CLOSING INDEX AND DOCUMENT BINDER TABLE OF CONTENTS
Registered Selling-Stockholder Secondary Offering of 6,250,000 Shares of Common Stock of PENTERRA PHARMACEUTICALS CORP. (Nasdaq: PNTR)
Aggregate Offering Amount: $260,000,000
Closing Date: October 17, 2023
Prepared by:
Brendan Walsh Calderwood & Harkness LLP One Liberty Plaza, 52nd Floor New York, NY 10006
Date of Index: October 27, 2023
INTRODUCTORY NOTE
This Closing Index and Document Binder Table of Contents constitutes the permanent record binder for the registered selling-stockholder secondary offering (the "Offering") of 6,250,000 shares of common stock, par value $0.001 per share (the "Shares"), of Penterra Pharmaceuticals Corp., a Delaware corporation ("PPC" or the "Company"), at a public offering price of $41.60 per share (the "Public Offering Price"). The Offering closed on October 17, 2023 (T+3 from pricing on October 12, 2023). The aggregate public offering price of the Shares offered in the base offering was $260,000,000.
The selling stockholders in the Offering (collectively, the "Selling Stockholders") were: Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC. The Company did not sell any shares in the Offering and did not receive any proceeds from the sale of Shares by the Selling Stockholders.
The underwriters in the Offering (collectively, the "Underwriters") were: Ridgeline Securities LLC (lead left book-runner), Broadmark Capital Inc. (joint book-runner), Linden Groves & Co. (co-manager), and Harborview Partners LLC (co-manager). The Underwriters were granted an over-allotment option to purchase up to 937,500 additional shares of common stock from the Selling Stockholders, exercisable for a period of 30 days from the date of the Underwriting Agreement.
The following counsel participated in the transaction:
• Issuer's Counsel: Calderwood & Harkness LLP ("C&H"), New York, New York
• Underwriters' Counsel: Caldwell, Pearce & Strauss LLP ("CPS"), New York, New York
• Selling Stockholders' Personal Counsel: Whitfield & Garza LLP ("W&G"), Houston, Texas
The Offering was conducted pursuant to PPC's shelf registration statement on Form S-3 (File No. 333-274851), which was declared effective by the Securities and Exchange Commission (the "SEC") on August 22, 2023, and a prospectus supplement filed with the SEC pursuant to Rule 424(b)(5) on October 12, 2023.
Documents in this binder are organized sequentially by tab number across eleven volumes. Executed originals or conformed copies are included where indicated. All documents are dated as of the dates indicated therein unless otherwise noted. Where a document was executed in counterparts, the compiled signature pages are included following the conformed body of the agreement. Certain tabs contain internal attorney work-product memoranda, which are designated as privileged and confidential and should be maintained separately from materials produced to third parties.
TAB-BY-TAB LISTING
VOLUME I — ENGAGEMENT AND ORGANIZATIONAL DOCUMENTS
Tab 1 — Engagement Letter
Engagement Letter dated September 5, 2023 from Calderwood & Harkness LLP to Penterra Pharmaceuticals Corp., setting forth the terms of C&H's representation of the Company as issuer's counsel in connection with the Selling Stockholders' registered secondary offering of shares of common stock of PPC. The engagement letter describes the scope of the representation, including preparation and review of the prospectus supplement, coordination with Underwriters' counsel and the Selling Stockholders' personal counsel, preparation of legal opinions and negative assurance letters, review of corporate authorizations and closing documents, and assistance with SEC filings in connection with the Offering. The engagement letter provides for a fee cap of $485,000 plus disbursements (including filing fees, printing costs, and other out-of-pocket expenses). The engagement letter was signed by Jennifer Kwon, Partner, Calderwood & Harkness LLP, on behalf of the firm, and accepted and agreed to by David Orenstein, General Counsel & Corporate Secretary, Penterra Pharmaceuticals Corp., on behalf of the Company.
Tab 2 — Transaction Timeline and Working Group List
Transaction Timeline and Working Group List (maintained in spreadsheet format) prepared and maintained by Audrey Zhou, Senior Associate, Calderwood & Harkness LLP. The timeline covers the full transaction period from the opening of the engagement on September 5, 2023 through the close of the matter on October 27, 2023, including key milestone dates for the confidential draft prospectus supplement, lock-up waiver request and consent process, SEC filing dates, roadshow period, pricing, closing, and binder preparation. The working group list contains full contact details (name, title, firm/company, address, direct telephone, email) for all members of the working group, including:
• Calderwood & Harkness LLP (Issuer's Counsel): Jennifer Kwon (Partner), Theodore Langston (Partner), Audrey Zhou (Senior Associate), Brendan Walsh (Associate)
• Penterra Pharmaceuticals Corp. (Issuer): David Orenstein (General Counsel & Corporate Secretary), Lisa Hargrove (Chief Financial Officer)
• Ridgeline Securities LLC (Lead Left Book-Runner): Jonathan Pryce-Hall (Managing Director), Angela Ferris (Vice President)
• Broadmark Capital Inc. (Joint Book-Runner): Samuel Okonkwo (Managing Director)
• Caldwell, Pearce & Strauss LLP (Underwriters' Counsel): Margaret Hui (Partner), Ryan Petrosian (Associate)
• Whitfield & Garza LLP (Selling Stockholders' Personal Counsel): Patricia Velázquez (Partner)
• Graystone & Whitmore LLP (Independent Registered Public Accounting Firm): Thomas Reiter (Engagement Partner)
VOLUME II — REGISTRATION STATEMENT AND PROSPECTUS FILINGS
Tab 3 — Base Prospectus
Base Prospectus included as part of the Registration Statement on Form S-3 (File No. 333-274851) filed by Penterra Pharmaceuticals Corp. (CIK: 0001987654) with the SEC, which was declared effective on August 22, 2023. The Base Prospectus covers the offer and sale of common stock, preferred stock, debt securities, warrants, and units of PPC, and provides general descriptions of the Company, risk factors, the securities that may be offered, the plan of distribution, and certain legal matters. The Base Prospectus, together with the Final Prospectus Supplement described at Tab 5, constitutes the statutory prospectus for the Offering within the meaning of Section 10(a) of the Securities Act of 1933, as amended (the "Securities Act").
Tab 4 — Preliminary Prospectus Supplement
Preliminary Prospectus Supplement filed with the SEC on October 2, 2023 relating to the proposed offering of 6,250,000 shares of common stock of PPC by the Selling Stockholders. The Preliminary Prospectus Supplement was prepared to supplement the Base Prospectus described at Tab 3 and contains a description of the Offering, the Selling Stockholders, the plan of distribution, risk factors specific to the Offering, information regarding the lock-up waiver, the new 90-day lock-up arrangement, and use of proceeds (noting that the Company would not receive any proceeds from the sale of Shares by the Selling Stockholders). A confidential draft of the Preliminary Prospectus Supplement was initially circulated among working group members on September 11, 2023 for review and comment, and was subsequently revised through multiple drafts prior to filing. An estimated price range of $40.00 to $43.00 per share was included in the Preliminary Prospectus Supplement.
Tab 5 — Final Prospectus Supplement
Final Prospectus Supplement dated October 12, 2023, filed with the SEC pursuant to Rule 424(b)(5) under the Securities Act, supplementing the Base Prospectus described at Tab 3. The Final Prospectus Supplement sets forth the final terms of the Offering, including the following:
• Shares Offered: 6,250,000 shares of common stock, par value $0.001 per share
• Public Offering Price: $41.60 per share
• Aggregate Offering Price (base): $260,000,000
• Underwriting discount: 2.50% ($1.04 per share; $6,500,000 in the aggregate)
• Net Proceeds to Selling Stockholders: $40.56 per share ($253,500,000 in the aggregate, before Selling Stockholder expenses)
• Over-Allotment Option: Up to 937,500 additional shares (representing 15% of the base offering), exercisable by the Underwriters for 30 days from the date of the Underwriting Agreement
• Use of Proceeds: The Company will not receive any proceeds from the sale of Shares by the Selling Stockholders
The Final Prospectus Supplement also contains the selling stockholder table setting forth the beneficial ownership of each Selling Stockholder before and after the Offering, risk factors specific to the Offering (including risks relating to selling pressure and potential dilution from the over-allotment option), a description of the lock-up waiver from the IPO lock-up agreements, the terms of the new 90-day lock-up arrangement entered into by the Selling Stockholders in connection with the Offering, a description of the plan of distribution, and a discussion of material U.S. federal income tax consequences to certain holders.
Tab 6 — Issuer Free Writing Prospectus / Pricing Term Sheet
Pricing Term Sheet dated October 12, 2023, filed with the SEC pursuant to Rule 433 under the Securities Act. The Pricing Term Sheet constitutes an "issuer free writing prospectus" within the meaning of Rule 433 and sets forth the final pricing terms of the Offering as follows:
• Issuer: Penterra Pharmaceuticals Corp.
• Shares Offered: 6,250,000 shares of common stock, par value $0.001 per share
• Public Offering Price per Share: $41.60
• Underwriting discount per Share: $1.04 (2.50%)
• Net Proceeds to Selling Stockholders per Share: $40.56
• Net Proceeds to Selling Stockholders (aggregate): $253,500,000
• Over-Allotment Option: 937,500 additional shares
• Trade Date: October 12, 2023
• Settlement Date: October 17, 2023
• CUSIP: 70831X 10 5
• Nasdaq Listing / Ticker Symbol: PNTR
VOLUME III — LOCK-UP WAIVER DOCUMENTS
Tab 7 — Lock-Up Waiver Request Letter to Ridgeline Securities LLC
Letter dated September 18, 2023 from Penterra Pharmaceuticals Corp. to Ridgeline Securities LLC, requesting the early release of the 180-day lock-up period applicable to the Selling Stockholders under the lock-up agreements executed in connection with PPC's initial public offering. The original lock-up period was scheduled to expire on October 14, 2023. The letter requests that the lock-up be released effective October 12, 2023, two days prior to the scheduled expiration, solely with respect to the shares to be sold by the Selling Stockholders in the secondary offering. The letter was signed by David Orenstein, General Counsel & Corporate Secretary, on behalf of Penterra Pharmaceuticals Corp.
Tab 8 — Lock-Up Waiver Request Letter to Broadmark Capital Inc.
Letter dated September 18, 2023 from Penterra Pharmaceuticals Corp. to Broadmark Capital Inc. (Attn: Samuel Okonkwo, Managing Director), requesting the early release of the 180-day lock-up period applicable to the Selling Stockholders, on the same terms and effective as of the same date (October 12, 2023) as described in the lock-up waiver request letter to Ridgeline Securities LLC at Tab 7. The letter was signed by David Orenstein on behalf of Penterra Pharmaceuticals Corp.
Tab 9 — Lock-Up Waiver Request Letter to Morningstar Zanthor & Co.
Letter dated September 18, 2023 from Penterra Pharmaceuticals Corp. to Morningstar Zanthor & Co. (Attn: Diane Chaudhary, Managing Director), 600 Lexington Avenue, New York, NY 10022, requesting the early release of the 180-day lock-up period applicable to the Selling Stockholders, on the same terms and effective as of the same date (October 12, 2023) as described in the lock-up waiver request letters at Tabs 7 and 8. Morningstar Zanthor & Co. served as a co-manager in PPC's initial public offering and is a party to the IPO lock-up agreements but is not participating as an underwriter in the secondary offering syndicate. The letter was signed by David Orenstein on behalf of Penterra Pharmaceuticals Corp.
Tab 10 — Lock-Up Waiver Consent — Ridgeline Securities LLC
Executed consent letter dated September 29, 2023 from Ridgeline Securities LLC, consenting to the early release of the 180-day lock-up period applicable to the Selling Stockholders effective as of October 12, 2023, solely with respect to the shares of PPC common stock to be sold by the Selling Stockholders in the secondary offering. The consent letter was signed by Jonathan Pryce-Hall, Managing Director, Ridgeline Securities LLC. The consent is conditioned upon the Selling Stockholders' entry into new 90-day lock-up agreements in connection with the secondary offering as described at Tab 16.
Tab 11 — Lock-Up Waiver Consent — Broadmark Capital Inc.
Executed consent letter dated September 29, 2023 from Broadmark Capital Inc., consenting to the early release of the 180-day lock-up period applicable to the Selling Stockholders effective as of October 12, 2023, solely with respect to the shares to be sold in the secondary offering. The consent letter was signed by Samuel Okonkwo, Managing Director, Broadmark Capital Inc. The consent is on the same terms and subject to the same conditions as the Ridgeline Securities consent described at Tab 10.
Tab 12 — Lock-Up Waiver Consent — Morningstar Zanthor & Co.
Executed consent letter dated September 29, 2023 from Morningstar Zanthor & Co., consenting to the early release of the 180-day lock-up period applicable to the Selling Stockholders effective as of October 12, 2023, solely with respect to the shares to be sold in the secondary offering. The consent letter was signed by Diane Chaudhary, Managing Director, Morningstar Zanthor & Co. The consent is on the same terms and subject to the same conditions as the consents described at Tabs 10 and 11.
VOLUME IV — UNDERWRITING AGREEMENT AND RELATED DOCUMENTS
Tab 13 — Underwriting Agreement (Execution Version)
Underwriting Agreement dated October 12, 2023 (the "Underwriting Agreement") among Penterra Pharmaceuticals Corp. (as Issuer), the Selling Stockholders (Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC), and the Underwriters (Ridgeline Securities LLC, as representative of the several underwriters named therein, Broadmark Capital Inc., Linden Groves & Co., and Harborview Partners LLC). The Underwriting Agreement provides for the sale by the Selling Stockholders of 6,250,000 shares of common stock of PPC at the Public Offering Price of $41.60 per share, less the underwriting discount of 2.50% ($1.04 per share). The Underwriting Agreement also grants the Underwriters an over-allotment option to purchase up to 937,500 additional shares from the Selling Stockholders at the Public Offering Price less the underwriting discount, exercisable for a period of 30 days from the date of the Underwriting Agreement. The Underwriting Agreement contains customary representations and warranties of the Company and the Selling Stockholders, covenants of the Company and the Selling Stockholders, conditions to closing, and indemnification and contribution provisions. The governing law of the Underwriting Agreement is the law of the State of Delaware.
Tab 14 — Underwriting Agreement — Executed Signature Pages
Compiled executed signature pages to the Underwriting Agreement described at Tab 13. The signature pages were executed in counterparts and are compiled herein for reference. The following parties executed the Underwriting Agreement:
• Penterra Pharmaceuticals Corp. (Issuer): Signed by Lisa Hargrove, Chief Financial Officer, on behalf of the Company
• Dr. Elena Castellano (Selling Stockholder): Individual signature
• Dr. Riccardo Castellano (Selling Stockholder): Individual signature
• Dr. Marco Castellano (Selling Stockholder): Individual signature
• Castellano Family Holdings LLC (Selling Stockholder): Signed by Dr. Elena Castellano as Managing Member
• Ridgeline Securities LLC: Signed by Jonathan Pryce-Hall, Managing Director, on behalf of itself and as representative of the several underwriters
• Broadmark Capital Inc.: Signed by Samuel Okonkwo, Managing Director
• Linden Groves & Co.: Signed by authorized signatory
• Harborview Partners LLC: Signed by authorized signatory
Tab 15 — Selling Stockholder Power of Attorney and Custody Agreement
Power of Attorney and Custody Agreement dated October 12, 2023, executed by each of the Selling Stockholders (Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC). Pursuant to the Power of Attorney and Custody Agreement, each Selling Stockholder appointed David Orenstein, General Counsel & Corporate Secretary of PPC, as such Selling Stockholder's attorney-in-fact, with full power and authority to execute and deliver, on behalf of such Selling Stockholder, the Underwriting Agreement, the Selling Stockholder certificates, and such other documents and instruments as may be necessary or appropriate in connection with the consummation of the Offering. Each Selling Stockholder also appointed Pinnacle Trust & Transfer Co. as custodian for the shares of PPC common stock to be delivered by such Selling Stockholder at the closing of the Offering, with authority to receive and hold the shares pending delivery through the Depository Trust Company.
Tab 16 — New Lock-Up Agreements (90-Day — Secondary Offering)
Form of 90-day lock-up agreement (the "New Lock-Up Agreement") executed by each Selling Stockholder in favor of Ridgeline Securities LLC and Broadmark Capital Inc., as representatives of the several Underwriters. Pursuant to the New Lock-Up Agreements, each Selling Stockholder agreed to a restriction on the offer, sale, pledge, or other disposition of shares of PPC common stock (and securities convertible into or exchangeable for shares of PPC common stock) retained by such Selling Stockholder following the Offering for a period of 90 days from the closing date (October 17, 2023), with such restriction expiring on January 15, 2024. The New Lock-Up Agreements contain customary exceptions, including transfers for estate planning purposes and transfers to affiliates, subject to the transferee agreeing to be bound by the terms of the lock-up. Separate executed copies of the New Lock-Up Agreement are included for each of the four Selling Stockholders:
(a) Dr. Elena Castellano
(b) Dr. Riccardo Castellano
(c) Dr. Marco Castellano
(d) Castellano Family Holdings LLC
VOLUME V — OPINIONS AND COMFORT LETTERS
Tab 17 — Issuer's Counsel Legal Opinion
Legal opinion of Calderwood & Harkness LLP dated October 17, 2023, addressed to the Underwriters (Ridgeline Securities LLC, Broadmark Capital Inc., Linden Groves & Co., and Harborview Partners LLC), delivered pursuant to Section 7(a) of the Underwriting Agreement. The legal opinion covers the following matters, among others:
(i) the 6,250,000 shares of common stock of PPC, par value $0.001 per share, to be sold by the Selling Stockholders in the Offering have been duly authorized and are validly issued, fully paid, and non-assessable;
(ii) PPC is a corporation duly incorporated, validly existing, and in good standing under the laws of the State of Delaware;
(iii) the execution, delivery, and performance by PPC of the Underwriting Agreement have been duly authorized by all necessary corporate action and do not conflict with PPC's Amended and Restated Certificate of Incorporation or Amended and Restated Bylaws; and
(iv) the Registration Statement on Form S-3 (File No. 333-274851) has been declared effective under the Securities Act, and no stop order suspending the effectiveness of the Registration Statement has been issued.
The legal opinion was signed by Jennifer Kwon, Partner, Calderwood & Harkness LLP. Customary qualifications, assumptions, and limitations are set forth in the opinion letter.
Tab 18 — Issuer's Counsel Negative Assurance Letter (10b-5 Letter)
Negative assurance letter of Calderwood & Harkness LLP dated October 17, 2023, addressed to the Underwriters, delivered pursuant to Section 7(b) of the Underwriting Agreement. In the negative assurance letter, issuer's counsel states that, based on its participation in the preparation of the Final Prospectus Supplement and the Base Prospectus and discussions with officers and other representatives of the Company and its independent registered public accounting firm, nothing came to counsel's attention that caused counsel to believe that the Final Prospectus Supplement dated October 12, 2023 or the Base Prospectus contained an untrue statement of a material fact or omitted to state a material fact required to be stated therein or necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading. The negative assurance letter covers the Final Prospectus Supplement and the Base Prospectus under the Registration Statement on Form S-3 (File No. 333-274851). The negative assurance letter contains customary qualifications, including that counsel's review did not extend to the financial statements and related notes, schedules, and other financial and statistical data included in the prospectus.
Tab 19 — Initial Comfort Letter — Graystone & Whitmore LLP
Comfort letter from Graystone & Whitmore LLP, the independent registered public accounting firm of Penterra Pharmaceuticals Corp., dated on or about October 2, 2023 (the date of the filing of the Preliminary Prospectus Supplement with the SEC). The comfort letter was prepared in accordance with AU-C Section 920, Letters for Underwriters and Certain Other Requesting Parties, issued by the American Institute of Certified Public Accountants. The comfort letter covers the audited and unaudited financial statements and certain financial data included in the Preliminary Prospectus Supplement, including procedures performed with respect to specified financial information appearing in the prospectus supplement. The engagement partner for Graystone & Whitmore LLP on this matter is Thomas Reiter.
Tab 20 — Bring-Down Comfort Letter — Graystone & Whitmore LLP
Bring-down comfort letter from Graystone & Whitmore LLP dated October 17, 2023 (the closing date), delivered pursuant to Section 7(c) of the Underwriting Agreement. The bring-down comfort letter confirms that, as of a date not more than three business days prior to the closing date, no material changes in the specified financial items covered by the initial comfort letter (Tab 19) have come to the attention of Graystone & Whitmore LLP, and that the statements in the initial comfort letter remain accurate as of the date of the bring-down letter, subject to certain specified changes and updates noted therein. The bring-down comfort letter was addressed to the Underwriters and the Selling Stockholders.
Tab 21 — Request Letter to Auditors for Comfort Letter
Letter from Calderwood & Harkness LLP (prepared by Audrey Zhou, Senior Associate) to Graystone & Whitmore LLP (Attn: Thomas Reiter, Engagement Partner) dated October 3, 2023. The request letter specifies the financial statements and financial data in the prospectus supplement to be covered by the comfort letter, the circle-up procedures to be performed by the auditors with respect to specified financial information, and the cut-off date for the comfort letter procedures. The request letter also identifies the persons to whom the comfort letter should be addressed and the delivery instructions.
Tab 22 — Bring-Down Comfort Letter Request
Letter from Calderwood & Harkness LLP (prepared by Audrey Zhou) to Graystone & Whitmore LLP dated October 15, 2023, requesting that Graystone & Whitmore LLP deliver a bring-down comfort letter, addressed to the Underwriters and the Selling Stockholders, dated as of the closing date of October 17, 2023, confirming that no material changes have occurred in the specified financial items since the date of the initial comfort letter (Tab 19). The request letter specifies that the bring-down letter should be delivered no later than 9:00 a.m. (Eastern Time) on October 17, 2023.
VOLUME VI — OFFICERS' AND DIRECTORS' CERTIFICATES AND CORPORATE DOCUMENTS
Tab 23 — Officer's Certificate of Penterra Pharmaceuticals Corp.
Officer's Certificate of Penterra Pharmaceuticals Corp. dated October 17, 2023, delivered pursuant to Section 7(d) of the Underwriting Agreement. The Officer's Certificate was signed by Dr. Marco Castellano, Chief Executive Officer, and Lisa Hargrove, Chief Financial Officer, on behalf of PPC. The Officer's Certificate certifies that: (i) the representations and warranties of PPC contained in the Underwriting Agreement are true and correct in all material respects as of the date of the Underwriting Agreement and as of the closing date with the same force and effect as though made on the closing date; (ii) PPC has complied in all material respects with all of its covenants and agreements contained in the Underwriting Agreement required to be performed on or before the closing date; and (iii) since the date of the most recent financial statements included in the Final Prospectus Supplement, there has been no material adverse change in the condition (financial or otherwise), results of operations, business, or prospects of PPC and its subsidiaries, taken as a whole.
Tab 24 — Secretary's Certificate of Penterra Pharmaceuticals Corp.
Secretary's Certificate of Penterra Pharmaceuticals Corp. dated October 17, 2023, signed by David Orenstein, General Counsel & Corporate Secretary. The Secretary's Certificate certifies the incumbency and authority of the officers of PPC who executed the Underwriting Agreement, the Officer's Certificate, and other documents on behalf of PPC in connection with the Offering. The Secretary's Certificate is accompanied by the following attachments:
(a) Certified copy of the Amended and Restated Certificate of Incorporation of Penterra Pharmaceuticals Corp., as currently in effect;
(b) Certified copy of the Amended and Restated Bylaws of Penterra Pharmaceuticals Corp., as currently in effect; and
(c) Certified copy of the resolutions of the Board of Directors of PPC described at Tab 25.
Tab 25 — Board Resolutions of Penterra Pharmaceuticals Corp.
Resolutions of the Board of Directors of Penterra Pharmaceuticals Corp. adopted at a duly convened meeting of the Board held on September 8, 2023. The resolutions authorize and approve, among other things:
(i) PPC's cooperation with and assistance in the registered secondary offering by the Selling Stockholders of up to 6,250,000 shares (plus up to 937,500 additional shares subject to the over-allotment option) of PPC common stock;
(ii) PPC's entry into the Underwriting Agreement;
(iii) the preparation, execution, and filing with the SEC of the prospectus supplement (including any preliminary prospectus supplement) and any issuer free writing prospectus in connection with the Offering;
(iv) the execution and delivery by authorized officers of PPC of the Officer's Certificate, Secretary's Certificate, and such other documents and instruments as may be necessary or appropriate in connection with the Offering;
(v) the engagement of Calderwood & Harkness LLP as issuer's counsel in connection with the Offering; and
(vi) the payment by PPC of issuer expenses in connection with the Offering in an aggregate amount not to exceed $765,000 (including legal fees, accounting fees, printing expenses, SEC filing fees, and other customary expenses).
Tab 26 — Good Standing Certificate — Delaware Secretary of State
Certificate of good standing for Penterra Pharmaceuticals Corp. issued by the Secretary of State of the State of Delaware, dated October 16, 2023. The good standing certificate confirms that PPC is a corporation duly formed and in good standing under the laws of the State of Delaware as of the date of the certificate, and that all applicable franchise taxes have been paid. The good standing certificate is accompanied by a Calderwood & Harkness LLP transmittal cover memorandum from Brendan Walsh summarizing the certificate and its use as a closing deliverable under the Underwriting Agreement.
VOLUME VII — SELLING STOCKHOLDER DOCUMENTS
Tab 27 — Selling Stockholder Representation Letter
Representation letter dated October 12, 2023, from each of the Selling Stockholders (Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC), addressed to Penterra Pharmaceuticals Corp. and the Underwriters. The Selling Stockholder Representation Letter contains the following representations and warranties made by each Selling Stockholder:
(a) Beneficial Ownership: Each Selling Stockholder represents the number of shares of PPC common stock beneficially owned by such Selling Stockholder as of the date of the letter:
• Dr. Elena Castellano: 14,200,000 shares
• Dr. Riccardo Castellano: 12,800,000 shares
• Dr. Marco Castellano: 4,500,000 shares
• Castellano Family Holdings LLC: 8,600,000 shares
(b) Authority to Sell: Each Selling Stockholder represents that such Selling Stockholder has full right, power, and authority to sell, assign, transfer, and deliver the shares being sold by such Selling Stockholder in the Offering.
(c) Absence of Encumbrances: Each Selling Stockholder represents that the shares to be sold by such Selling Stockholder in the Offering are free and clear of all liens, encumbrances, equities, security interests, and claims of any nature whatsoever.
(d) Accuracy of Information: Each Selling Stockholder represents that the information furnished by such Selling Stockholder for inclusion in the Final Prospectus Supplement is true, correct, and complete in all material respects and does not contain any untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary in order to make the statements therein not misleading.
(e) Compliance with Lock-Up Waiver Terms: Each Selling Stockholder represents that such Selling Stockholder has complied in all respects with the terms and conditions of the lock-up waiver granted by the IPO underwriters.
Tab 28 — Selling Stockholder Certificates
Certificates dated October 17, 2023, executed by each Selling Stockholder (or by David Orenstein as attorney-in-fact pursuant to the Power of Attorney and Custody Agreement described at Tab 15), delivered pursuant to Section 7(e) of the Underwriting Agreement. Each certificate certifies that: (i) the representations and warranties made by such Selling Stockholder in the Underwriting Agreement and in the Selling Stockholder Representation Letter (Tab 27) are true and correct in all material respects as of the closing date with the same force and effect as though made on the closing date; and (ii) all conditions to closing applicable to such Selling Stockholder under the Underwriting Agreement have been satisfied. Separate certificates are included for each of the following Selling Stockholders:
(a) Dr. Elena Castellano
(b) Dr. Riccardo Castellano
(c) Dr. Marco Castellano
(d) Castellano Family Holdings LLC
VOLUME VIII — TRANSFER AGENT AND DTC DOCUMENTS
Tab 29 — DTC Eligibility / Transfer Agent Direction Letter
Direction letter from Penterra Pharmaceuticals Corp. to Pinnacle Trust & Transfer Co. (1 Ashbury Asset Advisors Plaza, 30th Floor, New York, NY 10004), the transfer agent and registrar for PPC's common stock, dated October 16, 2023. The direction letter was signed by David Orenstein, General Counsel & Corporate Secretary, on behalf of PPC. The direction letter instructs Pinnacle Trust & Transfer Co. to facilitate the book-entry delivery of 6,250,000 shares of PPC common stock (CUSIP 70831X 10 5) through the facilities of the Depository Trust Company ("DTC") for settlement on October 17, 2023, in accordance with the terms of the Underwriting Agreement. The direction letter also confirms the DTC eligibility of PPC common stock and requests that Pinnacle Trust & Transfer Co. take all actions necessary to effect the timely delivery of the Shares to the accounts designated by the Underwriters at DTC.
VOLUME IX — SEC FILINGS AND SECTION 16 MATTERS
Tab 30 — Form 8-K — Current Report (Entry into Underwriting Agreement)
Form 8-K (Current Report) filed by Penterra Pharmaceuticals Corp. (CIK: 0001987654) with the SEC on October 12, 2023. The Form 8-K reports, under Item 8.01 (Other Events), the Company's entry into the Underwriting Agreement with the Selling Stockholders and the Underwriters in connection with the registered secondary offering of 6,250,000 shares of PPC common stock. The Form 8-K includes a brief description of the material terms of the Offering and a statement that the Company will not receive any proceeds from the sale of Shares by the Selling Stockholders. The Form 8-K was prepared by Calderwood & Harkness LLP and was reviewed by the Company and Underwriters' counsel prior to filing.
Tab 31 — Section 16 Form 4 Filing Memorandum
Internal memorandum from Brendan Walsh, Associate, Calderwood & Harkness LLP, to Jennifer Kwon, Partner, Calderwood & Harkness LLP, dated October 13, 2023. The memorandum addresses the Section 16 reporting obligations of the Selling Stockholders who are officers and/or directors of PPC in connection with their sales of PPC common stock in the Offering. As insiders of PPC, the following Selling Stockholders are required to file Form 4 (Statement of Changes in Beneficial Ownership) with the SEC to report their dispositions:
• Dr. Elena Castellano (Director and Co-Founder): Disposition of 3,000,000 shares
• Dr. Riccardo Castellano (Director and Co-Founder): Disposition of 2,500,000 shares
• Dr. Marco Castellano (Chief Executive Officer and Director): Disposition of 500,000 shares
The memorandum discusses the filing deadlines applicable to each Form 4 (no later than the second business day following the date of execution of the transaction), the procedures for preparation and EDGAR filing of each Form 4, and coordination with the Company's Corporate Secretary to ensure timely filing. The memorandum notes that Castellano Family Holdings LLC's disposition (250,000 shares) will be reported on the Form 4 of Dr. Elena Castellano as indirect beneficial ownership, consistent with prior filings.
VOLUME X — CLOSING MECHANICS AND CORRESPONDENCE
Tab 32 — Closing Checklist
Comprehensive closing checklist prepared by Audrey Zhou, Senior Associate, and Brendan Walsh, Associate, Calderwood & Harkness LLP. The closing checklist lists all closing deliverables required under the Underwriting Agreement and related transaction documents in connection with the October 17, 2023 closing, organized by category, and identifies for each deliverable: (i) the responsible party (or parties) for preparation and/or execution; (ii) the delivery status (draft, final, executed, or delivered); and (iii) the date delivered. The categories of closing deliverables covered by the closing checklist include:
• Officer's Certificate (Tab 23)
• Secretary's Certificate (Tab 24)
• Good Standing Certificate (Tab 26)
• Legal Opinion of Issuer's Counsel (Tab 17)
• Negative Assurance Letter of Issuer's Counsel (Tab 18)
• Initial Comfort Letter (Tab 19)
• Bring-Down Comfort Letter (Tab 20)
• Selling Stockholder Certificates (Tab 28)
• Lock-Up Waiver Consents (Tabs 10–12)
• New Lock-Up Agreements (Tab 16)
• Transfer Agent Direction Letter (Tab 29)
• Underwriting Agreement Execution Copies (Tabs 13–14)
• Power of Attorney and Custody Agreement (Tab 15)
• DTC Delivery Confirmation
• Funds Flow Confirmation
Tab 33 — Closing Memorandum
Closing Memorandum prepared by Calderwood & Harkness LLP dated October 17, 2023, summarizing the mechanics and settlement procedures for the closing of the Offering. The Closing Memorandum contains the following principal elements:
Settlement of Shares: 6,250,000 shares of PPC common stock were delivered by the Selling Stockholders through the facilities of the Depository Trust Company to the accounts of the several Underwriters at DTC on October 17, 2023, against payment of the aggregate purchase price.
Wire of Net Proceeds: Aggregate net proceeds of $253,500,000 (representing the aggregate public offering price of $260,000,000 less the aggregate underwriting discount of $6,500,000) were wired to the accounts of the Selling Stockholders (or their designees) on October 17, 2023.
Allocation of Underwriting Commissions: The aggregate underwriting commission of $6,500,000 (2.50% of the aggregate public offering price) was allocated among the Underwriters as follows:
Conditions Precedent: All conditions precedent to the obligations of the Underwriters and the Selling Stockholders under the Underwriting Agreement were confirmed to have been satisfied or waived as of the closing date, including delivery of the Officer's Certificate, Secretary's Certificate, Good Standing Certificate, legal opinions, comfort letters, Selling Stockholder Certificates, lock-up waiver consents, new lock-up agreements, and transfer agent direction letter.
Funds Flow Summary: A detailed funds flow summary is attached to the Closing Memorandum, setting forth the wire transfer instructions, amounts, and confirmations for all payments made in connection with the closing.
Tab 34 — Closing Confirmation Email
Email from Audrey Zhou, Senior Associate, Calderwood & Harkness LLP, to the full working group, sent on October 17, 2023. The recipients of the closing confirmation email are: David Orenstein and Lisa Hargrove (PPC); Jonathan Pryce-Hall and Angela Ferris (Ridgeline Securities); Samuel Okonkwo (Broadmark Capital); Margaret Hui and Ryan Petrosian (CPS); and Patricia Velázquez (W&G). The email confirms the successful closing and settlement of the Offering, including the delivery of 6,250,000 shares of PPC common stock at the Public Offering Price of $41.60 per share for aggregate gross proceeds of $260,000,000. The email further confirms that all closing deliverables were received, all conditions precedent were satisfied, and all funds were disbursed in accordance with the funds flow summary.
VOLUME XI — INTERNAL MEMORANDA (ATTORNEY WORK PRODUCT — PRIVILEGED)
PRIVILEGED AND CONFIDENTIAL — ATTORNEY WORK PRODUCT The memoranda contained in this Volume XI are protected by the attorney-client privilege and/or attorney work-product doctrine and are intended solely for use by Calderwood & Harkness LLP and its client, Penterra Pharmaceuticals Corp. These memoranda should not be disclosed to, or shared with, any third party without prior written authorization from Calderwood & Harkness LLP.
Tab 35 — Lock-Up Waiver Analysis Memorandum
Attorney work-product memorandum dated September 14, 2023, prepared by Audrey Zhou, Senior Associate, Calderwood & Harkness LLP, addressed to Jennifer Kwon, Partner, Calderwood & Harkness LLP. The memorandum provides a detailed analysis of the lock-up waiver mechanics under the 180-day lock-up agreements entered into by the Selling Stockholders in connection with PPC's initial public offering. The memorandum addresses the following topics:
(i) the contractual requirement under the IPO lock-up agreements for the consent of all three IPO underwriters (Ridgeline Securities LLC, Broadmark Capital Inc., and Morningstar Zanthor & Co.) as a condition to any early release of the lock-up restrictions;
(ii) the 14-day advance notice requirement under certain of the IPO lock-up agreements, and the process for seeking a waiver of such notice requirement in order to accommodate the timeline for the secondary offering;
(iii) applicable SEC disclosure obligations in connection with the lock-up waiver, including the requirement to disclose the early release in the prospectus supplement and, in certain circumstances, to file a Form 8-K;
(iv) considerations regarding the new 90-day lock-up to be entered into by the Selling Stockholders in connection with the secondary offering, including the scope of the lock-up restrictions, customary exceptions, and coordination with the IPO underwriters' consent conditions; and
(v) a recommended timeline and procedure for obtaining the lock-up waiver consents.
Tab 36 — Internal Deal Memorandum
Internal memorandum prepared by Audrey Zhou, Senior Associate, and Brendan Walsh, Associate, Calderwood & Harkness LLP, for the Calderwood & Harkness Capital Markets practice group. The memorandum provides a comprehensive summary of the transaction for internal reference and precedent purposes, covering the following topics:
(i) an overview of the deal structure, including the $260,000,000 selling-stockholder registered secondary offering of 6,250,000 shares of PPC common stock at $41.60 per share;
(ii) the lock-up waiver mechanics, including the process for obtaining consents from all three IPO underwriters and the entry into the new 90-day lock-up agreements;
(iii) the over-allotment option of 937,500 additional shares (15% of the base offering), exercisable by the Underwriters for 30 days from the date of the Underwriting Agreement;