EXHIBIT 10.4


 


SECURITIES
PURCHASE AGREEMENT


 


Dated as of January 17, 2017


 


Xtant Medical Holdings, Inc.


664 Cruiser Lane


Belgrade, Montana 59714


 


Ladies and Gentlemen:


 


The undersigned hereby confirms its agreement
with you as follows:


 


		1.	This Securities Purchase Agreement (this “Agreement”) is made as of the
date hereof between Xtant Medical Holdings, Inc., a Delaware corporation (the “Company”), and the Investor listed
on the signature page hereto (the “Investor”). The Investor holds Convertible Promissory Notes issued by the
Company pursuant to the Indenture, dated as of July 31, 2015, between the Company and Wilmington Trust, National Association (the
“Notes”), in the aggregate principal amount of $7,461,227.00.



 


		2.	The Company is proposing to issue and sell to the Investor shares of the Company’s
common stock, par value $0.000001 per share (the “Common Stock”), in the aggregate amount of $223,836.80 (the
“Securities”). The purchase price for the Securities shall be paid by a dollar-for-dollar offset against all
interest due to the Investor as of the closing under the Notes.



 


		3.	The Investor acknowledges that the Company will be concurrently issuing shares of Common Stock
to other investors on the same terms and conditions as described herein.



 


		4.	The Company and the Investor agree that, upon the terms and subject to the conditions set forth
herein, the Investor will purchase from the Company and the Company will issue and sell to the Investor the aggregate principal
amount of the Securities set forth below on the Investor’s signature page for the aggregate purchase price set forth below
on the Investor’s signature page. The Securities shall be purchased pursuant to the Terms and Conditions for Purchase of
Securities attached hereto as Annex A and incorporated herein by reference as if fully set forth herein.



 




     


     


    

 


Aggregate Amount of Securities the Investor Agrees to Purchase:
393,248


 


Aggregate Purchase Price of such Securities: $223,836.80


 


Please confirm that the foregoing correctly sets forth the agreement
between us by signing in the space provided below for that purpose.


 


	AGREED AND ACCEPTED BY:	 	 
	 	 	 
	
        Xtant Medical Holdings, Inc.

        a Delaware corporation
	 	Name of Investor: Park West Investors

                     Master Fund, Limited

	 	 	 	 	 
	By:	/s/ Daniel Goldberger	 	By:	/s/ Grace Jimenez
	Name:   Daniel Goldberger	 	Print Name:   Grace Jimenez
	Title:    Chief Executive Officer	 	Title:              Chief Financial Officer




 


Securities Purchase Agreement - Park
West Investors Master Fund, Limited


 




     


     


    

 


ANNEX A
TO THE SECURITIES PURCHASE AGREEMENT

TERMS AND CONDITIONS FOR PURCHASE OF SECURITIES


 


		1.	Authorization and Sale of Securities.
                                         The Company is proposing to sell Common Stock, in the aggregate amount of $223,836.80
                                         to the Investor.



 


		2.	Agreement to Sell and Purchase the Securities. Upon the terms and subject to the conditions
hereinafter set forth, at the Closing (as defined in Section 3.1), the Company will sell to the Investor, and the Investor
will purchase from the Company, the aggregate amount of Securities set forth on the Investor’s signature page hereto at the
purchase price set forth on such signature page.



 


		3.	Closings and Delivery of Securities and Funds.



 


		3.1	The completion of the purchase and sale of the Securities (the “Closing”) shall
occur on January 17, 2017 (the “Closing Date”).



 


		3.2	The Company’s obligation to issue and sell the Securities to the Investor shall be subject
to the following conditions, any one or more of which may be waived by the Company: (a) the accuracy of the representations and
warranties made by the Investor and (b) the fulfillment of those undertakings of the Investor to be fulfilled prior to the Closing.



 


		3.3	The Investor’s obligation to accept delivery of the Securities and to pay for the Securities
shall be subject to the following conditions: (a) each of the representations and warranties of the Company made in Section
4 shall be accurate in all material respects as of the Closing Date; (b) delivery of an officer’s certificate dated as
of the Closing Date regarding the accuracy in material respects of the Company’s representations and warranties and addressing
such other matters as are customarily addressed in closing certificates; (c) delivery to the Investor of a customary secretary’s
certificate in form reasonably acceptable to the Investor; and (d) the Company shall have furnished to the Investor such further
documents as the Investor may reasonably request.



 


		3.4	At the Closing, the purchase price for the Securities shall be paid by a dollar-for-dollar offset
against all interest due to the Investor as of the Closing under the Notes. Such offset shall have the same effect as if the Investor
paid cash to the Company for such Securities and the Company used such cash to pay to the Investor the interest so offset.



 




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		4.	Representations, Warranties and Covenants of the Company.



 


The Company hereby
represents and warrants to, and covenants with, the Investor that:


 


		4.1	Each of the Company and its subsidiaries has been duly organized, is validly existing and in good
standing as a corporation, partnership or limited liability company, as applicable, under the laws of its jurisdiction of organization
and is duly qualified to do business and in good standing as a foreign corporation or other business entity in each jurisdiction
in which its ownership or lease of property or the conduct of its businesses requires such qualification, except where the failure
to be so qualified or in good standing could not, individually or in the aggregate, reasonably be expected to (i) have a material
adverse effect on the condition (financial or otherwise), results of operations, stockholders’ equity, properties, business
or prospects of the Company and its subsidiaries taken as a whole or (ii) materially interfere with the consummation of the transactions
contemplated hereby (collectively, a “Material Adverse Effect”). Each of the Company and its subsidiaries has
all power and authority necessary to own or hold its properties and to conduct the businesses in which it is engaged. As of the
date of this Agreement, the Company has no subsidiaries other than Bacterin International, Inc., X-spine Systems Inc. and Xtant
Medical, Inc. and no “significant subsidiaries” (as defined in Rule 405 under the Securities Act) other than Bacterin
International, Inc. and X-spine Systems Inc.



 


		4.2	The Company has an authorized capitalization as set forth in the publicly available Annual Report
on Form 10-K filed with the Securities and Exchange Commission (the “Commission”) for the fiscal year ended
December 31, 2015, and all of the issued shares of capital stock of the Company have been duly authorized and validly issued and
are fully paid and non-assessable. All of the issued shares of capital stock or other ownership interest of each subsidiary of
the Company have been duly authorized and validly issued, are fully paid and non-assessable and are owned directly or indirectly
by the Company, free and clear of all liens, encumbrances, equities or claims, except for such liens, encumbrances, equities or
claims as could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect.



 


		4.3	The Company has all the requisite corporate power and authority to issue the Common Stock. The
Common Stock has been duly and validly authorized by the Company and, and will be validly issued, fully paid and non-assessable,
and the issuance of the Common Stock will not be subject to any preemptive or similar rights.



 


		4.4	The Company has all requisite corporate power to execute, deliver and perform its obligations under
this Agreement. This Agreement has been duly and validly authorized, executed and delivered by the Company.



 


		4.5	The issue and sale of the Common Stock, the execution, delivery and performance by the Company
of this Agreement and the consummation of the transactions contemplated hereby and thereby, will not (i) conflict with or result
in a breach or violation of any of the terms or provisions of, impose any lien, charge or encumbrance upon any property or assets
of the Company or its subsidiaries, or constitute a default under, any indenture, mortgage, deed of trust, loan agreement, license,
lease or other agreement or instrument to which the Company or any of its subsidiaries is a party or by which any of them is bound
or to which any of their respective properties or assets is subject, (ii) result in any violation of the provisions of the charter
or by-laws (or similar organizational documents) of the Company or any of its subsidiaries, or (iii) result in any violation of
any statute or any judgment, order, decree, rule or regulation of any court or governmental agency or body having jurisdiction
over the Company or any of its subsidiaries or any of their respective properties or assets, except, with respect to clauses (i)
and (iii), conflicts or violations that could not, individually or in the aggregate, reasonably be expected to have a Material
Adverse Effect.



 




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		4.6	Except for the filing of a prospectus supplement with the Commission respecting the Securities,
no consent, approval, authorization or order of, or filing, registration or qualification with any court or governmental agency
or body having jurisdiction over the Company or any of its subsidiaries or any of their respective properties or assets is required
for the issuance of the Common Stock, the execution, delivery and performance by the Company of this Agreement, and the consummation
of the transactions contemplated hereby.



 


		4.7	The Company maintains a system of internal control over financial reporting (as such term is defined
in Rule 13a-15(f) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”)) that complies with
the requirements of the Exchange Act and that has been designed by, or under the supervision of, the Company’s principal
executive and principal financial officers, to provide reasonable assurance regarding the reliability of financial reporting and
the preparation of financial statements for external purposes in accordance with generally accepted accounting principles in the
United States. The Company maintains internal accounting controls sufficient to provide reasonable assurance that (i) transactions
are executed in accordance with management’s general or specific authorization, (ii) transactions are recorded as necessary
to permit preparation of the Company’s financial statements in conformity with accounting principles generally accepted in
the United States and to maintain accountability for its assets, (iii) access to the Company’s assets is permitted only in
accordance with management’s general or specific authorization, and (iv) the recorded accountability for the Company’s
assets is compared with existing assets at reasonable intervals and appropriate action is taken with respect to any differences.
As of the date of the most recent balance sheet of the Company and its consolidated subsidiaries reviewed or audited by EKS&H
LLP and the audit committee of the board of directors of the Company, there were no material weaknesses in the Company’s
internal controls.



 


		4.8	The Company maintains disclosure controls and procedures (as such term is defined in Rule 13a-15(e)
under the Exchange Act), (ii) such disclosure controls and procedures are designed to ensure that the information required to be
disclosed by the Company and its subsidiaries in the reports they file or submit under the Exchange Act is accumulated and communicated
to management of the Company and its subsidiaries, including their respective principal executive officers and principal financial
officers, as appropriate, to allow timely decisions regarding required disclosure to be made; and (iii) such disclosure controls
and procedures are effective in all material respects to perform the functions for which they were established.



 




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		4.9	Since the date of the most recent balance sheet of the Company and its consolidated subsidiaries
reviewed or audited by EKS&H LLP and the audit committee of the board of directors of the Company, (i) the Company has not
been advised of or become aware of (A) any significant deficiencies in the design or operation of internal controls, that could
adversely affect the ability of the Company or any of its subsidiaries to record, process, summarize and report financial data,
or any material weaknesses in internal controls, and (B) any fraud, whether or not material, that involves management or other
employees who have a significant role in the internal controls of the Company and each of its subsidiaries; and (ii) there have
been no significant changes in internal controls or in other factors that could significantly affect internal controls, including
any corrective actions with regard to significant deficiencies and material weaknesses.



 


		4.10	There is and has been no failure on the part of the Company and any of its directors or officers,
in their capacities as such, to comply with any provision of the Sarbanes-Oxley Act of 2002 and the rules and regulations promulgated
in connection therewith.



 


		4.11	Since the date of the latest audited financial statements included in the Public Disclosure Documents
(as defined below) and except as disclosed therein, neither the Company nor any of its subsidiaries has (i) sustained any loss
or interference with its business from fire, explosion, flood or other calamity, whether or not covered by insurance, or from any
labor disturbance or dispute or court or governmental action, order or decree, (ii) issued or granted any securities (other than
pursuant to (x) employee benefit plans, qualified stock option plans, other employee compensation plans or non-employee director
compensation programs in existence on the date hereof and described in the Public Disclosure Documents or (y) options, warrants
or rights outstanding on the date hereof, (iii) incurred any liability or obligation, direct or contingent, other than liabilities
and obligations that were incurred in the ordinary course of business, (iv) entered into any transaction not in the ordinary course
of business (other than as described in the Public Disclosure Documents (without giving effect to any supplements or amendments
thereto after the execution and delivery of this Agreement)), or (v) declared or paid any dividend on its capital stock, and, since
such date, there has not been any change in the capital stock, partnership or limited liability company interests, as applicable,
or long-term debt of the Company or any of its subsidiaries (other than as described in the Public Disclosure Documents (without
giving effect to any supplements or amendments thereto after the execution and delivery of this Agreement)) or any adverse change,
or any development involving a prospective adverse change, in or affecting the condition (financial or otherwise), results of operations,
stockholders’ equity, properties, management, business or prospects of the Company and its subsidiaries, taken as a whole,
in each case except as could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect. The
reports required to be filed by the Company under the Exchange Act, including pursuant to Section 13(a) or 15(d) thereof, together
with any materials filed or furnished by the Company under the Exchange Act, whether or not any such reports were required, are
referred to herein, collectively, as the “Public Disclosure Documents”.



 




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		4.12	The Company and each of its subsidiaries has good and marketable title in fee simple to all real
property and good and marketable title to all personal property owned by them, in each case free and clear of all liens, encumbrances
and defects, except to the extent such liens, encumbrances and defects do not materially affect the value of such property and
do not materially interfere with the use made and proposed to be made of such property by the Company or any of its subsidiaries.
All assets held under lease by the Company or any of its subsidiaries are held by them under valid, subsisting and enforceable
leases, with such exceptions as do not materially interfere with the use made and proposed to be made of such assets by the Company
or any of its subsidiaries.



 


		4.13	The Company and each of its subsidiaries have, and have operated in compliance with, such permits,
licenses, patents, franchises, certificates of need, exemptions, clearances and other approvals or authorizations of governmental
or regulatory authorities (“Permits”) as are necessary under applicable law to own their properties and conduct
their businesses in the manner described in the Public Disclosure Documents, except for any of the foregoing that could not, individually
or in the aggregate, reasonably be expected to have a Material Adverse Effect. The Company and each of its subsidiaries have fulfilled
and performed all of its obligations with respect to the Permits, and no event has occurred that allows, or after notice or lapse
of time would allow, revocation or termination thereof or results in any other impairment of the rights of the holder or any such
Permits, except for any of the foregoing that could not, individually or in the aggregate, reasonably be expected to have a Material
Adverse Effect. Neither the Company, nor any of its subsidiaries has received written notice of any revocation, termination or
modification of any such Permits or otherwise has any reason to believe that any such Permits will be revoked, terminated or modified
or not be renewed in the ordinary course.



 




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		4.14	The Company and its subsidiaries own, or have obtained valid and enforceable licenses for, or other
rights to use, the inventions, patent applications, patents, trademarks (both registered and unregistered), tradenames, service
names, copyrights, trade secrets and other proprietary information described in Public Disclosure Documents as being owned or licensed
by them or which are necessary for the conduct of their respective businesses as currently conducted or as proposed to be conducted
(including the commercialization of products or services described in the Public Disclosure Documents as under development), except
where the failure to own, license or have such rights could not, individually or in the aggregate, reasonably be expected to have
a Material Adverse Effect (collectively, “Intellectual Property”). Except as disclosed in Public Disclosure
Documents, and except as could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect,
(i) there are no third parties who have or, to the Company’s knowledge, will be able to establish rights to any Intellectual
Property, except for, and to the extent of, the ownership rights of the owners of the Intellectual Property which the Public Disclosure
Documents disclose is licensed to the Company or any of its subsidiaries; (ii) to the Company’s knowledge, there is no infringement
by third parties of any Intellectual Property; (iii) there is no pending or, to the Company’s knowledge, threatened action,
suit, proceeding or claim by others challenging the Company’s or its subsidiaries’ rights in or to any Intellectual
Property, and the Company is unaware of any facts which could form a reasonable basis for any such action, suit, proceeding or
claim; (iv) there is no pending or, to the Company’s knowledge, threatened action, suit, proceeding or claim by others challenging
the validity, enforceability or scope of any Intellectual Property, and the Company is unaware of any facts which could form a
reasonable basis for any such action, suit, proceeding or claim; (v) there is no pending or, to the Company’s knowledge,
threatened action, suit, proceeding or claim by others that the Company or any of its subsidiaries infringes or otherwise violates
(or would, upon the commercialization of any product or service described in the Public Disclosure Documents as under development,
infringe or violate) any patent, trademark, tradename, service name, copyright, trade secret or other proprietary rights of others,
and the Company is unaware of any facts which could form a reasonable basis for any such action, suit, proceeding or claim; (vi)
the Company and its subsidiaries have complied with the terms of each agreement pursuant to which Intellectual Property has been
licensed to the Company or any of its subsidiaries, and all such agreements are in full force and effect; (vii) to the Company’s
knowledge, there is no patent or patent application that contains claims that interfere with the issued or pending claims of any
of the Intellectual Property or that challenges the validity, enforceability or scope of any of the Intellectual Property; and
(viii) to the Company’s knowledge, there is no prior art that may render any patent application within the Intellectual Property
unpatentable that has not been disclosed to the U.S. Patent and Trademark Office.



 




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		4.15	There are no legal or governmental proceedings pending to which the Company or any of its subsidiaries
is a party or of which any property or assets of the Company or any of its subsidiaries is the subject that could, individually
or in the aggregate, reasonably be expected to (i) have a Material Adverse Effect, except as described in the Public Disclosure
Documents, or (ii) have a material adverse effect on the performance by the Company of this Agreement or on the consummation of
any of the transactions contemplated hereby or thereby. To the Company’s knowledge, no such proceedings are threatened or
contemplated by governmental authorities or others.



 


		4.16	Neither the Company nor any of its subsidiaries: (i) is in violation of its charter or by-laws
(or similar organizational documents), (ii) is in default, and no event has occurred that, with notice or lapse of time or both,
would constitute such a default, in the due performance or observance of any term, covenant, condition or other obligation contained
in any indenture, mortgage, deed of trust, loan agreement, license or other agreement or instrument to which it is a party or by
which it is bound or to which any of its properties or assets is subject, or (iii) is in violation of any statute or any order,
rule or regulation of any court or governmental agency or body having jurisdiction over it or its property or assets or has failed
to obtain any license, permit, certificate, franchise or other governmental authorization or permit necessary to the ownership
of its property or to the conduct of its business, except in the case of clauses (ii) and (iii), to the extent any such default,
violation or failure could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect and
except as set forth in the Public Disclosure Documents.



 




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		4.17	The Company and its subsidiaries and their respective properties, assets and operations are in
compliance with, and the Company and each of its subsidiaries hold all permits, authorizations and approvals required under, Environmental
Laws (as defined below), except to the extent that failure to so comply or to hold such permits, authorizations or approvals could
not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect. To the Company’s knowledge,
there are no past, present or reasonably anticipated future events, conditions, circumstances, activities, practices, actions,
omissions or plans that, individually or in the aggregate, could reasonably be expected to give rise to any material costs or liabilities
to the Company or any of its subsidiaries under, or to interfere with or prevent compliance by the Company or any of its subsidiaries
with, Environmental Laws; except as could not, individually or in the aggregate, reasonably be expected to have a Material Adverse
Effect, neither the Company nor any of its subsidiaries (i) is the subject of any investigation, (ii) has received any notice or
claim, (iii) is a party to or affected by any pending or, to the Company’s knowledge, threatened action, suit or proceeding,
(iv) is bound by any judgment, decree or order or (v) has entered into any agreement, in each case relating to any alleged violation
of any Environmental Law or any actual or alleged release or threatened release or cleanup at any location of any Hazardous Materials
(as defined below) (as used herein, “Environmental Law” means any federal, state, local or foreign law, statute,
ordinance, rule, regulation, order, decree, judgment, injunction, permit, license, authorization or other binding requirement,
or common law, relating to health, safety or the protection, cleanup or restoration of the environment or natural resources, including
those relating to the distribution, processing, generation, treatment, storage, disposal, transportation, other handling or release
or threatened release of Hazardous Materials, and “Hazardous Materials” means any material (including, without
limitation, pollutants, contaminants, hazardous or toxic substances or wastes) that is regulated by or may give rise to liability
under any Environmental Law).



 


		4.18	The Company and each of its subsidiaries have filed all federal, state, local and foreign tax returns
required to be filed through the date hereof, subject to permitted extensions, and have paid all taxes due, and no tax deficiency
has been determined adversely to the Company or any of its subsidiaries, nor does the Company have any knowledge of any tax deficiencies
that have been, or could reasonably be expected to be asserted against the Company and each of its subsidiaries, that could, individually
or in the aggregate, reasonably be expected to have a Material Adverse Effect.



 


		4.19	Neither the Company nor any of its subsidiaries is, and, after giving effect to the offer and sale
of the Securities and the application of the proceeds therefrom, none of them will be, an “investment company” within
the meaning of the Investment Company Act of 1940, as amended, and the rules and regulations of the Commission thereunder.



 




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		4.20	The Company and its affiliates have not taken, directly or indirectly, any action designed to or
that has constituted or that could reasonably be expected to cause or result in the stabilization or manipulation of the price
of any security of the Company in connection with the offering of the Securities.



 


		4.21	Neither the Company nor any of its subsidiaries, nor, to the knowledge of the Company, after due
inquiry, any director, officer, agent, employee or other person associated with or acting on behalf of the Company or any of its
subsidiaries, has in the course of its actions for, or on behalf of, the Company or any of its subsidiaries: (i) used any corporate
funds for any unlawful contribution, gift, entertainment or other unlawful expense relating to political activity; (ii) made any
direct or indirect unlawful payment to any foreign or domestic government official, “foreign office” (as defined in
the Foreign Corrupt Practices Act of 1977, as amended, and the rules and regulations thereunder (collectively, the “FCPA”))
or employee from corporate funds; (iii) violated or is in violation of any provision of the FCPA, the Bribery Act 2010 of the United
Kingdom, as amended, or any other applicable anti-corruption or anti-bribery laws or statutes; or (iv) made any bribe, rebate,
payoff, influence payment, kickback or other unlawful payment to any domestic government official, foreign official or employee;
and the Company and its subsidiaries and, to the knowledge of the Company, the Company’s affiliates have conducted their
respective businesses in compliance with the FCPA, the Bribery Act 2010 of the United Kingdom, as amended, and any other applicable
anti-corruption or anti-bribery laws or statutes, and have instituted and maintain policies and procedures designed to ensure,
and which are reasonably expected to continue to ensure, continued compliance therewith.



 


		4.22	The operations of the Company and its subsidiaries are and have been conducted at all times in
compliance in all material respects with applicable financial recordkeeping and reporting requirements of the Currency and Foreign
Transactions Reporting Act of 1970, as amended, the money laundering statutes of all jurisdictions, the rules and regulations thereunder
and any related or similar rules, regulations or guidelines, issued, administered or enforced by any governmental agency (collectively,
the “Money Laundering Laws”); and no action, suit or proceeding by or before any court or governmental agency,
authority or body or any arbitrator involving the Company or any of its subsidiaries with respect to the Money Laundering Laws
is pending or, to the knowledge of the Company, threatened.



 




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		4.23	Neither the Company nor any of its subsidiaries nor, to the knowledge of the Company, after due
inquiry, any director, officer, agent, employee or affiliate of the Company or any of its subsidiaries (i) is currently subject
to or the target of any sanctions administered or enforced by the Office of Foreign Assets Control of the U.S. Treasury Department,
the U.S. Department of State, the United Nations Security Council, the European Union, Her Majesty’s Treasury, or other relevant
sanctions authority (collectively, “Sanctions”); or (ii) located, organized or resident in a country that is
the subject of Sanctions (including, without limitation, Cuba, Iran, North Korea, Sudan, and Syria); and the Company will not directly
or indirectly use the proceeds of the offering, or lend, contribute or otherwise make available such proceeds to any subsidiary,
joint venture partner or other person or entity, for the purpose of financing the activities of any person, or in any country or
territory, that currently is the subject or target of Sanctions or in any other manner that will result in a violation by any person
(including any person participating in the transaction whether as an underwriter, advisor, investor or otherwise) of Sanctions.
The Company and its subsidiaries have not knowingly engaged in for the past five (5) years, are not now knowingly engaged in, and
will not engage in, any dealings or transactions with any individual or entity, or in any country or territory, that at the time
of the dealing or transaction is or was the subject or target of Sanctions.



 


		4.24	There are no contracts or other documents that would be required to be described in a registration
statement filed under the Securities Act or filed as exhibits to a registration statement of the Company pursuant to Item 601(b)(10)
of Regulation S-K that have not been described in the Public Disclosure Documents.



 


		4.25	No relationship, direct or indirect, that would be required to be described in a registration statement
of the Company pursuant to Item 404 of Regulation S-K, exists between or among the Company and its subsidiaries, on the one hand,
and the directors, officers, stockholders, customers or suppliers of the Company and its subsidiaries, on the other hand, that
has not been described in the Public Disclosure Documents.



 


		4.26	No labor disturbance by or dispute with the employees of the Company or any of its subsidiaries
exists or, to the knowledge of the Company, is imminent that could, individually or in the aggregate, reasonably be expected to
have a Material Adverse Effect.



 


		4.27	None of the transactions contemplated by this Agreement (including, without limitation, the use
of the proceeds from the sale of the Securities), will violate or result in a violation of Section 7 of the Exchange Act, or any
regulation promulgated thereunder, including, without limitation, Regulations T, U and X of the Board of Governors of the Federal
Reserve System.



 


		4.28	The Company and each of its subsidiaries carry, or are covered by, insurance from insurers of recognized
financial responsibility in such amounts and covering such risks as is adequate for the conduct of their respective businesses
and the value of their respective properties and as is customary for companies engaged in similar businesses in similar industries.
All policies of insurance of the Company and its subsidiaries are in full force and effect; the Company and each of its subsidiaries
are in compliance with the terms of such policies in all material respects; and neither the Company nor any of its subsidiaries
has received notice from any insurer or agent of such insurer that capital improvements or other expenditures are required or necessary
to be made in order to continue such insurance. Except as could not, individually or in the aggregate, reasonably be expected to
have a Material Adverse Effect, there are no claims by the Company or any of its subsidiaries under any such policy or instrument
as to which any insurance company is denying liability or defending under a reservation of rights clause; and neither the Company
nor any such subsidiary has any reason to believe that it will not be able to renew its existing insurance coverage as and when
such coverage expires or to obtain similar coverage from similar insurers as may be necessary to continue its business at a cost
that could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect.



 




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		4.29	Each “employee benefit plan” (within the meaning of Section 3(3) of the Employee Retirement
Security Act of 1974, as amended (“ERISA”)) for which the Company or any member of its “Controlled Group”
(defined as any organization which is a member of a controlled group of corporations within the meaning of Section 414 of the Internal
Revenue Code of 1986, as amended (the “Code”)) would have any liability (each a “Plan”) has
been maintained in compliance with its terms and with the requirements of all applicable statutes, rules and regulations including
ERISA and the Code; (ii) no prohibited transaction, within the meaning of Section 406 of ERISA or Section 4975 of the Code, has
occurred with respect to any Plan excluding transactions effected pursuant to a statutory or administrative exemption; (iii) with
respect to each Plan subject to Title IV of ERISA: (A) no “reportable event” (within the meaning of Section 4043(c)
of ERISA) has occurred or is reasonably expected to occur, (B) no Plan is or is reasonably expected to be “at risk”
status (within the meaning of Section 430 of the Code or Section 303 of ERISA), (C) there has been no filing pursuant to Section
412(c) of the Code or Section 302(c) of ERISA of an application for a waiver of the minimum funding standard with respect to any
Plan or the receipt by the Company or any member of its Controlled Group from the Pension Benefit Guaranty Corporation or the plan
administrator of any notice relating to the intention to terminate any Plan or Plans or to appoint a trustee to administer any
Plan, (D) no conditions contained in Section 303(k)(1)(A) of ERISA for imposition of a lien shall have been met with respect to
any Plan and (E) neither the Company or any member of its Controlled Group has incurred, or reasonably expects to incur, any liability
under Title IV of ERISA (other than contributions to the Plan or premiums to the Pension Benefit Guaranty Corporation in the ordinary
course and without default) in respect of a Plan (including a “multiemployer plan”, within the meaning of Section 4001(c)(3)
of ERISA) (“Multiemployer Plan”); (iv) no Multiemployer Plan is, or is expected to be, “insolvent”
(within the meaning of Section 4245 of ERISA), in “reorganization” (within the meaning of Section 4241 of ERISA), or
in “endangered” or “critical” status (within the meaning of Section 432 of the Code or Section 304 of ERISA);
and (v) each Plan that is intended to be qualified under Section 401(a) of the Code is so qualified and nothing has occurred, whether
by action or by failure to act, which would cause the loss of such qualification.



 


		4.30	No subsidiary of the Company is currently prohibited, directly or indirectly, from paying any dividends
to the Company, from making any other distribution on such subsidiary’s capital stock or other ownership interests, from
repaying to the Company any loans or advances to such subsidiary from the Company or from transferring any of such subsidiary’s
property or assets to the Company or any other subsidiary of the Company, except as described in the Public Disclosure Documents.



 




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		4.31	Neither the Company nor any of its subsidiaries is a party to any contract, agreement or understanding
with any person (other than this Agreement) that could give rise to a valid claim against any of them for a brokerage commission,
finder’s fee or like payment in connection with the sale of the Securities.



 


		4.32	Neither the Company nor any of its subsidiaries is in violation of or has received notice of any
violation with respect to any federal or state law relating to discrimination in the hiring, promotion or pay of employees, nor
any applicable federal or state wage and hour laws, nor any state law precluding the denial of credit due to the neighborhood in
which a property is situated, the violation of any of which could, individually or in the aggregate, reasonably be expected to
have a Material Adverse Effect.



 


		4.33	Except as described in the Public Disclosure Documents, and except, in each case, where such event
could not, individually or in the aggregate, reasonably be expect to have a Material Adverse Effect, the Company and each of its
subsidiaries: (i) has not received any unresolved U.S. Food and Drug Administration (“FDA”) or similar
governmental agency or body (“Governmental Authority”) written notice of inspectional observations, Form 483,
written notice of adverse filing, warning letter, untitled letter or other similar correspondence or notice from the FDA, or any
other court or arbitrator or federal, state, local or foreign governmental or regulatory authority, alleging or asserting material
noncompliance with the Federal Food, Drug and Cosmetic Act (21 U.S.C. § 301 et seq.), or received any written requests or
requirements to make material changes to the Company products by the FDA or any other Governmental Authority, (ii) is and has been
in compliance with applicable health care laws, including, the Federal Food, Drug and Cosmetic Act (21 U.S.C. § 301 et seq.),
the federal Anti-kickback Statute (42 U.S.C. § 1320a-7b(b)), the civil False Claims Act (31 U.S.C. §§ 3729 et seq.),
the criminal False Claims Law (42 U.S.C. § 1320a-7b(a)), the Civil Monetary Penalties Law (42 U.S.C. § 1320a-7a), the
Physician Payment Sunshine Act (42 U.S.C. § 1320a-7h), all criminal laws relating to health care fraud and abuse, including
but not limited to 18 U.S.C. Sections 286 and 287, and the health care fraud criminal provisions under the Health Insurance Portability
and Accountability Act of 1996 (42 U.S.C. § 1320d et seq.) (“HIPAA”), the exclusion laws (42 U.S.C. §
1320a-7), Medicare (Title XVIII of the Social Security Act), Medicaid (Title XIX of the Social Security Act), HIPAA, as amended
by the Health Information Technology for Economic and Clinical Health Act of 2009, and the regulations promulgated pursuant to
such laws, and comparable state laws, and all other foreign, federal, state and local laws relating to the regulation of the Company
and its subsidiaries (collectively, “Health Care Laws”), (iii) has not engaged in activities which
are, as applicable, cause for false claims liability, civil penalties, or mandatory or permissive exclusion from Medicare, Medicaid,
or any other state health care program or federal health care program, (iv) possesses all Permits and supplements or amendments
thereto required by any such Health Care Laws and/or to carry on its businesses as currently conducted as described in the Public
Disclosure Documents (“Authorizations”), and such Authorizations are valid and in full force and effect and
neither the Company nor any of its subsidiaries is in violation of any term of any such Authorizations, (v) has not received written
notice of any ongoing claim, action, suit, proceeding, hearing, enforcement, investigation, arbitration or other action from any
Governmental Authority alleging that any product, operation or activity is in material violation of any Health Care Laws or Authorizations
and has no knowledge that any such Governmental Authority has threatened any such claim, litigation, arbitration, action, suit,
investigation or proceeding, (vi) has not received written notice that any Governmental Authority has taken, is taking or intends
to take action to limit, suspend, modify or revoke any Authorizations and has no knowledge that any such Governmental Authority
has threatened such action, (vii) has filed, obtained, maintained or submitted all reports, documents, forms, notices, applications,
records, claims, submissions and supplements or amendments thereto as required by any Health Care Laws or Authorizations and all
such reports, documents, forms, notices, applications, records, claims, submissions and supplements or amendments were complete,
correct and not misleading on the date filed (or were corrected or supplemented by a subsequent submission), (viii) has not, either
voluntarily or involuntarily, initiated, conducted, or issued or caused to be initiated, conducted or issued, any recall, market
withdrawal or replacement, safety alert, post sale warning, “dear doctor” letter, or other notice or action relating
to the alleged lack of safety, efficacy or regulatory compliance of any product or any alleged product defect or violation and,
to the Company’s knowledge, there are no facts which are reasonably likely to cause, and the Company has not received any
written notice from the FDA or any other Governmental Authority regarding, a material recall, market withdrawal or replacement
of any Company product sold or intended to be sold by the Company, a material change in the marketing classification or a material
adverse change in the labeling of any such Company products, or a termination or suspension of the manufacturing, marketing, or
distribution of such Company products, (ix) is not a party to any corporate integrity agreement, deferred prosecution agreement,
monitoring agreement, consent decree, settlement order, or similar agreements, or has any reporting obligations pursuant to any
such agreement, plan or correction or other remedial measure entered into with any Governmental Authority, (x) has not, nor has
any officer, director, employee, agent or, to the knowledge of the Company, any distributor of the Company, made an untrue statement
of a material fact or a fraudulent statement to the FDA or any other Governmental Authority, failed to disclose a material fact
required to be disclosed to the FDA or any other Governmental Authority, or committed an act, made a statement, or failed to make
a statement, in each such case, related to the business of the Company that, at the time such disclosure was made, would reasonably
be expected to provide a basis for the FDA to invoke its policy respecting “Fraud, Untrue Statements of Material Facts, Bribery,
and Illegal Gratuities”, set forth in 56 Fed. Reg. 46191 (September 10, 1991) or for the FDA or any other Governmental Authority
to invoke any similar policy, (xi) has not, nor has any officer, director, employee, or, to the knowledge of the Company, any agent
or distributor of the Company, been debarred or convicted of any crime or engaged in any conduct for which debarment is mandated
by 21 U.S.C. § 335a(a) or any similar law or authorized by 21 U.S.C. § 335a(b) or any similar law applicable in other
jurisdictions in which Company products or Company product candidates are sold or intended by the Company to be sold, and (xii)
neither the Company, its subsidiaries nor their officers, directors, employees, agents or contractors has been or is currently
debarred, suspended or excluded from participation in the Medicare and Medicaid programs or any other state or federal health care
program.



 




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		4.34	The preclinical tests and clinical trials conducted or sponsored by, or on behalf of the Company
and its subsidiaries were and, if still pending, are being conducted in all material respects in accordance with protocols filed
with the appropriate regulatory authorities for each such test or trial, as the case may be, and with standard medical and scientific
research procedures and applicable laws, regulations and Authorizations, including without limitation, those of the FDA; each description
of the results of such tests and trials contained in the Public Disclosure Documents is accurate and complete in all material respects
and fairly presents the data derived from such tests and trials, and the Company and its subsidiaries have no knowledge of any
other studies or tests, the results of which are inconsistent with, or otherwise call into question, the results described or referred
to in the Public Disclosure Documents; and neither the Company nor any of its subsidiaries has received any notices or other correspondence
from the FDA, the U.S. Department of Health and Human Services or any committee thereof or from any other U.S. or foreign government
or drug or medical device regulatory agency requiring the termination, suspension or modification of any clinical trials.



 


		4.35	The Company and its affiliates will not take, directly or indirectly, any action designed to or
that has constituted or that reasonably could be expected to cause or result in the stabilization or manipulation of the price
of any security of the Company in connection with the sale of the Securities.



 


		5.	Representations, Warranties and Covenants of the Investor.



 


Each Investor hereby
represents and warrants to, and covenants with, the Company that:


 


		5.1	When the Securities are issued in accordance with the terms of this Agreement, all interest obligations
owed by the Company to the Investor on account of the Notes will be current.



 


		5.2	The Investor has full right, power, authority and capacity to enter into this Agreement and to
consummate the transactions contemplated hereby and has taken all necessary action to authorize the execution, delivery and performance
of this Agreement, and this Agreement constitutes a valid, binding and enforceable obligation of the Investor, except as the enforceability
of the Agreement may be subject to or limited by bankruptcy, insolvency, reorganization, arrangement, moratorium or other similar
laws relating to or affecting the rights of creditors generally.



 




    	 	A-13	 



     


    

 


		5.3	The entry into and performance of this Agreement by the Investor and the consummation by the Investor
of the transactions contemplated hereby and thereby will not (i) result in a violation of the organizational documents of the Investor,
(ii) conflict with, or constitute a default under, or give to others any rights of termination, amendment, acceleration or cancellation
of any agreement, indenture or instrument to which the Investor is party, or (iii) result in the violation of any law, rule, regulation,
order, judgment or decree (including federal and state securities laws) applicable to the Investor, except in the case of clauses
(ii) and (iii) above, for such conflicts, defaults, rights or violations which would not, individually or in the aggregate, reasonably
be expected to have a material adverse effect on the ability of the Investor to perform its obligations hereunder.



 


		5.4	The Investor understands that nothing in this Agreement, information the Company has filed with
and furnished to the Commission or any other materials presented to the Investor in connection with the purchase and sale of the
Securities constitutes legal, tax or investment advice. The Investor has consulted such legal, tax and investment advisors as it,
in its sole discretion, has deemed necessary or appropriate in connection with its purchase of the Securities and has made its
own assessment and has satisfied itself concerning the relevant tax and other economic considerations relevant to its investment
in the Securities.



 


		6.	Survival of Representations, Warranties and Agreements. Notwithstanding any investigation
made by any party to this Agreement, all covenants, agreements, representations and warranties made by the Company and the Investor
herein shall survive the execution of this Agreement, the delivery to the Investor of the Securities being purchased and the payment
therefor.



 


		7.	Notices. All notices, requests, consents and other communications hereunder shall be in
writing, shall be delivered (A) if within the domestic United States, by first-class registered or certified mail, or nationally
recognized overnight express courier, postage prepaid, or by facsimile, or (B) otherwise by International Federal Express or facsimile,
and shall be deemed given (i) if delivered by first-class registered or certified mail, three (3) business days after so mailed,
(ii) if delivered by a nationally recognized overnight carrier, one business day after so mailed, (iii) if delivered by International
Federal Express, two (2) business days after so mailed and (iv) if delivered by facsimile, upon electronic confirmation of receipt
and shall be delivered as addressed as follows:



 


(a) if to
the Company, to:


 


Xtant Medical Holdings, Inc.


600 Cruiser Lane


Belgrade, Montana 59714


Attention: President


 


(b) if to
the Investor, at the Investor’s address on the signature page hereto, or at such other address or addresses as may have been
furnished to the Company in writing.


 




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		8.	Changes. Except as contemplated herein, this Agreement may not be modified or amended except
pursuant to an instrument in writing signed by the Company and the Investor.



 


		9.	Headings. The headings of the various sections of this Agreement have been inserted for
convenience or reference only and shall not be deemed to be part of this Agreement.



 


		10.	Severability. In case any provision contained in this Agreement should be invalid, illegal
or unenforceable in any respect, the validity, legality and enforceability of the remaining provisions contained herein shall not
in any way be affected or impaired thereby.



 


		11.	Applicable Law; Venue. This Agreement will be governed by and construed in accordance with
the laws of the State of New York applicable to contracts made and to be performed within the State of New York. Each of the Company
and each Investor agrees that any suit, action or proceeding arising out of or based upon this Agreement or the transactions contemplated
hereby may be instituted only in any State or U.S. federal court in The City of New York and County of New York and waives
any objection that such party may now or hereafter have to the laying of venue of any such suit, action or proceeding, and irrevocably
submits to the exclusive jurisdiction of such courts in any such suit, action or proceeding.



 


		12.	Waiver of Jury Trial. The Company and the Investor hereby irrevocably waive, to the fullest
extent permitted by applicable law, any and all right to trial by jury in any legal proceeding arising out of or relating to this
Agreement or the transactions contemplated hereby.



 


		13.	Counterparts. This Agreement may be signed in one or more counterparts, each of which
shall constitute an original and all of which together shall constitute one and the same agreement.



 


		14.	Payment of Expenses. The Company agrees to pay on demand all expenses of the Investor incurred
in connection with the Investor’s review, consideration and evaluation of this Agreement, including the rights and remedies
available to it in connection therewith, and the negotiation, preparation, execution and delivery of this Agreement.



 




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