Granted Patent
B2
US 11,142,549 · App. 16/921,450 · Granted Oct 12, 2021
Ultra-pure agonists of guanylate cyclase C, method of making and using same
Inventors:
Kunwar Shailubhai (Audubon, PA); Stephen Comiskey (Doylestown, PA); Rong Feng (Langhorne, PA); Juncai Bai (North Augusta, SC); Ruoping Zhang (North Augusta, SC); Jun Jia (Shanghai, CN); Junfeng Zhou (Shanghai, CN); Qiao Zhao (Shanghai, CN); Guoqing Zhang (Shanghai, CN)
Assignee:
Bausch Health Ireland Limited
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Abstract
The invention provides processes of purifying a peptide including a GCC agonist sequence selected from the group consisting of SEQ ID NOs: 1-251 described herein. The processes include a solvent exchange step before a freeze-drying (lyophilization) step.
Claims (8)
1. An oral formulation comprising:
(a) a purified peptide comprising the Guanylate Cyclase-C(GCC) agonist of amino acid sequence of SEQ ID NO: 1, wherein the purified peptide comprises less than 0.05% trifluoroacetic acid (TFA) by weight of the purified peptide; and
(b) one or more pharmaceutically acceptable excipients, wherein the one or more pharmaceutically acceptable excipients comprises microcrystalline cellulose.
2. The oral formulation of claim 1 , comprising 0.01 mg to 10 mg of the purified peptide.
3. The oral formulation of claim 2 , comprising 0.1 mg to 5 mg of the purified peptide.
4. The oral formulation of claim 3 , comprising 3 mg of the purified peptide.
5. The oral formulation of claim 1 , wherein the purified peptide has an average particle size of 80-120 μm.
6. The oral formulation of claim 1 , wherein the one or more pharmaceutically acceptable excipients further comprises magnesium stearate.
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 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT
Recorded Jun 9, 2023
From: BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED; MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; SALIX PHARMACEUTICALS, INC.; SOLTA MEDICAL, INC.; PRECISION DERMATOLOGY, INC.
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 063942/0001 →
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 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 (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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded May 23, 2022
From: SHAILUBHAI, KUNWAR; COMISKEY, STEPHEN; FENG, RONG
To: SYNERGY PHARMACEUTICALS, INC.
Reel/Frame 059982/0861 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded May 23, 2022
From: SYNERGY PHARMACEUTICALS, INC.
To: BAUSCH HEALTH IRELAND LIMITED
Reel/Frame 059983/0348 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded May 23, 2022
From: AMBIOPHARM, INC.
To: SYNERGY PHARMACEUTICALS, INC.
Reel/Frame 059983/0206 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded May 23, 2022
From: BAI, JUNCAI; ZHANG, RUOPING; JIA, JUN; ZHOU, JUNFENG; ZHAO, QIAO; ZHANG, GUOQING
To: AMBIOPHARM, INC.
Reel/Frame 059983/0092 →
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 →