NO320693B1 - Nye benzotiofenforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt deres anvendelser - Google Patents
Nye benzotiofenforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt deres anvendelser Download PDFInfo
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- NO320693B1 NO320693B1 NO20005166A NO20005166A NO320693B1 NO 320693 B1 NO320693 B1 NO 320693B1 NO 20005166 A NO20005166 A NO 20005166A NO 20005166 A NO20005166 A NO 20005166A NO 320693 B1 NO320693 B1 NO 320693B1
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- compounds
- pyridyl
- biphenyl
- ylmethoxy
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 36
- -1 aralkylene Chemical group 0.000 claims abstract description 17
- 239000002253 acid Substances 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
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 85
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 38
- 125000005605 benzo group Chemical group 0.000 claims description 14
- 239000004305 biphenyl Substances 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
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- 208000007536 Thrombosis Diseases 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 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
- 230000007170 pathology Effects 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
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- 229940100662 nasal drops Drugs 0.000 description 1
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- 239000002674 ointment Substances 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
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- 229940127126 plasminogen activator Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 229960000856 protein c Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 229960003766 thrombin (human) Drugs 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
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Classifications
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- 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
-
- 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
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
-
- 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
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—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
-
- 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)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan 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 |
---|---|---|---|
FR9912899A FR2799756B1 (fr) | 1999-10-15 | 1999-10-15 | Nouveaux derives benzothiopheniques, benzofuraniques et indoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20005166D0 NO20005166D0 (no) | 2000-10-13 |
NO20005166L NO20005166L (no) | 2001-04-17 |
NO320693B1 true NO320693B1 (no) | 2006-01-16 |
Family
ID=9550989
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20005166A NO320693B1 (no) | 1999-10-15 | 2000-10-13 | Nye benzotiofenforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt deres anvendelser |
Country Status (23)
Country | Link |
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US (1) | US6302837B1 (pt) |
EP (1) | EP1092716B1 (pt) |
JP (1) | JP3488683B2 (pt) |
KR (1) | KR100474753B1 (pt) |
CN (1) | CN1136213C (pt) |
AT (1) | ATE289305T1 (pt) |
AU (1) | AU774527B2 (pt) |
BR (1) | BR0005171A (pt) |
CA (1) | CA2323707C (pt) |
DE (1) | DE60018135T2 (pt) |
DK (1) | DK1092716T3 (pt) |
EA (1) | EA004147B1 (pt) |
ES (1) | ES2238261T3 (pt) |
FR (1) | FR2799756B1 (pt) |
HK (1) | HK1036447A1 (pt) |
HU (1) | HUP0004006A2 (pt) |
MX (1) | MXPA00010096A (pt) |
NO (1) | NO320693B1 (pt) |
NZ (1) | NZ507524A (pt) |
PL (1) | PL198579B1 (pt) |
PT (1) | PT1092716E (pt) |
SI (1) | SI1092716T1 (pt) |
ZA (1) | ZA200005668B (pt) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1129068A1 (en) * | 1998-11-12 | 2001-09-05 | Ariad Pharmaceuticals, Inc. | Bicyclic signal transduction inhibitors, composition containing them and uses thereof |
JP2001261674A (ja) * | 2000-03-22 | 2001-09-26 | Mitsui Chemicals Inc | ベンゾチオフェン誘導体およびそれを有効成分として含有する核内レセプター作動薬 |
AU2001268051A1 (en) * | 2000-06-28 | 2002-01-08 | Eli Lilly And Company | Spla2 inhibitors |
US6969730B2 (en) * | 2001-03-16 | 2005-11-29 | Abbott Laboratories | Amines as histamine-3 receptor ligands and their therapeutic applications |
EP1844771A3 (en) | 2001-06-20 | 2007-11-07 | Wyeth | Substituted indole acid derivatives as inhibitors of plasminogen activator 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) |
EP1397130B1 (en) | 2001-06-20 | 2007-07-25 | Wyeth | Substituted indole 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) | |
CN1723198A (zh) | 2002-12-10 | 2006-01-18 | 惠氏公司 | 用作纤溶酶原激活物抑制剂-1(pai-1)的抑制剂的芳基、芳氧基和烷氧基取代的1h-吲哚-3-基乙醛酸衍生物 |
DE60306548T2 (de) | 2002-12-10 | 2007-06-21 | Wyeth | Substituierte 3-carbonyl-1-yl-essigsäure-derivate als plasminogen aktivator inhibitor(pai-1) inhibitoren |
US7056943B2 (en) * | 2002-12-10 | 2006-06-06 | Wyeth | Substituted indole oxo-acetyl amino acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
ES2268480T3 (es) | 2002-12-10 | 2007-03-16 | Wyeth | Derivados del acido 3-alquilo- y 3-arilalquilo-1h-indol-1-il-acetico sustituidos como inhibidores del inhibidor del activador del plasminogeno-1 (pai-1). |
US7582773B2 (en) | 2003-09-25 | 2009-09-01 | Wyeth | Substituted phenyl indoles |
US7332521B2 (en) * | 2003-09-25 | 2008-02-19 | Wyeth | Substituted indoles |
US7442805B2 (en) * | 2003-09-25 | 2008-10-28 | Wyeth | Substituted sulfonamide-indoles |
US7141592B2 (en) | 2003-09-25 | 2006-11-28 | Wyeth | Substituted oxadiazolidinediones |
US7342039B2 (en) | 2003-09-25 | 2008-03-11 | Wyeth | Substituted indole oximes |
US7446201B2 (en) * | 2003-09-25 | 2008-11-04 | Wyeth | Substituted heteroaryl benzofuran acids |
US7351726B2 (en) * | 2003-09-25 | 2008-04-01 | Wyeth | Substituted oxadiazolidinediones |
US7268159B2 (en) | 2003-09-25 | 2007-09-11 | Wyeth | Substituted indoles |
US7534894B2 (en) | 2003-09-25 | 2009-05-19 | Wyeth | Biphenyloxy-acids |
US7420083B2 (en) | 2003-09-25 | 2008-09-02 | Wyeth | Substituted aryloximes |
US7411083B2 (en) | 2003-09-25 | 2008-08-12 | Wyeth | Substituted acetic acid derivatives |
US7265148B2 (en) * | 2003-09-25 | 2007-09-04 | Wyeth | Substituted pyrrole-indoles |
US7163954B2 (en) | 2003-09-25 | 2007-01-16 | Wyeth | Substituted naphthyl benzothiophene acids |
CA2577782A1 (en) | 2004-08-23 | 2006-03-02 | Wyeth | Pyrrolo-naphthyl acids as pai-1 inhibitors |
BRPI0514544A (pt) | 2004-08-23 | 2008-06-17 | Wyeth Corp | ácidos de oxazol-naftila como moduladores de inibidor tipo-1 de ativador de plasminogênio (pai-1) |
KR20070045353A (ko) | 2004-08-23 | 2007-05-02 | 와이어쓰 | 플라스미노겐 활성화제 억제제-1의 억제제로서티아졸로-나프틸 산 |
US7674822B2 (en) | 2004-11-24 | 2010-03-09 | Wyeth | PTP1b inhibitors |
AU2006279496A1 (en) | 2005-08-17 | 2007-02-22 | Wyeth | Substituted indoles and use thereof |
ES2376771T3 (es) * | 2006-08-21 | 2012-03-16 | Genentech, Inc. | Compuestos aza-benzofuranilo y métodos de utilización |
US7893085B2 (en) * | 2006-08-21 | 2011-02-22 | Genentech, Inc | Aza-benzothiophenyl compounds and methods of use |
CN101528746A (zh) * | 2006-09-15 | 2009-09-09 | 先灵公司 | 治疗脂质代谢障碍、疼痛、糖尿病和其它障碍的螺环氮杂环丁酮衍生物 |
CA2663502A1 (en) * | 2006-09-15 | 2008-03-20 | Schering Corporation | Azetidinone derivatives and methods of use thereof |
WO2008033465A1 (en) * | 2006-09-15 | 2008-03-20 | Schering Corporation | Azetidinone derivatives and methods of use thereof |
EP2379076B1 (en) | 2008-12-23 | 2014-11-12 | The Trustees of Columbia University in the City of New York | Phosphodiesterase inhibitors and uses thereof |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5095031A (en) * | 1990-08-20 | 1992-03-10 | Abbott Laboratories | Indole derivatives which inhibit leukotriene biosynthesis |
US5482920A (en) * | 1992-06-17 | 1996-01-09 | Ciba-Geigy Corporation | Triazinyl compounds with herbicidal activity |
US5334719A (en) * | 1992-06-17 | 1994-08-02 | Merck Frosst Canada, Inc. | Bicyclic(azaaromatic)indoles as inhibitors of leukotriene bisynthesis |
US5559127A (en) * | 1992-10-14 | 1996-09-24 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
US5288743A (en) * | 1992-11-20 | 1994-02-22 | Abbott Laboratories | Indole carboxylate derivatives which inhibit leukotriene biosynthesis |
GB9410387D0 (en) * | 1994-05-24 | 1994-07-13 | Xenova Ltd | Pharmaceutical compounds |
US6048877A (en) * | 1997-02-21 | 2000-04-11 | Bristol-Myers Squibb Company | Tetralone derivatives as antiarrhythmic agents |
FR2777886B1 (fr) * | 1998-04-27 | 2002-05-31 | Adir | Nouveaux derives benzothiopheniques, benzofuraniques et indoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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1999
- 1999-10-15 FR FR9912899A patent/FR2799756B1/fr not_active Expired - Fee Related
-
2000
- 2000-10-12 PL PL343147A patent/PL198579B1/pl unknown
- 2000-10-13 JP JP2000313668A patent/JP3488683B2/ja not_active Expired - Fee Related
- 2000-10-13 HU HU0004006A patent/HUP0004006A2/hu unknown
- 2000-10-13 PT PT00402831T patent/PT1092716E/pt unknown
- 2000-10-13 ZA ZA200005668A patent/ZA200005668B/xx unknown
- 2000-10-13 AT AT00402831T patent/ATE289305T1/de not_active IP Right Cessation
- 2000-10-13 EA EA200000947A patent/EA004147B1/ru unknown
- 2000-10-13 ES ES00402831T patent/ES2238261T3/es not_active Expired - Lifetime
- 2000-10-13 DE DE60018135T patent/DE60018135T2/de not_active Expired - Fee Related
- 2000-10-13 NO NO20005166A patent/NO320693B1/no unknown
- 2000-10-13 NZ NZ507524A patent/NZ507524A/en unknown
- 2000-10-13 CA CA002323707A patent/CA2323707C/fr not_active Expired - Fee Related
- 2000-10-13 KR KR10-2000-0060286A patent/KR100474753B1/ko not_active IP Right Cessation
- 2000-10-13 DK DK00402831T patent/DK1092716T3/da active
- 2000-10-13 EP EP00402831A patent/EP1092716B1/fr not_active Expired - Lifetime
- 2000-10-13 US US09/687,308 patent/US6302837B1/en not_active Expired - Fee Related
- 2000-10-13 AU AU66503/00A patent/AU774527B2/en not_active Ceased
- 2000-10-13 CN CNB001304577A patent/CN1136213C/zh not_active Expired - Fee Related
- 2000-10-13 SI SI200030642T patent/SI1092716T1/xx unknown
- 2000-10-16 MX MXPA00010096A patent/MXPA00010096A/es active IP Right Grant
- 2000-10-16 BR BR0005171-3A patent/BR0005171A/pt not_active Application Discontinuation
-
2001
- 2001-09-20 HK HK01106634A patent/HK1036447A1/xx not_active IP Right Cessation
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