IP Library Granted Patent US 10,597,424
Granted Patent B2
US 10,597,424 · App. 16/150,703 · Granted Mar 24, 2020

Agonists of guanylate cyclase and their uses

Inventor: Kunwar Shailubhai (Audubon, PA)
Assignee: Bausch Health Ireland Limited
C07K7/06A61K38/08A61K45/06C07K7/08
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Quick Facts
Patent No.
US 10,597,424
App. No.
16/150,703
Granted
Mar 24, 2020
Kind
B2
Abstract

This invention provides novel guanylate cyclase C (GC-C) agonists and their therapeutic use. The agonists may be used either alone or in combination with one or more additional agents.

Claims (47)

1. A peptide consisting essentially of the sequence of any one of SEQ ID NOs: 1-94, 119, and 120.

2. The peptide of claim 1 , wherein said peptide is

(SEQ ID NO: 1)

Asn 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -Leu 16 ,

(SEQ ID NO: 32)

Asn 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -Ser 16 ,

(SEQ ID NO: 119)

Asn 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -Thr 16 ,

(SEQ ID NO: 120)

Asn 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -Tyr 16 ,

(SEQ ID NO: 17)

dAsn 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -dLeu 16 ,

or

(SEQ ID NO: 56)

pyGlu 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -Leu 16 .

3. A pharmaceutical composition comprising: a peptide consisting essentially of the sequence of any one of SEQ ID NOs: 1-94, 119, and 120; and a pharmaceutical carrier, excipient, or diluent.

4. The peptide of claim 1 , wherein said peptide increases cGMP production in a cell.

5. The peptide of claim 1 , wherein said peptide is a bicyclic peptide.

6. A composition comprising an inert carrier coated with at least one peptide consisting essentially of the sequence of any one of SEQ ID NOs: 1-94, 119, and 120 and an enteric coating, wherein the composition releases the peptide at pH 5.0 or pH 7.0.

7. The composition of claim 6 , wherein said inert carrier is mannitol, lactose, a microcrystalline cellulose, or starch.

8. A method of treating a condition that responds to enhanced cGMP levels in a subject, the method comprising administering to the subject a therapeutically effective amount of at least one peptide consisting essentially of the sequence of any one of SEQ ID NOs: 1-94, 119, and 120.

9. The method of claim 8 , wherein said peptide is

(SEQ ID NO: 1)

Asn 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -Leu 16 ,

(SEQ ID NO: 32)

Asn 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -Ser 16 ,

(SEQ ID NO: 119)

Asn 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -Thr 16 ,

(SEQ ID NO: 120)

Asn 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -Tyr 16 ,

(SEQ ID NO: 17)

dAsn 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -dLeu 16 ,

or

(SEQ ID NO: 56)

pyGlu 1 -Asp 2 -Aad 3 -Cys 4 -Glu 5 -Leu 6 -Cys 7 -Val 8 -Asn 9 -

Val 10 -Ala 11 -Cys 12 -Thr 13 -Gly 14 -Cys 15 -Leu 16 .

Assignments (14)
U.S. PATENT SECURITY AGREEMENT Recorded Nov 25, 2025
From: BAUSCH HEALTH IRELAND LIMITED
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 073715/0375 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
Reel/Frame 073654/0300 →
RELEASE OF SECURITY INTEREST Recorded Apr 8, 2025
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: SOLTA MEDICAL, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH IRELAND LIMITED (F/K/A/ VALEANT PHARMACEUTICALS IRELAND LIMITED); SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD; SANTARUS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; HUMAX PHARMACEUTICAL S.A.; SOLTA MEDICAL IRELAND LIMITED; BAUSCH & LOMB MEXICO, S.A. DE C.V.; BAUSCH+LOMB OPS B.V.; BAUSCH HEALTH AMERICAS, INC.; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH HOLDCO LIMITED; BAUSCH HEALTH MAGYARORSZAG KFT (A/K/A BAUSCH HEALTH HUNGARY LLC); BAUSCH HEALTH POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA (F/K/A VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA); BAUSCH HEALTH US, LLC; BAUSCH HEALTH, CANADA INC. / SANTE BAUSCH, CANADA INC.; ICN POLFA RZESZOW SPOLKA AKCYJNA (A/K/A ICN POLFA RZESZOW S.A.); ORAPHARMA, INC.; PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA SPOLKA AKCYJNA (A/K/A PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA S.A.); SOLTA MEDICAL DUTCH HOLDINGS B.V.; V-BAC HOLDING CORP.; VRX HOLDCO LLC; 1261229 B.C. LTD.; 1530065 B.C. LTD.
Reel/Frame 070778/0199 →
SECURITY AGREEMENT (SECOND LIEN) Recorded Nov 4, 2022
From: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 062078/0276 →
SECURITY AGREEMENT (FIRST LIEN) Recorded Nov 4, 2022
From: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061882/0708 →
SECURITY AGREEMENT (SECOND LIEN) Recorded Oct 5, 2022
From: BAUSCH HEALTH US, LLC; BAUSCH HEALTH AMERICAS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; SOLTA MEDICAL, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061606/0468 →
SECURITY AGREEMENT (FIRST LIEN) Recorded Oct 4, 2022
From: BAUSCH HEALTH US, LLC; BAUSCH HEALTH AMERICAS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; SOLTA MEDICAL, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061595/0066 →
SECURITY INTEREST Recorded Jun 13, 2022
From: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON
Reel/Frame 060346/0705 →
SECURITY INTEREST Recorded Oct 5, 2021
From: BAUSCH & LOMB IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; DR. GERHARD MANN CHEM.-PHARM. FABRIK GMBH; TECHNOLAS PERFECT VISION GMBH
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 057821/0800 →
SECURITY INTEREST Recorded May 6, 2020
From: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH IRELAND LIMITED; SALIX PHARMACEUTICALS, LTD; SALIX PHARMACEUTICALS, INC.; SOLTA MEDICAL, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 052589/0884 →
SECURITY INTEREST Recorded May 6, 2020
From: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH IRELAND LIMITED; SALIX PHARMACEUTICALS, LTD; SALIX PHARMACEUTICALS, INC.; SOLTA MEDICAL, INC.
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 052589/0813 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 7, 2020
From: SYNERGY PHARMACEUTICALS INC.
To: BAUSCH HEALTH IRELAND LIMITED
Reel/Frame 051753/0817 →
RELEASE OF SECURITY INTEREST Recorded Mar 6, 2019
From: CRG SERVICING LLC
To: SYNERGY PHARMACEUTICALS INC.
Reel/Frame 048521/0005 →
SECURITY INTEREST Recorded Dec 10, 2018
From: SYNERGY PHARMACEUTICALS INC.
To: CRG SERVICING LLC
Reel/Frame 047729/0951 →
Continuity (5)
Continuation 15622526 · Jun 14, 2017
Continuation 14207753 · Mar 13, 2014
Provisional Application 61826749 · May 23, 2013
Provisional Application 61790266 · Mar 15, 2013
Related Publication 20190263861A1 · Aug 29, 2019
Cited By (1)
US 12,458,620