CA2250586C - Meta-substituted phenylene sulphonamide derivatives - Google Patents
Meta-substituted phenylene sulphonamide derivatives Download PDFInfo
- Publication number
- CA2250586C CA2250586C CA002250586A CA2250586A CA2250586C CA 2250586 C CA2250586 C CA 2250586C CA 002250586 A CA002250586 A CA 002250586A CA 2250586 A CA2250586 A CA 2250586A CA 2250586 C CA2250586 C CA 2250586C
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- CA
- Canada
- Prior art keywords
- amino
- phenyl
- aryl
- group
- sulfonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- -1 phenylene sulphonamide derivatives Chemical class 0.000 title claims description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 108010044426 integrins Proteins 0.000 claims abstract description 28
- 102000006495 integrins Human genes 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 111
- 125000003118 aryl group Chemical group 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 34
- 125000001188 haloalkyl group Chemical group 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 24
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 19
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229940124530 sulfonamide Drugs 0.000 claims description 16
- 150000003456 sulfonamides Chemical class 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 14
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
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- JDCCGUFYNGDABW-UHFFFAOYSA-N 3-[[3-[[3-(hydrazinylmethylideneamino)benzoyl]amino]phenyl]sulfonylamino]pent-4-ynoic acid Chemical compound NNC=NC1=CC=CC(C(=O)NC=2C=C(C=CC=2)S(=O)(=O)NC(CC(O)=O)C#C)=C1 JDCCGUFYNGDABW-UHFFFAOYSA-N 0.000 claims description 9
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
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- JJKFUGHDGGDLNQ-UHFFFAOYSA-N 2-[1-[3-[[3-(hydrazinylmethylideneamino)benzoyl]amino]phenyl]sulfonylpiperidin-2-yl]acetic acid Chemical compound NNC=NC1=CC=CC(C(=O)NC=2C=C(C=CC=2)S(=O)(=O)N2C(CCCC2)CC(O)=O)=C1 JJKFUGHDGGDLNQ-UHFFFAOYSA-N 0.000 claims description 3
- JJYAKWHUBRGONK-UHFFFAOYSA-N 3-[[3-[[3-(hydrazinylmethylideneamino)benzoyl]amino]phenyl]sulfonylamino]pent-4-enoic acid Chemical compound NNC=NC1=CC=CC(C(=O)NC=2C=C(C=CC=2)S(=O)(=O)NC(CC(O)=O)C=C)=C1 JJYAKWHUBRGONK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CSOJECDGWHHWRS-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylcarbamothioyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(=S)NC(=O)OC(C)(C)C CSOJECDGWHHWRS-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/42—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/46—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/47—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1441596P | 1996-03-29 | 1996-03-29 | |
| US60/014,415 | 1996-03-29 | ||
| PCT/US1997/003986 WO1997036861A1 (en) | 1996-03-29 | 1997-03-20 | Meta-substituted phenylene sulphonamide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2250586A1 CA2250586A1 (en) | 1997-10-09 |
| CA2250586C true CA2250586C (en) | 2007-04-17 |
Family
ID=21765351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002250586A Expired - Fee Related CA2250586C (en) | 1996-03-29 | 1997-03-20 | Meta-substituted phenylene sulphonamide derivatives |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US5843906A (enExample) |
| EP (1) | EP0889876B1 (enExample) |
| JP (1) | JP2000507952A (enExample) |
| AT (1) | ATE203515T1 (enExample) |
| AU (1) | AU2420897A (enExample) |
| CA (1) | CA2250586C (enExample) |
| DE (1) | DE69705829T2 (enExample) |
| DK (1) | DK0889876T3 (enExample) |
| ES (1) | ES2160949T3 (enExample) |
| GR (1) | GR3036887T3 (enExample) |
| PT (1) | PT889876E (enExample) |
| WO (1) | WO1997036861A1 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE203515T1 (de) * | 1996-03-29 | 2001-08-15 | Searle & Co | Meta-substituierte phenylsulphonamidderivate |
| GB9805655D0 (en) | 1998-03-16 | 1998-05-13 | Celltech Therapeutics Ltd | Chemical compounds |
| US6521626B1 (en) | 1998-03-24 | 2003-02-18 | Celltech R&D Limited | Thiocarboxamide derivatives |
| JP4064059B2 (ja) | 1998-04-09 | 2008-03-19 | 明治製菓株式会社 | インテグリンαＶβ３拮抗剤としてのアミノピペリジン誘導体 |
| GB9814414D0 (en) | 1998-07-03 | 1998-09-02 | Celltech Therapeutics Ltd | Chemical compounds |
| EP1100506A4 (en) * | 1998-07-29 | 2002-06-26 | Merck & Co Inc | INTEGRIN RECEPTOR ANTAGONISTS |
| GB9821061D0 (en) | 1998-09-28 | 1998-11-18 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9826174D0 (en) | 1998-11-30 | 1999-01-20 | Celltech Therapeutics Ltd | Chemical compounds |
| EA006294B1 (ru) | 1998-12-23 | 2005-10-27 | Дж.Д.Сирл Энд Ко. | Применение комбинации целекоксиба и гемцитабина в комбинированном способе лечебного воздействия при лечении рака поджелудочной железы |
| US6291503B1 (en) | 1999-01-15 | 2001-09-18 | Bayer Aktiengesellschaft | β-phenylalanine derivatives as integrin antagonists |
| US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
| WO2001010844A1 (fr) | 1999-08-05 | 2001-02-15 | Meiji Seika Kaisha, Ltd. | DERIVES D'ACIDE φ-AMINO-α-HYDROXYCARBOXYLIQUE POSSEDANT UN ANTAGONISME αvβ3 D'INTEGRINE |
| AU7353300A (en) * | 1999-09-08 | 2001-04-10 | Guilford Pharmaceuticals Inc. | Non-peptidic cyclophilin binding compounds and their use |
| EP1088821A1 (en) * | 1999-09-28 | 2001-04-04 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives |
| US6534513B1 (en) | 1999-09-29 | 2003-03-18 | Celltech R&D Limited | Phenylalkanoic acid derivatives |
| WO2001027082A1 (en) * | 1999-10-08 | 2001-04-19 | Meiji Seika Kaisha, Ltd. | 3-AMINOPIPERIDINE DERIVATIVES AS INTEGRIN αvβ3 ANTAGONISTS |
| US20050059669A1 (en) * | 1999-10-08 | 2005-03-17 | Keiichi Ajito | M-substituted benzoic acid derivatives having integrin alpha v beta 3 antagonistic activity |
| US6849639B2 (en) | 1999-12-14 | 2005-02-01 | Amgen Inc. | Integrin inhibitors and their methods of use |
| US6455539B2 (en) | 1999-12-23 | 2002-09-24 | Celltech R&D Limited | Squaric acid derivates |
| RU2240826C2 (ru) * | 2000-02-03 | 2004-11-27 | Эйсай Ко., Лтд. | Ингибитор экспрессии интегрина |
| EP1332132B1 (en) | 2000-04-17 | 2007-10-10 | UCB Pharma, S.A. | Enamine derivatives as cell adhesion molecules |
| US6403608B1 (en) | 2000-05-30 | 2002-06-11 | Celltech R&D, Ltd. | 3-Substituted isoquinolin-1-yl derivatives |
| US6545013B2 (en) | 2000-05-30 | 2003-04-08 | Celltech R&D Limited | 2,7-naphthyridine derivatives |
| AU2001267753A1 (en) | 2000-07-07 | 2002-01-21 | Celltech R And D Limited | Squaric acid derivatives containing a bicyclic heteroaromatic ring as integrin antagonists |
| EP1305291A1 (en) | 2000-08-02 | 2003-05-02 | Celltech R&D Limited | 3-substituted isoquinolin-1-yl derivatives |
| US6656971B2 (en) | 2001-01-25 | 2003-12-02 | Guilford Pharmaceuticals Inc. | Trisubstituted carbocyclic cyclophilin binding compounds and their use |
| ATE412895T1 (de) * | 2001-02-21 | 2008-11-15 | Eisai R&D Man Co Ltd | Verfahren zur untersuchung der wirkung eines angiogenese-hemmers unter vermittlung durch hemmung der integrin-expression |
| US6710061B2 (en) * | 2001-03-09 | 2004-03-23 | Ortho-Mcneil Pharamceutical, Inc. | Aminopyrrolidine sulfonamides as serine protease inhibitors |
| GB0127615D0 (en) * | 2001-07-09 | 2002-01-09 | Aventis Pharm Prod Inc | Substituted amides, sulfonamides and ureas useful for inhibiting kinase activity |
| US8252902B2 (en) | 2001-10-22 | 2012-08-28 | The Scripps Research Institute | Antibody targeting compounds |
| AU2002364260A1 (en) * | 2001-12-31 | 2003-07-30 | Bayer Pharmaceuticals Corporation | Avb3 and avb5 integrin antagonists and methods of treating diseases or conditions associated with avb3 and avb5 integrins |
| US20040001835A1 (en) * | 2002-03-04 | 2004-01-01 | Medimmune, Inc. | Prevention or treatment of cancer using integrin alphavbeta3 antagonists in combination with other agents |
| US20050084489A1 (en) * | 2002-03-04 | 2005-04-21 | Wilder Ronald L. | Methods of preventing or treating disorders by administering and integrin alphanubeta3 antagonist in combination with an HMG-CoA reductase inhibitor or a bisphosphonate |
| AU2004207002A1 (en) * | 2003-01-30 | 2004-08-12 | Medimmune, Inc. | Uses of integrin alphavbeta3 antagonists |
| UA87854C2 (en) | 2004-06-07 | 2009-08-25 | Мерк Энд Ко., Инк. | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators |
| US9296697B2 (en) | 2005-08-24 | 2016-03-29 | Abbott Laboratories | Hetaryl-substituted guanidine compounds and use thereof as binding partners for 5-HT5-receptors |
| WO2007048127A2 (en) * | 2005-10-20 | 2007-04-26 | The Scripps Research Institute | Fc labeling for immunostaining and immunotargeting |
| EP2222636B1 (en) | 2007-12-21 | 2013-04-10 | Ligand Pharmaceuticals Inc. | Selective androgen receptor modulators (sarms) and uses thereof |
| WO2010093706A2 (en) | 2009-02-10 | 2010-08-19 | The Scripps Research Institute | Chemically programmed vaccination |
| US10328082B2 (en) | 2014-05-30 | 2019-06-25 | Pfizer Inc. | Methods of use and combinations |
| MX2021012690A (es) | 2019-04-19 | 2022-01-31 | Ligand Pharm Inc | Formas cristalinas y metodos para producir formas cristalinas de un compuesto. |
| WO2023275715A1 (en) | 2021-06-30 | 2023-01-05 | Pfizer Inc. | Metabolites of selective androgen receptor modulators |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2456731A1 (fr) * | 1979-05-16 | 1980-12-12 | Choay Sa | Nouveaux derives substitues d'ary |
| DE3681408D1 (enExample) * | 1985-11-12 | 1991-10-17 | Ono Pharmaceutical Co. Ltd., Osaka, Jp | |
| NZ239846A (en) * | 1990-09-27 | 1994-11-25 | Merck & Co Inc | Sulphonamide derivatives and pharmaceutical compositions thereof |
| IL99537A (en) * | 1990-09-27 | 1995-11-27 | Merck & Co Inc | Fibrinogen receptor antagonists and pharmaceutical compositions containing them |
| WO1992008464A1 (en) * | 1990-11-15 | 1992-05-29 | Tanabe Seiyaku Co. Ltd. | Substituted urea and related cell adhesion modulation compounds |
| US5451677A (en) * | 1993-02-09 | 1995-09-19 | Merck & Co., Inc. | Substituted phenyl sulfonamides as selective β 3 agonists for the treatment of diabetes and obesity |
| WO1995032710A1 (en) * | 1994-05-27 | 1995-12-07 | Merck & Co., Inc. | Compounds for inhibiting osteoclast-mediated bone resorption |
| EP0889877B1 (en) * | 1996-03-29 | 2001-08-29 | G.D. Searle & Co. | META-SUBSTITUTED PHENYLENE DERIVATIVES AND THEIR USE AS ALPHAvBETA3 INTEGRIN ANTAGONISTS OR INHIBITORS |
| ATE203515T1 (de) * | 1996-03-29 | 2001-08-15 | Searle & Co | Meta-substituierte phenylsulphonamidderivate |
-
1997
- 1997-03-20 AT AT97919877T patent/ATE203515T1/de not_active IP Right Cessation
- 1997-03-20 AU AU24208/97A patent/AU2420897A/en not_active Abandoned
- 1997-03-20 WO PCT/US1997/003986 patent/WO1997036861A1/en not_active Ceased
- 1997-03-20 JP JP9535278A patent/JP2000507952A/ja not_active Abandoned
- 1997-03-20 PT PT97919877T patent/PT889876E/pt unknown
- 1997-03-20 CA CA002250586A patent/CA2250586C/en not_active Expired - Fee Related
- 1997-03-20 DK DK97919877T patent/DK0889876T3/da active
- 1997-03-20 DE DE69705829T patent/DE69705829T2/de not_active Expired - Fee Related
- 1997-03-20 EP EP97919877A patent/EP0889876B1/en not_active Expired - Lifetime
- 1997-03-20 ES ES97919877T patent/ES2160949T3/es not_active Expired - Lifetime
- 1997-03-27 US US08/824,626 patent/US5843906A/en not_active Expired - Fee Related
-
1998
- 1998-08-28 US US09/141,547 patent/US6677308B1/en not_active Expired - Fee Related
-
2001
- 2001-10-16 GR GR20010401757T patent/GR3036887T3/el not_active IP Right Cessation
-
2003
- 2003-09-08 US US10/657,570 patent/US20050176821A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20050176821A1 (en) | 2005-08-11 |
| WO1997036861A1 (en) | 1997-10-09 |
| AU2420897A (en) | 1997-10-22 |
| ATE203515T1 (de) | 2001-08-15 |
| EP0889876B1 (en) | 2001-07-25 |
| GR3036887T3 (en) | 2002-01-31 |
| EP0889876A1 (en) | 1999-01-13 |
| PT889876E (pt) | 2001-11-30 |
| DE69705829D1 (de) | 2001-08-30 |
| CA2250586A1 (en) | 1997-10-09 |
| US6677308B1 (en) | 2004-01-13 |
| JP2000507952A (ja) | 2000-06-27 |
| DK0889876T3 (da) | 2001-09-24 |
| US5843906A (en) | 1998-12-01 |
| DE69705829T2 (de) | 2002-04-04 |
| ES2160949T3 (es) | 2001-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20090320 |