negative-assurance-letter-10b5.docx

1018-00001 · Client 1018 · Opinions & Comfort Letters

negative-assurance-letter-10b5.docx DOCUMENT Capital Markets

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CALDERWOOD & HARKNESS LLP One Liberty Plaza, 52nd Floor New York, NY 10006 Telephone: (212) 558-4000 Facsimile: (212) 558-3588 www.calderwoodharkness.com

October 17, 2023

CONFIDENTIAL

Ridgeline Securities LLC 383 Madison Avenue New York, NY 10017

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

Linden Groves & Co. 745 Fifth Avenue New York, NY 10151

Harborview Partners LLC 1 Federal Street Boston, MA 02110

c/o Ridgeline Securities LLC, as Representative of the Several Underwriters

Ladies and Gentlemen:

Re: Penterra Pharmaceuticals Corp. — Selling Stockholder Secondary Offering of 6,250,000 Shares of Common Stock, par value $0.001 per share

1. Introduction and Context

We have acted as counsel to Penterra Pharmaceuticals Corp., a Delaware corporation (the "Company" or "PPC"), in connection with the registered public offering (the "Offering") of shares of common stock, par value $0.001 per share (the "Common Stock"), of the Company by certain selling stockholders. This letter is being delivered to you in connection with the Underwriting Agreement dated October 12, 2023 (the "Underwriting Agreement") among the Company, the selling stockholders named therein (Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC, collectively, the "Selling Stockholders"), and the several underwriters named in Schedule I thereto (the "Underwriters"), for whom Ridgeline Securities LLC is acting as Representative.

The Underwriting Agreement relates to the registered public offering by the Selling Stockholders of 6,250,000 shares of Common Stock (the "Shares"), plus up to an additional 937,500 shares of Common Stock subject to the Underwriters' over-allotment option granted pursuant to Section 2 of the Underwriting Agreement. This letter is delivered to you pursuant to Section 7(e) of the Underwriting Agreement as a condition to the obligations of the Underwriters to close the purchase of the Shares on the date hereof.

Calderwood & Harkness LLP has acted as counsel to the Company in connection with the preparation of the Registration Statement (as defined below), the Prospectus (as defined below), and the other offering documents relating to the Offering, and in connection with the negotiation and execution of the Underwriting Agreement.

2. Documents Reviewed

In connection with the preparation of this letter, we have reviewed the following documents:

(a) the Registration Statement on Form S-3 (File No. 333-274851) of the Company (the "Registration Statement"), including the base prospectus dated August 22, 2023, contained therein (the "Base Prospectus"), as filed with the Securities and Exchange Commission (the "SEC" or the "Commission") under the Securities Act of 1933, as amended (the "Securities Act"), and declared effective by the SEC on August 22, 2023;

(b) the preliminary prospectus supplement dated October 2, 2023, relating to the Offering, as filed with the SEC pursuant to Rule 424(b)(5) under the Securities Act (the "Preliminary Prospectus Supplement");

(c) the final prospectus supplement dated October 12, 2023 (the "Prospectus Supplement"), as filed with the SEC pursuant to Rule 424(b)(5) under the Securities Act, together with the Base Prospectus (the Prospectus Supplement together with the Base Prospectus, collectively, the "Prospectus");

(d) the Issuer Free Writing Prospectus, constituting a Pricing Term Sheet dated October 12, 2023, as filed with the SEC pursuant to Rule 433 under the Securities Act (the "Pricing Term Sheet");

(e) the Underwriting Agreement dated October 12, 2023;

(f) the documents incorporated by reference in the Registration Statement and the Prospectus as of the date hereof, including, without limitation:

(i) the Company's Annual Report on Form 10-K for the fiscal year ended December 31, 2022, as filed with the SEC on February 28, 2023;

(ii) the Company's Quarterly Report on Form 10-Q for the fiscal quarter ended March 31, 2023, as filed with the SEC on May 10, 2023;

(iii) the Company's Quarterly Report on Form 10-Q for the fiscal quarter ended June 30, 2023, as filed with the SEC on August 9, 2023;

(iv) the Company's Current Reports on Form 8-K filed with the SEC on March 14, 2023, May 22, 2023, July 7, 2023, August 15, 2023, September 18, 2023, and October 3, 2023;

(v) the description of the Company's Common Stock contained in the Company's Registration Statement on Form 8-A (File No. 001-39842), as filed with the SEC on November 10, 2020, including any amendments or reports filed for the purpose of updating such description; and

(vi) all other documents filed by the Company with the SEC pursuant to Sections 13(a), 13(c), 14, or 15(d) of the Securities Exchange Act of 1934, as amended (the "Exchange Act"), after the date of the initial filing of the Registration Statement and prior to the date hereof; and

(g) such other documents, records, corporate proceedings, certificates of officers of the Company, and instruments as we deemed necessary or appropriate for purposes of this letter.

We have also reviewed the forms of the certificates delivered by officers of the Company on the date hereof pursuant to the Underwriting Agreement.

3. Scope of Review and Participation

In addition to our review of the documents described in Section 2 above, we have participated in the preparation of the Registration Statement, the Base Prospectus, the Preliminary Prospectus Supplement, the Prospectus Supplement, and the Pricing Term Sheet, including review of successive drafts of each such document.

We have also participated in conferences and discussions with officers and other representatives of the Company, including David Orenstein, General Counsel and Corporate Secretary, Lisa Hargrove, Chief Financial Officer, and Dr. Marco Castellano, Chief Executive Officer, as well as representatives of Graystone & Whitmore LLP, the Company's independent registered public accounting firm, representatives of Caldwell, Pearce & Strauss LLP, counsel for the Underwriters, and representatives of the Underwriters, at which conferences and discussions the contents of the Registration Statement, the Prospectus, the Pricing Term Sheet, and related matters were discussed. These conferences and discussions included due diligence sessions held on October 3, 2023, October 6, 2023, and October 10, 2023, as well as telephonic conferences held at various times during the period from October 2, 2023 through October 16, 2023.

In addition, we have reviewed certain corporate records and documents of the Company that were furnished to us by the Company and its officers and representatives in connection with this Offering, including, without limitation, the Amended and Restated Certificate of Incorporation and Amended and Restated Bylaws of the Company, minutes of meetings of the Board of Directors of the Company and committees thereof, and certain material contracts of the Company.

Notwithstanding the foregoing, we did not participate in the preparation of the financial statements, financial statement schedules, or other financial or accounting data (including the notes thereto and the reports of independent registered public accounting firms thereon) included or incorporated by reference in the Registration Statement or the Prospectus, and we have not independently verified the accuracy, completeness, or fairness of such financial statements, financial statement schedules, or other financial or accounting data. Our review of the financial statements and financial data was limited to reading such information for the purpose of determining whether, on its face, it appeared to be consistent in all material respects with the non-financial statement portions of the Registration Statement and the Prospectus with which we were involved.

4. Limitations and Qualifications

This letter is subject to the following limitations and qualifications:

(a) This letter is not a guarantee, and the negative assurance set forth herein is not based on an independent investigation or verification of the facts stated in or omitted from the Registration Statement or the Prospectus. We have assumed the genuineness of all signatures, the legal capacity of all natural persons, the authenticity of all documents submitted to us as originals, and the conformity to original documents of all documents submitted to us as certified, photostatic, facsimile, or electronic copies. We have relied, to the extent we deemed appropriate, upon certificates of public officials and officers and representatives of the Company as to matters of fact.

(b) The scope of our engagement as described herein was limited and did not include an audit, an examination, or any other procedures of the type that would be undertaken by an independent registered public accounting firm in accordance with the standards of the Public Company Accounting Oversight Board. Nor did our engagement include any other procedures designed or intended to discover undisclosed liabilities, undisclosed pending or threatened litigation, regulatory proceedings, or other matters that may be material to the Company or the Offering. Our participation in due diligence conferences and discussions does not constitute an independent verification of any of the matters discussed therein.

(c) We do not express any opinion or belief regarding the financial statements or financial data of the Company (including the notes thereto and the auditor's reports thereon), financial statement schedules, or any other financial, statistical, or accounting information included or incorporated by reference in the Registration Statement or the Prospectus, including, without limitation, any pro forma financial information, any selected financial data, any "Management's Discussion and Analysis of Financial Condition and Results of Operations" to the extent it constitutes financial data, and any financial information contained in any exhibit to or document incorporated by reference in the Registration Statement or the Prospectus. All such financial statements, financial data, and related information are expressly excluded from the scope of this letter.

(d) We do not express any opinion or belief with respect to any Statement of Eligibility on Form T-1 (if any) included as an exhibit to the Registration Statement, or with respect to any statistical data, or any information regarding clinical trials, scientific or medical data, pharmacological data, pre-clinical studies, toxicology reports, regulatory filings or determinations by the United States Food and Drug Administration or any other governmental authority, or other technical information included or incorporated by reference in the Registration Statement or the Prospectus. Such information involves matters of a scientific, medical, or technical nature that are outside the scope of our legal expertise, and we have made no effort to independently verify or evaluate such information.

(e) We are members of the Bar of the State of New York, and we do not express any opinion or belief as to the laws of any jurisdiction other than (i) the laws of the State of New York, (ii) the General Corporation Law of the State of Delaware, and (iii) the federal laws of the United States of America, including the Securities Act, the Exchange Act, and the rules and regulations promulgated thereunder by the SEC. We express no opinion as to the laws of any other state or jurisdiction, including, without limitation, the Blue Sky or securities laws of any state, the patent, trademark, or intellectual property laws of any jurisdiction, the laws governing the regulation of pharmaceutical products in any jurisdiction, or the tax laws of any jurisdiction.

(f) We have assumed that each of the documents we have reviewed was duly and validly authorized, executed, and delivered by each party thereto (other than the Company, with respect to which we have reviewed relevant corporate proceedings), and that each such document constitutes the legal, valid, and binding obligation of each party thereto, enforceable in accordance with its terms.

5. Negative Assurance Statement

On the basis of the review and participation described in Sections 2 and 3 above, and subject to the limitations, qualifications, and exclusions set forth in Section 4 above and elsewhere in this letter, and in reliance upon the representations and warranties of the Company and the Selling Stockholders contained in the Underwriting Agreement and the certificates delivered to us by officers of the Company in connection with the closing of the Offering, we advise you that nothing has come to our attention that causes us to believe that:

(a) the Registration Statement (File No. 333-274851), as of the date it became effective under the Securities Act (August 22, 2023), including the documents incorporated by reference therein at such date and any information deemed to be a part thereof pursuant to Rule 430B under the Securities Act, contained an untrue statement of a material fact or omitted to state a material fact required to be stated therein or necessary to make the statements therein not misleading (within the meaning of Section 11 of the Securities Act);

(b) the Prospectus (consisting of the Prospectus Supplement dated October 12, 2023 together with the Base Prospectus dated August 22, 2023), including the documents incorporated by reference therein, as of its date and as of the date hereof, contained or contains an untrue statement of a material fact or omitted or omits to state a material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading (within the meaning of Section 12(a)(2) of the Securities Act and Rule 10b-5 under the Exchange Act); or

(c) any amendment or supplement to the Registration Statement or the Prospectus filed with the SEC between the effective date of the Registration Statement and the date hereof (including any post-effective amendment or any amended or supplemented prospectus) contained, at the respective time such amendment or supplement was filed with the SEC, an untrue statement of a material fact or omitted to state a material fact required to be stated therein or necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading.

The statements set forth in clauses (a) through (c) above do not apply to (i) the financial statements, financial statement schedules, and other financial or accounting data (including the notes thereto and the auditor's reports thereon) included or incorporated by reference in the Registration Statement or the Prospectus, (ii) any Statement of Eligibility on Form T-1, (iii) any statistical data, (iv) any information regarding clinical trials, scientific or medical data, or other technical information included or incorporated by reference in the Registration Statement or the Prospectus, or (v) any information that we have not reviewed or in the preparation of which we did not participate, all of which are expressly excluded from the scope of this letter.

We note that the negative assurance statements set forth above are made with reference to the standards of liability established under Section 11 of the Securities Act (in respect of the Registration Statement) and Section 12(a)(2) of the Securities Act and Rule 10b-5 promulgated under the Exchange Act (in respect of the Prospectus). The negative assurance set forth herein is based on our professional judgment as lawyers and should not be construed as a factual representation or warranty regarding the accuracy or completeness of the Registration Statement or the Prospectus.

6. Reliance and Benefit

This letter is furnished to the Underwriters solely for their benefit and solely in connection with the Offering and may not be used, circulated, quoted, referred to, or relied upon by any other person or entity, or for any other purpose, without our prior written consent in each instance. Without limiting the generality of the foregoing, this letter may not be furnished to, or relied upon by, any purchaser or prospective purchaser of the Shares.

This letter is given as of the date hereof, and we assume no obligation to update, supplement, revise, or reaffirm this letter to reflect any facts or circumstances that may hereafter come to our attention or any changes in applicable law that may hereafter occur, whether or not such facts, circumstances, or changes may affect the conclusions set forth herein. We express no opinion or belief as to any matter not expressly set forth herein, and no opinion or belief is to be inferred or implied beyond the matters expressly stated in this letter.

7. No Attorney-Client Relationship with Underwriters

We wish to clarify that Calderwood & Harkness LLP has acted solely as counsel to the Company in connection with the Offering. We do not represent, and have not represented, any of the Underwriters, the Selling Stockholders, or any other party in connection with the Offering. The Underwriters are separately represented by Caldwell, Pearce & Strauss LLP as counsel for the Underwriters, and the Selling Stockholders are separately represented by Whitfield & Garza LLP as personal counsel to the Selling Stockholders. The delivery of this letter to the Underwriters does not create an attorney-client relationship between Calderwood & Harkness LLP and any of the Underwriters.

Very truly yours,

CALDERWOOD & HARKNESS LLP

By: ________

Name: Jennifer Kwon

Title: Partner

One Liberty Plaza, 52nd Floor New York, NY 10006

cc: David Orenstein, General Counsel & Corporate Secretary, Penterra Pharmaceuticals Corp., 400 Connell Drive, Suite 4200, Berkeley Heights, NJ 07922

cc: Patricia Velázquez, Esq., Whitfield & Garza LLP, 800 Third Avenue, New York, NY 10022 (Selling Stockholders' Personal Counsel)

cc: Margaret Hui, Esq., Caldwell, Pearce & Strauss LLP, 599 Lexington Avenue, New York, NY 10022 (Underwriters' Counsel)

CALDERWOOD & HARKNESS LLP One Liberty Plaza, 52nd Floor New York, NY 10006 Telephone: (212) 558-4000 Facsimile: (212) 558-3588 www.calderwoodharkness.com
October 17, 2023
CONFIDENTIAL
Ridgeline Securities LLC 383 Madison Avenue New York, NY 10017
Broadmark Capital Inc. 200 Park Avenue New York, NY 10166
Linden Groves & Co. 745 Fifth Avenue New York, NY 10151
Harborview Partners LLC 1 Federal Street Boston, MA 02110
c/o Ridgeline Securities LLC, as Representative of the Several Underwriters
Ladies and Gentlemen:
Re: Penterra Pharmaceuticals Corp. — Selling Stockholder Secondary Offering of 6,250,000 Shares of Common Stock, par value $0.001 per share
1. Introduction and Context
We have acted as counsel to Penterra Pharmaceuticals Corp., a Delaware corporation (the "Company" or "PPC"), in connection with the registered public offering (the "Offering") of shares of common stock, par value $0.001 per share (the "Common Stock"), of the Company by certain selling stockholders. This letter is being delivered to you in connection with the Underwriting Agreement dated October 12, 2023 (the "Underwriting Agreement") among the Company, the selling stockholders named therein (Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC, collectively, the "Selling Stockholders"), and the several underwriters named in Schedule I thereto (the "Underwriters"), for whom Ridgeline Securities LLC is acting as Representative.
The Underwriting Agreement relates to the registered public offering by the Selling Stockholders of 6,250,000 shares of Common Stock (the "Shares"), plus up to an additional 937,500 shares of Common Stock subject to the Underwriters' over-allotment option granted pursuant to Section 2 of the Underwriting Agreement. This letter is delivered to you pursuant to Section 7(e) of the Underwriting Agreement as a condition to the obligations of the Underwriters to close the purchase of the Shares on the date hereof.
Calderwood & Harkness LLP has acted as counsel to the Company in connection with the preparation of the Registration Statement (as defined below), the Prospectus (as defined below), and the other offering documents relating to the Offering, and in connection with the negotiation and execution of the Underwriting Agreement.
2. Documents Reviewed
In connection with the preparation of this letter, we have reviewed the following documents:
(a) the Registration Statement on Form S-3 (File No. 333-274851) of the Company (the "Registration Statement"), including the base prospectus dated August 22, 2023, contained therein (the "Base Prospectus"), as filed with the Securities and Exchange Commission (the "SEC" or the "Commission") under the Securities Act of 1933, as amended (the "Securities Act"), and declared effective by the SEC on August 22, 2023;
(b) the preliminary prospectus supplement dated October 2, 2023, relating to the Offering, as filed with the SEC pursuant to Rule 424(b)(5) under the Securities Act (the "Preliminary Prospectus Supplement");
(c) the final prospectus supplement dated October 12, 2023 (the "Prospectus Supplement"), as filed with the SEC pursuant to Rule 424(b)(5) under the Securities Act, together with the Base Prospectus (the Prospectus Supplement together with the Base Prospectus, collectively, the "Prospectus");
(d) the Issuer Free Writing Prospectus, constituting a Pricing Term Sheet dated October 12, 2023, as filed with the SEC pursuant to Rule 433 under the Securities Act (the "Pricing Term Sheet");
(e) the Underwriting Agreement dated October 12, 2023;
(f) the documents incorporated by reference in the Registration Statement and the Prospectus as of the date hereof, including, without limitation:
(i) the Company's Annual Report on Form 10-K for the fiscal year ended December 31, 2022, as filed with the SEC on February 28, 2023;
(ii) the Company's Quarterly Report on Form 10-Q for the fiscal quarter ended March 31, 2023, as filed with the SEC on May 10, 2023;
(iii) the Company's Quarterly Report on Form 10-Q for the fiscal quarter ended June 30, 2023, as filed with the SEC on August 9, 2023;
(iv) the Company's Current Reports on Form 8-K filed with the SEC on March 14, 2023, May 22, 2023, July 7, 2023, August 15, 2023, September 18, 2023, and October 3, 2023;
(v) the description of the Company's Common Stock contained in the Company's Registration Statement on Form 8-A (File No. 001-39842), as filed with the SEC on November 10, 2020, including any amendments or reports filed for the purpose of updating such description; and
(vi) all other documents filed by the Company with the SEC pursuant to Sections 13(a), 13(c), 14, or 15(d) of the Securities Exchange Act of 1934, as amended (the "Exchange Act"), after the date of the initial filing of the Registration Statement and prior to the date hereof; and
(g) such other documents, records, corporate proceedings, certificates of officers of the Company, and instruments as we deemed necessary or appropriate for purposes of this letter.
We have also reviewed the forms of the certificates delivered by officers of the Company on the date hereof pursuant to the Underwriting Agreement.
3. Scope of Review and Participation
In addition to our review of the documents described in Section 2 above, we have participated in the preparation of the Registration Statement, the Base Prospectus, the Preliminary Prospectus Supplement, the Prospectus Supplement, and the Pricing Term Sheet, including review of successive drafts of each such document.
We have also participated in conferences and discussions with officers and other representatives of the Company, including David Orenstein, General Counsel and Corporate Secretary, Lisa Hargrove, Chief Financial Officer, and Dr. Marco Castellano, Chief Executive Officer, as well as representatives of Graystone & Whitmore LLP, the Company's independent registered public accounting firm, representatives of Caldwell, Pearce & Strauss LLP, counsel for the Underwriters, and representatives of the Underwriters, at which conferences and discussions the contents of the Registration Statement, the Prospectus, the Pricing Term Sheet, and related matters were discussed. These conferences and discussions included due diligence sessions held on October 3, 2023, October 6, 2023, and October 10, 2023, as well as telephonic conferences held at various times during the period from October 2, 2023 through October 16, 2023.
In addition, we have reviewed certain corporate records and documents of the Company that were furnished to us by the Company and its officers and representatives in connection with this Offering, including, without limitation, the Amended and Restated Certificate of Incorporation and Amended and Restated Bylaws of the Company, minutes of meetings of the Board of Directors of the Company and committees thereof, and certain material contracts of the Company.
Notwithstanding the foregoing, we did not participate in the preparation of the financial statements, financial statement schedules, or other financial or accounting data (including the notes thereto and the reports of independent registered public accounting firms thereon) included or incorporated by reference in the Registration Statement or the Prospectus, and we have not independently verified the accuracy, completeness, or fairness of such financial statements, financial statement schedules, or other financial or accounting data. Our review of the financial statements and financial data was limited to reading such information for the purpose of determining whether, on its face, it appeared to be consistent in all material respects with the non-financial statement portions of the Registration Statement and the Prospectus with which we were involved.
4. Limitations and Qualifications
This letter is subject to the following limitations and qualifications:
(a) This letter is not a guarantee, and the negative assurance set forth herein is not based on an independent investigation or verification of the facts stated in or omitted from the Registration Statement or the Prospectus. We have assumed the genuineness of all signatures, the legal capacity of all natural persons, the authenticity of all documents submitted to us as originals, and the conformity to original documents of all documents submitted to us as certified, photostatic, facsimile, or electronic copies. We have relied, to the extent we deemed appropriate, upon certificates of public officials and officers and representatives of the Company as to matters of fact.
(b) The scope of our engagement as described herein was limited and did not include an audit, an examination, or any other procedures of the type that would be undertaken by an independent registered public accounting firm in accordance with the standards of the Public Company Accounting Oversight Board. Nor did our engagement include any other procedures designed or intended to discover undisclosed liabilities, undisclosed pending or threatened litigation, regulatory proceedings, or other matters that may be material to the Company or the Offering. Our participation in due diligence conferences and discussions does not constitute an independent verification of any of the matters discussed therein.
(c) We do not express any opinion or belief regarding the financial statements or financial data of the Company (including the notes thereto and the auditor's reports thereon), financial statement schedules, or any other financial, statistical, or accounting information included or incorporated by reference in the Registration Statement or the Prospectus, including, without limitation, any pro forma financial information, any selected financial data, any "Management's Discussion and Analysis of Financial Condition and Results of Operations" to the extent it constitutes financial data, and any financial information contained in any exhibit to or document incorporated by reference in the Registration Statement or the Prospectus. All such financial statements, financial data, and related information are expressly excluded from the scope of this letter.
(d) We do not express any opinion or belief with respect to any Statement of Eligibility on Form T-1 (if any) included as an exhibit to the Registration Statement, or with respect to any statistical data, or any information regarding clinical trials, scientific or medical data, pharmacological data, pre-clinical studies, toxicology reports, regulatory filings or determinations by the United States Food and Drug Administration or any other governmental authority, or other technical information included or incorporated by reference in the Registration Statement or the Prospectus. Such information involves matters of a scientific, medical, or technical nature that are outside the scope of our legal expertise, and we have made no effort to independently verify or evaluate such information.
(e) We are members of the Bar of the State of New York, and we do not express any opinion or belief as to the laws of any jurisdiction other than (i) the laws of the State of New York, (ii) the General Corporation Law of the State of Delaware, and (iii) the federal laws of the United States of America, including the Securities Act, the Exchange Act, and the rules and regulations promulgated thereunder by the SEC. We express no opinion as to the laws of any other state or jurisdiction, including, without limitation, the Blue Sky or securities laws of any state, the patent, trademark, or intellectual property laws of any jurisdiction, the laws governing the regulation of pharmaceutical products in any jurisdiction, or the tax laws of any jurisdiction.
(f) We have assumed that each of the documents we have reviewed was duly and validly authorized, executed, and delivered by each party thereto (other than the Company, with respect to which we have reviewed relevant corporate proceedings), and that each such document constitutes the legal, valid, and binding obligation of each party thereto, enforceable in accordance with its terms.
5. Negative Assurance Statement
On the basis of the review and participation described in Sections 2 and 3 above, and subject to the limitations, qualifications, and exclusions set forth in Section 4 above and elsewhere in this letter, and in reliance upon the representations and warranties of the Company and the Selling Stockholders contained in the Underwriting Agreement and the certificates delivered to us by officers of the Company in connection with the closing of the Offering, we advise you that nothing has come to our attention that causes us to believe that:
(a) the Registration Statement (File No. 333-274851), as of the date it became effective under the Securities Act (August 22, 2023), including the documents incorporated by reference therein at such date and any information deemed to be a part thereof pursuant to Rule 430B under the Securities Act, contained an untrue statement of a material fact or omitted to state a material fact required to be stated therein or necessary to make the statements therein not misleading (within the meaning of Section 11 of the Securities Act);
(b) the Prospectus (consisting of the Prospectus Supplement dated October 12, 2023 together with the Base Prospectus dated August 22, 2023), including the documents incorporated by reference therein, as of its date and as of the date hereof, contained or contains an untrue statement of a material fact or omitted or omits to state a material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading (within the meaning of Section 12(a)(2) of the Securities Act and Rule 10b-5 under the Exchange Act); or
(c) any amendment or supplement to the Registration Statement or the Prospectus filed with the SEC between the effective date of the Registration Statement and the date hereof (including any post-effective amendment or any amended or supplemented prospectus) contained, at the respective time such amendment or supplement was filed with the SEC, an untrue statement of a material fact or omitted to state a material fact required to be stated therein or necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading.
The statements set forth in clauses (a) through (c) above do not apply to (i) the financial statements, financial statement schedules, and other financial or accounting data (including the notes thereto and the auditor's reports thereon) included or incorporated by reference in the Registration Statement or the Prospectus, (ii) any Statement of Eligibility on Form T-1, (iii) any statistical data, (iv) any information regarding clinical trials, scientific or medical data, or other technical information included or incorporated by reference in the Registration Statement or the Prospectus, or (v) any information that we have not reviewed or in the preparation of which we did not participate, all of which are expressly excluded from the scope of this letter.
We note that the negative assurance statements set forth above are made with reference to the standards of liability established under Section 11 of the Securities Act (in respect of the Registration Statement) and Section 12(a)(2) of the Securities Act and Rule 10b-5 promulgated under the Exchange Act (in respect of the Prospectus). The negative assurance set forth herein is based on our professional judgment as lawyers and should not be construed as a factual representation or warranty regarding the accuracy or completeness of the Registration Statement or the Prospectus.
6. Reliance and Benefit
This letter is furnished to the Underwriters solely for their benefit and solely in connection with the Offering and may not be used, circulated, quoted, referred to, or relied upon by any other person or entity, or for any other purpose, without our prior written consent in each instance. Without limiting the generality of the foregoing, this letter may not be furnished to, or relied upon by, any purchaser or prospective purchaser of the Shares.
This letter is given as of the date hereof, and we assume no obligation to update, supplement, revise, or reaffirm this letter to reflect any facts or circumstances that may hereafter come to our attention or any changes in applicable law that may hereafter occur, whether or not such facts, circumstances, or changes may affect the conclusions set forth herein. We express no opinion or belief as to any matter not expressly set forth herein, and no opinion or belief is to be inferred or implied beyond the matters expressly stated in this letter.
7. No Attorney-Client Relationship with Underwriters
We wish to clarify that Calderwood & Harkness LLP has acted solely as counsel to the Company in connection with the Offering. We do not represent, and have not represented, any of the Underwriters, the Selling Stockholders, or any other party in connection with the Offering. The Underwriters are separately represented by Caldwell, Pearce & Strauss LLP as counsel for the Underwriters, and the Selling Stockholders are separately represented by Whitfield & Garza LLP as personal counsel to the Selling Stockholders. The delivery of this letter to the Underwriters does not create an attorney-client relationship between Calderwood & Harkness LLP and any of the Underwriters.
Very truly yours,
CALDERWOOD & HARKNESS LLP
By: ________
Name: Jennifer Kwon
Title: Partner
One Liberty Plaza, 52nd Floor New York, NY 10006
cc: David Orenstein, General Counsel & Corporate Secretary, Penterra Pharmaceuticals Corp., 400 Connell Drive, Suite 4200, Berkeley Heights, NJ 07922
cc: Patricia Velázquez, Esq., Whitfield & Garza LLP, 800 Third Avenue, New York, NY 10022 (Selling Stockholders' Personal Counsel)
cc: Margaret Hui, Esq., Caldwell, Pearce & Strauss LLP, 599 Lexington Avenue, New York, NY 10022 (Underwriters' Counsel)

CONFIDENTIAL

CALDERWOOD & HARKNESS LLP

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