Contract analysis

I. EXECUTIVE SUMMARY Calderwood & Harkness LLP ("C&H") has been engaged as issuer's counsel to Penterra Pharmaceuticals Corp. ("Penterra," "PPC," or the "Company"), a Delaware corporation listed on the Nasdaq Global Select Market (ticker: PNTR), in connection with a registered selling-stockholder secondary offering of shares of common stock (the "Offering"). The engagement was opened on September 5, 2023, and the eng

II. BACKGROUND ON PENTERRA PHARMACEUTICALS CORP. A. Company Overview The full legal name of the issuer is Penterra Pharmaceuticals Corp. PPC is a corporation organized under the laws of the State of Delaware. Its principal executive offices are located at 400 Meridian Parkway, Suite 1200, Princeton, New Jersey 08540. PPC's registered agent in Delaware is actionaltional Registered Agents Inc., located at 251 Little Fa

III. DEAL STRUCTURE AND ECONOMICS A. Offering Type The Offering is structured as a registered selling-stockholder secondary offering (commonly referred to as a "follow-on" offering). No primary shares will be sold by PPC, and the Company will receive no proceeds from the Offering. All shares are being sold by the Selling Stockholders identified in Section IV below. The Offering will be effected as a shelf takedown un

IV. SELLING STOCKHOLDERS A. Identification and Share Holdings The Selling Stockholders in the Offering are four members and entities of the Castellano founding family. The following table sets forth the identity of each Selling Stockholder, their respective pre-offering share holdings, the number of shares offered in the base offering, the maximum number of shares subject to the Over-Allotment Option, and their post-

V. LOCK-UP WAIVER MECHANICS A. Original IPO Lock-Up In connection with PPC's IPO, which closed on April 17, 2023, all directors, officers, and holders of 5% or more of PPC common stock entered into customary 180-day lock-up agreements. These agreements restrict the lock-up parties from, among other things, offering, selling, contracting to sell, pledging, granting any option to purchase, making any short sale, or oth

VI. UNDERWRITING SYNDICATE A. Book-Running Managers The underwriting syndicate for the Offering consists of two book-running managers and two co-managers. Lead Left Book-Runner: Ridgeline Securities LLC 383 Madison Avenue New York, New York 10017 • Lead Banker: Jonathan Pryce-Hall, Managing Director • Syndicate Desk: Angela Ferris, Vice President Ridgeline served as lead left book-runner for PPC's IPO in April 2023 a

VII. KEY TRANSACTION DOCUMENTS This section summarizes the principal transaction documents that will be prepared, negotiated, and delivered in connection with the Offering. C&H is responsible for the preparation of documents on behalf of PPC as issuer, and will coordinate with Caldwell, Pearce & Strauss (underwriters' counsel) and Whitfield & Garza (selling stockholders' counsel) on all multi-party documents. A. Pros

I. SEC Filings The following filings with the SEC will be made in connection with the Offering: • Issuer Free Writing Prospectus / Pricing Term Sheet: A pricing term sheet will be filed as an issuer free writing prospectus pursuant to Rule 433 under the Securities Act on the pricing date (October 12, 2023). The pricing term sheet will set forth the final public offering price, the underwriting discount, the net proce

VIII. TRANSACTION TIMELINE The following table sets forth the key dates and milestones for the Offering. All dates are subject to change based on market conditions, SEC review, and the progress of deal negotiations. The timeline is aggressive but achievable, provided that (i) all workstreams proceed in parallel, (ii) SEC comments on the prospectus supplement are minimal or non-existent, and (iii) the lock-up waiver p

IX. ISSUER EXPENSES PPC will bear all expenses of the Offering other than the underwriting discount, which is borne by the Selling Stockholders. This allocation of expenses is customary for selling-stockholder secondary offerings. The estimated issuer expenses are as follows: The PPC Board of Directors, in its resolutions adopted on September 8, 2023, authorized the payment of issuer expenses in connection with the O

X. ENGAGEMENT ECONOMICS (CALDERWOOD & HARKNESS) C&H's engagement as issuer's counsel is governed by the engagement letter dated September 5, 2023, which provides for a capped fee arrangement plus disbursements. Fee Arrangement: Capped fee of $485,000, plus reasonable out-of-pocket disbursements. The capped fee covers all legal services provided by C&H in connection with the Offering, including the preparation and fil

XI. OTHER SERVICE PROVIDERS The following table summarizes the other principal service providers engaged in connection with the Offering: Graystone & Whitmore LLP serves as PPC's independent registered public accounting firm and will deliver initial and bring-down comfort letters in connection with the Offering. The comfort letter process is being coordinated between C&H, Caldwell Pearce & Strauss, and Graystone. Pin

XII. KEY LEGAL CONSIDERATIONS AND OPEN ITEMS This section summarizes the principal legal considerations and open items that require attention from the C&H deal team as the transaction progresses. A. Lock-Up Waiver Disclosure The early release of the IPO lock-up restrictions is a material fact that must be disclosed in the prospectus supplement. The SEC has historically taken the position that lock-up waivers or early

XIII. WORKING GROUP CONTACT LIST The following table sets forth the principal working group members for the Offering. All parties should be included on deal-related communications unless otherwise directed. This memorandum is intended solely for internal use within Calderwood & Harkness LLP. It does not constitute legal advice to any client. The information contained herein is based on publicly available information