IP Library › Granted Patent US 6,989,451
Granted Patent B2
US 6,989,451 · App. 10/455,149 · Granted Jan 24, 2006

Heterocyclic compounds and uses thereof

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Quick Facts
Patent No.
US 6,989,451
App. No.
10/455,149
Granted
Jan 24, 2006
Kind
B2
Abstract

Substituted isothiazole compounds and compositions are provided, wherein particularly preferred compositions and methods are directed towards inhibition of various protein kinases (especially MEK and/or ERK). Consequently, particularly preferred methods include treatment of diseases associated with abnormality in MEK and/or ERK function.

Claims (32)

1. A compound selected from the group consisting of the following, or a salt thereof:

5-(3-methylphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-methoxyphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-methoxyphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3-methoxyphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-nitrophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(1-naphthyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-phenyl-2-methoxyphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2,6-di-isopropylphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-dimethylamino-1-naphthyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-dimethylamino-1-naphthyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-trichloromethyl-phenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-aminophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-acetyl-phenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-methoxycarbonyl-phenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-fluorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-methoxycarbonyl-phenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2,4-dichlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(1-indanyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(pyridin-3-yl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3-trichloromethyl-4-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3,5-dichlorophenyl)amino-3-hydroxy-4-cyano-isothiazole; and

5-(4-bromophenyl)amino-3-hydroxy-4-cyano-isothiazole.

2. A compound selected from the group consisting of the following, or a salt thereof:

5-(4-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3-trichloromethyl-4-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3,5-dichlorophenyl)amino-3-hydroxy-4-cyano-isothiazole; and

5-(4-bromophenyl)amino-3-hydroxy-4-cyano-isothiazole.

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
Reel/Frame 073637/0126 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMA POLAND SPOLKA Z ORGANICZONA ODPOWIEDZIALNOSCIA; VALEANT SP. Z.O.O.
Reel/Frame 073637/0222 →
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 Jul 3, 2019
From: BAUSCH HEALTH IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT PHARMACEUTICALS LUXEMBOURG S.À R.L.; VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA; VALEANT SP. Z O. O.
To: THE BANK OF NEW YORK MELLON, AS COLLATERAL AGENT
Reel/Frame 049672/0652 →
SECURITY INTEREST Recorded Mar 11, 2019
From: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 048556/0758 →
SECURITY INTEREST Recorded Jul 19, 2017
From: VALEANT PHARMACEUTICALS INTERNATIONAL
To: THE BANK OF NEW YORK MELLON
Reel/Frame 043045/0913 →