Document:

Exhibit
4.1

 

FORM
OF WARRANT

 

EXERCISABLE
ON OR AFTER NOVEMBER 22, 2022

AND UNTIL 5:00 P.M. (NEW YORK TIME) ON THE EXPIRATION DATE

 

TFF
PHARMACEUTICALS, INC.

WARRANT TO PURCHASE COMMON STOCK

 

Warrant No.:__________

Number
of Shares of Common Stock:_________

Date
of Issuance: ______, 2022 (“Issuance Date”)

 

TFF
Pharmaceuticals, Inc., a corporation duly organized and validly existing under the laws of the State of Delaware (the “Company”),
hereby certifies that, for good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, [HOLDER], the
registered holder hereof or its permitted assigns (the “Holder”), is entitled, subject to the terms set forth below,
to purchase from the Company, at a per share purchase price equal to $[●] (the “Exercise Price”), subject to
the terms, conditions and adjustments set forth below in this Warrant, [●] fully paid non-assessable shares of Common Stock (as
defined below), subject to adjustment as provided herein (the “Warrant Shares”). This Warrant is one of the Warrants
to Purchase Common Stock (the “Warrants”) issued pursuant to (i) that certain Underwriting Agreement, dated
as of November 17, 2022, by and between the Company and JonesTrading Institutional Services LLC, as representatives of the several underwriters
named therein, (ii) the Company’s Registration Statement on Form S-3 (File number 333-249870) (the “Registration Statement”).
This Warrant shall initially be issued and maintained in the form of a security held in book-entry form at the Company’s transfer
agent, Pacific Stock Transfer (“Warrant Agent”), subject to a Holder’s right to elect to receive a Warrant in certificated
form pursuant to the terms of the Warrant Agent Agreement between the Company and the Warrant Agent.

 

The
Company shall register this Warrant, upon records to be maintained by the Warrant Agent for that purpose (the “Warrant Register”),
in the name of the record Holder (which shall include the initial Holder or, as the case may be, any registered assignee to which this
Warrant is permissibly assigned hereunder) from time to time. The Company may deem and treat the registered Holder of this Warrant as
the absolute owner hereof for the purpose of any exercise hereof or any distribution to the Holder, and for all other purposes, absent
actual notice to the contrary. Upon thirty (30) days’ notice to the Holder, the Company may appoint a new warrant agent. Any corporation
into which the Company or any new warrant agent may be merged or any corporation resulting from any consolidation to which the Company
or any new warrant agent shall be a party or any corporation to which the Company or any new warrant agent transfers substantially all
of its corporate trust or shareholders’ services business shall be a successor warrant agent under this Warrant without any further
act. Any such successor warrant agent shall promptly cause notice of its succession as warrant agent to be mailed (by first class mail,
postage prepaid) to the Holder at the Holder’s last address as shown on the Warrant Register.

 

1.
Date of Warrant Exercise. This Warrant shall become exercisable on the Base Date (the “Exercise Date”). As
used in this Warrant, the term “Base Date” shall mean November 22, 2022 (the date of the issuance of this Warrant.

 

     

     

    

 

2.
Expiration of Warrant. This Warrant shall expire on the five (5) year anniversary of the Base Date (the “Expiration Date”).

 

3.
Exercise of Warrant. This Warrant shall be exercisable pursuant to the terms of this Section 3.

 

3.1
Manner of Exercise.

 

(a)
This Warrant may only be exercised by the Holder hereof on or after the Exercise Date and on or prior to the Expiration Date, in accordance
with the terms and conditions hereof, in whole or in part (but not as to fractional shares) with respect to any portion of this Warrant,
during the Company’s normal business hours on any day other than a Saturday or a Sunday or a day on which commercial banking institutions
in New York, New York are authorized by law to be closed (a “Business Day”), by surrender of this Warrant to the Company
at its office maintained pursuant to Section 10.2(a) hereof, accompanied by a written exercise notice in the form attached as Exhibit
A to this Warrant (or a reasonable facsimile thereof) duly executed by the Holder, together with the payment of the aggregate Exercise
Price for the number of Warrant Shares purchased upon exercise of this Warrant. Upon surrender of this Warrant, the Company shall cancel
this Warrant document and shall, in the event of partial exercise, replace it with a new Warrant document in accordance with Section
3.3.

 

(b)
Except as provided for in Section 3.1(c) below, each exercise of this Warrant must be accompanied by payment in full of the aggregate
Exercise Price in cash by check or wire transfer in immediately available funds for the number of Warrant Shares being purchased by the
Holder upon such exercise.

 

(c)
If at the time of exercise hereof there is no effective registration statement registering, or the prospectus contained therein is not
available for, the issuance of the Warrant Shares to the Holder, then this Warrant may only be exercised, in whole or in part, at such
time by means of a “cashless exercise” in which the Holder shall be entitled to receive a number of Warrant Shares, equal
to the quotient (X) obtained by dividing [(A-B) (Y)] by (A), where:

  

	 	X
    =	the
    number of Warrant Shares to be issued to the Holder (rounded to the nearest whole share).
	 	 	 
	 	Y
    =	the
    number of Warrant Shares with respect to which this Warrant is being exercised.

 

	 	A
    =	the
    Fair Market Value of the Common Stock.

 

	 	B
    =	the
    Exercise Price.

 

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For
purposes of this Warrant, the term “Fair Market Value” means with respect to a particular date, the average closing
price of the Common Stock for the ten (10) trading days immediately preceding the applicable exercise herein as officially reported by
the principal securities exchange on which the Common Stock is then listed or admitted to trading, or, if the Common Stock is not listed
or admitted to trading on any securities exchange as determined in good faith by resolution of the Board of Directors of the Company,
based on the best information available to it.

 

If
Warrant Shares are issued in such a cashless exercise, the parties acknowledge and agree that in accordance with Section 3(a)(9) of the
Securities Act of 1933, as amended, and the rules and regulations promulgated thereunder (collectively, the “Securities Act”),
the Warrant Shares shall take on the registered characteristics of the Warrants being exercised. The Company agrees not to take any position
contrary to this Section 3.1(c).

 

3.2
When Exercise Effective. Each exercise of this Warrant shall be deemed to have been effected immediately prior to the close of
business on the Business Day on which this Warrant shall have been duly surrendered to the Company as provided in Sections 3.1 and 12
hereof, and, at such time, the Holder in whose name any certificate or certificates for Warrant Shares shall be issuable upon exercise
as provided in Section 3.3 hereof shall be deemed to have become the holder or holders of record thereof of the number of Warrant Shares
purchased upon exercise of this Warrant.

 

3.3
Delivery of Common Stock Certificates and New Warrant. As soon as reasonably practicable after each exercise of this Warrant,
in whole or in part, and in any event within three (3) Business Days thereafter, the Company, at its expense (including the payment by
it of any applicable issue taxes), will cause to be issued in the name of and delivered to the Holder hereof or, subject to Sections
9 and 10 hereof, as the Holder (upon payment by the Holder of any applicable transfer taxes) may direct:

 

(a)
a certificate or certificates (with appropriate restrictive legends, as applicable) for the number of duly authorized, validly issued,
fully paid and non-assessable Warrant Shares to which the Holder shall be entitled upon exercise; and

 

(b)
in case exercise is in part only, a new Warrant document of like tenor, dated the date hereof, for the remaining number of Warrant Shares
issuable upon exercise of this Warrant after giving effect to the partial exercise of this Warrant (including the delivery of any Warrant
Shares as payment of the Exercise Price for such partial exercise of this Warrant).

 

4.
Certain Adjustments. For so long as this Warrant is outstanding:

 

4.1
Mergers or Consolidations. If at any time after the date hereof there shall be a capital reorganization (other than a combination
or subdivision of Common Stock otherwise provided for herein) resulting in a reclassification to or change in the terms of securities
issuable upon exercise of this Warrant (a “Reorganization”), or a merger or consolidation of the Company with another
corporation, association, partnership, organization, business, individual, government or political subdivision thereof or a governmental
agency (a “Person” or the “Persons”) (other than a merger with another Person in which the Company
is a continuing corporation and which does not result in any reclassification or change in the terms of securities issuable upon exercise
of this Warrant or a merger effected exclusively for the purpose of changing the domicile of the Company) (a “Merger”),
then, as a part of such Reorganization or Merger, lawful provision and adjustment shall be made so that the Holder shall thereafter be
entitled to receive, upon exercise of this Warrant, the number of shares of stock or any other equity or debt securities or property
receivable upon such Reorganization or Merger by a holder of the number of shares of Common Stock which might have been purchased upon
exercise of this Warrant immediately prior to such Reorganization or Merger. In any such case, appropriate adjustment shall be made in
the application of the provisions of this Warrant with respect to the rights and interests of the Holder after the Reorganization or
Merger to the end that the provisions of this Warrant (including adjustment of the Exercise Price then in effect and the number of Warrant
Shares) shall be applicable after that event, as near as reasonably may be, in relation to any shares of stock, securities, property
or other assets thereafter deliverable upon exercise of this Warrant. The provisions of this Section 4.1 shall similarly apply to successive
Reorganizations and/or Mergers.

 

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4.2
Splits and Subdivisions; Dividends. In the event the Company should at any time or from time to time effectuate a split or subdivision
of the outstanding shares of Common Stock or pay a dividend in or make a distribution payable in additional shares of Common Stock or
other securities, or rights convertible into, or entitling the holder thereof to receive, directly or indirectly, additional shares of
Common Stock (hereinafter referred to as “Common Stock Equivalents”) without payment of any consideration by such
holder for the additional shares of Common Stock or Common Stock Equivalents (including the additional shares of Common Stock issuable
upon conversion or exercise thereof), then, as of the applicable record date (or the date of such distribution, split or subdivision
if no record date is fixed), the per share Exercise Price shall be appropriately decreased and the number of Warrant Shares shall be
appropriately increased in proportion to such increase (or potential increase) of outstanding shares; provided, however, that no adjustment
shall be made in the event the split, subdivision, dividend or distribution is not effectuated.

 

4.3
Combination of Shares. If the number of shares of Common Stock outstanding at any time after the date hereof is decreased by a
combination of the outstanding shares of Common Stock, the per share Exercise Price shall be appropriately increased and the number of
shares of Warrant Shares shall be appropriately decreased in proportion to such decrease in outstanding shares.

 

4.4
Adjustments for Other Distributions. In the event the Company shall declare a distribution payable in securities of other Persons,
evidences of indebtedness issued by the Company or other Persons, assets (excluding cash dividends or distributions to the holders of
Common Stock paid out of current or retained earnings and declared by the Company’s Board of Directors) or options or rights not
referred to in Sections 4.2 or 4.3 then, in each such case for the purpose of this Section 4.4, upon exercise of this Warrant, the Holder
shall be entitled to a proportionate share of any such distribution as though the Holder was the actual record holder of the number of
Warrant Shares as of the record date fixed for the determination of the holders of Common Stock of the Company entitled to receive such
distribution.

 

5.
No Impairment. The Company will not, by amendment of its certificate of incorporation or by-laws or through any consolidation,
merger, reorganization, transfer of assets, dissolution, issue or sale of securities or any other voluntary action, avoid or seek to
avoid the observance or performance of any of the terms of this Warrant, but will at all times in good faith assist in the carrying out
of all of the terms and in the taking of all actions necessary or appropriate in order to protect the rights of the Holder against impairment.

 

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6.
Notice as to Adjustments. With respect to each adjustment pursuant to Section 4 of this Warrant, the Company, at its expense,
will promptly compute the adjustment or re-adjustment in accordance with the terms of this Warrant and furnish the Holder with a certificate
certified and confirmed by the Secretary or Chief Financial Officer of the Company setting forth, in reasonable detail, the event requiring
the adjustment or re-adjustment and the amount of such adjustment or re-adjustment, the method of calculation thereof and the facts upon
which the adjustment or re-adjustment is based, and the Exercise Price and the number of Warrant Shares or other securities purchasable
hereunder after giving effect to such adjustment or re-adjustment, which report shall be mailed by first class mail, postage prepaid
to the Holder.

 

7.
Reservation of Shares. The Company shall, solely for the purpose of effecting the exercise of this Warrant, at all times during
the term of this Warrant, reserve and keep available out of its authorized shares of Common Stock, free from all taxes, liens and charges
with respect to the issue thereof and not subject to preemptive rights of shareholders of the Company, such number of its shares of Common
Stock as shall from time to time be sufficient to effect in full the exercise of this Warrant. If at any time the number of authorized
but unissued shares of Common Stock shall not be sufficient to effect in full the exercise of this Warrant, in addition to such other
remedies as shall be available to Holder, the Company will promptly take such corporate action as may, in the opinion of its counsel,
be necessary to increase the number of authorized but unissued shares of Common Stock to such number of shares as shall be sufficient
for such purposes, including without limitation, using its Reasonable Commercial Efforts (as defined in Section 15 hereof) to obtain
the requisite shareholder approval necessary to increase the number of authorized shares of Common Stock. The Company hereby represents
and warrants that all shares of Common Stock issuable upon proper exercise of this Warrant shall be duly authorized and, when issued
and paid for upon proper exercise, shall be validly issued, fully paid and nonassessable.

 

8.
Holder’s Exercise Limitations. The Company shall not effect any exercise of this Warrant, and a Holder shall not have the
right to exercise any portion of this Warrant, pursuant to Section 3 or otherwise, to the extent that after giving effect to such issuance
after exercise as set forth on the applicable Notice of Exercise, the Holder (together with the Holder’s Affiliates, and any other
Persons acting as a group together with the Holder or any of the Holder’s Affiliates (such Persons, “Attribution Parties”)),
would beneficially own in excess of the Beneficial Ownership Limitation (as defined below). For purposes of the foregoing sentence, the
number of shares of Common Stock beneficially owned by the Holder and its Affiliates and Attribution Parties shall include the number
of shares of Common Stock issuable upon exercise of this Warrant with respect to which such determination is being made, but shall exclude
the number of shares of Common Stock which would be issuable upon (i) exercise of the remaining, nonexercised portion of this Warrant
beneficially owned by the Holder or any of its Affiliates or Attribution Parties and (ii) exercise or conversion of the unexercised or
nonconverted portion of any other securities of the Company subject to a limitation on conversion or exercise analogous to the limitation
contained herein beneficially owned by the Holder or any of its Affiliates or Attribution Parties. Except as set forth in the preceding
sentence, for purposes of this Section 8, beneficial ownership shall be calculated in accordance with Section 13(d) of the Securities
Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder (collectively, the “Exchange Act”),
it being acknowledged by the Holder that the Company is not representing to the Holder that such calculation is in compliance with Section
13(d) of the Exchange Act and the Holder is solely responsible for any schedules required to be filed in accordance therewith. To the
extent that the limitation contained in this Section 8 applies, the determination of whether this Warrant is exercisable (in relation
to other securities owned by the Holder together with any Affiliates and Attribution Parties) and of which portion of this Warrant is
exercisable shall be in the sole discretion of the Holder, and the submission of a Notice of Exercise shall be deemed to be the Holder’s
determination of whether this Warrant is exercisable (in relation to other securities owned by the Holder together with any Affiliates
and Attribution Parties) and of which portion of this Warrant is exercisable, in each case subject to the Beneficial Ownership Limitation,
and the Company shall have no obligation to verify or confirm the accuracy of such determination. In addition, a determination as to
any group status as contemplated above shall be determined in accordance with Section 13(d) of the Exchange Act and the rules and regulations
promulgated thereunder. For purposes of this Section 8, in determining the number of outstanding shares of Common Stock, a Holder may
rely on the number of outstanding shares of Common Stock as reflected in (A) the Company’s most recent periodic or annual report
filed with the Commission, as the case may be, (B) a more recent public announcement by the Company or (C) a more recent written notice
by the Company or the Transfer Agent setting forth the number of shares of Common Stock outstanding. Upon the written or oral request
of a Holder, the Company shall within one (1) Trading Day confirm orally and in writing to the Holder the number of shares of Common
Stock then outstanding. In any case, the number of outstanding shares of Common Stock shall be determined after giving effect to the
conversion or exercise of securities of the Company, including this Warrant, by the Holder or its Affiliates or Attribution Parties since
the date as of which such number of outstanding shares of Common Stock was reported. The “Beneficial Ownership Limitation”
shall be 9.99% of the number of shares of the Common Stock outstanding immediately after giving effect to the issuance of shares of Common
Stock issuable upon exercise of this Warrant. The limitations contained in this paragraph shall apply to a successor holder of this Warrant.
For purposes of this Section 8, “Affiliate” means any Person that, directly or indirectly through one or more intermediaries,
controls or is controlled by or is under common control with a Person, as such terms are used in and construed under Rule 405 under the
Securities Act.

 

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9.
Transfer of Warrant.

 

9.1
Restrictive Legends. This Warrant and each Warrant issued upon transfer or in substitution for this Warrant pursuant to Section
10 hereof, each certificate for Common Stock issued upon the exercise of the Warrant and each certificate issued upon the transfer of
any such Common Stock shall be transferable only upon satisfaction of the conditions specified in this Section 9. Each of the foregoing
securities shall be stamped or otherwise imprinted with a legend reflecting the restrictions on transfer set forth herein and any restrictions
required under the Securities Act or other applicable securities laws.

 

9.2
Notice of Proposed Transfer. Prior to any transfer of any securities which are not registered under an effective registration
statement under the Securities Act (“Restricted Securities”), which transfer may only occur if there is an
exemption from the registration provisions of the Securities Act and all other applicable securities laws, the Holder will give written
notice to the Company of the Holder’s intention to effect a transfer (and shall describe the manner and circumstances of the proposed
transfer). The following provisions shall apply to any proposed transfer of Restricted Securities:

 

(i)
If in the opinion of counsel for the Holder reasonably satisfactory to the Company the proposed transfer may be effected without registration
of the Restricted Securities under the Securities Act (which opinion shall state in detail the basis of the legal conclusions reached
therein), the Holder shall thereupon be entitled to transfer the Restricted Securities in accordance with the terms of the notice delivered
by the Holder to the Company. Each certificate representing the Restricted Securities issued upon or in connection with any transfer
shall bear the restrictive legends required by Section 9.1 hereof.

 

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(ii)
If the opinion called for in (i) above is not delivered, the Holder shall not be entitled to transfer the Restricted Securities until
either: (x) receipt by the Company of a further notice from such Holder pursuant to the foregoing provisions of this Section 9.2 and
fulfillment of the provisions of clause (i) above, or (y) such Restricted Securities have been effectively registered under the Securities
Act.

 

10.
Ownership, Transfer, Sale and Substitution of Warrant.

 

10.1
Ownership of Warrant. The Company may treat any Person in whose name this Warrant is registered in the Warrant Register maintained
pursuant to Section 10.2(b) hereof as the owner and holder thereof for all purposes, notwithstanding any notice to the contrary, except
that, if and when any Warrant is properly assigned in blank, the Company may (but shall not be obligated to) treat the bearer thereof
as the owner of such Warrant for all purposes, notwithstanding any notice to the contrary. Subject to Sections 9 and 10 hereof, this
Warrant, if properly assigned, may be exercised by a new holder without a new Warrant first having been issued.

 

10.2
Office; Exchange of Warrant.

 

(a)
The Company will maintain its principal office at the location identified in the prospectus relating to the Offering or at such other
offices as set forth in the Company’s most current filing (as of the date notice is to be given) under the Exchange Act, or as
the Company otherwise notifies the Holder.

 

(b)
The Company shall cause to be kept at its office maintained pursuant to Section 10.2(a) hereof the Warrant Register. The Person in whose
name the Warrant shall be so registered shall be deemed and treated as the owner and holder thereof for all purposes of this Warrant,
and the Company shall not be affected by any notice or knowledge to the contrary.

 

(c)
Upon the surrender of this Warrant, properly endorsed, for registration of transfer or for exchange at the office of the Company maintained
pursuant to Section 10.2(a) hereof, the Company at its expense will (subject to compliance with Section 9 hereof, if applicable) execute
and deliver to or upon the order of the Holder thereof a new Warrant of like tenor, in the name of such holder or as such holder (upon
payment by such holder of any applicable transfer taxes) may direct, calling in the aggregate on the face thereof for the number of shares
of Common Stock called for on the face of the Warrant so surrendered (after giving effect to any previous adjustment(s) to the number
of Warrant Shares).

 

10.3
Replacement of Warrant. Upon receipt of evidence reasonably satisfactory to the Company of the loss, theft, destruction or mutilation
of this Warrant and, in the case of any such loss, theft or destruction of this Warrant, upon delivery of indemnity reasonably satisfactory
to the Company in form and amount or, in the case of any mutilation, upon surrender of this Warrant for cancellation at the office of
the Company maintained pursuant to Section 10.2(a) hereof, the Company will execute and deliver, in lieu thereof, a new Warrant of like
tenor and dated the date hereof.

 

10.4
Opinions. In connection with the sale of the Warrant Shares by Holder, the Company agrees to cooperate with the Holder, and at
the Company’s expense, to have its counsel provide any legal opinions required to remove the restrictive legends from the Warrant
Shares in connection with a sale, transfer or legend removal request of Holder.

 

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11.
  Redemption of Warrants.

 

(a)
Beginning on the one-year anniversary of this Warrant, outstanding Warrants may be redeemed at the option of the Company, in whole or
in part on a pro-rata basis, by giving not less than 30 days’ prior notice as provided in Section 13 below, which notice may not
be given before, but may be given at any time after the date on which the closing price of the Company’s common stock on the principal
exchange or trading facility on which it is then traded has equaled or exceeded $4.00 for ten consecutive Trading Days. For purposes
of this Section 11, (a) “Trading Day” means (i) a day on which the shares of Common Stock are traded on the Trading
Market on which the shares of Common Stock are then listed or quoted, or (ii) if the shares of Common Stock are not listed on any such
Trading Market, a day on which the shares of Common Stock are traded in the over-the-counter market, as reported by the OTC Markets;
provided, that in the event that the shares of Common Stock are not listed or quoted as set forth in clause (i) or (ii) hereof, then
Trading Day shall mean a Business Day. and (b) “Trading Market” means the New York Stock Exchange, the NYSE American,
the Nasdaq Capital Market, the Nasdaq Global Market or the Nasdaq Global Select Market.

 

(b)
The price at which a Warrant may be redeemed (the “Redemption Price”) is $0.025 per Warrant. On and after the date
upon which such Warrant is redeemed by the Company (the “Redemption Date”), the Holder of a redeemed Warrant shall
be entitled to payment of the Redemption Price upon surrender of the Warrant to the Company.

 

(c)
Notice of redemption of Warrants shall be given at least 30 days’ prior to the Redemption Date by the Company (i) notifying the
Warrant Holders of such redemption via publication of a press release and (ii) taking such other steps as may be required under applicable
law.

 

(d)
From and after the Redemption Date, all Warrants noticed for redemption that have not theretofore been exercised by the Holder shall,
upon payment of the aggregate Redemption Price therefor, cease to represent the right to purchase any shares of Common Stock and shall
be deemed cancelled and void and of no further force or effect without any further act or deed on the part of the Company.

 

(e)
The Holder undertakes to return the certificate representing any redeemed Warrants to the Company upon their redemption and to indemnify
the Company with respect to any losses, claims, damages or liabilities arising from the Holder’s failure to return such certificate.
In the event the certificate so returned represents a number of Warrants in excess of the number being redeemed, the Company shall as
promptly as practicable issue to the Holder a new certificate in book-entry form for the number of unredeemed Warrants.

 

12. No
Rights or Liabilities as Stockholder. No Holder shall be entitled to vote or be deemed the holder of any equity securities which
may at any time be issuable on the exercise hereof, nor shall anything contained herein be construed to confer upon the Holder, as such,
any of the rights of a stockholder of the Company or any right to vote for the election of directors or upon any matter submitted to
stockholders at any meeting thereof, or to give or withhold consent to any corporate action (whether upon any recapitalization, issuance
of stock, reclassification of stock, change of par value, consolidation, merger, conveyance, or otherwise) or to receive notice of meetings
until the Warrant shall have been exercised and the shares of Common Stock purchasable upon the exercise hereof shall have become deliverable,
as provided herein.

 

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13.
Notices. Any notice or other communication in connection with this Warrant shall be given in writing and directed to the parties
hereto as follows: (a) if to the Holder, at the address of the holder in the warrant register maintained pursuant to Section 10 hereof,
or (b) if to the Company, to the attention of its Chief Executive Officer at its office maintained pursuant to Section 10.2(a) hereof;
provided, that the exercise of the Warrant shall also be effected in the manner provided in Section 3 hereof. Notices shall be
deemed properly delivered and received when delivered to the notice party (i) if personally delivered, upon receipt or refusal to accept
delivery, (ii) if sent via facsimile, upon mechanical confirmation of successful transmission thereof generated by the sending telecopy
machine, (iii) if sent by a commercial overnight courier for delivery on the next Business Day, on the first Business Day after deposit
with such courier service, (iv) if sent by registered or certified mail, five (5) Business Days after deposit thereof in the U.S. mail,
or (v) if sent by email, the date of transmission if such notice or communication is delivered via email at the email address specified
in the Underwriting Agreement prior to 5:00 p.m. (prevailing Pacific time) on a Business Day, or the next Business Day after the date
of transmission if such notice or communication is delivered via email at the email address specified in the Underwriting Agreement on
a day that is not a Business Day or later than 5:00 p.m. (prevailing Pacific time) on a Business Day.

 

14.
Payment of Taxes. The Company will pay all documentary stamp taxes attributable to the issuance of shares of Common Stock underlying
this Warrant upon exercise of this Warrant; provided, however, that the Company shall not be required to pay any tax which may
be payable in respect of any transfer involved in the transfer or registration of this Warrant or any certificate for shares of Common
Stock underlying this Warrant in a name other that of the Holder. The Holder is responsible for all other tax liability that may arise
as a result of holding or transferring this Warrant or receiving shares of Common Stock underlying this Warrant upon exercise hereof.

 

15.
Miscellaneous. This Warrant and any term hereof may be changed, waived, discharged or terminated only by an instrument in writing
signed by the party against which enforcement of the change, waiver, discharge or termination is sought. This Warrant shall be construed
and enforced in accordance with and governed by the laws of the State of New York. Each of the parties consents to the exclusive jurisdiction
of the Federal or state courts whose districts encompass any part of the County of New York located in the City of New York, New York
in connection with any dispute arising under this Agreement and hereby waives, to the maximum extent permitted by law, any objection,
including any objection based on forum non conveniens, to the bringing of any such proceeding in such jurisdictions. Each party
to this Agreement irrevocably consents to the service of process in any such proceeding by any manner permitted by law. The section headings
in this Warrant are for purposes of convenience only and shall not constitute a part hereof. In case any one or more of the provisions
of this Warrant shall be invalid or unenforceable in any respect, the validity and enforceability of the remaining terms and provisions
of this Warrant shall not in any way be affected or impaired thereby, and the parties will attempt in good faith to agree upon a valid
and enforceable provision which shall be a commercially reasonable substitute therefor, and upon so agreeing, shall incorporate such
substitute provision in this Warrant. When used herein, the term “Reasonable Commercial Efforts” means, with respect
to the applicable obligation of the Company, reasonable commercial efforts for similarly situated, publicly-traded companies.

 

(Signature
on Following Page)

 

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IN
WITNESS WHEREOF, the Company has caused this Underwriter Warrant to be duly executed as of the date first above written.

 

	 	TFF PHARMACEUTICALS, INC.
	 	 	 
	 	By:	 
	 	 	Name:	 Glenn Mattes
	 	 	Title: 	Chief Executive Officer

 

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EXHIBIT
A

FORM OF EXERCISE NOTICE

[To be executed only upon exercise of Warrant]

 

To
TFF PHARMACEUTICALS, INC.:

 

The
undersigned registered holder of the within Warrant hereby irrevocably exercises the Warrant pursuant to Section 3.1 of the Warrant with
respect to [_____] Warrant Shares, at an exercise price of $1.29 per share, and requests that the certificates for such Warrant Shares
be issued, subject to Sections 9 and 10, in the name of and delivered to:

 

	 	 
	 	 
	 	 
	 	 

 

The
undersigned is hereby making payment for the Warrant Shares in the following manner:

 

[check
one]

 

		☐	by
cash in accordance with Section 3.1(b) of the Warrant

 

		☐	via
cashless exercise in accordance with Section 3.1(c) of the Warrant in the following manner:

 

	 	 
	 	 
	 	 

 

The
undersigned hereby represents and warrants that it is, and has been since its acquisition of the Warrant, the record and beneficial owner
of the Warrant.

 

	

    Dated:
	 	 

 

	 	 
	Print
    or Type Name	 

 

	 	 

(Signature
must conform in all respects to name of holder as specified on the face of Warrant)

 

	 	 

(Street
Address)

 

	 	 	 	 
	(City)	(State)	(Zip
    Code)	 

 

     

     

    

 

EXHIBIT
B

FORM OF ASSIGNMENT

[To be executed only upon transfer of Warrant]

 

For
value received, the undersigned registered holder of the within Warrant hereby sells, assigns and transfers unto_________________ [include
name and addresses] the rights represented by the Warrant to purchase________ shares of Common Stock of TFF PHARMACEUTICALS, INC. to
which the Warrant relates, and appoints Attorney to make such transfer on the books of TFF PHARMACEUTICALS, INC. maintained for the purpose,
with full power of substitution in the premises.

 

Dated:

 

	 	 
	 	(Signature
    must conform in all respects to name of holder as specified on the face of Warrant)
	 	 
	 	 
	 	(Street
    Address)

 

	 	 	 	 	 
	 	(City)	(State)	(Zip
    Code)	 

 

Signed
in the presence of:

 

	 	 
	 	Signature
    of Transferee)
	 	 
	 	 
	 	(Street
    Address)

 

	 	 	 	 	 
	 	(City)	(State)	(Zip
    Code)	 

 

	Signed
    in the presence of:Exhibit
4.6

 

AMENDMENT
NO. 4 TO THE GAUCHO GROUP HOLDINGS, INC.

(FORMERLY
ALGODON WINES & LUXURY DEVELOPMENT GROUP, INC.) 

2018
AWLD EQUITY INCENTIVE PLAN

 

Section
4(a) of the Plan, as previously amended, is hereby further amended as follows:

 

Section
4.Shares Available for Awards

 

	(a)	Shares
    Available. Subject to adjustment as provided in Section 4(c) of the Plan, the aggregate number of Shares that may be issued under
    the Plan, excluding shares issued under the Pre-Existing Plans, shall be 10,176,391 Shares (25% of the Common Stock outstanding on
    a fully-diluted basis as of the date of stockholder approval of August 30, 2022), plus an automatic annual increase to be added on
    January 1 of each year equal to 2.5% of the total number of Shares outstanding on such date (including for this purpose any Shares
    issuable upon conversion of any outstanding capital stock of the Company).
	 	 
	(i)	Any
    Shares subject to an Award issued under this Plan or the Pre-Existing Plans that are canceled, forfeited or expire prior to exercise
    or realization, either in full or in part, shall be added to the total number of Shares available for an Award to be made under the
    Plan.
	 	 
	(ii)	Shares
    to be issued under the Plan must be authorized but unissued Shares.
	 	 
	(iii)	Notwithstanding
    the foregoing, (A) the number of Shares available for granting Incentive Stock Options under the Plan shall not exceed the aggregate
    number of Shares that may be issued under the Plan not taking into account any automatic increase in the share reserve, subject to
    adjustment as provided in Section 4(c) of the Plan and subject to the provisions of Section 422 or 424 of the Code or any successor
    provision and (B) the number of Shares available for granting Restricted Stock and Restricted Stock Units shall not exceed 500,000,
    subject to adjustment as provided in Section 4(c) of the Plan. Shares tendered by Participants as full or partial payment to the
    Company upon exercise of an Award, and Shares withheld by or otherwise remitted to the Company to satisfy a Participant’s tax
    withholding obligations with respect to an Award, shall not then become available for issuance under the Plan. Any Shares withheld
    or otherwise remitted to the Company to satisfy tax withholding obligations, to pay the exercise price of an Award, or Shares of
    Common Stock subject to a broker-assisted cashless exercise of an Award shall reduce the number of Shares available for issuance
    under the Plan.
	 	 
	(iv)	The
    maximum number of Shares subject to an Award granted during a Fiscal Year to any Director (exclusive of Shares subject to an Award
    issued to any Director in his or her capacity as an Employee of the Company), together with any cash fees paid to such Director during
    the Fiscal Year shall not exceed a total value of $100,000 (calculating the value of any Awards based on the grant date fair value
    for financial reporting purposes).

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