NO319101B1 - Nye benzotiofenforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt anvendelse av forbindelsene - Google Patents
Nye benzotiofenforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt anvendelse av forbindelsene Download PDFInfo
- Publication number
- NO319101B1 NO319101B1 NO19991957A NO991957A NO319101B1 NO 319101 B1 NO319101 B1 NO 319101B1 NO 19991957 A NO19991957 A NO 19991957A NO 991957 A NO991957 A NO 991957A NO 319101 B1 NO319101 B1 NO 319101B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compounds
- pyridinyl
- group
- benzo
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 title claims description 124
- 238000000034 method Methods 0.000 title claims description 43
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title abstract description 6
- -1 1-6C arylalkylene Chemical group 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 25
- 125000005605 benzo group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 208000007536 Thrombosis Diseases 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 230000007170 pathology Effects 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 150000003138 primary alcohols Chemical class 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- XYEAUXYPORAKOD-ZTKZIYFRSA-N (e)-3-[3-(4-hydroxyphenoxy)-5,6-bis(phenylmethoxy)-1-benzothiophen-2-yl]-2-pyridin-4-ylprop-2-enoic acid Chemical compound C=1C=NC=CC=1/C(C(=O)O)=C\C(=C(C1=CC=2OCC=3C=CC=CC=3)OC=3C=CC(O)=CC=3)SC1=CC=2OCC1=CC=CC=C1 XYEAUXYPORAKOD-ZTKZIYFRSA-N 0.000 claims description 2
- GGYUGABEHLLYJX-YRRMYEEHSA-N (e)-3-[5,6-bis(phenylmethoxy)-3-(4-phenylmethoxyphenoxy)-1-benzothiophen-2-yl]-2-pyridin-4-ylprop-2-enoic acid Chemical compound C=1C=NC=CC=1/C(C(=O)O)=C\C(=C(C1=CC=2OCC=3C=CC=CC=3)OC=3C=CC(OCC=4C=CC=CC=4)=CC=3)SC1=CC=2OCC1=CC=CC=C1 GGYUGABEHLLYJX-YRRMYEEHSA-N 0.000 claims description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- SCOXUJLHNHFVDK-VUTHCHCSSA-N (e)-3-[3-(6-methylpyridin-3-yl)oxy-5,6-bis(phenylmethoxy)-1-benzothiophen-2-yl]-2-pyridin-4-ylprop-2-enoic acid Chemical compound C1=NC(C)=CC=C1OC(C1=CC(OCC=2C=CC=CC=2)=C(OCC=2C=CC=CC=2)C=C1S1)=C1\C=C(\C(O)=O)C1=CC=NC=C1 SCOXUJLHNHFVDK-VUTHCHCSSA-N 0.000 claims 1
- LTAHKZSKQPFEDZ-MWAVMZGNSA-N (e)-3-[6-methoxy-5-phenylmethoxy-3-(4-phenylmethoxyphenoxy)-1-benzothiophen-2-yl]-2-pyridin-4-ylprop-2-enoic acid Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1OC=1C=2C=C(OCC=3C=CC=CC=3)C(OC)=CC=2SC=1\C=C(\C(O)=O)C1=CC=NC=C1 LTAHKZSKQPFEDZ-MWAVMZGNSA-N 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 abstract 2
- 125000000732 arylene group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 2
- 150000002475 indoles Chemical class 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000002431 aminoalkoxy group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 abstract 1
- 239000000047 product Substances 0.000 description 29
- 238000004452 microanalysis Methods 0.000 description 26
- 239000003153 chemical reaction reagent Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000758 substrate Substances 0.000 description 18
- 102000012335 Plasminogen Activator Inhibitor 1 Human genes 0.000 description 14
- 108010022233 Plasminogen Activator Inhibitor 1 Proteins 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000011734 sodium Substances 0.000 description 9
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- 230000015572 biosynthetic process Effects 0.000 description 7
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- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 6
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- 239000002244 precipitate Substances 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/64—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9805239A FR2777886B1 (fr) | 1998-04-27 | 1998-04-27 | Nouveaux derives benzothiopheniques, benzofuraniques et indoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO991957D0 NO991957D0 (no) | 1999-04-23 |
| NO991957L NO991957L (no) | 1999-10-28 |
| NO319101B1 true NO319101B1 (no) | 2005-06-20 |
Family
ID=9525701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19991957A NO319101B1 (no) | 1998-04-27 | 1999-04-23 | Nye benzotiofenforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt anvendelse av forbindelsene |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6048875A (pt) |
| EP (1) | EP0955299B1 (pt) |
| JP (1) | JP3957424B2 (pt) |
| CN (1) | CN1211362C (pt) |
| AT (1) | ATE214387T1 (pt) |
| AU (1) | AU744456B2 (pt) |
| BR (1) | BR9901298A (pt) |
| CA (1) | CA2270086C (pt) |
| DE (1) | DE69901006T2 (pt) |
| DK (1) | DK0955299T3 (pt) |
| ES (1) | ES2174579T3 (pt) |
| FR (1) | FR2777886B1 (pt) |
| HK (1) | HK1022694A1 (pt) |
| HU (1) | HUP9901403A1 (pt) |
| NO (1) | NO319101B1 (pt) |
| NZ (1) | NZ335388A (pt) |
| PT (1) | PT955299E (pt) |
| ZA (1) | ZA992941B (pt) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6162930A (en) | 1998-03-06 | 2000-12-19 | Baylor University | Anti-mitotic agents which inhibit tubulin polymerization |
| FR2799756B1 (fr) * | 1999-10-15 | 2001-12-14 | Adir | Nouveaux derives benzothiopheniques, benzofuraniques et indoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| JP2004505888A (ja) * | 2000-03-10 | 2004-02-26 | ベイラー・ユニバーシテイ | チューブリン結合リガンドおよび対応するプロドラッグ構造 |
| CA2445712A1 (en) * | 2001-05-31 | 2002-12-05 | Cellegy Pharmaceuticals, Inc. | Store operated calcium influx inhibitors and methods of use |
| ATE367812T1 (de) * | 2001-06-20 | 2007-08-15 | Wyeth Corp | Substituierte indolsäurederivate als inhibitoren von plasminogen-aktivator-inhibitor-1 (pai-1) |
| TWI224101B (en) | 2001-06-20 | 2004-11-21 | Wyeth Corp | Substituted naphthyl indole derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1) |
| WO2004052856A1 (en) * | 2002-12-10 | 2004-06-24 | Wyeth | Substituted indole oxo-acetyl amino acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| UA80453C2 (en) * | 2002-12-10 | 2007-09-25 | Derivatives of substituted dyhydropyranoindol-3,4-dion as inhibitors of plasminogen activator inhibitor-1 (pai-1) | |
| CA2509238A1 (en) * | 2002-12-10 | 2004-06-24 | Wyeth | Substituted 3-carbonyl-1h-indol-1-yl acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| US7348351B2 (en) | 2002-12-10 | 2008-03-25 | Wyeth | Substituted 3-alkyl and 3-arylalkyl 1H-indol-1yl acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
| CA2509191A1 (en) * | 2002-12-10 | 2004-06-24 | Wyeth | Aryl, aryloxy, and alkyloxy substituted 1h-indol-3-yl glyoxylic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| US7420083B2 (en) | 2003-09-25 | 2008-09-02 | Wyeth | Substituted aryloximes |
| US7411083B2 (en) | 2003-09-25 | 2008-08-12 | Wyeth | Substituted acetic acid derivatives |
| US7582773B2 (en) | 2003-09-25 | 2009-09-01 | Wyeth | Substituted phenyl indoles |
| US7163954B2 (en) | 2003-09-25 | 2007-01-16 | Wyeth | Substituted naphthyl benzothiophene acids |
| US7268159B2 (en) | 2003-09-25 | 2007-09-11 | Wyeth | Substituted indoles |
| US7442805B2 (en) | 2003-09-25 | 2008-10-28 | Wyeth | Substituted sulfonamide-indoles |
| US7351726B2 (en) | 2003-09-25 | 2008-04-01 | Wyeth | Substituted oxadiazolidinediones |
| US7141592B2 (en) | 2003-09-25 | 2006-11-28 | Wyeth | Substituted oxadiazolidinediones |
| US7534894B2 (en) | 2003-09-25 | 2009-05-19 | Wyeth | Biphenyloxy-acids |
| US7446201B2 (en) | 2003-09-25 | 2008-11-04 | Wyeth | Substituted heteroaryl benzofuran acids |
| US7265148B2 (en) | 2003-09-25 | 2007-09-04 | Wyeth | Substituted pyrrole-indoles |
| US7342039B2 (en) | 2003-09-25 | 2008-03-11 | Wyeth | Substituted indole oximes |
| US7332521B2 (en) | 2003-09-25 | 2008-02-19 | Wyeth | Substituted indoles |
| AU2005277139A1 (en) * | 2004-08-23 | 2006-03-02 | Wyeth | Thiazolo-naphthyl acids as inhibitors of plasminogen activator inhibitor-1 |
| CN101044136A (zh) * | 2004-08-23 | 2007-09-26 | 惠氏公司 | 作为pai－1抑制剂的吡咯基－萘基酸 |
| US7754747B2 (en) | 2004-08-23 | 2010-07-13 | Wyeth Llc | Oxazolo-naphthyl acids |
| WO2007022321A2 (en) * | 2005-08-17 | 2007-02-22 | Wyeth | Substituted indoles and use thereof |
| EP2069354B1 (en) * | 2006-08-21 | 2011-11-02 | Genentech, Inc. | Aza-benzofuranyl compounds and methods of use |
| MX2009001875A (es) * | 2006-08-21 | 2009-03-02 | Genentech Inc | Compuestos de aza-benzotiofenilo y metodos de uso de los mismos. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4663344A (en) * | 1985-03-11 | 1987-05-05 | Merck & Co., Inc. | Anti-inflammatory and analgesic 3-hydroxybenzo[b]thiophene derivatives, compositions, and method of use therefor |
| IT1227362B (it) * | 1988-11-18 | 1991-04-08 | Istituto Biochimico Italiano | Derivati indolici, processo per la loro preparazione e loro uso comefarmaci antitrombotici |
| US5356926A (en) * | 1992-02-24 | 1994-10-18 | Warner-Lambert Company | 3-alkyloxy-, aryloxy-, or arylalkyloxy-benzo [β]thiophene-2-carboxamides as inhibitors of cell adhesion |
-
1998
- 1998-04-27 FR FR9805239A patent/FR2777886B1/fr not_active Expired - Fee Related
-
1999
- 1999-04-23 NO NO19991957A patent/NO319101B1/no unknown
- 1999-04-26 JP JP11736799A patent/JP3957424B2/ja not_active Expired - Fee Related
- 1999-04-26 DK DK99401010T patent/DK0955299T3/da active
- 1999-04-26 PT PT99401010T patent/PT955299E/pt unknown
- 1999-04-26 CA CA002270086A patent/CA2270086C/fr not_active Expired - Fee Related
- 1999-04-26 EP EP99401010A patent/EP0955299B1/fr not_active Expired - Lifetime
- 1999-04-26 AT AT99401010T patent/ATE214387T1/de not_active IP Right Cessation
- 1999-04-26 ZA ZA9902941A patent/ZA992941B/xx unknown
- 1999-04-26 DE DE69901006T patent/DE69901006T2/de not_active Expired - Fee Related
- 1999-04-26 ES ES99401010T patent/ES2174579T3/es not_active Expired - Lifetime
- 1999-04-26 US US09/299,271 patent/US6048875A/en not_active Expired - Fee Related
- 1999-04-26 NZ NZ335388A patent/NZ335388A/xx unknown
- 1999-04-27 HU HU9901403A patent/HUP9901403A1/hu unknown
- 1999-04-27 CN CNB991051815A patent/CN1211362C/zh not_active Expired - Fee Related
- 1999-04-27 AU AU24021/99A patent/AU744456B2/en not_active Ceased
- 1999-04-27 BR BR9901298-7A patent/BR9901298A/pt not_active Application Discontinuation
-
2000
- 2000-03-21 HK HK00101709A patent/HK1022694A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2174579T3 (es) | 2002-11-01 |
| US6048875A (en) | 2000-04-11 |
| BR9901298A (pt) | 2000-05-02 |
| PT955299E (pt) | 2002-07-31 |
| NO991957L (no) | 1999-10-28 |
| CN1235156A (zh) | 1999-11-17 |
| ZA992941B (en) | 1999-10-26 |
| FR2777886A1 (fr) | 1999-10-29 |
| EP0955299A1 (fr) | 1999-11-10 |
| JP3957424B2 (ja) | 2007-08-15 |
| ATE214387T1 (de) | 2002-03-15 |
| HK1022694A1 (en) | 2000-08-18 |
| NZ335388A (en) | 2000-03-27 |
| EP0955299B1 (fr) | 2002-03-13 |
| HU9901403D0 (en) | 1999-06-28 |
| CA2270086A1 (fr) | 1999-10-27 |
| NO991957D0 (no) | 1999-04-23 |
| AU2402199A (en) | 1999-11-04 |
| JPH11349586A (ja) | 1999-12-21 |
| CA2270086C (fr) | 2005-04-05 |
| DK0955299T3 (da) | 2002-06-24 |
| AU744456B2 (en) | 2002-02-21 |
| DE69901006T2 (de) | 2002-11-07 |
| DE69901006D1 (de) | 2002-04-18 |
| CN1211362C (zh) | 2005-07-20 |
| HUP9901403A1 (hu) | 2000-06-28 |
| FR2777886B1 (fr) | 2002-05-31 |
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