Document:

EXHIBIT 10.1

 

TWENTy-SECOND
AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT

 

This TWENTy-SECOND
AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”) is made and entered into as of January
30, 2018 (the “Amendment Closing Date”) by and among Bacterin
International, Inc., a Nevada corporation (the “Borrower”), ROS
acquisition offshore lp, a Cayman Islands Exempted Limited Partnership (“ROS”), ORBIMED ROYALTY
OPPORTUNITIES II, LP, a Delaware limited partnership (“Royalty Opportunities”), and, in their capacity as
Guarantors under the Credit Agreement (as defined below), XTANT MEDICAL HOLDINGS, INC., a Delaware corporation (“Holdings”),
X-SPINE SYSTEMS, INC., an Ohio corporation (“X-Spine” or the “Additional Delayed Draw Borrower”
and, together with the Borrower, the “Borrowers”) and XTANT MEDICAL, INC., a Delaware corporation (“Xtant”
and, along with Holdings and X-Spine, collectively, the “Guarantors”).

 

WHEREAS, the Borrowers,
ROS and Royalty Opportunities are party to that certain Amended and Restated Credit Agreement, dated as of July 27, 2015, as amended
by that certain First Amendment to Amended and Restated Credit Agreement, dated as of March 31, 2016, that certain Second Amendment
to Amended and Restated Credit Agreement, dated as of May 25, 2016, that certain Third Amendment to Amended and Restated Credit
Agreement, dated as of June 30, 2016, that certain Fourth Amendment to Amended and Restated Credit Agreement, dated as of July
29, 2016, that certain Fifth Amendment to the Amended and Restated Credit Agreement, dated as of August 12, 2016, that certain
Sixth Amendment to the Amended and Restated Credit Agreement, dated as of September 27, 2016, that certain Seventh Amendment to
the Amended and Restated Credit Agreement, dated as of December 31, 2016, that certain Eighth Amendment to Amended and Restated
Credit Agreement, dated as of January 13, 2017, that certain Ninth Amendment to Amended and Restated Credit Agreement, dated as
of January 31, 2017, that certain Tenth Amendment to Amended and Restated Credit Agreement, dated as of February 14, 2017, that
certain Eleventh Amendment to Amended and Restated Credit Agreement, dated as of February 28, 2017, that certain Twelfth Amendment
and Waiver to Amended and Restated Credit Agreement, dated as of March 31, 2017, that certain Thirteenth Amendment to Amended and
Restated Credit Agreement, dated as of April 30, 2017, that certain Fourteenth Amendment to Amended and Restated Credit Agreement,
dated as of May 11, 2017, that certain Fifteenth Amendment to Amended and Restated Credit Agreement, dated as of June 30, 2017,
that certain Sixteenth Amendment to Amended and Restated Credit Agreement, dated as of July 15, 2017, that certain Seventeenth
Amendment and Waiver to Amended and Restated Credit Agreement, dated as of August 11, 2017, that certain Eighteenth Amendment to
Amended and Restated Credit Agreement, dated as of September 29, 2017, that certain Nineteenth Amendment to Amended and Restated
Credit Agreement, dated as of October 31, 2017, that certain Waiver, dated as of November 14, 2017, that certain Twentieth Amendment
and Waiver to Amended and Restated Credit Agreement, dated as of November 30, 2017, and that certain Twenty-First Amendment to
Amended and Restated Credit Agreement, dated as of December 28, 2017 (the “Credit Agreement”), pursuant to which
(i) ROS and Royalty Opportunities, as Lenders under the Credit Agreement, have extended credit to the Borrowers on the terms set
forth therein and (ii) each Lender has appointed ROS as the administrative agent (the “Administrative Agent”)
for the Lenders;

 

     

     

    

 

WHEREAS, the Guarantors
and the Administrative Agent entered into an Amended and Restated Guarantee, dated as of July 31, 2015 and supplemented on September
11, 2015, pursuant to which the Guarantors have agreed to guarantee the Obligations of the Borrowers under the Credit Agreement;

 

WHEREAS, pursuant
to Section 11.1 of the Credit Agreement, the Credit Agreement may be amended by an instrument in writing signed by each of the
Borrowers and the Administrative Agent (acting on behalf of the Lenders); and

 

WHEREAS, the Borrowers
and the Lenders desire to amend certain provisions of the Credit Agreement as provided in this Amendment.

 

NOW, THEREFORE,
in consideration of the mutual agreements herein contained, and for other good and valuable consideration, the receipt and sufficiency
of which are hereby acknowledged, the parties hereto agree as follows:

 

1.          Definitions;
Loan Document. Capitalized terms used herein without definition shall have the meanings assigned to such terms in the Credit
Agreement. This Amendment shall constitute a Loan Document for all purposes of the Credit Agreement and the other Loan Documents.

 

2.          Amendments
to Section 3.6. Section 3.6 of the Credit Agreement is hereby amended by deleting the last sentence from such Section 3.6
in its entirety and inserting the following as the last sentence thereof:

 

“Notwithstanding
the foregoing, interest accrued on the Loans for the Fiscal Quarters ended on December 31, 2016, March 31, 2017, June 30, 2017,
September 30, 2017 and December 31, 2017 and otherwise required to be paid in cash on January 2, 2017, March 31, 2017, June 30,
2017, October 2, 2017 and January 2, 2018, respectively, shall instead be required to be paid in cash on February 28, 2018, plus
interest accrued on such interest from January 2, 2017, March 31, 2017, June 30, 2017, October 2, 2017 and January 2, 2018, as
applicable, to the date of payment thereof at a rate equal to the Applicable Margin plus the higher of (i) the LIBO Rate for the
Fiscal Quarter ended on December 31, 2016, the Fiscal Quarter ended on March 31, 2017, the Fiscal Quarter ended on June 30, 2017,
the Fiscal Quarter ended on September 30, 2017 or the Fiscal Quarter ended on December 31, 2017, as applicable, and (ii) 1.00%.”

 

3.          Amendments
to Section 8.4(b). Section 8.4(b) of the Credit Agreement is hereby amended by deleting the first two sentences from such
Section 8.4(b) in their entirety and inserting the following as the first two sentences thereof:

 

“At
all times prior to February 28, 2018, the Liquidity shall not be less than $100,000. At all times after February 28, 2018, the
Liquidity shall not be less than $5,000,000.”

 

4.          Conditions
to Effectiveness of Amendment. This Amendment shall become effective upon receipt by the Borrowers, the Administrative
Agent, the Lenders and the Guarantors of a counterpart signature of the others to this Amendment duly executed and delivered by
each of the Borrowers, the Lenders, the Administrative Agent and the Guarantors.

 

    	 	-2-	 

     

    

 

5.          Expenses.
The Borrowers agree to pay on demand all expenses of the Administrative Agent (including, without limitation, the fees and out-of-pocket
expenses of Covington & Burling LLP, counsel to the Administrative Agent) incurred in connection with the Administrative Agent’s
review, consideration and evaluation of this Amendment, including the rights and remedies available to it in connection therewith,
and the negotiation, preparation, execution and delivery of this Amendment.

 

6.          Representations
and Warranties. The Borrowers and the Guarantors represent and warrant to each Lender as follows:

 

(a)        After
giving effect to this Amendment, the representations and warranties of the Borrowers and the Guarantors contained in the Credit
Agreement or any other Loan Document shall, (i) with respect to representations and warranties that contain a materiality qualification,
be true and correct in all respects on and as of the date hereof, and (ii) with respect to representations and warranties that
do not contain a materiality qualification, be true and correct in all material respects on and as of the date hereof, and except
that the representations and warranties limited by their terms to a specific date shall be true and correct as of such date.

 

(b)        Before
and after giving effect to this Amendment, no Default or Event of Default under the Credit Agreement has occurred or will occur
or be continuing.

 

7.          No
Implied Amendment or Waiver. Except as expressly set forth in this Amendment, this Amendment shall not, by implication
or otherwise, limit, impair, constitute a waiver of or otherwise affect any rights or remedies of the Administrative Agent or the
Lenders under the Credit Agreement or the other Loan Documents, or alter, modify, amend or in any way affect any of the terms,
obligations or covenants contained in the Credit Agreement or the other Loan Documents, all of which shall continue in full force
and effect. Nothing in this Amendment shall be construed to imply any willingness on the part of the Administrative Agent or the
Lenders to agree to or grant any similar or future amendment, consent or waiver of any of the terms and conditions of the Credit
Agreement or the other Loan Documents.

 

8.         Waiver and Release. TO INDUCE THE ADMINISTRATIVE AGENT, ACTING ON BEHALF OF THE LENDERS, TO
AGREE TO THE TERMS OF THIS AMENDMENT, THE BORROWERS, THE GUARANTORS AND THEIR AFFILIATES (COLLECTIVELY, THE RELEASING
PARTIES”) REPRESENT AND WARRANT THAT AS OF THE DATE HEREOF THERE ARE NO CLAIMS OR OFFSETS AGAINST OR RIGHTS OF
RECOUPMENT WITH RESPECT TO OR DEFENSES OR COUNTERCLAIMS TO THEIR OBLIGATIONS UNDER THE LOAN DOCUMENTS AND IN ACCORDANCE
THEREWITH THEY:

 

(a)        WAIVE
ANY AND ALL SUCH CLAIMS, OFFSETS, RIGHTS OF RECOUPMENT, DEFENSES OR COUNTERCLAIMS, WHETHER KNOWN OR UNKNOWN, ARISING PRIOR TO THE
DATE HEREOF; AND

 

    	 	-3-	 

     

    

 

(b)        FOREVER
RELEASE, RELIEVE, AND DISCHARGE THE ADMINISTRATIVE AGENT, THE LENDERS, THEIR OFFICERS, DIRECTORS, SHAREHOLDERS, MEMBERS, PARTNERS,
PREDECESSORS, SUCCESSORS, ASSIGNS, ATTORNEYS, ACCOUNTANTS, AGENTS, EMPLOYEES, AND REPRESENTATIVES (COLLECTIVELY, THE "RELEASED
PARTIES"), AND EACH OF THEM, FROM ANY AND ALL CLAIMS, LIABILITIES, DEMANDS, CAUSES OF ACTION, DEBTS, OBLIGATIONS, PROMISES,
ACTS, AGREEMENTS, AND DAMAGES, OF WHATEVER KIND OR NATURE, WHETHER KNOWN OR UNKNOWN, SUSPECTED OR UNSUSPECTED, CONTINGENT OR FIXED,
LIQUIDATED OR UNLIQUIDATED, MATURED OR UNMATURED, WHETHER AT LAW OR IN EQUITY, WHICH THE RELEASING PARTIES EVER HAD, NOW HAVE,
OR MAY, SHALL, OR CAN HEREAFTER HAVE, DIRECTLY OR INDIRECTLY ARISING OUT OF OR IN ANY WAY BASED UPON, CONNECTED WITH, OR RELATED
TO MATTERS, THINGS, ACTS, CONDUCT, AND/OR OMISSIONS AT ANY TIME FROM THE BEGINNING OF THE WORLD THROUGH AND INCLUDING THE DATE
HEREOF, INCLUDING WITHOUT LIMITATION ANY AND ALL CLAIMS AGAINST THE RELEASED PARTIES ARISING UNDER OR RELATED TO THE LOAN DOCUMENTS
OR THE TRANSACTIONS CONTEMPLATED THEREBY.

 

(c)        IN
CONNECTION WITH THE RELEASE CONTAINED HEREIN, THE RELEASING PARTIES ACKNOWLEDGE THAT THEY ARE AWARE THAT THEY MAY HEREAFTER DISCOVER
CLAIMS PRESENTLY UNKNOWN OR UNSUSPECTED, OR FACTS IN ADDITION TO OR DIFFERENT FROM THOSE WHICH THEY KNOW OR BELIEVE TO BE TRUE,
WITH RESPECT TO THE MATTERS RELEASED HEREIN. NEVERTHELESS, IT IS THE INTENTION OF THE RELEASING PARTIES, THROUGH THIS AGREEMENT
AND WITH ADVICE OF COUNSEL, FULLY, FINALLY, AND FOREVER TO RELEASE ALL SUCH MATTERS, AND ALL CLAIMS RELATED THERETO, WHICH DO NOW
EXIST, OR HERETOFORE HAVE EXISTED. IN FURTHERANCE OF SUCH INTENTION, THE RELEASES HEREIN GIVEN SHALL BE AND REMAIN IN EFFECT AS
A FULL AND COMPLETE RELEASE OR WITHDRAWAL OF SUCH MATTERS NOTWITHSTANDING THE DISCOVERY OR EXISTENCE OF ANY SUCH ADDITIONAL OR
DIFFERENT CLAIMS OR FACTS RELATED THERETO.

 

(d)        THE
RELEASING PARTIES COVENANT AND AGREE NOT TO BRING ANY CLAIM, ACTION, SUIT, OR PROCEEDING AGAINST THE RELEASED PARTIES, DIRECTLY
OR INDIRECTLY, REGARDING OR RELATED IN ANY MANNER TO THE MATTERS RELEASED HEREBY, AND FURTHER COVENANT AND AGREE THAT THIS AGREEMENT
IS A BAR TO ANY SUCH CLAIM, ACTION, SUIT, OR PROCEEDING.

 

(e)        THE
RELEASING PARTIES REPRESENT AND WARRANT TO THE RELEASED PARTIES THAT THEY HAVE NOT HERETOFORE ASSIGNED OR TRANSFERRED, OR PURPORTED
TO ASSIGN OR TRANSFER, TO ANY PERSON OR ENTITY ANY CLAIMS OR OTHER MATTERS HEREIN RELEASED.

 

    	 	-4-	 

     

    

 

9.         Counterparts;
Governing Law. This Amendment may be executed in any number of counterparts and by different parties hereto on separate
counterparts, each of such when so executed and delivered shall be an original, but all of such counterparts shall together constitute
but one and the same agreement. Delivery of an executed counterpart of a signature page of this Amendment by fax transmission or
other electronic mail transmission (e.g., “pdf” or “tif”) shall be effective as delivery of a manually
executed counterpart of this Amendment. THIS AMENDMENT SHALL BE GOVERNED BY, AND CONSTRUED IN ACCORDANCE WITH, THE INTERNAL LAWS
OF THE STATE OF NEW YORK (INCLUDING FOR SUCH PURPOSE SECTIONS 5-1401 AND 5-1402 OF THE GENERAL OBLIGATIONS LAW OF THE STATE OF
NEW YORK).

 

[Remainder
of Page Intentionally Left Blank]

 

    	 	-5-	 

     

    

 

IN WITNESS WHEREOF, the parties
hereto have caused this Amendment to be executed by their respective officers thereunto duly authorized as of the day and year
first above written.

 

	 	
        BACTERIN INTERNATIONAL, INC.,

        as the Borrower

	 	 	 
	 	By:	/s/ Carl D. O’Connell
	 	Name:	Carl D. O’Connell
	 	Title:	Chief Executive Officer
	 	 	 
	 	
        XTANT MEDICAL HOLDINGS, INC.,

        (fka: Bacterin International Holdings, Inc.) as a Guarantor

	 	 	 
	 	By:	/s/ Carl D. O’Connell
	 	Name:	Carl D. O’Connell
	 	Title:	Chief Executive Officer
	 	 	 
	 	
        X-SPINE SYSTEMS, INC.,

        as a Guarantor and the Additional Delayed Draw Borrower

	 	 	 
	 	By:	/s/ Carl D. O’Connell
	 	Name:	Carl D. O’Connell
	 	Title:	Chief Executive Officer
	 	 	 
	 	
        XTANT MEDICAL, INC.,

        as a Guarantor

	 	 	 
	 	By:	/s/ Carl D. O’Connell
	 	Name:	Carl D. O’Connell
	 	Title:	Chief Executive Officer

 

Signature Page to Twenty-Second Amendment
to A&R Credit Agreement

 

     

     

    

 

	 	ROS Acquisition Offshore LP,
 as a Lender and as the Administrative Agent
	 	 	 
	 	By OrbiMed Advisors LLC, solely in its
	 	capacity as Investment Manager
	 	 	 
	 	By:	/s/ W. Carter Neild
	 	Name:	W. Carter Neild
	 	Title:	Member
	 	 	 
	 	ORBIMED ROYALTY OPPORTUNITIES II, LP,
 as a Lender
	 	 	 
	 	By OrbiMed ROF II LLC,
	 	its General Partner
	 	By OrbiMed Advisors LLC,
	 	its Managing Member
	 	 	 
	 	By:	/s/ W. Carter Neild
	 	Name:	W. Carter Neild
	 	Title:	Member

 

Signature Page to Twenty-Second Amendment
to A&R Credit AgreementEXHIBIT 10.2

 

 

 

XTANT MEDICAL HOLDINGS, INC.

 

(formerly known as Bacterin International
Holdings, Inc.)

 

6.00% CONVERTIBLE SENIOR NOTES DUE 2021

 

———————————————————

 

AMENDMENT NUMBER 6 TO INDENTURE

 

Dated as of January 30, 2018

 

———————————————————

 

WILMINGTON TRUST, NATIONAL ASSOCIATION

as Trustee

 

 

 

     

     

    

 

THIS AMENDMENT NUMBER
6 TO INDENTURE (this “Amendment”), dated as of January 30, 2018, is between Xtant Medical Holdings, Inc., a
Delaware corporation formerly known as Bacterin International Holdings, Inc. (the “Company”), and Wilmington
Trust, National Association, a national banking association, as trustee (the “Trustee”).

 

RECITALS

 

WHEREAS, the Company
and the Trustee entered into an Indenture, dated as of July 31, 2015, and as amended by Amendment Number 1 to Indenture, dated
as of August 16, 2017, Amendment Number 2 to Indenture, dated as of October 2, 2017, Amendment Number 3 to Indenture, dated as
of October 31, 2017, Amendment Number 4 and Waiver to Indenture, dated as of December 1, 2017, and Amendment Number 5 to Indenture,
dated as of December 29, 2017 (the “Indenture”), pursuant to which $68,000,000 in principal amount of 6.00%
Senior Notes due 2021 (the “Notes”), have been issued;

 

WHEREAS, Section 9.02
of the Indenture provides that the Company, upon the written consent of each affected Holder and when authorized by a Board Resolution,
may amend Section 2.04(a)(ii) of the Indenture;

 

WHEREAS, all acts and
things prescribed by the Indenture, by law and by the Certificate of Incorporation and the Bylaws of the Company and of the Trustee
necessary to make this Amendment a valid instrument legally binding on the Company and the Trustee, in accordance with its terms,
have been duly done and performed;

 

WHEREAS, there is currently
outstanding under the Indenture $68,000,000 aggregate principal amount of the Notes, and the Holders of 100% of the Notes have
previously provided written consent to this Amendment;

 

WHEREAS, the Company
has provided to the Trustee the Officer’s Certificate and Opinion of Counsel required by Section 9.09 of the Indenture with
respect to the execution of this Amendment;  

 

WHEREAS, the Company
desires to execute this Amendment embodying the modifications of the Indenture approved as aforesaid and has requested that the
Trustee execute this Amendment pursuant to clauses (b) and (f) of Section 9.02 of the Indenture; and

 

WHEREAS, all capitalized
terms used but not defined herein shall have the meanings given to them in the Indenture.

 

NOW, THEREFORE, to
comply with the provisions of the Indenture and in consideration of the above premises, the Company and the Trustee covenant and
agree for the equal and proportionate benefit of the respective Holders of the Notes as follows:

 

ARTICLE 1.

 

Section 1.01This
Amendment amends the Indenture and does and shall be deemed to form a part of, and shall be construed in connection with and as
part of, the Indenture for any and all purposes.

 

    	 	1	 

     

    

 

Section 1.02This
Amendment shall become effective immediately upon its execution and delivery by the Company and the Trustee.

 

ARTICLE 2.

 

Section 2.01Amendment
of Section 2.04(a)(ii). Section 2.04(a)(ii) of the Indenture is hereby amended by deleting the last sentence from such Section
2.04(a)(ii) (which sentence, for the avoidance of doubt, was previously added by Amendment Number 5 to Indenture) in its entirety
and inserting the following thereof:

 

Notwithstanding anything to
the contrary in this Indenture, (A) interest accrued on the Notes otherwise required to be paid in cash on July 15, 2017 (the second
semi-annual Interest Payment Date in 2017) shall instead be required to be paid in cash on February 28, 2018, plus interest accrued
on such interest from July 15, 2017 to the date of payment thereof at a rate equal to 6.00% per annum plus 100 basis points, (B)
the record date for the payment of such amount shall be June 30, 2017 and (C) no Event of Default shall occur (and be waived for
all purposes under the Indenture) as a result of the non-payment of such interest on July 15, 2017. Further, notwithstanding anything
to the contrary in this Indenture, (A) interest accrued on the Notes otherwise required to be paid in cash on January 15, 2018
(the first semi-annual Interest Payment Date in 2018) shall instead be required to be paid in cash on February 28, 2018, plus interest
accrued on such interest from January 15, 2018 to the date of payment thereof at a rate equal to 6.00% per annum plus 100 basis
points, (B) the record date for the payment of such amount shall be December 31, 2017 and (C) no Event of Default shall occur (and
be waived for all purposes under the Indenture) as a result of the non-payment of such interest on January 15, 2018.

 

ARTICLE 3.

 

Section 3.01Except
as specifically modified herein, the Indenture and the Notes are in all respects ratified and confirmed (mutatis mutandis) and
shall remain in full force and effect in accordance with their terms with all capitalized terms used herein without definition
having the same respective meanings ascribed to them as in the Indenture.

 

Section 3.02No
duties, responsibilities or liabilities are assumed, or shall be construed to be assumed, by the Trustee by reason of this Amendment.
This Amendment is executed and accepted by the Trustee subject to all the terms and conditions set forth in the Indenture with
the same force and effect as if those terms and conditions were repeated at length herein and made applicable to the Trustee with
respect hereto. The Trustee is not responsible in any manner whatsoever for or in respect of the validity or sufficiency of this
Amendment or for or in respect of the recitals contained herein.

 

Section 3.03THIS
AMENDMENT SHALL BE GOVERNED BY, AND CONSTRUED IN ACCORDANCE WITH, THE LAWS OF THE STATE OF NEW YORK.

 

    	 	2	 

     

    

 

Section 3.04The
parties may sign any number of copies of this Amendment. Each signed copy shall be an original, but all of such executed copies
together shall represent the same agreement.

 

[Remainder of Page Intentionally Left
Blank; Signature Page Follows]

 

    	 	3	 

     

    

 

IN WITNESS WHEREOF,
the undersigned have executed this Amendment as of the day and year first written above.

 

	 	XTANT MEDICAL HOLDINGS, INC., formerly known as Bacterin International Holdings, Inc.
	 	 	 
	 	By:	/s/ Carl D. O’Connell
	 	Name:	Carl D. O’Connell
	 	Title:	Chief Executive Officer
	 	 	 
	 	WILMINGTON TRUST, NATIONAL ASSOCIATION, as Trustee
	 	 	 
	 	By:	/s/ Lynn M. Steiner
	 	Name:	Lynn M. Steiner
	 	Title:	Vice President

 

[Signature
Page to Amendment Number 6 to Indenture]

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