Document:

Exhibit 10.1

 

 

 

CLARUS THERAPEUTICS, INC.

 

to

 

U.S.
BANK NATIONAL ASSOCIATION,

 

as Trustee and as Collateral Agent

 

 

 

Supplemental Indenture No. 3

Dated as of September 28, 2021

 

 

 

Supplemental to the Indenture dated as of
March 12, 2020

Relating to the 12.5% Senior Secured Notes due 2025

 

 

 

Providing for Certain Amendments to said Indenture

 

 

 

     

     

    

 

Supplemental
Indenture No. 3

 

This SUPPLEMENTAL INDENTURE
No. 3 dated as of September 28, 2021 is between Clarus Therapeutics, Inc., a Delaware corporation with an address at 555 Skokie Boulevard,
Suite 340, Northbrook, Illinois 60062 (the “Issuer”), and U.S. Bank National Association, as trustee (the “Trustee”)
and as collateral agent (the “Collateral Agent”). This Supplemental Indenture No. 3 supplements and amends that certain Indenture
dated as of March 12, 2020 among the Issuer, the Trustee and the Collateral Agent, as amended and supplemented by Supplemental Indenture
No. 1 dated as of May 27, 2021 and Supplemental Indenture No. 2 dated as of September 9, 2021, in each case, from the Issuer to the Trustee
and the Collateral Agent (as so supplemented and amended, the “Original Indenture”). The Original Indenture and any and all
indentures and instruments supplemental thereto (including this Supplemental Indenture No. 3) are hereinafter sometimes collectively called
the “Indenture”.

 

RECITALS OF THE ISSUER

 

WHEREAS, the Original Indenture
was authorized, executed and delivered by the Issuer to provide for the issuance from time to time of the Securities (such term and all
other capitalized terms used herein without definition having the respective meanings assigned to them in the Original Indenture);

 

WHEREAS, the Issuer desires
to amend certain provisions of the Original Indenture as set forth in this Supplemental Indenture No. 3;

 

WHEREAS, there are no Guarantors
currently a party to the Original Indenture;

 

WHEREAS, Section 9.02 of the
Original Indenture permits the Issuer, the Collateral Agent, the Guarantors and the Trustee to amend or supplement the Original Indenture
with the written consent of the Holders of the requisite principal amount of the Securities then outstanding voting as a single class;

 

WHEREAS, the Issuer has obtained
the written consent of the Holders of 100% of the principal amount of the Securities currently outstanding voting as a single class to
the amendment of the provisions of the Original Indenture as set forth in this Supplemental Indenture No. 3 (as evidenced by an Officer’s
Certificate and Opinion of Counsel delivered to the Trustee);

 

WHEREAS, pursuant to that
certain direction letter dated as of September 28, 2021, among other things, Holders of 100% of the principal amount of the Securities
currently outstanding directed the Trustee pursuant to Section 6.05 of the Original Indenture to execute this Supplemental Indenture No.
3 and the Trustee accepted such direction pursuant to the terms and conditions provided therein; and

 

WHEREAS, the Issuer has satisfied
the other conditions set forth in the Original Indenture to the valid execution and delivery of this Supplemental Indenture No. 3 by the
Issuer, the Collateral Agent and the Trustee;

 

NOW, THEREFORE, THIS SUPPLEMENTAL
INDENTURE NO. 3 WITNESSETH, that, for good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, it
is mutually covenanted and agreed as follows:

 

ARTICLE
One

 

SECTION 1.01. A new
Section 4.23 is added to the Original Indenture as follows:

 

SECTION 4.23. Refinancing
Process. The Issuer shall, either directly or indirectly through an Affiliate, (i) engage a financial advisor or similar agent reasonably
satisfactory to the Holders as determined in good faith to assist the Issuer (or such Affiliate) with the refinancing, redemption or other
repayment of all of the outstanding Securities (a “Debt Refinance”), and (ii) commence an active and continuous process intended
to effectuate a Debt Refinance, in each case, beginning no later than October 15, 2021. The Issuer and/or any of its Affiliates shall
not commence or conduct any process to sell, offer for sale, market or promote any Equity Interest of the Issuer or such Affiliate without
simultaneously commencing and conducting a Debt Refinance process.

 

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SECTION 1.02. The
first sentence of Section 8.01(c) of the Original Indenture is amended and restated as follows:

 

Subject to Section 8.01(b)
and Section 8.02, the Issuer at any time may terminate (i) all its obligations under the Securities and this Indenture (with respect to
such Securities) (“legal defeasance option”) or (ii) its obligations under Sections 4.02, 4.03, 4.04, 4.05, 4.06, 4.07, 4.10,
4.11, 4.13, 4.14, 4.15, 4.16, 4.17, 4.18, 4.19, 4.21, 4.22 and 4.23 and the operation of Section 4.08, Article 5 and Sections 6.01(c),
6.01(d), 6.01(e) (with respect to Restricted Subsidiaries of the Issuer only), 6.01(f) (with respect to Restricted Subsidiaries of the
Issuer only), 6.01(g), 6.01(h), 6.01(i), 6.01(j), 6.01(k) and 6.01(l) (“covenant defeasance option”).

 

SECTION 1.03. A new
last sentence is added to Paragraph 1(b) of each of the Securities (and the form of Security attached as Exhibit A to the Original Indenture)
as follows:

 

Notwithstanding
the foregoing or anything to the contrary in this Security or the Indenture, the interest payment amount that was due and payable on the
Securities on September 1, 2021 (exclusive of the interest payable in respect of $10,000,000 aggregate principal amount of the Securities
that were exchanged and cancelled pursuant to Section 4 of the Transaction Support Agreement) shall be due and payable in cash on March
1, 2022 together with interest accrued on such amount in cash from and including September 1, 2021 until payment thereof at a rate per
annum equal to 18.5% (collectively, the “September 1, 2021 Interest Payment Amount”) (and, for the avoidance of doubt, in
addition to the interest payment amount due and payable on the Securities on March 1, 2022). For all purposes under the Indenture, until
paid, the September 1, 2021 Interest Payment Amount shall be treated as “accrued and unpaid interest” or “accrued but
unpaid interest” in respect of the Securities, including for purposes of Article 3, Section 4.08 and Section 6.02 of the Indenture
and Paragraph 5 of each of the Securities.

 

SECTION 1.04. The
first sentence of paragraph 4 of each of the Securities (and the form of Security attached as Exhibit A to the Original Indenture) is
hereby deleted in its entirety and replaced with the following:

 

The Issuer issued
the Securities under the Indenture dated as of March 12, 2020 (as amended from time to time, including by Supplemental Indenture No. 1
thereto dated as of May 27, 2021, by Supplemental Indenture No. 2 thereto dated as of September 9, 2021 and by Supplemental Indenture
No. 3 thereto dated as of September 28, 2021, the “Indenture”) among the Issuer, the guarantors that may be party thereto
from time to time, the Trustee and the Collateral Agent.

 

SECTION 1.05. 

 

(i) Without
prejudice to the terms of this Supplemental Indenture No. 3, the Issuer confirms that the security created by or pursuant to the Security
Documents remains in full force and effect and continues to secure the Obligations.

 

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(ii) Without
prejudice to the terms of the Security Documents, the Issuer confirms that the security created by or pursuant to the Security Documents
extends to secure the Obligations as amended or supplemented by the terms of this Supplemental Indenture No. 3.

 

ARTICLE
Two

 

SECTION 2.01. This
Supplemental Indenture No. 3 is a supplement to the Original Indenture. As supplemented by this Supplemental Indenture No. 3, the Original
Indenture is in all respects ratified, approved and confirmed, and the Original Indenture and this Supplemental Indenture No. 3 shall
together constitute the Indenture. This Supplemental Indenture No. 3 shall in no way be construed or interpreted as an extinctive novation
of any of the obligations or agreements of the Issuer set forth in the Original Indenture.

 

SECTION 2.02. Sections
12.01, 12.07, 12.09, 12.10, 12.11, 12.12, 12.13 and 12.15 of the Original Indenture shall be applicable to this Supplemental Indenture
No. 3, as though fully set forth herein. The words “execution”, “signed” and “signature” and words
of like import in this Supplemental Indenture No. 3 or in any other certificate, agreement or document related to this Supplemental Indenture
No. 3 shall include images of manually executed signatures transmitted by facsimile or other electronic format (including “pdf”,
“tif” or “jpg”) and other electronic signatures (including DocuSign and AdobeSign, or such other digital signature
provider as specified in writing to Trustee by the Issuer). The use of electronic signatures and electronic records (including any contract
or other record created, generated, sent, communicated, received or stored by electronic means) shall be of the same legal effect, validity
and enforceability as a manually executed signature or use of a paper-based record-keeping system to the fullest extent permitted by applicable
Law, including the Electronic Signatures in Global and National Commerce Act, the New York State Electronic Signatures and Records Act
and any other applicable Law, including any state Law based on the Uniform Electronic Transactions Act or the Uniform Commercial Code.
The Issuer agrees to assume all risks arising out of the use of using digital signatures and electronic methods to submit communications
to each other, including without limitation the risk of the Trustee acting on unauthorized instructions (other than any instructions actually
known by the Trustee to be unauthorized or otherwise invalid), and the risk of interception and misuse by third parties; provided that
neither the Issuer assumes any such risks if the Issuer incurs any loss, liability or expense as a result of the Trustee’s, the
Collateral Agent’s and/or any related Person’s own willful misconduct or gross negligence (as determined by a final, non-appealable
order of a court of competent jurisdiction).

 

SECTION 2.03. The
recitals contained in this Supplemental Indenture No. 3 shall be taken as the statements of the Issuer. The Trustee and the Collateral
Agent assume no responsibility for the correctness of such recitals and make no representations as to the validity or sufficiency of this
Supplemental Indenture No. 3.

 

{SIGNATURE PAGES FOLLOW}

 

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IN WITNESS WHEREOF, the parties
hereto have caused this Supplemental Indenture No. 3 to be duly executed as of the date first written above.

 

	 	CLARUS THERAPEUTICS, INC.
	 	 	 
	 	By:	/s/ Robert E. Dudley
	 	 	Name: Robert E. Dudley
	 	 	Title: President and Chief Executive Officer

 

{Signature Page to Supplemental Indenture No. 3}

 

     

     

    

  

	 	U.S. BANK NATIONAL ASSOCIATION,
	 	as Trustee
	 	 	 
	 	By:	/s/ Diana Jacobs
	 	 	Name: Diana Jacobs
	 	 	Title: Vice President
	 	 	 
	 	U.S. BANK NATIONAL ASSOCIATION,
	 	as Collateral Agent
	 	 	 
	 	By:	/s/ Diana Jacobs
	 	 	Name: Diana Jacobs
	 	 	Title: Vice President

 

{Signature Page to Supplemental Indenture No. 3}Exhibit 10.1

 

PROMISSORY NOTE

 

	$1,240,695.50	 	As of September 29, 2021

 

Tuscan Holdings Corp. II (“Maker”)
promises to pay to the order of Tuscan Holdings Acquisition II LLC or its successors or assigns (“Payee”) the principal sum
of One Million Two Hundred Forty Thousand Six Hundred Ninety Five Dollars and Fifty Cents ($1,240,695.50) in lawful money of the United
States of America, on the terms and conditions described below.

 

1. Principal.
The principal balance of this Note shall be repayable on the consummation of the Maker’s initial merger, capital stock exchange,
asset acquisition or other similar business combination with one or more businesses or entities (a “Business Combination”).
Payee understands that if a Business Combination is not consummated, this Note will not be repaid and all amounts owed hereunder will
be forgiven except to the extent that the Maker has funds available to it outside of its trust account established in connection with
its initial public offering.

 

2. Interest.
No interest shall accrue on the unpaid principal balance of this Note.

 

3. Application
of Payments. All payments shall be applied first to payment in full of any costs incurred in the collection of any sum due under this
Note, including (without limitation) reasonable attorneys’ fees, then to the payment in full of any late charges and finally to
the reduction of the unpaid principal balance of this Note.

 

4. Events
of Default. The following shall constitute Events of Default:

 

(a) Failure
to Make Required Payments. Failure by Maker to pay the principal of this Note within five (5) business days following the date when
due.

 

(b) Voluntary
Bankruptcy, Etc. The commencement by Maker of a voluntary case under the Federal Bankruptcy Code, as now constituted or hereafter
amended, or any other applicable federal or state bankruptcy, insolvency, reorganization, rehabilitation or other similar law, or the
consent by it to the appointment of or taking possession by a receiver, liquidator, assignee, trustee, custodian, sequestrator (or other
similar official) of Maker or for any substantial part of its property, or the making by it of any assignment for the benefit of creditors,
or the failure of Maker generally to pay its debts as such debts become due, or the taking of corporate action by Maker in furtherance
of any of the foregoing.

 

(c) Involuntary
Bankruptcy, Etc. The entry of a decree or order for relief by a court having jurisdiction in the premises in respect of maker
in an involuntary case under the Federal Bankruptcy Code, as now or hereafter constituted, or any other applicable federal or state bankruptcy,
insolvency or other similar law, or appointing a receiver, liquidator, assignee, custodian, trustee, sequestrator (or similar official)
of Maker or for any substantial part of its property, or ordering the winding-up or liquidation of its affairs, and the continuance of
any such decree or order unstayed and in effect for a period of 60 consecutive days.

 

5. Remedies.

 

(a) Upon
the occurrence of an Event of Default specified in Section 4(a), Payee may, by written notice to Maker, declare this Note to be due and
payable, whereupon the principal amount of this Note, and all other amounts payable thereunder, shall become immediately due and payable
without presentment, demand, protest or other notice of any kind, all of which are hereby expressly waived, anything contained herein
or in the documents evidencing the same to the contrary notwithstanding.

 

(b) Upon
the occurrence of an Event of Default specified in Sections 4(b) and 4(c), the unpaid principal balance of, and all other sums payable
with regard to, this Note shall automatically and immediately become due and payable, in all cases without any action on the part of Payee.

 

     

     

    

 

6. Intentionally
Omitted.

 

7. Waivers.
Maker and all endorsers and guarantors of, and sureties for, this Note waive presentment for payment, demand, notice of dishonor, protest,
and notice of protest with regard to the Note, all errors, defects and imperfections in any proceedings instituted by Payee under the
terms of this Note, and all benefits that might accrue to Maker by virtue of any present or future laws exempting any property, real or
personal, or any part of the proceeds arising from any sale of any such property, from attachment, levy or sale under execution, or providing
for any stay of execution, exemption from civil process, or extension of time for payment; and Maker agrees that any real estate that
may be levied upon pursuant to a judgment obtained by virtue hereof, on any writ of execution issued hereon, may be sold upon any such
writ in whole or in part in any order desired by Payee.

 

8. Unconditional
Liability. Maker hereby waives all notices in connection with the delivery, acceptance, performance, default, or enforcement of the
payment of this Note, and agrees that its liability shall be unconditional, without regard to the liability of any other party, and shall
not be affected in any manner by any indulgence, extension of time, renewal, waiver or modification granted or consented to by Payee,
and consents to any and all extensions of time, renewals, waivers, or modifications that may be granted by Payee with respect to the payment
or other provisions of this Note, and agree that additional makers, endorsers, guarantors, or sureties may become parties hereto without
notice to them or affecting their liability hereunder.

 

9. Notices.
Any notice called for hereunder shall be deemed properly given if (i) sent by certified mail, return receipt requested, (ii) personally
delivered, (iii) dispatched by any form of private or governmental express mail or delivery service providing receipted delivery, (iv)
sent by telefacsimile or (v) sent by e-mail, to the following addresses or to such other address as either party may designate by notice
in accordance with this Section:

 

If to Maker:

 

Tuscan Holdings Corp. II

135 E. 57th Street, 17th Floor

New York, New York 10022

 

If to Payee:

 

Tuscan Holdings Acquisition II LLC

135 E. 57th Street, 17th Floor

New York, New York 10022

 

Notice shall be deemed given on the earlier of
(i) actual receipt by the receiving party, (ii) the date shown on a telefacsimile transmission confirmation, (iii) the date on which an
e-mail transmission was received by the receiving party’s on-line access provider (iv) the date reflected on a signed delivery receipt,
or (vi) two (2) Business Days following tender of delivery or dispatch by express mail or delivery service.

 

10. Construction.
This Note shall be construed and enforced in accordance with the domestic, internal law, but not the law of conflict of laws, of the State
of New York.

 

11. Severability.
Any provision contained in this Note which is prohibited or unenforceable in any jurisdiction shall, as to such jurisdiction, be ineffective
to the extent of such prohibition or unenforceability without invalidating the remaining provisions hereof, and any such prohibition or
unenforceability in any jurisdiction shall not invalidate or render unenforceable such provision in any other jurisdiction.

 

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IN WITNESS WHEREOF, Maker,
intending to be legally bound hereby, has caused this Note to be duly executed the day and year first above written.

 

	 	TUSCAN HOLDINGS CORP. II
	 	 	 
	 	By:	/s/ Stephen Vogel
	 	Name:	Stephen Vogel
	 	Title:	Chief Executive Officer

 

 

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