SK285029B6 - Antagonisty receptorov vitronektínu, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Info

Publication number

SK285029B6

SK285029B6 SK425-99A SK42599A SK285029B6 SK 285029 B6 SK285029 B6 SK 285029B6 SK 42599 A SK42599 A SK 42599A SK 285029 B6 SK285029 B6 SK 285029B6

Authority

SK

Slovakia

Prior art keywords

benzazepine

oxo

tetrahydro

propyloxy

methyl

Prior art date

1996-10-02

Links

• Espacenet
• Global Dossier
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• 238000002360 preparation method Methods 0.000 title claims abstract description 94
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
• 230000008569 process Effects 0.000 title claims abstract description 5
• 102100022337 Integrin alpha-V Human genes 0.000 title description 21
• 108010048673 Vitronectin Receptors Proteins 0.000 title description 21
• 239000002464 receptor antagonist Substances 0.000 title description 3
• 229940044551 receptor antagonist Drugs 0.000 title description 3
• 238000011282 treatment Methods 0.000 claims abstract description 21
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• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 10
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• 238000004519 manufacturing process Methods 0.000 claims abstract description 9
• 230000033115 angiogenesis Effects 0.000 claims abstract description 7
• 150000001875 compounds Chemical class 0.000 claims description 324
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 100
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• 125000000217 alkyl group Chemical group 0.000 claims description 58
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 239000002253 acid Substances 0.000 claims description 30
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• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
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• 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 2
• 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 2
• AETRKKIQMLUFRW-UHFFFAOYSA-N methyl 2-[2-benzyl-8-[3-[(2-methylpropan-2-yl)oxycarbonyl-pyridin-2-ylamino]propoxy]-3-oxo-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C1=C2CN(CC=3C=CC=CC=3)C(=O)C(CC(=O)OC)CC2=CC=C1OCCCN(C(=O)OC(C)(C)C)C1=CC=CC=N1 AETRKKIQMLUFRW-UHFFFAOYSA-N 0.000 description 2
• HAWPDYJYKUZVGJ-UHFFFAOYSA-N methyl 2-[2-methyl-3-oxo-8-[3-(pyridin-2-ylamino)propoxy]-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C1=C2CN(C)C(=O)C(CC(=O)OC)CC2=CC=C1OCCCNC1=CC=CC=N1 HAWPDYJYKUZVGJ-UHFFFAOYSA-N 0.000 description 2
• QGRKKKRUWQWGRT-UHFFFAOYSA-N methyl 2-[2-methyl-8-[3-[(4-nitrophenyl)methoxycarbonylamino]propoxy]-3-oxo-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C1=C2CN(C)C(=O)C(CC(=O)OC)CC2=CC=C1OCCCNC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 QGRKKKRUWQWGRT-UHFFFAOYSA-N 0.000 description 2
• VYGWPDHNDHJBCN-UHFFFAOYSA-N methyl 2-[8-(3-aminopropoxy)-2-methyl-3-oxo-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C1N(C)C(=O)C(CC(=O)OC)CC2=CC=C(OCCCN)C=C21 VYGWPDHNDHJBCN-UHFFFAOYSA-N 0.000 description 2
• FZJXJGONQXSZKU-UHFFFAOYSA-N methyl 2-[8-[2-(1h-benzimidazol-2-yl)ethoxy]-3-oxo-1,2,4,5-tetrahydro-2-benzazepin-4-yl]acetate Chemical compound C1=C2CNC(=O)C(CC(=O)OC)CC2=CC=C1OCCC1=NC2=CC=CC=C2N1 FZJXJGONQXSZKU-UHFFFAOYSA-N 0.000 description 2
• HVKLJINKLPNYLY-UHFFFAOYSA-N methyl 2-[8-[3-[(2-methylpropan-2-yl)oxycarbonyl-pyridin-2-ylamino]propoxy]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-3-oxo-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical compound C1=C2CN(CC(=O)OC(C)(C)C)C(=O)C(CC(=O)OC)CC2=CC=C1OCCCN(C(=O)OC(C)(C)C)C1=CC=CC=N1 HVKLJINKLPNYLY-UHFFFAOYSA-N 0.000 description 2
• JILRDIJMUXXSCC-UHFFFAOYSA-N methyl 2-[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 compound C1=C2CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)C(CC(=O)OC)CC2=CC=C1OCCCN(C(=O)OC(C)(C)C)C1=CC=CC=N1 JILRDIJMUXXSCC-UHFFFAOYSA-N 0.000 description 2
• WFERTFJUYHIUHU-UHFFFAOYSA-N methyl 2-[8-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propoxy]-3-oxo-1,2,4,5-tetrahydro-2-benzazepin-4-yl]acetate Chemical compound C1NC(=O)C(CC(=O)OC)CC2=CC=C(OCCCNC(=O)OC(C)(C)C)C=C21 WFERTFJUYHIUHU-UHFFFAOYSA-N 0.000 description 2
• 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 2
• AHKQHMWRKXSXEF-UHFFFAOYSA-N methyl 2-[8-[3-[3,3-dimethylbutanoyl(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(=O)CC(C)(C)C)C1=CC=CC=N1 AHKQHMWRKXSXEF-UHFFFAOYSA-N 0.000 description 2
• 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 2
• NSKVDUPDIQAOEQ-UHFFFAOYSA-N methyl 2-[8-[3-[methyl(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)C1=CC=CC=N1 NSKVDUPDIQAOEQ-UHFFFAOYSA-N 0.000 description 2
• NLQPTCGXBABSPV-UHFFFAOYSA-N methyl 2-[8-hydroxy-3-oxo-2-(2,2,2-trifluoroethyl)-4,5-dihydro-1h-2-benzazepin-4-yl]acetate Chemical class C1N(CC(F)(F)F)C(=O)C(CC(=O)OC)CC2=CC=C(O)C=C21 NLQPTCGXBABSPV-UHFFFAOYSA-N 0.000 description 2
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