NO320194B1 - Vitronektin reseptor antagonister, anvendelse og fremstilling derav samt farmasoytisk sammensetning - Google Patents
Vitronektin reseptor antagonister, anvendelse og fremstilling derav samt farmasoytisk sammensetning Download PDFInfo
- Publication number
- NO320194B1 NO320194B1 NO19991590A NO991590A NO320194B1 NO 320194 B1 NO320194 B1 NO 320194B1 NO 19991590 A NO19991590 A NO 19991590A NO 991590 A NO991590 A NO 991590A NO 320194 B1 NO320194 B1 NO 320194B1
- Authority
- NO
- Norway
- Prior art keywords
- tetrahydro
- oxo
- benzazepine
- propyloxy
- acetic acid
- Prior art date
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- 238000002360 preparation method Methods 0.000 title description 74
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- 108010048673 Vitronectin Receptors Proteins 0.000 title description 18
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- -1 (C1-C4)alkylsulfoxyl Chemical group 0.000 claims description 43
- 238000004519 manufacturing process Methods 0.000 claims description 27
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
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- KIWDZMAJDQPBPT-NRFANRHFSA-N methyl 2-[(4s)-3-oxo-8-[[4-(trifluoromethyl)phenyl]methoxy]-2-[[4-(trifluoromethyl)phenyl]methyl]-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C([C@H](C(N(CC=1C=CC(=CC=1)C(F)(F)F)CC1=C2)=O)CC(=O)OC)C1=CC=C2OCC1=CC=C(C(F)(F)F)C=C1 KIWDZMAJDQPBPT-NRFANRHFSA-N 0.000 description 1
- SCGBFQUOTIZFLZ-INIZCTEOSA-N methyl 2-[(4s)-8-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound CNC1=CC=CC(CCOC=2C=C3CN(CC(F)(F)F)C(=O)[C@H](CC(=O)OC)CC3=CC=2)=N1 SCGBFQUOTIZFLZ-INIZCTEOSA-N 0.000 description 1
- QXECIBGVADGKOC-QHCPKHFHSA-N methyl 2-[(4s)-8-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-3-oxo-2-(2-phenylethyl)-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound CNC1=CC=CC(CCOC=2C=C3CN(CCC=4C=CC=CC=4)C(=O)[C@H](CC(=O)OC)CC3=CC=2)=N1 QXECIBGVADGKOC-QHCPKHFHSA-N 0.000 description 1
- YQGKSHJEPSPUAN-NRFANRHFSA-N methyl 2-[(4s)-8-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-3-oxo-2-[[4-(trifluoromethyl)phenyl]methyl]-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound CNC1=CC=CC(CCOC=2C=C3CN(CC=4C=CC(=CC=4)C(F)(F)F)C(=O)[C@H](CC(=O)OC)CC3=CC=2)=N1 YQGKSHJEPSPUAN-NRFANRHFSA-N 0.000 description 1
- JILRDIJMUXXSCC-VWLOTQADSA-N methyl 2-[(4s)-8-[3-[(2-methylpropan-2-yl)oxycarbonyl-pyridin-2-ylamino]propoxy]-3-oxo-2-[[4-(trifluoromethyl)phenyl]methyl]-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical class C([C@H](C(N(CC=1C=CC(=CC=1)C(F)(F)F)CC1=C2)=O)CC(=O)OC)C1=CC=C2OCCCN(C(=O)OC(C)(C)C)C1=CC=CC=N1 JILRDIJMUXXSCC-VWLOTQADSA-N 0.000 description 1
- IWUCMTSBIKTGIS-DEOSSOPVSA-N methyl 2-[(4s)-8-[3-[(4-nitrophenyl)methoxycarbonylamino]propoxy]-3-oxo-2-[[4-(trifluoromethyl)phenyl]methyl]-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C([C@H](C(N(CC=1C=CC(=CC=1)C(F)(F)F)CC1=C2)=O)CC(=O)OC)C1=CC=C2OCCCNC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 IWUCMTSBIKTGIS-DEOSSOPVSA-N 0.000 description 1
- SFFLORBVBCOJJW-JTQLQIEISA-N methyl 2-[(4s)-8-hydroxy-2-methyl-3-oxo-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C1N(C)C(=O)[C@H](CC(=O)OC)CC2=CC=C(O)C=C21 SFFLORBVBCOJJW-JTQLQIEISA-N 0.000 description 1
- QNNFQRACPNCRIL-SFHVURJKSA-N methyl 2-[(4s)-8-methoxy-3-oxo-2-(2-phenylethyl)-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C([C@H](C1=O)CC(=O)OC)C2=CC=C(OC)C=C2CN1CCC1=CC=CC=C1 QNNFQRACPNCRIL-SFHVURJKSA-N 0.000 description 1
- KCKAGGQLHRMFEB-UHFFFAOYSA-N methyl 2-[8-(3-aminopropoxy)-3-oxo-1,2,4,5-tetrahydro-2-benzazepin-4-yl]acetate Chemical compound C1NC(=O)C(CC(=O)OC)CC2=CC=C(OCCCN)C=C21 KCKAGGQLHRMFEB-UHFFFAOYSA-N 0.000 description 1
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- HCOAGHSXSNNRLI-UHFFFAOYSA-N methyl 2-[8-[2-(2-amino-1,3-thiazol-4-yl)ethoxy]-2-methyl-3-oxo-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C1=C2CN(C)C(=O)C(CC(=O)OC)CC2=CC=C1OCCC1=CSC(N)=N1 HCOAGHSXSNNRLI-UHFFFAOYSA-N 0.000 description 1
- SAYVBDJYDMVNKE-UHFFFAOYSA-N methyl 2-[8-[3-[(4-aminopyridin-2-yl)amino]propoxy]-2-methyl-3-oxo-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C1=C2CN(C)C(=O)C(CC(=O)OC)CC2=CC=C1OCCCNC1=CC(N)=CC=N1 SAYVBDJYDMVNKE-UHFFFAOYSA-N 0.000 description 1
- WYMBGZKYOCPSPU-UHFFFAOYSA-N methyl 2-[8-[3-[(4-aminopyridin-2-yl)amino]propoxy]-3-oxo-1,2,4,5-tetrahydro-2-benzazepin-4-yl]acetate Chemical compound C1=C2CNC(=O)C(CC(=O)OC)CC2=CC=C1OCCCNC1=CC(N)=CC=N1 WYMBGZKYOCPSPU-UHFFFAOYSA-N 0.000 description 1
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- DZDXMIPOOKZPKF-UHFFFAOYSA-N methyl 2-[8-[3-[(4-methylpyridin-2-yl)amino]propoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical class C1=C2CN(CC(F)(F)F)C(=O)C(CC(=O)OC)CC2=CC=C1OCCCNC1=CC(C)=CC=N1 DZDXMIPOOKZPKF-UHFFFAOYSA-N 0.000 description 1
- YVJPNBILAQNTNW-UHFFFAOYSA-N methyl 2-[8-[3-[2-methylpropoxycarbonyl(pyridin-2-yl)amino]propoxy]-3-oxo-2-[[4-(trifluoromethyl)phenyl]methyl]-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical class C1=C2CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)C(CC(=O)OC)CC2=CC=C1OCCCN(C(=O)OCC(C)C)C1=CC=CC=N1 YVJPNBILAQNTNW-UHFFFAOYSA-N 0.000 description 1
- HBWGJDYATCLISW-UHFFFAOYSA-N methyl 2-[8-[3-[benzoyl(pyridin-2-yl)amino]propoxy]-3-oxo-2-[[4-(trifluoromethyl)phenyl]methyl]-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C1=C2CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)C(CC(=O)OC)CC2=CC=C1OCCCN(C=1N=CC=CC=1)C(=O)C1=CC=CC=C1 HBWGJDYATCLISW-UHFFFAOYSA-N 0.000 description 1
- NDWSPVHHOTWHFE-UHFFFAOYSA-N methyl 2-[8-methoxy-3-oxo-2-(2,2,2-trifluoroethyl)-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C1N(CC(F)(F)F)C(=O)C(CC(=O)OC)CC2=CC=C(OC)C=C21 NDWSPVHHOTWHFE-UHFFFAOYSA-N 0.000 description 1
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- IGOIXJSMQHYRKP-UHFFFAOYSA-N tert-butyl n-[(2-bromo-5-methoxyphenyl)methyl]-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound COC1=CC=C(Br)C(CN(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=C1 IGOIXJSMQHYRKP-UHFFFAOYSA-N 0.000 description 1
- JPPYGSZTJXBKCU-UHFFFAOYSA-N tert-butyl n-[(2-bromo-5-methoxyphenyl)methyl]-n-methylcarbamate Chemical compound COC1=CC=C(Br)C(CN(C)C(=O)OC(C)(C)C)=C1 JPPYGSZTJXBKCU-UHFFFAOYSA-N 0.000 description 1
- YDLIGFUPCAQSBU-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate;potassium Chemical compound [K].CC(C)(C)OC(=O)NC(=O)OC(C)(C)C YDLIGFUPCAQSBU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61K33/00—Medicinal preparations containing inorganic active ingredients
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- A61K33/243—Platinum; Compounds thereof
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- 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
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- 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
- C07D401/12—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 chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Inorganic Chemistry (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
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US2732096P | 1996-10-02 | 1996-10-02 | |
US4377697P | 1997-04-11 | 1997-04-11 | |
PCT/US1997/018001 WO1998014192A1 (en) | 1996-10-02 | 1997-10-01 | Vitronectin receptor antagonists |
Publications (3)
Publication Number | Publication Date |
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NO991590D0 NO991590D0 (no) | 1999-03-31 |
NO991590L NO991590L (no) | 1999-05-31 |
NO320194B1 true NO320194B1 (no) | 2005-11-14 |
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NO19991590A NO320194B1 (no) | 1996-10-02 | 1999-03-31 | Vitronektin reseptor antagonister, anvendelse og fremstilling derav samt farmasoytisk sammensetning |
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EP (1) | EP0957917B1 (cs) |
JP (2) | JP4491072B2 (cs) |
KR (1) | KR100589578B1 (cs) |
CN (1) | CN1114403C (cs) |
AP (1) | AP1463A (cs) |
AR (1) | AR008878A1 (cs) |
AT (1) | ATE312089T1 (cs) |
AU (1) | AU733417B2 (cs) |
BG (1) | BG64581B1 (cs) |
BR (1) | BR9712248B1 (cs) |
CA (1) | CA2267224C (cs) |
CO (1) | CO4900046A1 (cs) |
CY (1) | CY2576B1 (cs) |
CZ (1) | CZ299076B6 (cs) |
DE (1) | DE69734833T2 (cs) |
DK (1) | DK0957917T3 (cs) |
DZ (1) | DZ2320A1 (cs) |
EA (1) | EA002419B1 (cs) |
ES (1) | ES2252775T3 (cs) |
HK (1) | HK1023730A1 (cs) |
HU (1) | HU229221B1 (cs) |
ID (1) | ID19623A (cs) |
IL (1) | IL129243A (cs) |
MA (1) | MA24361A1 (cs) |
MY (1) | MY137606A (cs) |
NO (1) | NO320194B1 (cs) |
NZ (1) | NZ334953A (cs) |
PE (1) | PE10499A1 (cs) |
PL (1) | PL190859B1 (cs) |
RO (1) | RO119881B1 (cs) |
SA (1) | SA98180936B1 (cs) |
SK (1) | SK285029B6 (cs) |
TR (1) | TR199900737T2 (cs) |
TW (1) | TW487702B (cs) |
UA (1) | UA60311C2 (cs) |
UY (2) | UY24735A1 (cs) |
WO (1) | WO1998014192A1 (cs) |
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UA60311C2 (uk) * | 1996-10-02 | 2003-10-15 | Смітклайн Бічам Корпорейшн | Антагоністи рецептора вітронектину, спосіб одержання цих сполук та фармацевтична композиція |
TW527355B (en) | 1997-07-02 | 2003-04-11 | Bristol Myers Squibb Co | Inhibitors of farnesyl protein transferase |
CA2303846A1 (en) * | 1997-09-24 | 1999-04-01 | Smithkline Beecham Corporation | Vitronectin receptor antagonist |
JP2002500162A (ja) * | 1997-09-24 | 2002-01-08 | スミスクライン・ビーチャム・コーポレイション | ビトロネクチン受容体アンタゴニスト |
US6372719B1 (en) * | 1998-03-04 | 2002-04-16 | Jay Cunningham | ανβ3 integrin antagonists in combination with chemotherapeutic agents |
DE19842415A1 (de) * | 1998-09-16 | 2000-03-23 | Merck Patent Gmbh | Pharmazeutische Zubereitung |
CZ20012320A3 (cs) * | 1998-12-23 | 2002-10-16 | G. D. Searle & Co. | Léčivo s obsahem inhibitoru cyklooxygenázy-2 a jednoho nebo více antineoplastických činidel pro kombinační terapii při léčení neoplasie |
AU747503B2 (en) * | 1999-02-03 | 2002-05-16 | Merck & Co., Inc. | Benzazepine derivatives as alpha-V integrin receptor antagonists |
EP1143946B1 (en) * | 1999-04-30 | 2004-01-28 | The Regents Of The University Of Michigan | Use of benzodiazepines for treating autoimmune diseases induced by apoptosis |
AU6523200A (en) * | 1999-08-06 | 2001-03-05 | Smithkline Beecham Corporation | Vitronectin receptor antagonists useful for the treatment of strokes |
US6514964B1 (en) | 1999-09-27 | 2003-02-04 | Amgen Inc. | Fused cycloheptane and fused azacycloheptane compounds and their methods of use |
DE10028575A1 (de) | 2000-06-14 | 2002-03-14 | Basf Ag | Integrinliganden |
DE10027514A1 (de) * | 2000-06-06 | 2002-01-03 | Basf Ag | Liganden von Integrinrezeptoren |
FR2806082B1 (fr) * | 2000-03-07 | 2002-05-17 | Adir | Nouveaux composes bicycliques antagonistes des recepteurs de la vitronectine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
CA2436130A1 (en) | 2001-01-29 | 2002-08-08 | 3-Dimensional Pharmaceuticals, Inc. | Substituted indoles and their use as integrin antagonists |
WO2002083125A1 (en) * | 2001-04-10 | 2002-10-24 | Smithkline Beecham Corporation | Method of inhibiting adhesion formation |
SE0101386D0 (sv) | 2001-04-20 | 2001-04-20 | Astrazeneca Ab | New compounds |
WO2002090325A2 (en) * | 2001-05-03 | 2002-11-14 | Merck & Co., Inc. | Benzazepinone alpha v integrin receptor antagonists |
EP2428226A1 (en) | 2001-10-22 | 2012-03-14 | The Scripps Research Institute | Antibody targeting compounds |
GB0215867D0 (en) * | 2002-07-09 | 2002-08-14 | Glaxosmithkline Spa | Novel method and compounds |
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SG63579A1 (en) * | 1992-12-21 | 1999-03-30 | Smithkline Beecham Corp | Bicyclic fibrinogen antagonists |
EP0762882A4 (en) * | 1994-06-29 | 2002-09-11 | Smithkline Beecham Corp | Vibronectin Receptor Antagonists |
WO1996000730A1 (en) * | 1994-06-29 | 1996-01-11 | Smithkline Beecham Corporation | Vitronectin receptor antagonists |
EP0777657A1 (en) * | 1994-08-22 | 1997-06-11 | Smithkline Beecham Corporation | Bicyclic compounds |
WO1996026190A1 (en) * | 1995-02-22 | 1996-08-29 | Smithkline Beecham Corporation | Integrin receptor antagonists |
UA60311C2 (uk) * | 1996-10-02 | 2003-10-15 | Смітклайн Бічам Корпорейшн | Антагоністи рецептора вітронектину, спосіб одержання цих сполук та фармацевтична композиція |
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