1018-00001 · Client 1018 · Closing Documents

officer-certificate-ppc.docx DOCUMENT Capital Markets

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OFFICER'S CERTIFICATE OF PENTERRA PHARMACEUTICALS CORP.

Delivered Pursuant to Section 7(d) of the Underwriting Agreement dated October 12, 2023

October 17, 2023

Issued in connection with the registered selling-stockholder secondary offering of 6,250,000 shares of common stock, par value $0.001 per share, of Penterra Pharmaceuticals Corp.

TO:

Ridgeline Securities LLC 383 Madison Avenue New York, NY 10017

Broadmark Capital Inc. 200 Park Avenue New York, NY 10166

As representatives of the several underwriters named in Schedule I to the Underwriting Agreement (as defined below)

With a copy to:

Caldwell, Pearce & Strauss LLP 1251 Avenue of the Americas, 40th Floor New York, NY 10020

Attention: Margaret Hui

Calderwood & Harkness LLP One Liberty Plaza, 52nd Floor New York, NY 10006

Attention: Jennifer Kwon

Ladies and Gentlemen:

The undersigned, Dr. Marco Castellano, in his capacity as Chief Executive Officer of Penterra Pharmaceuticals Corp., a corporation organized and existing under the laws of the State of Delaware ("PPC" or the "Company"), and Lisa Hargrove, in her capacity as Chief Financial Officer of PPC, do hereby certify as follows in connection with the Underwriting Agreement dated October 12, 2023 (the "Underwriting Agreement"), among (i) Penterra Pharmaceuticals Corp., as issuer, (ii) the selling stockholders named therein (being Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC, each a "Selling Stockholder" and collectively, the "Selling Stockholders"), and (iii) Ridgeline Securities LLC and Broadmark Capital Inc., as representatives (the "Representatives") of the several underwriters named in Schedule I to the Underwriting Agreement (being Ridgeline Securities LLC, Broadmark Capital Inc., Linden Groves & Co., and Harborview Partners LLC, collectively, the "Underwriters").

This Officer's Certificate is delivered to the Representatives on the date hereof pursuant to Section 7(d) of the Underwriting Agreement as a condition to the obligations of the Underwriters at the closing of the offering on October 17, 2023 (the "Closing Date"). This certificate is being delivered in connection with and as contemplated by the Underwriting Agreement and is intended to be relied upon by the Underwriters and their respective counsel in connection with the closing of the transactions contemplated thereby.

Reference is made to the prospectus supplement dated October 12, 2023 (the "Prospectus Supplement"), filed with the Securities and Exchange Commission (the "SEC") pursuant to Rule 424(b)(5) under the Securities Act of 1933, as amended (the "Securities Act"), supplementing the base prospectus forming part of the registration statement on Form S-3 (File No. 333-274851) (together with all amendments thereto, the "Registration Statement"), which Registration Statement was declared effective by the SEC on August 22, 2023 (the base prospectus and the Prospectus Supplement, together with any documents incorporated by reference therein, collectively, the "Prospectus").

The offering to which this certificate relates consists of 6,250,000 shares of common stock, par value $0.001 per share, of PPC (the "Shares"), offered by the Selling Stockholders at a public offering price of $41.60 per share, for aggregate gross proceeds of $260,000,000, with an over-allotment option granted by the Selling Stockholders to the Underwriters covering up to an additional 937,500 shares of common stock (the "Option Shares"), exercisable in whole or in part within thirty (30) days from the date of the Underwriting Agreement.

Capitalized terms used but not otherwise defined herein shall have the meanings assigned to such terms in the Underwriting Agreement.

Section 1. Certification of Representations and Warranties

Each of the undersigned hereby certifies, in his or her capacity as an officer of PPC and not in any individual capacity, as follows:

(a) The representations and warranties of the Company set forth in Section 1 of the Underwriting Agreement are true and correct in all material respects as of the date of the Underwriting Agreement (October 12, 2023) and as of the Closing Date (October 17, 2023), with the same force and effect as though expressly made on and as of the Closing Date, except for any representations and warranties that by their terms speak as of a specific date, which representations and warranties are true and correct in all material respects as of such specified date.

(b) No representation or warranty of the Company contained in the Underwriting Agreement, or in any certificate, document, or instrument delivered by or on behalf of the Company pursuant to the Underwriting Agreement, contains any untrue statement of a material fact or omits to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading, in each case as of the date of the Underwriting Agreement and as of the Closing Date.

(c) Without limiting the generality of the foregoing, the undersigned confirm that the representations and warranties of the Company relating to (i) the Company's capitalization, (ii) the authorization and valid issuance of the Shares, (iii) the accuracy and completeness of the Registration Statement and the Prospectus Supplement, (iv) the Company's compliance with applicable laws and regulations, (v) the Company's intellectual property and proprietary rights, (vi) the Company's tax matters, (vii) the Company's internal controls over financial reporting and disclosure controls and procedures, and (viii) the Company's compliance with the applicable listing requirements of the Nasdaq Global Select Market, are true and correct in all material respects as of the Closing Date.

Section 2. Certification of Compliance with Covenants

Each of the undersigned hereby certifies as follows:

(a) The Company has performed and complied in all material respects with all agreements, covenants, conditions, and obligations required by the Underwriting Agreement to be performed, satisfied, or complied with by the Company at or prior to the Closing Date, including, without limitation, those set forth in Section 4 of the Underwriting Agreement.

(b) Without limiting the generality of the foregoing, the Company has:

(i) timely filed the Prospectus Supplement (including the final prospectus supplement dated October 12, 2023) with the SEC pursuant to Rule 424(b)(5) under the Securities Act within the time period required by such Rule, and the Company has confirmed that such filing was accepted by the SEC's EDGAR filing system;

(ii) cooperated fully with the Selling Stockholders and the Underwriters in connection with the offering, including providing reasonable access to the Company's books, records, properties, and personnel and facilitating due diligence reviews conducted by the Underwriters and their counsel;

(iii) complied in all material respects with all applicable requirements of the Securities Act, the Securities Exchange Act of 1934, as amended (the "Exchange Act"), and the rules and regulations of the SEC promulgated thereunder, including, without limitation, Regulation S-K, Regulation S-X, Rule 10b-5, Rule 415, Rule 424, and Rule 433, in each case as applicable to the Registration Statement, the Prospectus Supplement, and the transactions contemplated by the Underwriting Agreement;

(iv) maintained the listing of its common stock on the Nasdaq Global Select Market under the trading symbol "PNTR," including the listing of the Shares to be sold in the offering, and has filed all required supplemental listing applications and forms with the Nasdaq Stock Market LLC in connection therewith, and no proceedings for the delisting of the Company's common stock from the Nasdaq Global Select Market have been instituted or, to the knowledge of the undersigned, are threatened or contemplated;

(v) filed or caused to be filed all required SEC filings in connection with the offering, including the filing of the Prospectus Supplement, any free writing prospectuses, and all documents required to be incorporated by reference in the Prospectus Supplement; and

(vi) refrained from taking any action that would cause the Company to become an "ineligible issuer" as defined in Rule 405 under the Securities Act.

Section 3. Certification Regarding Registration Statement and Prospectus Supplement

Each of the undersigned hereby certifies as follows:

(a) The Registration Statement on Form S-3 (File No. 333-274851), as of the date it was declared effective by the SEC (August 22, 2023), and each amendment thereto, at the time each such amendment became effective, did not contain any untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary to make the statements therein not misleading. As of the Closing Date, the Registration Statement does not contain any untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary to make the statements therein not misleading.

(b) The Prospectus Supplement, including the preliminary prospectus supplement filed with the SEC on October 2, 2023, and the final prospectus supplement dated October 12, 2023, as of their respective dates of filing with the SEC and as of the Closing Date, did not and does not contain any untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading. The base prospectus forming part of the Registration Statement, as supplemented by the Prospectus Supplement, did not and does not, as of the Closing Date, contain any untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading.

(c) No issuer free writing prospectus (as defined in Rule 433 under the Securities Act), including the Pricing Term Sheet dated October 12, 2023, filed with the SEC pursuant to Rule 433 under the Securities Act, when considered together with the Prospectus Supplement as of its date or as of the Closing Date, contained or contains any untrue statement of a material fact or omits to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading. The Company has not distributed any issuer free writing prospectus other than those listed in Schedule II to the Underwriting Agreement.

(d) Each document, if any, filed or to be filed pursuant to the Exchange Act and incorporated by reference in the Registration Statement or the Prospectus Supplement, when such document was filed with the SEC, complied in all material respects with the Exchange Act and the applicable rules and regulations of the SEC promulgated thereunder, and no such document, when considered together with all other documents then filed and incorporated by reference, contained or contains any untrue statement of a material fact or omitted or omits to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading.

Section 4. Absence of Material Adverse Change

Each of the undersigned hereby certifies as follows:

(a) Since the date of the most recent financial statements of the Company included or incorporated by reference in the Prospectus Supplement — being (i) the unaudited condensed consolidated financial statements for the six months ended June 30, 2023, as set forth in the Company's Quarterly Report on Form 10-Q for the quarter ended June 30, 2023 (reflecting first-half 2023 consolidated revenue of $312.6 million and first-half 2023 consolidated net income of $67.8 million), and (ii) the audited consolidated financial statements for the fiscal year ended December 31, 2022, as set forth in the Company's Annual Report on Form 10-K for the fiscal year ended December 31, 2022 (reflecting fiscal year 2022 consolidated revenue of $387.4 million and fiscal year 2022 consolidated net income of $42.1 million) — there has been no Material Adverse Change (as defined in Section 1(a)(xii) of the Underwriting Agreement) in the condition (financial or otherwise), earnings, business, properties, management, operations, assets, liabilities, or prospects of the Company and its subsidiaries taken as a whole, whether or not arising from transactions in the ordinary course of business.

(b) Since the date of the most recent financial statements described in subsection (a) above, there has been no development or event involving a prospective Material Adverse Change in or affecting the condition (financial or otherwise), earnings, business, properties, management, operations, assets, liabilities, or prospects of the Company and its subsidiaries taken as a whole.

(c) The Company's total shares of common stock issued and outstanding as of the Closing Date are 120,000,000 shares, par value $0.001 per share, which is consistent in all respects with the disclosure regarding the Company's capitalization set forth in the Prospectus Supplement. The Company has no shares of preferred stock outstanding as of the Closing Date.

(d) The Company's market capitalization as publicly reported by the Nasdaq Global Select Market has not experienced any decline that constitutes, or would reasonably be expected to constitute, a Material Adverse Change in the condition (financial or otherwise), business, properties, or prospects of the Company and its subsidiaries taken as a whole.

Section 5. Absence of Certain Events

Each of the undersigned hereby certifies as follows:

(a) Since the date of the Underwriting Agreement (October 12, 2023) and through the Closing Date (October 17, 2023):

(i) No stop order suspending the effectiveness of the Registration Statement has been issued by the SEC, and no proceedings for that purpose have been instituted, are pending, or, to the knowledge of the undersigned, have been threatened or are contemplated by the SEC or any other governmental authority. No notice of objection of the SEC to the use of the Registration Statement or any post-effective amendment thereto pursuant to Rule 401(g)(2) under the Securities Act has been received by the Company.

(ii) No order preventing or suspending the use of the Prospectus Supplement or any issuer free writing prospectus has been issued by the SEC or any state securities commission or other regulatory authority, and no proceedings for that purpose have been instituted, are pending, or, to the knowledge of the undersigned, have been threatened or are contemplated.

(iii) No action, suit, proceeding, inquiry, or investigation at law or in equity, or before or by any federal, state, local, or foreign court, governmental authority, regulatory body, administrative agency, self-regulatory organization, or arbitral tribunal, has been instituted, is pending, or, to the knowledge of the undersigned, is threatened or contemplated, that (A) would reasonably be expected to prevent or materially impair the consummation of the transactions contemplated by the Underwriting Agreement, including the sale and delivery of the Shares by the Selling Stockholders to the Underwriters and the public offering thereof, or (B) would reasonably be expected to result in a Material Adverse Change in the condition (financial or otherwise), earnings, business, properties, management, operations, assets, liabilities, or prospects of the Company and its subsidiaries taken as a whole.

(iv) The Company has not incurred any material liabilities or obligations, whether direct or contingent, absolute or conditional, or otherwise, that are not in the ordinary course of business consistent with past practice, except as disclosed in the Prospectus Supplement or the Underwriting Agreement.

(v) No nationally recognized statistical rating organization (as defined in Section 3(a)(62) of the Exchange Act) has downgraded, or publicly announced any intention to review for possible downgrade or placed on negative watch, any debt securities, preferred stock, or other securities of the Company or any of its subsidiaries.

Section 6. Absence of Certain Distributions

Each of the undersigned hereby certifies as follows:

(a) Since the date of the Underwriting Agreement (October 12, 2023), the Company has not:

(i) declared, set aside, paid, or made any dividend or other distribution (whether in cash, stock, property, or otherwise) on or with respect to any shares of its capital stock or other equity interests;

(ii) issued any shares of capital stock, or any options, warrants, rights, or other securities convertible into, exercisable for, or exchangeable for shares of capital stock of the Company (other than (A) the issuance of shares of common stock upon the exercise of outstanding stock options or the settlement of outstanding restricted stock units in each case pursuant to the Company's existing employee benefit plans as previously disclosed in the Prospectus Supplement, and (B) shares of common stock issued pursuant to the Company's employee stock purchase plan); or

(iii) directly or indirectly repurchased, redeemed, or otherwise acquired, or entered into any agreement, arrangement, or understanding to repurchase, redeem, or otherwise acquire, any of its outstanding shares of capital stock or other equity securities,

in each case except as otherwise specifically disclosed in the Prospectus Supplement or the Underwriting Agreement or as previously approved by the Board of Directors of the Company and disclosed to the Representatives in writing.

Section 7. Company Organizational Matters

Each of the undersigned hereby certifies as follows:

(a) PPC has been duly incorporated and is validly existing as a corporation in good standing under the laws of the State of Delaware, with full corporate power and authority to own, lease, and operate its properties and assets and to conduct its business as described in the Prospectus Supplement.

(b) PPC is duly qualified to transact business and is in good standing as a foreign corporation in each jurisdiction in which the conduct of its business or its ownership or leasing of property requires such qualification, except where the failure to be so qualified or in good standing would not, individually or in the aggregate, reasonably be expected to result in a Material Adverse Change.

(c) The Company's Third Amended and Restated Certificate of Incorporation (as amended) and the Company's Amended and Restated Bylaws, each as currently in effect, have not been amended, modified, supplemented, or otherwise changed since the date of the Underwriting Agreement (October 12, 2023), and true and correct copies of such documents, as currently in effect, have been delivered to counsel for the Underwriters.

(d) The Company's registered agent in the State of Delaware is Registered Agents Inc., with offices located at 251 Little Falls Drive, Wilmington, Delaware 19808.

(e) The Company's principal executive offices and corporate headquarters are located at 400 Meridian Parkway, Suite 1200, Princeton, New Jersey 08540.

(f) Each of the Company's subsidiaries is a corporation, limited liability company, or other entity duly organized, validly existing, and in good standing (where applicable) under the laws of its jurisdiction of organization, with full power and authority to own, lease, and operate its properties and conduct its business as described in the Prospectus Supplement.

Section 8. Additional Certifications Regarding the Offering

Each of the undersigned hereby certifies as follows:

(a) The Company is not receiving any of the proceeds from the sale of the Shares by the Selling Stockholders in the offering. All net proceeds from the sale of the Shares (after deduction of the underwriting discount of 2.50% of the public offering price, being $1.04 per share, and any applicable transfer taxes) are being paid directly to the Selling Stockholders, pro rata in accordance with the number of Shares sold by each such Selling Stockholder as set forth in the Underwriting Agreement.

(b) The total issuer expenses borne by the Company in connection with the offering (excluding the underwriting discount, which is borne by the Selling Stockholders) are estimated to be $765,000, consisting of the following:

The foregoing expenses are within the amount authorized and approved by the Board of Directors of the Company for payment in connection with the offering, as reflected in the resolutions adopted by the Board of Directors on September 28, 2023.

(c) The Company has delivered to Pinnacle Trust & Transfer Co. (the Company's transfer agent and registrar for its common stock) all necessary instructions, authorizations, and documentation to facilitate the book-entry delivery of the Shares through the facilities of The Depository Trust Company ("DTC") for settlement on the Closing Date. The Shares bear CUSIP number 70831X 10 5 and are eligible for book-entry settlement and clearance through DTC. The Company has confirmed with Pinnacle Trust & Transfer Co. that all Shares to be delivered on the Closing Date will be made available in book-entry form through DTC no later than 10:00 a.m. (New York City time) on the Closing Date.

Section 9. Awareness Statement / Knowledge Qualifier

(a) Each of the undersigned has made due and diligent inquiry of such officers, directors, employees, agents, and other representatives of the Company (including, without limitation, the Company's General Counsel, Vice President of Regulatory Affairs, Vice President of Commercial Operations, and Controller) as the undersigned deemed necessary or appropriate to enable the undersigned to make the certifications contained herein on a fully informed basis. The undersigned have also reviewed such corporate records, documents, agreements, filings, correspondence, and other materials as the undersigned deemed necessary or appropriate in connection with the preparation and delivery of this certificate.

(b) This certificate is being delivered on behalf of the Company, solely in the official capacities of the undersigned as officers of the Company, and not in any individual or personal capacity. No personal liability shall attach to, or be incurred by, either of the undersigned by reason of the execution, delivery, or performance of this certificate. Nothing contained in this certificate shall be deemed to create any obligation or liability of the undersigned in their individual capacities.

(c) This certificate may be relied upon by the Representatives and the other Underwriters, and their respective counsel, solely for purposes of determining whether the conditions to the obligations of the Underwriters under Section 7 of the Underwriting Agreement have been satisfied as of the Closing Date, and for no other purpose. This certificate shall not be deemed to constitute a guaranty, surety, or insurance of any kind in favor of any person or entity.

[Remainder of page intentionally left blank; signature page follows]

SIGNATURE PAGE TO OFFICER'S CERTIFICATE

PENTERRA PHARMACEUTICALS CORP.

IN WITNESS WHEREOF, the undersigned have executed this Officer's Certificate as of the date first set forth above.

PENTERRA PHARMACEUTICALS CORP.

By: ________

Name: Dr. Marco Castellano

Title: Chief Executive Officer

Date: October 17, 2023

PENTERRA PHARMACEUTICALS CORP.

By: ________

Name: Lisa Hargrove

Title: Chief Financial Officer

Date: October 17, 2023

Expense Category	Payee	Estimated Amount
Nasdaq supplemental listing fees	The Nasdaq Stock Market LLC	$45,000
Legal fees and expenses of Company counsel	Calderwood & Harkness LLP	$485,000
Accounting fees and expenses	Graystone & Whitmore LLP	$175,000
Printing and EDGAR filing fees	Apex Financial Printing Inc.	$35,000
Miscellaneous expenses	Various	$25,000
Total Estimated Issuer Expenses	$765,000

OFFICER'S CERTIFICATE OF PENTERRA PHARMACEUTICALS CORP.
Delivered Pursuant to Section 7(d) of the Underwriting Agreement dated October 12, 2023
October 17, 2023
Issued in connection with the registered selling-stockholder secondary offering of 6,250,000 shares of common stock, par value $0.001 per share, of Penterra Pharmaceuticals Corp.
TO:
Ridgeline Securities LLC 383 Madison Avenue New York, NY 10017
Broadmark Capital Inc. 200 Park Avenue New York, NY 10166
As representatives of the several underwriters named in Schedule I to the Underwriting Agreement (as defined below)
With a copy to:
Caldwell, Pearce & Strauss LLP 1251 Avenue of the Americas, 40th Floor New York, NY 10020
Attention: Margaret Hui
Calderwood & Harkness LLP One Liberty Plaza, 52nd Floor New York, NY 10006
Attention: Jennifer Kwon
Ladies and Gentlemen:
The undersigned, Dr. Marco Castellano, in his capacity as Chief Executive Officer of Penterra Pharmaceuticals Corp., a corporation organized and existing under the laws of the State of Delaware ("PPC" or the "Company"), and Lisa Hargrove, in her capacity as Chief Financial Officer of PPC, do hereby certify as follows in connection with the Underwriting Agreement dated October 12, 2023 (the "Underwriting Agreement"), among (i) Penterra Pharmaceuticals Corp., as issuer, (ii) the selling stockholders named therein (being Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC, each a "Selling Stockholder" and collectively, the "Selling Stockholders"), and (iii) Ridgeline Securities LLC and Broadmark Capital Inc., as representatives (the "Representatives") of the several underwriters named in Schedule I to the Underwriting Agreement (being Ridgeline Securities LLC, Broadmark Capital Inc., Linden Groves & Co., and Harborview Partners LLC, collectively, the "Underwriters").
This Officer's Certificate is delivered to the Representatives on the date hereof pursuant to Section 7(d) of the Underwriting Agreement as a condition to the obligations of the Underwriters at the closing of the offering on October 17, 2023 (the "Closing Date"). This certificate is being delivered in connection with and as contemplated by the Underwriting Agreement and is intended to be relied upon by the Underwriters and their respective counsel in connection with the closing of the transactions contemplated thereby.
Reference is made to the prospectus supplement dated October 12, 2023 (the "Prospectus Supplement"), filed with the Securities and Exchange Commission (the "SEC") pursuant to Rule 424(b)(5) under the Securities Act of 1933, as amended (the "Securities Act"), supplementing the base prospectus forming part of the registration statement on Form S-3 (File No. 333-274851) (together with all amendments thereto, the "Registration Statement"), which Registration Statement was declared effective by the SEC on August 22, 2023 (the base prospectus and the Prospectus Supplement, together with any documents incorporated by reference therein, collectively, the "Prospectus").
The offering to which this certificate relates consists of 6,250,000 shares of common stock, par value $0.001 per share, of PPC (the "Shares"), offered by the Selling Stockholders at a public offering price of $41.60 per share, for aggregate gross proceeds of $260,000,000, with an over-allotment option granted by the Selling Stockholders to the Underwriters covering up to an additional 937,500 shares of common stock (the "Option Shares"), exercisable in whole or in part within thirty (30) days from the date of the Underwriting Agreement.
Capitalized terms used but not otherwise defined herein shall have the meanings assigned to such terms in the Underwriting Agreement.
Section 1. Certification of Representations and Warranties
Each of the undersigned hereby certifies, in his or her capacity as an officer of PPC and not in any individual capacity, as follows:
(a) The representations and warranties of the Company set forth in Section 1 of the Underwriting Agreement are true and correct in all material respects as of the date of the Underwriting Agreement (October 12, 2023) and as of the Closing Date (October 17, 2023), with the same force and effect as though expressly made on and as of the Closing Date, except for any representations and warranties that by their terms speak as of a specific date, which representations and warranties are true and correct in all material respects as of such specified date.
(b) No representation or warranty of the Company contained in the Underwriting Agreement, or in any certificate, document, or instrument delivered by or on behalf of the Company pursuant to the Underwriting Agreement, contains any untrue statement of a material fact or omits to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading, in each case as of the date of the Underwriting Agreement and as of the Closing Date.
(c) Without limiting the generality of the foregoing, the undersigned confirm that the representations and warranties of the Company relating to (i) the Company's capitalization, (ii) the authorization and valid issuance of the Shares, (iii) the accuracy and completeness of the Registration Statement and the Prospectus Supplement, (iv) the Company's compliance with applicable laws and regulations, (v) the Company's intellectual property and proprietary rights, (vi) the Company's tax matters, (vii) the Company's internal controls over financial reporting and disclosure controls and procedures, and (viii) the Company's compliance with the applicable listing requirements of the Nasdaq Global Select Market, are true and correct in all material respects as of the Closing Date.
Section 2. Certification of Compliance with Covenants
Each of the undersigned hereby certifies as follows:
(a) The Company has performed and complied in all material respects with all agreements, covenants, conditions, and obligations required by the Underwriting Agreement to be performed, satisfied, or complied with by the Company at or prior to the Closing Date, including, without limitation, those set forth in Section 4 of the Underwriting Agreement.
(b) Without limiting the generality of the foregoing, the Company has:
(i) timely filed the Prospectus Supplement (including the final prospectus supplement dated October 12, 2023) with the SEC pursuant to Rule 424(b)(5) under the Securities Act within the time period required by such Rule, and the Company has confirmed that such filing was accepted by the SEC's EDGAR filing system;
(ii) cooperated fully with the Selling Stockholders and the Underwriters in connection with the offering, including providing reasonable access to the Company's books, records, properties, and personnel and facilitating due diligence reviews conducted by the Underwriters and their counsel;
(iii) complied in all material respects with all applicable requirements of the Securities Act, the Securities Exchange Act of 1934, as amended (the "Exchange Act"), and the rules and regulations of the SEC promulgated thereunder, including, without limitation, Regulation S-K, Regulation S-X, Rule 10b-5, Rule 415, Rule 424, and Rule 433, in each case as applicable to the Registration Statement, the Prospectus Supplement, and the transactions contemplated by the Underwriting Agreement;
(iv) maintained the listing of its common stock on the Nasdaq Global Select Market under the trading symbol "PNTR," including the listing of the Shares to be sold in the offering, and has filed all required supplemental listing applications and forms with the Nasdaq Stock Market LLC in connection therewith, and no proceedings for the delisting of the Company's common stock from the Nasdaq Global Select Market have been instituted or, to the knowledge of the undersigned, are threatened or contemplated;
(v) filed or caused to be filed all required SEC filings in connection with the offering, including the filing of the Prospectus Supplement, any free writing prospectuses, and all documents required to be incorporated by reference in the Prospectus Supplement; and
(vi) refrained from taking any action that would cause the Company to become an "ineligible issuer" as defined in Rule 405 under the Securities Act.
Section 3. Certification Regarding Registration Statement and Prospectus Supplement
Each of the undersigned hereby certifies as follows:
(a) The Registration Statement on Form S-3 (File No. 333-274851), as of the date it was declared effective by the SEC (August 22, 2023), and each amendment thereto, at the time each such amendment became effective, did not contain any untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary to make the statements therein not misleading. As of the Closing Date, the Registration Statement does not contain any untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary to make the statements therein not misleading.
(b) The Prospectus Supplement, including the preliminary prospectus supplement filed with the SEC on October 2, 2023, and the final prospectus supplement dated October 12, 2023, as of their respective dates of filing with the SEC and as of the Closing Date, did not and does not contain any untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading. The base prospectus forming part of the Registration Statement, as supplemented by the Prospectus Supplement, did not and does not, as of the Closing Date, contain any untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading.
(c) No issuer free writing prospectus (as defined in Rule 433 under the Securities Act), including the Pricing Term Sheet dated October 12, 2023, filed with the SEC pursuant to Rule 433 under the Securities Act, when considered together with the Prospectus Supplement as of its date or as of the Closing Date, contained or contains any untrue statement of a material fact or omits to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading. The Company has not distributed any issuer free writing prospectus other than those listed in Schedule II to the Underwriting Agreement.
(d) Each document, if any, filed or to be filed pursuant to the Exchange Act and incorporated by reference in the Registration Statement or the Prospectus Supplement, when such document was filed with the SEC, complied in all material respects with the Exchange Act and the applicable rules and regulations of the SEC promulgated thereunder, and no such document, when considered together with all other documents then filed and incorporated by reference, contained or contains any untrue statement of a material fact or omitted or omits to state a material fact necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading.
Section 4. Absence of Material Adverse Change
Each of the undersigned hereby certifies as follows:
(a) Since the date of the most recent financial statements of the Company included or incorporated by reference in the Prospectus Supplement — being (i) the unaudited condensed consolidated financial statements for the six months ended June 30, 2023, as set forth in the Company's Quarterly Report on Form 10-Q for the quarter ended June 30, 2023 (reflecting first-half 2023 consolidated revenue of $312.6 million and first-half 2023 consolidated net income of $67.8 million), and (ii) the audited consolidated financial statements for the fiscal year ended December 31, 2022, as set forth in the Company's Annual Report on Form 10-K for the fiscal year ended December 31, 2022 (reflecting fiscal year 2022 consolidated revenue of $387.4 million and fiscal year 2022 consolidated net income of $42.1 million) — there has been no Material Adverse Change (as defined in Section 1(a)(xii) of the Underwriting Agreement) in the condition (financial or otherwise), earnings, business, properties, management, operations, assets, liabilities, or prospects of the Company and its subsidiaries taken as a whole, whether or not arising from transactions in the ordinary course of business.
(b) Since the date of the most recent financial statements described in subsection (a) above, there has been no development or event involving a prospective Material Adverse Change in or affecting the condition (financial or otherwise), earnings, business, properties, management, operations, assets, liabilities, or prospects of the Company and its subsidiaries taken as a whole.
(c) The Company's total shares of common stock issued and outstanding as of the Closing Date are 120,000,000 shares, par value $0.001 per share, which is consistent in all respects with the disclosure regarding the Company's capitalization set forth in the Prospectus Supplement. The Company has no shares of preferred stock outstanding as of the Closing Date.
(d) The Company's market capitalization as publicly reported by the Nasdaq Global Select Market has not experienced any decline that constitutes, or would reasonably be expected to constitute, a Material Adverse Change in the condition (financial or otherwise), business, properties, or prospects of the Company and its subsidiaries taken as a whole.
Section 5. Absence of Certain Events
Each of the undersigned hereby certifies as follows:
(a) Since the date of the Underwriting Agreement (October 12, 2023) and through the Closing Date (October 17, 2023):
(i) No stop order suspending the effectiveness of the Registration Statement has been issued by the SEC, and no proceedings for that purpose have been instituted, are pending, or, to the knowledge of the undersigned, have been threatened or are contemplated by the SEC or any other governmental authority. No notice of objection of the SEC to the use of the Registration Statement or any post-effective amendment thereto pursuant to Rule 401(g)(2) under the Securities Act has been received by the Company.
(ii) No order preventing or suspending the use of the Prospectus Supplement or any issuer free writing prospectus has been issued by the SEC or any state securities commission or other regulatory authority, and no proceedings for that purpose have been instituted, are pending, or, to the knowledge of the undersigned, have been threatened or are contemplated.
(iii) No action, suit, proceeding, inquiry, or investigation at law or in equity, or before or by any federal, state, local, or foreign court, governmental authority, regulatory body, administrative agency, self-regulatory organization, or arbitral tribunal, has been instituted, is pending, or, to the knowledge of the undersigned, is threatened or contemplated, that (A) would reasonably be expected to prevent or materially impair the consummation of the transactions contemplated by the Underwriting Agreement, including the sale and delivery of the Shares by the Selling Stockholders to the Underwriters and the public offering thereof, or (B) would reasonably be expected to result in a Material Adverse Change in the condition (financial or otherwise), earnings, business, properties, management, operations, assets, liabilities, or prospects of the Company and its subsidiaries taken as a whole.
(iv) The Company has not incurred any material liabilities or obligations, whether direct or contingent, absolute or conditional, or otherwise, that are not in the ordinary course of business consistent with past practice, except as disclosed in the Prospectus Supplement or the Underwriting Agreement.
(v) No nationally recognized statistical rating organization (as defined in Section 3(a)(62) of the Exchange Act) has downgraded, or publicly announced any intention to review for possible downgrade or placed on negative watch, any debt securities, preferred stock, or other securities of the Company or any of its subsidiaries.
Section 6. Absence of Certain Distributions
Each of the undersigned hereby certifies as follows:
(a) Since the date of the Underwriting Agreement (October 12, 2023), the Company has not:
(i) declared, set aside, paid, or made any dividend or other distribution (whether in cash, stock, property, or otherwise) on or with respect to any shares of its capital stock or other equity interests;
(ii) issued any shares of capital stock, or any options, warrants, rights, or other securities convertible into, exercisable for, or exchangeable for shares of capital stock of the Company (other than (A) the issuance of shares of common stock upon the exercise of outstanding stock options or the settlement of outstanding restricted stock units in each case pursuant to the Company's existing employee benefit plans as previously disclosed in the Prospectus Supplement, and (B) shares of common stock issued pursuant to the Company's employee stock purchase plan); or
(iii) directly or indirectly repurchased, redeemed, or otherwise acquired, or entered into any agreement, arrangement, or understanding to repurchase, redeem, or otherwise acquire, any of its outstanding shares of capital stock or other equity securities,
in each case except as otherwise specifically disclosed in the Prospectus Supplement or the Underwriting Agreement or as previously approved by the Board of Directors of the Company and disclosed to the Representatives in writing.
Section 7. Company Organizational Matters
Each of the undersigned hereby certifies as follows:
(a) PPC has been duly incorporated and is validly existing as a corporation in good standing under the laws of the State of Delaware, with full corporate power and authority to own, lease, and operate its properties and assets and to conduct its business as described in the Prospectus Supplement.
(b) PPC is duly qualified to transact business and is in good standing as a foreign corporation in each jurisdiction in which the conduct of its business or its ownership or leasing of property requires such qualification, except where the failure to be so qualified or in good standing would not, individually or in the aggregate, reasonably be expected to result in a Material Adverse Change.
(c) The Company's Third Amended and Restated Certificate of Incorporation (as amended) and the Company's Amended and Restated Bylaws, each as currently in effect, have not been amended, modified, supplemented, or otherwise changed since the date of the Underwriting Agreement (October 12, 2023), and true and correct copies of such documents, as currently in effect, have been delivered to counsel for the Underwriters.
(d) The Company's registered agent in the State of Delaware is Registered Agents Inc., with offices located at 251 Little Falls Drive, Wilmington, Delaware 19808.
(e) The Company's principal executive offices and corporate headquarters are located at 400 Meridian Parkway, Suite 1200, Princeton, New Jersey 08540.
(f) Each of the Company's subsidiaries is a corporation, limited liability company, or other entity duly organized, validly existing, and in good standing (where applicable) under the laws of its jurisdiction of organization, with full power and authority to own, lease, and operate its properties and conduct its business as described in the Prospectus Supplement.
Section 8. Additional Certifications Regarding the Offering
Each of the undersigned hereby certifies as follows:
(a) The Company is not receiving any of the proceeds from the sale of the Shares by the Selling Stockholders in the offering. All net proceeds from the sale of the Shares (after deduction of the underwriting discount of 2.50% of the public offering price, being $1.04 per share, and any applicable transfer taxes) are being paid directly to the Selling Stockholders, pro rata in accordance with the number of Shares sold by each such Selling Stockholder as set forth in the Underwriting Agreement.
(b) The total issuer expenses borne by the Company in connection with the offering (excluding the underwriting discount, which is borne by the Selling Stockholders) are estimated to be $765,000, consisting of the following:
The foregoing expenses are within the amount authorized and approved by the Board of Directors of the Company for payment in connection with the offering, as reflected in the resolutions adopted by the Board of Directors on September 28, 2023.
(c) The Company has delivered to Pinnacle Trust & Transfer Co. (the Company's transfer agent and registrar for its common stock) all necessary instructions, authorizations, and documentation to facilitate the book-entry delivery of the Shares through the facilities of The Depository Trust Company ("DTC") for settlement on the Closing Date. The Shares bear CUSIP number 70831X 10 5 and are eligible for book-entry settlement and clearance through DTC. The Company has confirmed with Pinnacle Trust & Transfer Co. that all Shares to be delivered on the Closing Date will be made available in book-entry form through DTC no later than 10:00 a.m. (New York City time) on the Closing Date.
Section 9. Awareness Statement / Knowledge Qualifier
(a) Each of the undersigned has made due and diligent inquiry of such officers, directors, employees, agents, and other representatives of the Company (including, without limitation, the Company's General Counsel, Vice President of Regulatory Affairs, Vice President of Commercial Operations, and Controller) as the undersigned deemed necessary or appropriate to enable the undersigned to make the certifications contained herein on a fully informed basis. The undersigned have also reviewed such corporate records, documents, agreements, filings, correspondence, and other materials as the undersigned deemed necessary or appropriate in connection with the preparation and delivery of this certificate.
(b) This certificate is being delivered on behalf of the Company, solely in the official capacities of the undersigned as officers of the Company, and not in any individual or personal capacity. No personal liability shall attach to, or be incurred by, either of the undersigned by reason of the execution, delivery, or performance of this certificate. Nothing contained in this certificate shall be deemed to create any obligation or liability of the undersigned in their individual capacities.
(c) This certificate may be relied upon by the Representatives and the other Underwriters, and their respective counsel, solely for purposes of determining whether the conditions to the obligations of the Underwriters under Section 7 of the Underwriting Agreement have been satisfied as of the Closing Date, and for no other purpose. This certificate shall not be deemed to constitute a guaranty, surety, or insurance of any kind in favor of any person or entity.
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SIGNATURE PAGE TO OFFICER'S CERTIFICATE
PENTERRA PHARMACEUTICALS CORP.
IN WITNESS WHEREOF, the undersigned have executed this Officer's Certificate as of the date first set forth above.
PENTERRA PHARMACEUTICALS CORP.
By: ________
Name: Dr. Marco Castellano
Title: Chief Executive Officer
Date: October 17, 2023
PENTERRA PHARMACEUTICALS CORP.
By: ________
Name: Lisa Hargrove
Title: Chief Financial Officer
Date: October 17, 2023
Expense Category | Payee | Estimated Amount
Nasdaq supplemental listing fees | The Nasdaq Stock Market LLC | $45,000
Legal fees and expenses of Company counsel | Calderwood & Harkness LLP | $485,000
Accounting fees and expenses | Graystone & Whitmore LLP | $175,000
Printing and EDGAR filing fees | Apex Financial Printing Inc. | $35,000
Miscellaneous expenses | Various | $25,000
Total Estimated Issuer Expenses | $765,000

OFFICER'S CERTIFICATE OF PENTERRA PHARMACEUTICALS CORP.

SIGNATURE PAGE TO OFFICER'S CERTIFICATE

PENTERRA PHARMACEUTICALS CORP.

PENTERRA PHARMACEUTICALS CORP.

PENTERRA PHARMACEUTICALS CORP.

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