Exhibit 10.1

SECURITIES PURCHASE AGREEMENT

This SECURITIES PURCHASE AGREEMENT (this “Agreement”) is dated as of January 16,
2020 (the “Agreement Date”), by and among Iterum Therapeutics Bermuda Limited, a
company formed under the laws of Bermuda (the “Company”), as issuer, Iterum
Therapeutics plc, an Irish public limited company (“Iterum”), as guarantor,
Iterum Therapeutics International Limited, a company formed under the laws of
Ireland, as guarantor, Iterum Therapeutics US Limited, a company formed under
the laws of Delaware, as guarantor, and Iterum Therapeutics US Holding Limited,
a company formed under the laws of Delaware, as guarantor (the guarantors other
than Iterum, collectively, the “Subsidiary Guarantors” and, together with
Iterum, the “Guarantors”) and the Persons set forth on Schedule 1 of this
Agreement (together with their successors and assigns, the “Purchasers” and,
together with the Company and Iterum, the “Parties”).

W I T N E S S E T H:

WHEREAS, the Company wishes to sell to the Purchasers Units (as defined below)
consisting of (A) Notes (as defined below) in the aggregate original principal
amount of Fifty One Million Eight Hundred and Eighty Eight Thousand Dollars
($51,888,000) and (B) an aggregate of Two Million Five Hundred Ninety Four
Thousand Four Hundred (2,594,400) RLNs (as defined below) in accordance with
Section 2.1 of this Agreement; and

WHEREAS, the Purchasers desire to purchase the Notes and the RLNs from the
Company.

NOW, THEREFORE, in consideration of the mutual covenants and agreements set
forth herein, the Parties agree as follows:

ARTICLE 1

DEFINITIONS

Section 1.1 General Definitions. Wherever used in this Agreement, the Exhibits
or the Schedules attached hereto, unless the context otherwise requires, the
following terms have the following meanings:

“Accredited Investor Questionnaire” means a questionnaire used to determine a
Purchaser’s status as an accredited investor, in a form satisfactory to the
Company and Iterum.

“Affiliate” means any Person or entity that, directly or indirectly through one
or more intermediaries, controls or is controlled by or is under common control
with a person or entity, as such terms are used in and construed under Rule 144
under the Securities Act. With respect to a Purchaser that is not a Wellington
Entity, any investment fund or managed account that is managed on a
discretionary basis by the same investment manager as such Purchaser will be
deemed to be an Affiliate of such Purchaser. As used in this definition of
“Affiliate,” the term “control” means the possession, directly or indirectly, of
the power to direct or cause the direction of the management and policies of a
Person, whether through ownership of voting securities or partnership or other
ownership interest, by contract, or otherwise.

 

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“Agreement” shall have the meaning set forth in the introductory paragraph.

“Agreement Date” shall have the meaning set forth in the introductory paragraph.

“Applicable Laws” means all statutes, rules and regulations of Governmental
Authorities in the United States or elsewhere applicable to the Company, the
Guarantors and their respective Subsidiaries.

“Authorized Shares Approval” means such approvals as may be required from
Iterum’s shareholders (i) to increase the authorized number of Ordinary Shares
under Iterum’s Constitution such that the number of unissued Ordinary Shares
that are available for issuance by Iterum, less the number of shares that are
issuable upon exercise, conversion or exchange of outstanding options, warrants
or other securities or are reserved under any equity incentive plan maintained
by Iterum, is greater than the total number of Ordinary Shares that are issuable
upon exchange of the then-outstanding 6.500% Exchangeable Senior Subordinated
Notes issued under the Indenture (disregarding any limitations on exchange in
Section 14.01(c) of the Indenture) and (ii) to amend Article 7 of Iterum’s
Articles of Association to authorize Iterum’s Board of Directors to allot and
issue such newly created Ordinary Shares generally and to do so on a non
pre-emptive basis as if Section 1022 of the Irish Companies Act 2014 did not
apply.

“Available Shares” means a number of Ordinary Shares equal to the number of
authorized but unissued Ordinary Shares that are available for issuance by
Iterum (excluding any shares that are issuable upon exercise, conversion or
exchange of outstanding options, warrants or other securities or are reserved
under any equity plan maintained by Iterum or reserved for exchange of any Notes
issued pursuant to the Rights Offering).

“Business Day” means any day other than a Saturday, a Sunday or a day on which
the Federal Reserve Bank of New York is authorized or required by law,
regulation or executive order to close or be closed.

“Closing Date” shall have the meaning set forth in Section 2.1 of this
Agreement.

“Commission” means the United States Securities and Exchange Commission.

“Dollars” and the “$” sign mean the lawful currency of the United States of
America.

“Exchange Act” means the Securities Exchange Act of 1934, as amended, including
the rules and regulations promulgated thereunder.

“Exchange Shares” means the Ordinary Shares issuable upon exchange of the Notes
pursuant to the terms thereof.

“Governmental Authority” means any government, governmental department,
ministry, cabinet, commission, board, bureau, agency, tribunal, regulatory
authority, instrumentality, judicial, legislative, fiscal, or administrative
body or entity, whether domestic or foreign, federal, state or local, having
jurisdiction over the matter or matters and Person or Persons in question.

 

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“Investment Company Act” means the Investment Company Act of 1940, as amended,
including the rules and regulations promulgated thereunder.

“Indenture” means the indenture, dated as of the Closing Date, among the
Company, Iterum, the Subsidiary Guarantors and U.S. Bank National Association,
as trustee, under which the Notes are to be issued, substantially in the form
attached hereto as Exhibit F.

“Investor Rights Agreement” means the Investor Rights Agreement, dated as of the
Closing Date, by and among the Company, Iterum and each of the Purchasers,
substantially in the form attached hereto as Exhibit A.

“Irish Takeover Rules” means the Irish Takeover Panel Act, 1997, Takeover Rules
2013.

“Knowledge” means, with respect to the Company or any Guarantor, the actual
knowledge of Judith Matthews or Corey Fishman, in each case, after reasonable
due inquiry.

“Material Adverse Effect” means a material adverse effect on (i) the condition,
financial or otherwise, operating results, assets, liabilities, operations or
business of Iterum and its Subsidiaries, taken as a whole, or (ii) the ability
of Iterum to perform any of its material obligations under any of the
Transaction Documents.

“Material Contract” means any contract of Iterum or its Subsidiaries that has
been filed or was required to have been filed as an exhibit to the SEC Reports
pursuant to Item 601(b)(4) or Item 601(b)(10) of Regulation S-K. For the
avoidance of doubt, the Pfizer License shall at all times be deemed a Material
Contract.

“Notes” means the 6.500% Exchangeable Senior Subordinated Notes due 2025, fully
and unconditionally guaranteed on an unsecured senior basis by the Guarantors,
issued by the Company to the Purchasers under the Indenture.

“Ordinary Shares” means the ordinary shares, $0.01 nominal value, of Iterum.

“Organizational Documents” means the constitution, bylaws or similar documents,
each as amended to date, of the Company and the Guarantors.

“Parties” shall have the meaning set forth in the introductory paragraph.

“Person” means and includes any natural person, individual, partnership, joint
venture, corporation, trust, limited liability company, limited company, joint
stock company, unincorporated organization, Governmental Authority or any
political subdivision or agency thereof, or any other entity.

“Pfizer License” means that License Agreement, by and among Iterum, Iterum
Therapeutics International Limited and Pfizer Inc., dated as of November 18,
2015, as it may be amended from time to time.

“Placement Agent” means SVB Leerink LLC.

 

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“Purchasers” shall have the meaning set forth in the introductory paragraph.

“Regulation D” means Regulation D promulgated under the Securities Act.

“Regulation S” means Regulation S promulgated under the Securities Act.

“Required Purchasers” means, at any time, Purchasers holding (i) Notes
representing more than 66 2/3% of the aggregate principal amount of the Notes
purchased under this Agreement, and (ii) RLNs representing more than 66 2/3% of
the aggregate Principal Amount of the RLNs (as defined therein) purchased under
this Agreement.

“Rights Offering” means the public offering of subscription rights to purchase
Units by Iterum and the Company to holders of Ordinary Shares on a pro rata
basis in accordance with their share ownership as of a record date to be
determined by the Board of Directors of Iterum or a committee thereof; provided,
that the Purchasers and their Affiliates shall not purchase any Units pursuant
to the Rights Offering (regardless of whether or not under Irish or other
applicable law such subscription rights are required to be offered to the
Purchasers).

“RLNs” means the limited recourse royalty-linked subordinated notes issued to
the Purchasers under the RLN Indenture.

“RLN Indenture” means the Limited Recourse Royalty-Linked Subordinated Notes
Indenture, dated as of the Closing Date, by and among the Company, Iterum, the
Subsidiary Guarantors, Iterum Holders’ Representative LLC, as Holders’
Representative, and Computershare Trust Company, N.A., as trustee, substantially
in the form attached hereto as Exhibit G.

“Rule 144A” means Rule 144A promulgated by the Commission pursuant to the
Securities Act, as such rule may be amended from time to time, or any similar
rule or regulation hereafter adopted by the Commission having substantially the
same effect as such rule.

“Rule 9 Whitewash” means such approvals and waivers as may be required under the
Takeover Rules or by the Irish Takeover Panel to facilitate the issue of
Exchange Shares without triggering a requirement for a mandatory offer under
Rule 9 of the Irish Takeover Rules.

“SEC Reports” shall have the meaning set forth in Section 3.1(a) of this
Agreement.

“Securities” means the Notes, the Exchange Shares and the RLNs.

“Securities Act” means the Securities Act of 1933, as amended, including the
rules and regulations promulgated thereunder.

“Securityholder Questionnaire” means a questionnaire substantially in the form
attached hereto as Exhibit B.

“Shareholder Approval” means such approval as may be required from time to time
by the applicable rules and regulations of the Nasdaq Stock Market (or any
successor entity) from Iterum’s shareholders with respect to the issuance of the
Units (including the Notes) in

 

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connection with the sale to the Purchasers hereunder and/or the issuance of all
Ordinary Shares issuable in connection with the exchange of any Notes issued to
the Purchasers hereunder.

“Subsidiary or Subsidiaries” means, with respect to a Person, any entity of
which securities or other ownership interests having ordinary voting power to
elect a majority of the board of directors or other individuals performing
similar functions are at the time directly or indirectly owned or controlled by
such Person.

“SVB Facility” means that certain Loan and Security Agreement among the
Subsidiary Guarantors, the Company and Silicon Valley Bank, dated as of
April 27, 2018 (as may be amended, modified, restated, replaced, or supplemented
from time to time, including any deferrals, renewals, refinancings or extensions
thereof).

“Transaction Documents” means this Agreement, the Notes, the RLNs, the
Indenture, the RLN Indenture and the Investor Rights Agreement.

“Units” means units consisting of Notes and RLNs.

“Wellington Entities” means Salthill Investors (Bermuda) L.P. and Salthill
Partners, L.P.

Section 1.2 Interpretation. In this Agreement, unless the context otherwise
requires, all words and personal pronouns relating thereto shall be read and
construed as the number and gender of the party or parties requires and the verb
shall be read and construed as agreeing with the required word and pronoun; the
division of this Agreement into Articles and Sections and the use of headings
and captions is for convenience of reference only and shall not modify or affect
the interpretation or construction of this Agreement or any of its provisions;
the words “herein,” “hereof,” “hereunder,” “hereinafter” and “hereto” and words
of similar import refer to this Agreement as a whole and not to any particular
Article or Section hereof; the words “include,” “including,” and derivations
thereof shall be deemed to have the phrase “without limitation” attached thereto
unless otherwise expressly stated; references to a specified Article, Exhibit,
Section or Schedule shall be construed as a reference to that specified Article,
Exhibit, Section or Schedule of this Agreement; and any reference to any of the
Transaction Documents means such document as the same shall be amended,
supplemented or modified and from time to time in effect.

Section 1.3 Business Day Adjustment. If the day by which any payment or other
performance is due to be made is not a Business Day, that payment or performance
shall be made by the next succeeding Business Day.

ARTICLE 2

AGREEMENT FOR THE PURCHASE OF THE UNITS

Section 2.1 Purchase and Sale of the Units. Subject to the conditions set forth
in Article 4 of this Agreement, the Company shall issue and sell to each
Purchaser, and each Purchaser shall purchase from the Company, such Units as
indicated opposite such Purchaser’s name on Schedule 1 hereto under the heading
“Units Purchased”. Each “Unit” shall consist of $1,000 principal amount of Notes
and 50 RLNs. The closing shall occur on a date (“Closing

 

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Date”) not more than five (5) Business Days following the Agreement Date, or
such later date as mutually agreed by the Parties in writing. The purchase price
per Unit shall be $1,000, consisting of a purchase price per $1,000 principal
amount of Notes of $768.73 and a purchase price per 50 RLNs of $231.27.

Section 2.2 On the Closing Date, each Purchaser shall deliver or cause to be
delivered to the Company (or to Iterum if so directed by the Company), via wire
transfer of immediately available funds pursuant to the wire instructions
delivered to such Purchaser by the Company on or prior to the Closing Date, an
amount equal to the purchase price to be paid by the Purchaser for the Units to
be acquired by it as set forth opposite the name of such Purchaser under the
heading “Aggregate Purchase Price” on Schedule 1 attached hereto.

Section 2.3 At or before the closing, the Company shall deliver or cause to be
delivered to each Purchaser (A) Notes representing the aggregate principal
amount included in the number of Units being purchased by such Purchaser,
registered in the name of the Purchaser, and (B) a number of RLNs included in
the number of Units being purchased by such Purchaser.

ARTICLE 3

REPRESENTATIONS AND WARRANTIES

Section 3.1 Representations and Warranties of the Company. Unless otherwise
noted, the Company and the Guarantors hereby represent and warrant, on a joint
and several basis, as of the Agreement Date that:

(a) Since May 24, 2018, Iterum has timely filed all required reports, schedules,
forms, statements and other documents (including exhibits and all other
information incorporated therein), and any required amendments to any of the
foregoing, with the Commission (collectively, the “SEC Reports”). As of their
respective filing dates, each of the SEC Reports complied in all material
respects with the requirements of the Exchange Act or the Securities Act, as
applicable, and no SEC Reports, when filed, declared effective or mailed, as
applicable, contained any 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 light of the circumstances under which they were
made, not misleading. There are no material open, outstanding or unresolved
Commission comments to any SEC Reports. To the Knowledge of Iterum, none of the
SEC Reports is the subject of any ongoing, pending or threatened, review,
comment, or investigation by the Commission or any other Governmental Authority.

(b) The financial statements of Iterum contained or incorporated by reference in
the SEC Reports complied as to form with the published rules and regulations of
the Commission with respect thereto, were prepared in accordance with GAAP
applied on a consistent basis throughout the periods involved and fairly present
in all material respects the financial position and the results of operations,
changes in shareholders’ equity, and cash flows of Iterum at the respective
dates of and for the periods referred to in such financial statements (except as
may be indicated in the notes thereto and for the omission of notes and audit

 

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adjustments in the case of unaudited quarterly financial statements to the
extent permitted by Regulation S-X or Regulation S-K promulgated by the
Commission, as applicable).

(c) Since December 31, 2018, neither Iterum nor, to the Knowledge of Iterum,
Iterum’s independent registered public accounting firm has identified or been
made aware of (A) any significant deficiency or material weakness in the system
of internal control over financial reporting used by Iterum and its Subsidiaries
that has not been subsequently remediated; or (B) any fraud, whether or not
material, that involves Iterum’s management or other employees who have a role
in the preparation of financial statements or the internal control over
financial reporting utilized by Iterum and its Subsidiaries.

(d) The Company, the Guarantors and each of their respective Subsidiaries have
been duly organized, are validly existing and in good standing under the laws of
their respective jurisdictions of organization (to the extent that such
qualification is required in the relevant jurisdiction of organization), have
the corporate power and authority to own their property and to conduct their
business. The Company, the Guarantors and each of their respective Subsidiaries
are duly qualified to transact business and are in good standing in each
jurisdiction in which the conduct of their business or their ownership or
leasing of property requires such qualification, except to the extent that the
failure to so qualify or be in good standing would not, individually or in the
aggregate, result in a Material Adverse Effect.

(e) Each of the Transaction Documents has been duly authorized by the Company
and the Guarantors and, when duly executed and delivered in accordance with its
terms by the parties thereto, will constitute a valid and legally binding
obligation of the Company and the Guarantors, enforceable against the Company
and the Guarantors in accordance with its terms, except as such enforceability
may be limited by (i) applicable insolvency, bankruptcy, reorganization,
moratorium or other similar laws affecting the enforcement of creditors’ rights
generally, or (ii) applicable equitable principles relating to enforceability
(whether considered in a proceeding at law or in equity).

(f) The authorized, issued and outstanding share capital of Iterum conforms to
the description thereof contained in the SEC Reports, and since March 31, 2019,
to Iterum’s Knowledge, there has been no material change to the number or
percentage of shares beneficially owned by any Person listed in the “Share
Ownership of Certain Beneficial Owners and Management” section of Iterum’s 2019
proxy statement, as filed with the Commission on April 25, 2019 (other than as
set forth in any such Person’s beneficial ownership reports as filed with the
Commission). All of the capital stock of the Company is owned by Iterum or a
Subsidiary of Iterum. All of the issued shares of share capital of Iterum have
been duly authorized and validly issued and are fully paid and non-assessable.
None of the outstanding share capital of Iterum was issued in violation of any
preemptive rights, rights of first refusal or other similar rights to subscribe
for or purchase securities of, or other equity interests in, Iterum. Except as
disclosed in the SEC Reports, there are no authorized or outstanding options,
warrants, preemptive rights, rights of first refusal or other rights to
purchase, or securities convertible into or exchangeable or exercisable for, any
capital stock of Iterum or any of its Subsidiaries (other than options or equity
awards granted under Iterum’s equity incentive plans).

 

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(g) Assuming the valid passing of the Authorized Shares Approval by the
requisite majority of shareholders at a duly convened shareholder meeting, the
Exchange Shares will be duly authorized and reserved and, when issued upon
exchange of the Notes in accordance with the terms of the Notes and the
Indenture, will be validly issued, fully paid and not subject to calls for any
additional payments (non-assessable), and the issuance of such Ordinary Shares
will not be subject to any preemptive or similar rights.

(h) The execution and delivery by the Company and the Guarantors of, and the
performance by the Company and the Guarantors of their respective obligations
under, the Transaction Documents will not contravene any Organizational
Documents of the Company or the Guarantors or any Material Contract, or any
judgment, order or decree of any Governmental Authority, agency or court having
jurisdiction over the Company or the Guarantors or any of their respective
Subsidiaries, and no consent, approval, authorization or order of, or
qualification with, any Governmental Authority is required for the performance
by the Company or the Guarantors of its obligations under this Agreement, except
those that have already been obtained or made or as may be required by the
securities or Blue Sky laws of the various states in connection with the offer
and sale of the Securities, or the filing with the Commission of one or more
registration statements pursuant to, and in accordance with, the Investor Rights
Agreement. Neither the Company nor the Guarantors are in violation of its
Organizational Documents. Neither the Company nor the Guarantors are in breach
of or otherwise in default, and no event has occurred which, with notice or
lapse of time or both, would constitute such a default in the performance of any
Material Contract, except (i) with respect to any Material Contract other than
the Pfizer License, for any such default that would not, individually or in the
aggregate, have a Material Adverse Effect, and (ii) with respect to the Pfizer
License, for any default that is immaterial and would not give the counterparty
thereto any right to terminate, amend or modify the Pfizer License or any rights
or obligations of any Guarantor thereunder.

(i) Since December 31, 2018, there have not been any changes, conditions, events
or circumstances which have had, or would reasonably be expected to have, a
Material Adverse Effect, except in each case as described in the SEC Reports.

(j) Neither the Company nor the Guarantors are, and immediately after issuance
of the Notes and the RLNs, neither the Company nor the Guarantors will be, an
“investment company” within the meaning of the Investment Company Act.

(k) Since December 31, 2018, (i) Iterum has not incurred any material liability
or obligation, direct or contingent, nor entered into any material transaction;
(ii) Iterum has not purchased any of its issued share capital (except in
connection with the departure of an employee or consultant and pursuant to the
terms of an existing agreement between such Person and Iterum of which the
Purchaser has been advised in writing), nor declared, paid or otherwise made any
dividend or distribution of any kind on its share capital other than ordinary
and customary dividends; and (iii) there has not been any material change in
Iterum’s share capital (other than options or equity awards granted under
Iterum’s equity incentive plans), or the short-term debt or long-term debt of
Iterum, except in each case as described in the SEC Reports.

(l) Except as described in the SEC Reports, neither the Company nor Iterum has
sold, issued or distributed any Ordinary Shares during the six-month period
preceding the

 

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Agreement Date, including any sales pursuant to (i) Rule 144A, (ii) Regulation D
or (iii) Regulation S, other than Ordinary Shares issued pursuant to (1) the
Company’s or Iterum’s employee benefit plans, qualified stock option plans or
other employee compensation plans, (2) outstanding options, rights or warrants
or (3) transactions in connection with commercial relationships not exceeding 5%
in the aggregate of Iterum’s Ordinary Shares.

(m) Assuming the accuracy of the representations and warranties of the
Purchasers set forth in Section 3.2 of this Agreement and the Purchasers’
compliance with their agreements set forth therein, (i) the Notes and the RLNs
will be issued in compliance with all applicable federal and state securities
laws and (ii) it is not necessary, in connection with the issuance and sale of
the Notes and the RLNs to the Purchasers, to register the Securities under the
Securities Act.

(n) The issuance of the Notes, the RLNs and the Exchange Shares will not
obligate the Company or Iterum to issue Ordinary Shares or any other securities
to any Person (other than the Purchasers or pursuant to the Rights Offering) and
will not result in a right of any holder of the Company’s or Iterum’s
securities, including the Ordinary Shares, to adjust the exercise, conversion,
exchange or reset price under any of such securities. Except (i) the Investor
Rights Agreement and (ii) as otherwise disclosed in the SEC Reports, there are
no stockholders’ agreements, voting agreements or other similar agreements with
respect to Iterum’s share capital, including the Ordinary Shares, to which
Iterum is a party or, to Iterum’s Knowledge, between or among any of Iterum’s
shareholders.

(o) None of the Company, the Guarantors or any of their respective Affiliates
(other than the Purchasers) has, directly or through any agent, sold, offered
for sale, solicited offers to buy or otherwise negotiated in respect of, any
security (as defined in the Securities Act), that is or will be integrated with
the sale of the Notes and the RLNs in a manner that would require registration
of the Notes or the RLNs under the Securities Act.

(p) None of the Company, the Guarantors or any of their respective Affiliates
(other than the Purchasers) or any other Person authorized to act on its or
their behalf has (i) solicited offers for, or offered or sold, the Notes or the
RLNs by means of any form of general solicitation or general advertising within
the meaning of Rule 502(c) of Regulation D or in any manner involving a public
offering within the meaning of Section 4(a)(2) of the Securities Act or
(ii) engaged in any directed selling efforts within the meaning of Regulation S,
and all such Persons have complied with the offering restrictions requirement of
Regulation S.

(q) Neither the Company nor the Guarantors have taken, directly or indirectly,
without giving any effect to the activities of the Purchasers, any action
designed to or that would reasonably be expected to cause or result in
stabilization or manipulation of the price of any security of the Company or the
Guarantors to facilitate the sale or resale of the Notes or the RLNs.

(r) No Person, other than the Placement Agent and its Affiliates, has or will
have, as a result of the transactions contemplated by this Agreement or any of
the other Transaction Documents, any right, interest or claim against or upon
the Company or the

 

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Guarantors for any commission, fee or other compensation as a finder or broker
because of any act or omission by the Company, the Guarantors or their
respective stockholders or Affiliates.

(s) Neither (i) the Company, the Guarantors or, to the Company’s or the
Guarantors’ Knowledge, their respective Affiliates (other than the Purchasers)
or (ii) to the Company’s or the Guarantors’ Knowledge, any of their respective
directors, executive officers, other officers that may serve as a director or
officer of any company in which it invests, general partners or managing
members, nor (iii) to Iterum’s Knowledge, any beneficial owner of 20% or more of
Iterum’s voting equity securities (in accordance with Rule 506(d) of the
Securities Act), is subject to any of the “bad actor” disqualification events
described in Rule 506(d)(1)(i) through (viii) under the Securities Act.

(t) There is no pending or, to the Knowledge of the Company, threatened action,
suit, proceeding or investigation that, individually or in the aggregate, would
constitute or would reasonably be expected to reduce the amount of any Payment
(as defined in the RLN Indenture), including any action involving any of the
Products (as defined in the RLN Indenture) or any intellectual property related
to any of the Products.

(u) Subject to the Pfizer License and the SVB Facility, the Company and the
Guarantors are the exclusive owners of and hold all right, title (legal and
equitable) and interest in and to the rights in the Gross Revenues (as defined
in the RLN Indenture), free and clear of all liens.

(v) Subject to the Pfizer License and the SVB Facility, the Company and the
Guarantors are the exclusive owners of the entire right, title and interest in
and to each of the Products, all data associated therewith, and all intellectual
property rights covering or relating to the Products, free and clear of all
liens.

(w) All patents owned or controlled by the Company and the Guarantors covering
any Product that have been issued or granted by the appropriate patent office
are valid and enforceable.

(x) The manufacture, use, offer for sale, sale and/or importation of any of the
Products will not infringe on any patent or other intellectual property rights
of any third party. Neither Company nor Guarantor has received written or oral
notice of any action, suit or proceeding that claims that the manufacture, use,
marketing, sale, offer for sale, importation or distribution of any Product
infringes on any patent or other intellectual property rights of any third party
or constitutes misappropriation of any third party’s trade secrets or other
intellectual property rights.

(y) The Guarantors are in compliance with all material terms of and obligations
under the Pfizer License, are, the exclusive licensees of all intellectual
property rights purported to be licensed in the Pfizer License, and have not
materially breached and are not in default under any material provision of the
Pfizer License. To the Knowledge of the Guarantors, the Pfizer License is valid,
enforceable and in good standing.

(z) No event has occurred that would give Pfizer the right to unilaterally
terminate the Pfizer License. The Guarantors have not received any notice of an
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Pfizer to terminate the Pfizer License, and the Guarantors have not agreed with
Pfizer to terminate the Pfizer License in whole or in part.

(aa) The Guarantors are in compliance in all material respects with all
applicable healthcare laws and regulations and with the codes of conduct
published by the Pharmaceutical Research and Manufacturers of America.

Section 3.2 Representations and Warranties of the Purchasers. Each Purchaser,
severally and not jointly, hereby represents and warrants on behalf of itself to
the Company and the Guarantors as of the Agreement Date that:

(a) Such Purchaser, if an entity, is duly organized and validly existing under
the laws of the jurisdiction of its formation.

(b) Each of the Transaction Documents to which it is a party has been duly
authorized, executed and delivered by such Purchaser and constitutes the valid
and legally binding obligation of such Purchaser, enforceable against such
Purchaser in accordance with its terms, except as such enforceability may be
limited by (i) applicable insolvency, bankruptcy, reorganization, moratorium or
other similar laws affecting the enforcement of creditors’ rights generally, or
(ii) applicable equitable principles relating to enforceability (whether
considered in a proceeding at law or in equity).

(c) Such Purchaser has full power and authority to purchase the Notes and the
RLNs and to enter into and perform its other obligations under each of the
Transaction Documents and carry out the other transactions contemplated thereby.

(d) Each of the Notes, the RLNs and Exchange Shares to be received by such
Purchaser hereunder will be acquired for such Purchaser’s own account, and not
with a view to the resale or distribution of any part thereof in violation of
the Securities Act, and such Purchaser has no agreement or understanding,
directly or indirectly, or present intention of selling, granting any
participation in or otherwise distributing the Notes, the RLNs or Exchange
Shares in violation of applicable federal, state, European or Irish securities
laws; provided, however, nothing contained herein shall be deemed a
representation or warranty by such Purchaser to hold the Securities for any
period of time and such Purchaser reserves the right to dispose of the
Securities at any time in accordance with, or pursuant to, a registration
statement or an applicable exemption under the Securities Act and any applicable
European and Irish laws.

(e) Such Purchaser can bear the economic risk and complete loss of its
investment in the Securities and has such knowledge and experience in financial
and business matters that it is capable of evaluating the merits and risks of
the investment contemplated hereby.

(f) Such Purchaser understands that the Securities are characterized as
“restricted securities” under the U.S. federal securities laws inasmuch as they
are being acquired from the Company or Iterum in a transaction not involving a
public offering and that under such laws and applicable regulations such
securities may be resold without registration under the Securities Act only in
certain limited circumstances.

 

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(g) Such Purchaser understands that, except as provided below, certificates
evidencing the Securities may bear the following or any similar legend:

(i) “These securities represented hereby [and the securities issuable upon
exchange of these securities] have not been registered with the Securities and
Exchange Commission or the securities commission of any State in reliance upon
an exemption from registration under the Securities Act of 1933, as amended,
and, accordingly, may not be transferred unless (i) such securities have been
registered for sale pursuant to the Securities Act of 1933, as amended,
(ii) such securities may be sold pursuant to Rule 144, (iii) the Issuer has
received an opinion of counsel reasonably satisfactory to it that such transfer
may lawfully be made without registration under the Securities Act of 1933, as
amended, or (iv) the securities are transferred without consideration to an
affiliate of such holder or a custodial nominee (which for the avoidance of
doubt shall require neither consent nor the delivery of an opinion).”; or

(ii) If required by the authorities of any State in connection with the issuance
of sale of the Securities, the legend required by such State authority.

(h) Such Purchaser understands that the Securities are being offered and sold to
it in reliance on specific exemptions from the registration requirements of
United States federal and state securities laws and that the Company and the
Guarantors are relying in part upon the truth and accuracy of, and such
Purchasers’ compliance with, the representations, warranties, agreements,
acknowledgments and understandings of such Purchaser set forth herein in order
to determine the availability of such exemptions and the eligibility of such
Purchaser to acquire the Securities.

(i) Such Purchaser has (i) received all the information from the Company, the
Guarantors and their management that the Purchaser considers necessary or
appropriate for deciding whether to purchase the Notes and the RLNs hereunder,
including the SEC Reports and (ii) had an opportunity to ask questions and
receive answers from the Company and the Guarantors regarding the Company and
the Guarantors, their financial condition, results of operations and prospects,
and the terms and conditions of the offering of the Notes and the RLNs
sufficient to enable it to evaluate its investment; provided, that the foregoing
does not limit or modify the representations and warranties made by the Company
and the Guarantors in Section 3.1 of this Agreement or the right of each of the
Purchasers to rely thereon.

(j) Such Purchaser did not learn of the offering and sale of the Notes and the
RLNs as a result of any general solicitation or general advertising.

(k) Such Purchaser is an “accredited investor” as such term is defined in
Regulation D.

(l) Except in so far as such Purchaser is eligible to receive Ordinary Shares
upon exchange of the Notes to be purchased by such Purchaser hereunder and any
seats on the Iterum Board of Directors pursuant to the Investor Rights
Agreement, such Purchaser has no present intent to effect a “change of control”
of the Company or Iterum as such term is understood under the rules promulgated
pursuant to Section 13(d) of the Exchange Act.

 

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(m) Such Purchaser acknowledges that, subject to the terms of the Indenture,
Iterum shall not issue to any holder of a Note issued hereunder, and no such
holder may acquire, a number of Ordinary Shares upon exchange of a Note and
Iterum shall not otherwise issue any Ordinary Shares pursuant to the Indenture,
to the extent that (1) upon such issuance, the number of Ordinary Shares then
beneficially owned by the holder and its affiliates and any other Persons or
entities whose beneficial ownership of Ordinary Shares would be aggregated with
the holder’s for purposes of Section 13(d) of the Exchange Act (including any
shares held by any “group” of which the holder is a member, but excluding shares
beneficially owned by virtue of the ownership of securities or rights to acquire
securities that have limitations on the right to exchange, convert, exercise or
purchase similar to the limitation set forth in the Indenture) would exceed
19.99% of the total number of Ordinary Shares issued and outstanding, (2) such
issuance, when aggregated with any other Ordinary Shares theretofore or
simultaneously therewith issued to or otherwise beneficially owned by the holder
and its affiliates and any other Persons or entities whose beneficial ownership
of Ordinary Shares would be aggregated with the holder’s for purposes of
Section 13(d) of the Exchange Act (including any shares held by any “group” of
which the holder is a member, but excluding shares beneficially owned by virtue
of the ownership of securities or rights to acquire securities that have
limitations on the right to exchange, convert, exercise or purchase similar to
the limitation set forth in the Indenture) would otherwise result in a “change
of control” of Iterum within the meaning of Nasdaq Listing Rule 5635(b) or
(3) the issuance of such Ordinary Shares would, together with any other issuance
of Ordinary Shares to any holders of Notes issued hereunder upon the exchange of
all such Notes, exceed 19.99% of the issued and outstanding Ordinary Shares
immediately prior to the Closing Date (the “Aggregate Ownership Cap”), except
that such limitations shall not apply in the event that Iterum (a) obtains the
Shareholder Approval or (b) with respect to the Aggregate Ownership Cap, obtains
a waiver from the Nasdaq Stock Market LLC of all applicable listing rules
requiring such stockholder approval. Until one of the exceptions in clauses
(a) or (b) of the proceeding sentence applies, upon an exchange of a Note to
which the Aggregate Ownership Cap applies the Purchaser shall, subject to the
terms of Section 14.01 and Section 14.02 of the Indenture, be entitled to
receive up to a number of Ordinary Shares equal to (x) the number of issued and
outstanding Ordinary Shares immediately prior to the Closing Date (subject to
adjustment in the event of any stock dividend, stock split, combination or other
similar recapitalization) multiplied by (y) the quotient obtained by dividing
the principal amount of such Note by the initial aggregate principal of all
Notes issued hereunder immediately following their original issuance, and for
the avoidance of doubt, such Purchaser shall retain any portion of such Note not
exchanged for Ordinary Shares as a result of the application of the foregoing
formula.

(n) Such Purchaser acknowledges that, subject to the terms of the Indenture,
Iterum shall not issue to any holder of a Note issued hereunder, and no such
holder may acquire, a number of Ordinary Shares upon exchange of a Note and
Iterum shall not otherwise deliver any Ordinary Shares pursuant hereto, to the
extent that the issuance of such Ordinary Shares would, together with any other
issuance of Ordinary Shares by Iterum to any holders of Notes issued hereunder
upon the exchange of all such Notes, exceed the Available Shares, except that
such limitation shall not apply in the event that Iterum obtains the Authorized
Shares Approval (the “Available Shares Ownership Cap”). Until the exception in
the proceeding sentence applies, upon an exchange of a Note to which the
Available Shares Ownership Cap applies the Purchaser shall in no event, subject
to the terms of Section 14.01 and Section 14.02 of the Indenture, be entitled to
receive a number of Ordinary Shares (determined in the aggregate for all such

 

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exchanges of a Specified Note by such holder) in excess of (x) the Available
Shares (subject to adjustment in the event of any stock dividend, stock split,
combination or other similar recapitalization) multiplied by (y) the quotient
obtained by dividing the principal amount of such Specified Note by the initial
aggregate principal of all Specified Notes immediately following their original
issuance

(o) Such Purchaser acknowledges that Exchange Shares issued upon the exchange of
any Note shall not be voted in connection with or counted in support of the
Shareholder Approval.

(p) Such Purchaser has not taken any of the actions set forth in, and is not
subject to, any of the “bad actor” disqualification events described in Rule
506(d)(1)(i) through (viii) under the Securities Act. The Purchaser’s responses
in the questionnaire delivered to the Company by the Purchaser related to
qualification under Rule 506(d)(1) of the Securities Act are true and correct as
of the Agreement Date and will remain true and correct as of the Closing Date.

(q) Such Purchaser will only purchase Units pursuant to this Agreement in an
amount set forth in Schedule 1 and will not purchase or allow any of its
Affiliates to purchase any Units pursuant to the Rights Offering (regardless of
whether or not under Irish or other applicable law subscription rights to
purchase Units are required to be offered to such Purchaser).

(r) Such Purchaser hereby acknowledges and agrees that (a) the Placement Agent
is acting solely as placement agent in connection with the execution, delivery
and performance of the Transaction Documents and is not acting as an underwriter
or in any other capacity and is not and shall not be construed as a fiduciary
for such Purchaser, the Company or any other person or entity in connection with
the execution, delivery and performance of the Transaction Documents, (b) the
Placement Agent has not made and will not make any representation or warranty,
whether express or implied, of any kind or character, and has not provided any
advice or recommendation in connection with the execution, delivery and
performance of the Transaction Documents, (c) the Placement Agent will not have
any responsibility with respect to (i) any representations, warranties or
agreements made by any person or entity under or in connection with the
execution, delivery and performance of the Transaction Documents, or the
execution, legality, validity or enforceability (with respect to any person)
thereof, or (ii) the business, affairs, financial condition, operations,
properties or prospects of, or any other matter concerning the Company, and
(d) the Placement Agent will not have any liability or obligation (including
without limitation, for or with respect to any losses, claims, damages,
obligations, penalties, judgments, awards, liabilities, costs, expenses or
disbursements incurred by such Purchaser, the Company or any other person or
entity), whether in contract, tort or otherwise, to such Purchaser, or to any
person claiming through it, in respect of the execution, delivery and
performance of the Transaction Documents.

 

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ARTICLE 4

CONDITIONS OF PURCHASE OF THE UNITS.

Section 4.1 Conditions to the Sale of the Notes. The obligation of the Company
to issue and sell the Units to each Purchaser shall be subject to the
fulfillment of the following conditions:

(a) The Company shall have received executed counterparts of the Investor Rights
Agreement from each Purchaser;

(b) The Company shall have received from each Purchaser a fully completed and
duly executed Securityholder Questionnaire and Accredited Investor
Questionnaire;

(c) The Purchaser shall have delivered the purchase price for the Units to the
Company in accordance with this Agreement;

(d) The representations and warranties made by the Purchaser in Section 3.2
hereof shall be true and correct as of the Agreement Date and as of the Closing
Date as though made on and as of such Closing Date, except to the extent such
representations and warranties are specifically made as of a particular date, in
which case such representations and warranties shall be true and correct as of
such date; and

(e) The Purchasers shall have performed or complied with all agreements and
covenants required by this Agreement to be performed or complied with by them at
or prior to the Closing Date.

Section 4.2 Conditions to the Purchase of the Units. The obligation of the
Purchasers to purchase the Units shall be subject to the fulfillment of the
following conditions:

(a) The Purchasers shall have received copies of the Investor Rights Agreement,
the RLN Indenture and the Indenture executed by the Company and the Guarantors
and the applicable trustee (in the case of the RLN Indenture and the Indenture)
and the Holders’ Representative (in the case of the RLN Indenture), dated as of
the Closing Date;

(b) No Material Adverse Effect shall have occurred following the Agreement Date;

(c) The representations and warranties made by the Company in Section 3.1 hereof
shall be true and correct as of the Agreement Date and as of the Closing Date as
though made on and as of such Closing Date, except to the extent such
representations and warranties are specifically made as of a particular date, in
which case such representations and warranties shall be true and correct as of
such date;

(d) The Company and the Guarantors shall have performed or complied with all
agreements and covenants required by this Agreement to be performed or complied
with by it and them at or prior to the Closing Date;

 

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(e) Iterum shall have requested and caused Wilmer Cutler Pickering Hale and Dorr
LLP, U.S. counsel for Iterum, to furnish to the Purchasers its opinion, dated
the Closing Date and addressed to the Purchasers, in substantially the form
attached hereto as Exhibit C;

(f) Iterum shall have requested and caused A&L Goodbody, Irish counsel for
Iterum, to furnish to the Purchasers its opinion, dated the Closing Date and
addressed to the Purchasers, in substantially the form attached hereto as
Exhibit D;

(g) Iterum shall have requested and caused Conyers Dill & Pearman, Bermuda
counsel for Iterum, to furnish to the Purchasers its opinion, dated the Closing
Date and addressed to the Purchasers, in substantially the form attached hereto
as Exhibit E;

(h) Iterum shall have executed and delivered the Investor Rights Agreement;

(i) Iterum shall have obtained and delivered to Purchasers the written consent
of Silicon Valley Bank (in its capacity as party to the SVB Facility), to the
execution of this Agreement by the Company and the Guarantors and the
consummation of the activities and transactions contemplated by each of the
Transaction Documents;

(j) The aggregate consideration paid by the Purchasers for the purchase of Units
pursuant to this Agreement, collectively, shall be at least $10,000,000; and

(k) Iterum shall have delivered a statement setting forth for the Notes and the
RLNs, as of the Closing Date (i) with respect to the RLNs only, the fair market
value of each RLN as determined by an independent valuation firm, (ii) with
respect to the Notes, the total amount of original issue discount, and
(iii) with respect to the Notes, the yield to maturity.

Section 4.3 Mutual Conditions to Closing. The obligation of the Company to issue
and sell the Units to each Purchaser and the obligation of the Purchasers to
purchase the Units shall be subject to the fulfillment of the following
conditions:

(a) There shall be no action, suit, proceeding or investigation by a
Governmental Authority pending or currently threatened in writing against the
Company, a Guarantor or the Purchasers that questions the validity of any of the
Transaction Documents, the right of the Company, a Guarantor or the Purchasers
to enter into any of the Transaction Documents or to consummate the transactions
contemplated hereby or thereby or which, if determined adversely, would impose
substantial monetary damages on the Company, a Guarantor or the Purchasers as a
result of the consummation of the transactions contemplated by any of the
Transaction Documents; and

(b) No provision of any Applicable Law, and no judgment, injunction (whether
preliminary or permanent), order or decree, that prohibits, makes illegal or
enjoins the consummation of the transactions contemplated by any of the
Transaction Documents shall be in effect.

 

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ARTICLE 5

Covenants

Section 5.1 Reservation of Ordinary Shares for Exchange. Subject to (i) the
valid passing of the Authorized Shares Approval by the requisite majority of
shareholders at a duly convened shareholder meeting and (ii) the Available
Shares Ownership Cap, Iterum covenants that it will at all times reserve and
keep available out of its authorized but unissued Ordinary Shares and/or
Ordinary Shares then held in treasury, solely for the purpose of delivery upon
exchange of the Notes as herein provided, such number of Ordinary Shares as
shall then be deliverable upon the exchange of the Notes. Assuming the valid
passing of the Authorized Shares Approval by the requisite majority of
shareholders at a duly convened shareholder meeting, all Ordinary Shares which
shall be so deliverable shall, when issued, be duly and validly issued and fully
paid and not subject to calls for any additional payments (non-assessable).

Section 5.2 Shareholder Approval. Iterum shall take all action reasonably
necessary or appropriate in accordance with the applicable rules and regulations
of the Irish Takeover Rules, Nasdaq Stock Market (or any successor entity) to
solicit the Shareholder Approval, the Authorized Shares Approval and the Rule 9
Whitewash. In furtherance (and without limitation) of the foregoing, (i) Iterum
and the Purchasers will use their commercially reasonable efforts to seek all
waivers and derogations from the Irish Takeover Panel in connection with any
proposed Rule 9 Whitewash and (ii) Iterum will use its commercially reasonable
efforts to hold meetings of shareholders no later than June 10, 2020, at which
meetings proposals for obtaining the Shareholder Approval, the Authorized Shares
Approval and the Rule 9 Whitewash shall be considered, with, subject to
compliance with its fiduciary duties, the recommendation of Iterum’s Board of
Directors that such proposals be approved, and Iterum shall solicit proxies from
its shareholders in connection therewith in the same manner as any other
management proposals in such proxy statement. The circular to independent
shareholders of Iterum in respect of the Rule 9 Whitewash shall include all
information required and requested by the Irish Takeover Panel, and the
Purchasers shall promptly provide any information reasonably requested by Iterum
for this purpose.

Section 5.3 Registration Statement. To the extent not prohibited by any
applicable law or applicable interpretations of the Commission or any other
applicable governing authority, Iterum shall prepare and file with the
Commission a registration statement under the Securities Act covering the sale
of securities in connection with the Rights Offering and shall use commercially
reasonable efforts to make such registration statement effective and complete
the Rights Offering prior to the date that is six months following the Closing
Date.

Section 5.4 Compliance. Each Purchaser agrees with Iterum (i) that such
Purchaser will sell any Securities only pursuant to either the registration
requirements of the Securities Act and (if applicable) European and Irish
securities laws, including any applicable prospectus delivery requirements, or
an applicable exemption therefrom, (ii) that if Securities are sold pursuant to
a registration statement, they will be sold in compliance with the plan of
distribution set forth therein and (iii) that if, after the effective date of a
registration statement covering the resale of the Securities, such registration
statement ceases to be effective and the issuer has

 

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provided notice to such Purchaser to that effect, such Purchaser will sell the
Securities only in compliance with an applicable exemption from the registration
requirements of the Securities Act unless and until such registration statement
again becomes effective or another registration statement covering the resale of
the Securities subsequently becomes effective.

Section 5.5 Voting. Each Purchaser other than the Wellington Entities covenants
and agrees soley with Iterum that at any meeting of the holders of the capital
stock of Iterum, however called, and in any other action by written consent of
the holders of the capital stock of Iterum, such Purchaser shall vote all
outstanding Ordinary Shares (other than Exchange Shares issued upon the exchange
of any Note) that are owned beneficially or of record by such Purchaser in favor
of the Shareholder Approval and the Authorized Shares Approval and the Rule 9
Whitewash. Each Purchaser shall, promptly, if requested by the Irish Takeover
Panel, confirm in writing that it shall not accept any mandatory offer required
under Rule 9 of the Irish Takeover Rules on the issue of any Exchange Shares.

ARTICLE 6

MISCELLANEOUS

Section 6.1 Notices. Any notices required or permitted to be given under the
terms hereof shall be sent by certified or registered United States mail (return
receipt requested) or delivered personally or by courier (including a recognized
overnight delivery service) or by electronic mail and shall be effective five
(5) days after being placed in the mail, if mailed by certified or registered
United States mail, or upon receipt, if delivered personally or by courier
(including a recognized overnight delivery service), or when received by
electronic mail if received during normal business hours of the recipient on a
Business Day, or if not so received, on the next Business Day, in each case
addressed to a Party. All notices shall be addressed to the Party to be notified
at the address as follows, or at such other address as such Party may designate
by giving the other Party written notice thereof in accordance with the terms of
this Section 6.1:

If to the Company or the Guarantors:

Iterum Therapeutics plc

Block 2, Floor 3, Harcourt Centre, Harcourt Street

Dublin 2, Ireland

Attention: Corey N. Fishman, President and Chief Executive Officer

Email:

With copies to:

Legal Department

Iterum Therapeutics plc

Block 2, Floor 3, Harcourt Centre, Harcourt Street

Dublin 2, Ireland

Email:

 

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Wilmer Cutler Pickering Hale and Dorr LLP

7 World Trade Center

250 Greenwich Street

New York, New York 10007

Attn: Brian Johnson, Esq.

Email:

If to the Purchasers: To the address set forth immediately below such
Purchaser’s name on the signature pages hereto.

Section 6.2 Waiver of Notice. Whenever any notice is required to be given to any
of the Purchasers, the Company or a Guarantor under any provision of this
Agreement, a waiver thereof in writing signed by the Person or Persons entitled
to such notice, whether before or after the time stated therein, shall be deemed
equivalent to the giving of such notice.

Section 6.3 Fees and Expenses.

(a) The Company, Iterum Therapeutics US Limited or Iterum Therapeutics US
Holding Limited shall reimburse New Leaf Ventures III, L.P. and New Leaf
Biopharma Opportunities II, L.P. (together “New Leaf”) for all reasonable and
documented third party legal or other advisory fees and expenses incurred by New
Leaf in connection with the sale of the Units pursuant to this Agreement, in an
amount not to exceed $450,000.

(b) The Company, Iterum Therapeutics US Limited or Iterum Therapeutics US
Holding Limited shall reimburse Sarissa Capital Management LP for all reasonable
and documented third party legal or other advisory fees and expenses incurred
thereby (or by any Affiliate thereof) in connection with the sale of the Units
pursuant to this Agreement, in an amount not to exceed $260,000.

Section 6.4 Amendment and Waiver. Any term of this Agreement may be amended and
the observance of any term of this Agreement may be waived (either generally or
in a particular instance and either retroactively or prospectively) only with
the written consent of the Company, the Guarantors and the Required Purchasers.

Section 6.5 Governing Law; Consent to Jurisdiction; Waiver of Jury Trial. All
questions concerning the construction, validity, enforcement and interpretation
of this Agreement shall be governed by and construed and enforced in accordance
with the internal laws of the State of New York without regard to the choice of
law principles thereof. Each Party agrees that all legal proceedings concerning
the interpretations, enforcement and defense of the transactions contemplated by
this Agreement (whether brought against a Party hereto or its respective
Affiliates, directors, officers, shareholders, employees or agents) shall be
commenced exclusively in the state and federal courts sitting in the City of New
York. Each Party hereby irrevocably submits to the exclusive jurisdiction of the
state and federal courts sitting in the City of New York, borough of Manhattan
for the adjudication of any dispute hereunder or in connection herewith or with
any transaction contemplated hereby or discussed herein, and hereby irrevocably
waives, and agrees not to assert in any suit, action or other proceeding, any
claim that it is not personally subject to the jurisdiction of any such court,
that such suit, action or

 

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proceeding is improper or is an inconvenient venue for such proceeding. Each
Party hereby irrevocably waives personal service of process and consents to
process being served in any such suit, action or other proceeding by mailing a
copy thereof via registered or certified United States mail or overnight
delivery (with evidence of delivery) to such Party at the address in effect for
notices to it under this Agreement and agrees that such service shall constitute
good and sufficient service of process and notice thereof. Nothing contained
herein shall be deemed to limit in any way any right to serve process in any
other manner permitted by law. THE PARTIES HEREBY WAIVE ALL RIGHTS TO A TRIAL BY
JURY.

Section 6.6 Successors and Assigns. This Agreement shall bind and inure to the
respective successors and assigns of the Parties. The Company and the Guarantors
may assign this Agreement at any time in connection with a sale or acquisition
of the Company or a Guarantor, as applicable, whether by merger, consolidation,
sale of all or substantially all of the Company’s or such Guarantor’s assets, or
similar transaction, without the consent of the Purchasers; provided, that, the
successor or acquirer agrees in writing to assume all of the Company’s or such
Guarantor’s, as applicable, rights and obligations under this Agreement.

Section 6.7 Entire Agreement. The Transaction Documents contain the entire
understanding of the Parties with respect to the matters covered thereby and
supersede any and all other written and oral communications, negotiations,
commitments and writings with respect thereto. Except as otherwise provided
herein, the provisions of this Agreement may be waived, modified, supplemented
or amended only by an instrument in writing signed by an authorized
representative of each Party.

Section 6.8 Severability. If any provision of this Agreement shall be invalid,
illegal or unenforceable in any respect under any law, the validity, legality
and enforceability of the remaining provisions shall not in any way be affected
or impaired thereby.

Section 6.9 Counterparts. This Agreement may be executed in several
counterparts, and by each Party on separate counterparts, each of which and any
photocopies or other electronic transmission (including by PDF) thereof shall be
deemed an original, but all of which together shall constitute one and the same
agreement.

Section 6.10 Survival.

(a) This Agreement and all agreements, representations and warranties made
herein, and in any document, certificate or statement delivered pursuant thereto
or in connection herewith, shall be considered to have been relied upon by the
other Parties and shall survive the execution and delivery of this Agreement and
the purchase of the Units hereunder regardless of any investigation made by any
such other Party or on its behalf, and shall continue in force until the
applicable statute of limitations.

(b) The obligations of the Company, the Guarantors and the Purchasers under this
Article 6 shall survive and remain in full force and effect regardless of the
consummation of the transactions contemplated hereby, the repayment of the Notes
or the termination of this Agreement or any provision hereof.

 

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Section 6.11 No Waiver. Neither the failure of, nor any delay on the part of,
any Party in exercising any right, power or privilege under this Agreement shall
operate as a waiver thereof, nor shall any single or partial exercise of any
right, power or privilege under this Agreement preclude other or further
exercise thereof or the exercise of any other right, power or privilege; nor
shall any waiver of any right, power or privilege under this Agreement
constitute a waiver of any other right, power or privilege under this Agreement.
All rights and remedies herein provided are cumulative and not exclusive of any
rights or remedies otherwise provided by law.

Section 6.12 Several Obligations. The obligations of the Purchasers under the
Transaction Documents shall be several and not joint.

Section 6.13 Disclosure/Publicity. By no later than 9:00 a.m., New York City
time, on the first trading day after the date of this Agreement, Iterum shall
disclose publicly, by press release or a Current Report on Form 8-K reasonably
acceptable to the Purchasers, all material terms of the transactions
contemplated hereby and by the other Transaction Documents and any other
material, non-public information that Iterum, the Company or any Guarantor has
provided to the Purchasers in connection with their consideration of the
transactions contemplated by this Agreement or any of the other Transaction
Documents. Notwithstanding the foregoing, Iterum shall not publicly disclose the
name of any Purchaser or any Affiliate or investment adviser of a Purchaser, or
include the name of a Purchaser or any Affiliate or investment adviser of a
Purchaser in any press release or in any filing with the Commission or any
regulatory agency or trading market, without the prior written consent
(including by e-mail) of such Purchaser, except as required by the federal
securities laws, rules or regulations and to the extent such disclosure is
required by other laws, rules or regulations, at the request of the staff of the
Commission or regulatory agency or under Nasdaq regulations, in which case
Iterum shall provide the Purchaser with prior written notice (including by
e-mail) of such permitted disclosure, and shall reasonably consult with
Purchaser regarding such disclosure.

Section 6.14 Benefit of Agreement. The Placement Agent is an intended
third-party beneficiary of the representations and warranties of the Company and
the Guarantors and of each Purchaser set forth in Section 3.1 and Section 3.2,
respectively, of this Agreement.

[Signature Page Follows]

 

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IN WITNESS WHEREOF, the Purchasers, the Company, Iterum and the Subsidiary
Guarantors have caused this Agreement to be duly executed as of the 16th day of
January, 2020.

 

COMPANY: ITERUM THERAPEUTICS BERMUDA LIMITED By:  

/s/ Louise Barrett

Name: Louise Barrett Title: Director ITERUM: ITERUM THERAPEUTICS PLC By:  

/s/ David Kelly

Name: David Kelly Title: Director SUBSIDIARY GUARANTOR: ITERUM THERAPEUTICS
INTERNATIONAL LIMITED By:  

/s/ Louise Barrett

Name: Louise Barrett Title: Director SUBSIDIARY GUARANTOR: ITERUM THERAPEUTICS
US LIMITED By:  

/s/ Judy Matthews

Name: Judy Matthews Title: Director

 

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SUBSIDIARY GUARANTOR: ITERUM THERAPEUTICS US HOLDING LIMITED By:  

/s/ Judy Matthews

Name: Judy Matthews Title: Director PURCHASERS: ADVENT LIFE SCIENCES LLP By:  

/s/ Kaasim Mahmood

Name: Kaasim Mahmood Title: Partner ADVENT LIFE SCIENCES FUND II LP By: Advent
Life Sciences LLP, its General Partner By:  

/s/ Kaasim Mahmood

Name: Kaasim Mahmood Title: Partner ARIX BIOSCIENCE HOLDINGS LIMITED By:  

/s/ Robert Lyne

Name: Robert Lyne Title: Chief Operating Officer & General Counsel

 

- 23 -

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CANAAN X L.P. By: Canaan Partners X LLC, its general partner By:  

/s/ Brent Ahrens

Name: Brent Ahrens Title: Managing Member FRAZIER HEALTHCARE VII, L.P. By: FHM
VII, LP, its general partner By: FHM VII, LLC, its general partner By:  

/s/ Patrick Heron

Name: Patrick Heron Title: Manager FRAZIER HEALTHCARE VII-A, L.P. By: FHM VII,
LP, its general partner By: FHM VII, LLC, its general partner By:  

/s/ Patrick Heron

Name: Patrick Heron Title: Manager

 

- 24 -

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NEW LEAF VENTURES III, L.P. By: New Leaf Venture Associates III, L.P. Its:
General Partner By: New Leaf Venture Management III, L.L.C. Its: General Partner
By:  

/s/ Craig L. Slutzkin

Name:   Craig L. Slutzkin Title:   Chief Operating Officer/Chief Financial
Officer NEW LEAF BIOPHARMA OPPORTUNITIES II, L.P. By: New Leaf BPO Associates
II, L.P. Its: General Partner By: New Leaf BPO Management II, L.L.C. Its:
General Partner By:  

/s/ Craig L. Slutzkin

Name: Craig L. Slutzkin Title:   Chief Operating Officer/Chief Financial Officer
SOFINNOVA VENTURE PARTNERS IX, L.P. By:   Sofinnova Management IX, L.L.C.   its
General Partner By:  

/s/ James I. Healy

Name: James I. Healy Title: Managing Member

 

- 25 -

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DOMAIN PARTNERS IX, L.P. By: One Palmer Square Associates IX, L.L.C. By:  

/s/ Lisa A. Kraeutler

Name:   Lisa A. Kraeutler Title:   Attorney-in-fact PIVOTAL BIOVENTURE PARTNERS
FUND I, LP By: Pivotal bioVenture Partners Fund I GP, LP By: Pivotal bioVenture
Partners Fund I GP U.G.P., Ltd. By:  

/s/ Robert Hopfner

Name:   Robert Hopfner Title:   Managing Partner SALTHILL INVESTORS (BERMUDA)
L.P. By:   Wellington Management Company LLP,   as investment adviser By:  

/s/ Emily Babalas

Name:   Emily Babalas Title:   Managing Director & Counsel SALTHILL PARTNERS,
L.P. By:   Wellington Management Company LLP,   as investment adviser By:  

/s/ Emily Babalas

Name:   Emily Babalas Title:   Managing Director & Counsel

 

- 26 -

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SARISSA CAPITAL OFFSHORE MASTER FUND LP By:  

/s/ Patrice Bonfiglio

Name: Patrice Bonfiglio Title:   Chief Financial Officer SARISSA CAPITAL
CATAPULT FUND LLC By:  

/s/ Patrice Bonfiglio

Name: Patrice Bonfiglio Title:   Chief Financial Officer SARISSA CAPITAL HAWKEYE
FUND LP By:  

/s/ Patrice Bonfiglio

Name: Patrice Bonfiglio Title:   Chief Financial Officer RA CAPITAL HEALTHCARE
FUND, L.P. By: RA Capital Healthcare Fund GP, LLC Its General Partner By:  

/s/ Peter Kolchinsky

Name: Peter Kolchinsky Title:   Manager

 

- 27 -

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BLACKWELL PARTNERS LLC – SERIES A By:  

/s/ Justin B. Nixon

Name: Justin B. Nixon Title:   Investment Manager        DUMAC, Inc., Authorized
Signatory By:  

/s/ Jannine M. Lall

Name: Jannine M. Lall Title:   Investment Manager        DUMAC, Inc., Authorized
Signatory 2B LLC By: SilverArc Capital Management, LLC acting as Investment
manager. By:  

/s/ Andrew Timpson

Name: Andrew Timpson Title:   Chief Operating Officer 683 CAPITAL PARTNERS, LP
By:  

/s/ Joseph Patt

Name: Joseph Patt Title:   Member of the General Partner CVI INVESTMENTS, INC.
By: Heights Capital Management, Inc., its authorized signatory By:  

/s/ Martin Kobinger

Name: Martin Kobinger Title:   Investment Manager

 

- 28 -

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EMPERY MASTER ONSHORE, LLC By: Empery Asset Management LP, its authorized agent
By:  

/s/ Brett Director

Name: Brett Director Title:   General Counsel EMPERY TAX EFFICIENT, LP By:
Empery Asset Management LP, its authorized agent By:  

/s/ Brett Director

Name: Brett Director Title:   General Counsel EMPERY TAX EFFICIENT II, LP By:
Empery Asset Management LP, its authorized agent By:  

/s/ Brett Director

Name: Brett Director Title:   General Counsel NORTH SOUND TRADING, LP By:  

/s/ Brian Miller

Name: Brian Miller Title:   President of the General Partner

 

- 29 -

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LINCOLN PARK CAPITAL FUND, LLC By: Lincoln Park Capital, LLC By: Rockledge
Capital Corporation By:  

/s/ Joshua Scheinfeld

Name: Joshua Scheinfeld Title:   President S.H.N FINANCIAL INVESTMENTS LTD By:  

/s/ Nir Shamir

Name: Nir Shamir Title:   Owner SABBY VOLATILITY WARRANT MASTER FUND, LTD. By:  

/s/ Robert Grundstein

Name: Robert Grundstein Title:   COO of Investment Manager SILVERARC CAPITAL
ALPHA FUND I, L.P. By: SilverArc Capital Management, LLC acting as Investment
manager. By:  

/s/ Andrew Timpson

Name: Andrew Timpson Title:   Chief Operating Officer

 

- 30 -

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SILVERARC CAPITAL ALPHA FUND II, L.P. By: SilverArc Capital Management, LLC
acting as Investment manager. By:  

/s/ Andrew Timpson

Name:   Andrew Timpson Title:   Chief Operating Officer GARY D. COHN By:  

/s/ Gary D. Cohn

Name:   Gary D. Cohn

 

- 31 -

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SCHEDULE 1

 

PURCHASER

   UNITS
PURCHASED      AGGREGATE
PURCHASE
PRICE  

Advent Life Sciences LLP

     53      $ 53,000  

Advent Life Sciences Fund II LP

     1,495      $ 1,495,000  

Arix Bioscience Holdings Limited

     1,900      $ 1,900,000  

Canaan X L.P.

     2,000      $ 2,000,000  

Frazier Healthcare VII, L.P.

     1,167      $ 1,167,000  

Frazier Healthcare VII-A, L.P.

     333      $ 333,000  

New Leaf Ventures III, L.P.

     2,208      $ 2,208,000  

New Leaf Biopharma Opportunities II, L.P.

     792      $ 792,000  

Sofinnova Venture Partners IX, L.P.

     1,750      $ 1,750,000  

Domain Partners IX, L.P.

     1,000      $ 1,000,000  

Pivotal bioVenture Partners Fund I, LP

     1,000      $ 1,000,000  

Sarissa Capital Offshore Master Fund LP

     9,000      $ 9,000,000  

Sarissa Capital Catapult Fund LLC

     3,439      $ 3,439,000  

Sarissa Capital Hawkeye Fund LP

     2,561      $ 2,561,000  

RA Capital Healthcare Fund, L.P.

     8,486      $ 8,486,000  

Blackwell Partners LLC – Series A

     1,514      $ 1,514,000  

Empery Master Onshore, LLC

     361      $ 361,000  

Empery Tax Efficient, LP

     55      $ 55,000  

Empery Tax Efficient II, LP

     334      $ 334,000  

Lincoln Park Capital Fund, LLC

     250      $ 250,000  

683 Capital Partners, LP

     1,000      $ 1,000,000  

SilverArc Capital Alpha Fund I, L.P.

     19      $ 19,000  

SilverArc Capital Alpha Fund II, L.P.

     165      $ 165,000  

2b LLC

     16      $ 16,000  

Sabby Volatility Warrant Master Fund, Ltd.

     1,500      $ 1,500,000  

S.H.N Financial investments ltd

     500      $ 500,000  

North Sound Trading, LP

     4,000      $ 4,000,000  

CVI Investments, Inc.

     2,000      $ 2,000,000  

Salthill Investors (Bermuda) L.P.

     920      $ 920,000  

Salthill Partners, L.P.

     570      $ 570,000  

Gary D. Cohn

     1,500      $ 1,500,000  

Total

     51,888      $ 51,888,000