OA12189A - Vitronectin receptor antagonists. - Google Patents

Vitronectin receptor antagonists. Download PDF

Info

Publication number: OA12189A
Authority: OA; OAPI
Prior art keywords: phenyl; pyridin; methylamino; ethoxy; galkyl
Prior art date: 1998-03-10

Application number

OA00000248A

Other languages

English (en)

Inventor

William H Miller

John G Gleason

Dirk Heerding

James M Samanen

Irene N Uzinskas

Peter J Manley

Original Assignee

Smithkline Beecham Corp

Priority date (The priority date 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 date listed.)

1998-03-10

Filing date

1999-03-10

Publication date

2006-05-09

1999-03-10 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

2006-05-09 Publication of OA12189A publication Critical patent/OA12189A/en

Links

102100022337 Integrin alpha-V Human genes 0.000 title abstract description 16
108010048673 Vitronectin Receptors Proteins 0.000 title abstract description 16
239000002464 receptor antagonist Substances 0.000 title description 2
229940044551 receptor antagonist Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 349
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
238000011282 treatment Methods 0.000 claims abstract description 23
201000010099 disease Diseases 0.000 claims abstract description 20
206010028980 Neoplasm Diseases 0.000 claims abstract description 14
208000001132 Osteoporosis Diseases 0.000 claims abstract description 10
208000037803 restenosis Diseases 0.000 claims abstract description 10
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 7
206010061218 Inflammation Diseases 0.000 claims abstract description 6
230000004054 inflammatory process Effects 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims description 176
238000000034 method Methods 0.000 claims description 112
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
239000002253 acid Substances 0.000 claims description 64
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 58
-1 methylenedioxy Chemical group 0.000 claims description 54
229910052760 oxygen Inorganic materials 0.000 claims description 39
229910052786 argon Inorganic materials 0.000 claims description 28
125000001475 halogen functional group Chemical group 0.000 claims description 27
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
229910052717 sulfur Inorganic materials 0.000 claims description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
102100025248 C-X-C motif chemokine 10 Human genes 0.000 claims description 19
101000858088 Homo sapiens C-X-C motif chemokine 10 Proteins 0.000 claims description 19
210000000988 bone and bone Anatomy 0.000 claims description 19
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
125000006239 protecting group Chemical group 0.000 claims description 14
102100040615 Homeobox protein MSX-2 Human genes 0.000 claims description 13
101000967222 Homo sapiens Homeobox protein MSX-2 Proteins 0.000 claims description 13
208000015842 craniosynostosis 2 Diseases 0.000 claims description 13
239000002246 antineoplastic agent Substances 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
229940034982 antineoplastic agent Drugs 0.000 claims description 11
JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
230000005764 inhibitory process Effects 0.000 claims description 11
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
208000028257 Joubert syndrome with oculorenal defect Diseases 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
230000008569 process Effects 0.000 claims description 9
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DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 8
229960004316 cisplatin Drugs 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 6
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229960000303 topotecan Drugs 0.000 claims description 3
QQEIIOWLNXVJET-FQEVSTJZSA-N (3s)-4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]-3-phenylbutanoic acid Chemical compound CNC1=CC=CC(CCOC=2C=CC(C[C@@H](CC(O)=O)C=3C=CC=CC=3)=CC=2)=N1 QQEIIOWLNXVJET-FQEVSTJZSA-N 0.000 claims description 2
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IPDKGBVODWCUPX-UHFFFAOYSA-N 3-(4-bromophenyl)-4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]butanoic acid Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CC(O)=O)C=3C=CC(Br)=CC=3)=CC=2)=N1 IPDKGBVODWCUPX-UHFFFAOYSA-N 0.000 claims description 2
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FKIUJPKATZMXEU-UHFFFAOYSA-N 3-cyclopropyl-4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]butanoic acid Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CC(O)=O)C3CC3)=CC=2)=N1 FKIUJPKATZMXEU-UHFFFAOYSA-N 0.000 claims description 2
MWIDYJJFSZUTTH-UHFFFAOYSA-N 3-methyl-4-[4-[2-[6-(methylamino)pyridin-3-yl]ethoxy]phenyl]butanoic acid Chemical compound C1=NC(NC)=CC=C1CCOC1=CC=C(CC(C)CC(O)=O)C=C1 MWIDYJJFSZUTTH-UHFFFAOYSA-N 0.000 claims description 2
MNMNKSRAIMNXQS-UHFFFAOYSA-N 3-methyl-4-[4-[3-(pyridin-2-ylamino)propoxy]phenyl]butanoic acid Chemical compound C1=CC(CC(CC(O)=O)C)=CC=C1OCCCNC1=CC=CC=N1 MNMNKSRAIMNXQS-UHFFFAOYSA-N 0.000 claims description 2
SUEPPQJCLHQCOC-UHFFFAOYSA-N 4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]-3-(4-propan-2-ylphenyl)butanoic acid Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CC(O)=O)C=3C=CC(=CC=3)C(C)C)=CC=2)=N1 SUEPPQJCLHQCOC-UHFFFAOYSA-N 0.000 claims description 2
BUAVKXYCGMZUOY-UHFFFAOYSA-N 4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]-3-thiophen-2-ylbutanoic acid Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CC(O)=O)C=3SC=CC=3)=CC=2)=N1 BUAVKXYCGMZUOY-UHFFFAOYSA-N 0.000 claims description 2
UMSOUUMTSPJKIP-UHFFFAOYSA-N 4-[4-[3-[(4-methylpyridin-2-yl)amino]propoxy]phenyl]-3-(4-propan-2-ylphenyl)butanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(CC(O)=O)CC(C=C1)=CC=C1OCCCNC1=CC(C)=CC=N1 UMSOUUMTSPJKIP-UHFFFAOYSA-N 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
230000008485 antagonism Effects 0.000 claims 4
CVIPGYDGAAPSKL-UHFFFAOYSA-N 2-[benzyl-[[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]methyl]amino]acetic acid Chemical compound CNC1=CC=CC(CCOC=2C=CC(CN(CC(O)=O)CC=3C=CC=CC=3)=CC=2)=N1 CVIPGYDGAAPSKL-UHFFFAOYSA-N 0.000 claims 1
SDFOJSFWUHHYNZ-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]butanoic acid Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CC(O)=O)C=3SC4=CC=CC=C4N=3)=CC=2)=N1 SDFOJSFWUHHYNZ-UHFFFAOYSA-N 0.000 claims 1
VEEBAWVYVGVHBT-UHFFFAOYSA-N 3-(furan-2-yl)-4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]butanoic acid Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CC(O)=O)C=3OC=CC=3)=CC=2)=N1 VEEBAWVYVGVHBT-UHFFFAOYSA-N 0.000 claims 1
MVJOIQPJZKTESD-UHFFFAOYSA-N 3-methyl-4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]but-3-enoic acid Chemical compound CNC1=CC=CC(CCOC=2C=CC(C=C(C)CC(O)=O)=CC=2)=N1 MVJOIQPJZKTESD-UHFFFAOYSA-N 0.000 claims 1
GQAGHOJOIIYQFT-UHFFFAOYSA-N 3-methyl-4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]butanoic acid Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(C)CC(O)=O)=CC=2)=N1 GQAGHOJOIIYQFT-UHFFFAOYSA-N 0.000 claims 1
HCPRPQNWWRMIHG-UHFFFAOYSA-N 3-phenyl-3-[4-[4-(pyridin-2-ylamino)butyl]anilino]propanoic acid Chemical compound C=1C=CC=CC=1C(CC(=O)O)NC(C=C1)=CC=C1CCCCNC1=CC=CC=N1 HCPRPQNWWRMIHG-UHFFFAOYSA-N 0.000 claims 1
IAMUMIBDQILHMZ-UHFFFAOYSA-N 3-phenyl-4-[4-[3-(pyridin-1-ium-2-ylamino)propoxy]phenyl]butanoate Chemical compound C=1C=CC=CC=1C(CC(=O)O)CC(C=C1)=CC=C1OCCCNC1=CC=CC=N1 IAMUMIBDQILHMZ-UHFFFAOYSA-N 0.000 claims 1
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SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
230000033115 angiogenesis Effects 0.000 claims 1
125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
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230000014399 negative regulation of angiogenesis Effects 0.000 claims 1
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FEDPQILTURDKKH-UHFFFAOYSA-N ethyl 4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]-3-(4-methyl-1,3-thiazol-2-yl)butanoate Chemical compound N=1C(C)=CSC=1C(CC(=O)OCC)CC(C=C1)=CC=C1OCCC1=CC=CC(NC)=N1 FEDPQILTURDKKH-UHFFFAOYSA-N 0.000 description 2
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FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
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208000027202 mammary Paget disease Diseases 0.000 description 2
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JOTQJBDUSFHREU-LLVKDONJSA-N methyl (3R)-4-(4-hydroxyphenyl)-3-(1,3-thiazol-2-yl)butanoate Chemical compound C([C@H](CC(=O)OC)C=1SC=CN=1)C1=CC=C(O)C=C1 JOTQJBDUSFHREU-LLVKDONJSA-N 0.000 description 2
JOTQJBDUSFHREU-NSHDSACASA-N methyl (3S)-4-(4-hydroxyphenyl)-3-(1,3-thiazol-2-yl)butanoate Chemical compound C([C@@H](CC(=O)OC)C=1SC=CN=1)C1=CC=C(O)C=C1 JOTQJBDUSFHREU-NSHDSACASA-N 0.000 description 2
LEFNJHVMJFCUFV-DUXPYHPUSA-N methyl (e)-4-(4-hydroxyphenyl)but-2-enoate Chemical compound COC(=O)\C=C\CC1=CC=C(O)C=C1 LEFNJHVMJFCUFV-DUXPYHPUSA-N 0.000 description 2
DDMFLDILYVCMIW-HWKANZROSA-N methyl (e)-4-(4-methoxyphenyl)but-2-enoate Chemical compound COC(=O)\C=C\CC1=CC=C(OC)C=C1 DDMFLDILYVCMIW-HWKANZROSA-N 0.000 description 2
AHANXHACCTXGAE-UHFFFAOYSA-N methyl 2-(4-hydroxy-2-phenoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C=C1OC1=CC=CC=C1 AHANXHACCTXGAE-UHFFFAOYSA-N 0.000 description 2
XGDZEDRBLVIUMX-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C=C1 XGDZEDRBLVIUMX-UHFFFAOYSA-N 0.000 description 2
LDKQBNAANQSXSA-UHFFFAOYSA-N methyl 2-(4-methoxy-2-phenoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(OC)C=C1OC1=CC=CC=C1 LDKQBNAANQSXSA-UHFFFAOYSA-N 0.000 description 2
MHJNOSUWMQMJSD-UHFFFAOYSA-N methyl 2-[(4-hydroxy-2-methoxyphenyl)methylamino]acetate Chemical compound COC(=O)CNCC1=CC=C(O)C=C1OC MHJNOSUWMQMJSD-UHFFFAOYSA-N 0.000 description 2
KXRWSHXHMXMWCM-UHFFFAOYSA-N methyl 2-[n-[(4-hydroxyphenyl)methyl]anilino]acetate Chemical compound C=1C=CC=CC=1N(CC(=O)OC)CC1=CC=C(O)C=C1 KXRWSHXHMXMWCM-UHFFFAOYSA-N 0.000 description 2
DTHOJDDHHZQFDG-UHFFFAOYSA-N methyl 2-[n-[(4-methoxyphenyl)methyl]anilino]acetate Chemical compound C=1C=CC=CC=1N(CC(=O)OC)CC1=CC=C(OC)C=C1 DTHOJDDHHZQFDG-UHFFFAOYSA-N 0.000 description 2
KNKIXYMOHMYZJR-UHFFFAOYSA-N methyl 2-thiophen-2-ylacetate Chemical compound COC(=O)CC1=CC=CS1 KNKIXYMOHMYZJR-UHFFFAOYSA-N 0.000 description 2
YJYIUNANXAURRI-UHFFFAOYSA-N methyl 3-(furan-2-yl)-4-(4-methoxyphenyl)butanoate Chemical compound C=1C=COC=1C(CC(=O)OC)CC1=CC=C(OC)C=C1 YJYIUNANXAURRI-UHFFFAOYSA-N 0.000 description 2
PLNJUBIUGVATKW-UHFFFAOYSA-N methyl 3-(furan-2-yl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=CO1 PLNJUBIUGVATKW-UHFFFAOYSA-N 0.000 description 2
YBHMPCBPKFDLND-UHFFFAOYSA-N methyl 3-[(4-methoxyphenyl)methyl]pent-4-ynoate Chemical compound COC(=O)CC(C#C)CC1=CC=C(OC)C=C1 YBHMPCBPKFDLND-UHFFFAOYSA-N 0.000 description 2
PKRJJKXKYXRLNF-UHFFFAOYSA-N methyl 3-[[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]methyl]-5-phenylpentanoate Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CCC=3C=CC=CC=3)CC(=O)OC)=CC=2)=N1 PKRJJKXKYXRLNF-UHFFFAOYSA-N 0.000 description 2
ASGUADOJYRUTNV-UHFFFAOYSA-N methyl 3-[[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]methyl]pent-4-enoate Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CC(=O)OC)C=C)=CC=2)=N1 ASGUADOJYRUTNV-UHFFFAOYSA-N 0.000 description 2
BXJWQYPYYCKLNP-UHFFFAOYSA-N methyl 3-benzyl-4-(4-hydroxyphenyl)butanoate Chemical compound C=1C=C(O)C=CC=1CC(CC(=O)OC)CC1=CC=CC=C1 BXJWQYPYYCKLNP-UHFFFAOYSA-N 0.000 description 2
PRCHFYCKORQMRZ-UHFFFAOYSA-N methyl 3-benzyl-4-(4-methoxyphenyl)butanoate Chemical compound C=1C=C(OC)C=CC=1CC(CC(=O)OC)CC1=CC=CC=C1 PRCHFYCKORQMRZ-UHFFFAOYSA-N 0.000 description 2
BFJDQSGLWWVPIB-UHFFFAOYSA-N methyl 3-benzyl-4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]butanoate Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CC(=O)OC)CC=3C=CC=CC=3)=CC=2)=N1 BFJDQSGLWWVPIB-UHFFFAOYSA-N 0.000 description 2
GBFKHOMPLQCKFU-UHFFFAOYSA-N methyl 3-cyclopropyl-4-(4-methoxyphenyl)butanoate Chemical compound C1CC1C(CC(=O)OC)CC1=CC=C(OC)C=C1 GBFKHOMPLQCKFU-UHFFFAOYSA-N 0.000 description 2
POUYDQBUSCRIOT-UHFFFAOYSA-N methyl 3-formyl-4-(4-methoxyphenyl)butanoate Chemical compound COC(=O)CC(C=O)CC1=CC=C(OC)C=C1 POUYDQBUSCRIOT-UHFFFAOYSA-N 0.000 description 2
RQWVXEOOYSWNFP-UHFFFAOYSA-N methyl 3-methyl-4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]but-3-enoate Chemical compound CNC1=CC=CC(CCOC=2C=CC(C=C(C)CC(=O)OC)=CC=2)=N1 RQWVXEOOYSWNFP-UHFFFAOYSA-N 0.000 description 2
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JZLXJJNNVDYIBN-UHFFFAOYSA-N methyl 4-(4-hydroxyphenyl)-3-(4-propan-2-ylphenyl)butanoate Chemical group C=1C=C(C(C)C)C=CC=1C(CC(=O)OC)CC1=CC=C(O)C=C1 JZLXJJNNVDYIBN-UHFFFAOYSA-N 0.000 description 2
UZHISWLCHOMTIO-UHFFFAOYSA-N methyl 4-(4-hydroxyphenyl)butanoate Chemical compound COC(=O)CCCC1=CC=C(O)C=C1 UZHISWLCHOMTIO-UHFFFAOYSA-N 0.000 description 2
UIRKJYZBNHUAAY-UHFFFAOYSA-N methyl 4-(4-methoxyphenyl)-3-(1,3-oxazol-2-yl)butanoate Chemical compound N=1C=COC=1C(CC(=O)OC)CC1=CC=C(OC)C=C1 UIRKJYZBNHUAAY-UHFFFAOYSA-N 0.000 description 2
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NFZWIMOIORHGEH-UHFFFAOYSA-N n-methoxy-n-methyl-2-(4-phenylmethoxyphenyl)acetamide Chemical compound C1=CC(CC(=O)N(C)OC)=CC=C1OCC1=CC=CC=C1 NFZWIMOIORHGEH-UHFFFAOYSA-N 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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150000002431 hydrogen Chemical class 0.000 description 1
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238000010255 intramuscular injection Methods 0.000 description 1
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238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
206010023332 keratitis Diseases 0.000 description 1
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239000011968 lewis acid catalyst Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
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239000006166 lysate Substances 0.000 description 1
208000002780 macular degeneration Diseases 0.000 description 1
RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
229940071648 metered dose inhaler Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
VEHNJODPIZBWOL-WEVVVXLNSA-N methyl (e)-4-(4-phenylmethoxyphenyl)but-2-enoate Chemical compound C1=CC(C/C=C/C(=O)OC)=CC=C1OCC1=CC=CC=C1 VEHNJODPIZBWOL-WEVVVXLNSA-N 0.000 description 1
FJEOSEAUTNEZDF-UHFFFAOYSA-N methyl 2-[2-phenoxy-4-[5-(pyridin-2-ylamino)pentoxy]phenyl]acetate Chemical compound C1=C(OC=2C=CC=CC=2)C(CC(=O)OC)=CC=C1OCCCCCNC1=CC=CC=N1 FJEOSEAUTNEZDF-UHFFFAOYSA-N 0.000 description 1
OWFPSZQZAFEKHK-UHFFFAOYSA-N methyl 2-[4-tri(propan-2-yl)silyloxyphenyl]acetate Chemical compound COC(=O)CC1=CC=C(O[Si](C(C)C)(C(C)C)C(C)C)C=C1 OWFPSZQZAFEKHK-UHFFFAOYSA-N 0.000 description 1
HRWSGUWYKPQLHP-UHFFFAOYSA-N methyl 2-[[2-methoxy-4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]methylamino]acetate Chemical compound CNC1=CC=CC(CCOC=2C=C(OC)C(CNCC(=O)OC)=CC=2)=N1 HRWSGUWYKPQLHP-UHFFFAOYSA-N 0.000 description 1
AJHZGVMKIXHMNP-UHFFFAOYSA-N methyl 2-anilinoacetate;hydrochloride Chemical compound Cl.COC(=O)CNC1=CC=CC=C1 AJHZGVMKIXHMNP-UHFFFAOYSA-N 0.000 description 1
CQLQMKNWVKHXAL-UHFFFAOYSA-N methyl 3-(furan-2-yl)-4-(4-hydroxyphenyl)butanoate Chemical compound C=1C=COC=1C(CC(=O)OC)CC1=CC=C(O)C=C1 CQLQMKNWVKHXAL-UHFFFAOYSA-N 0.000 description 1
OYVBPFWLDNQBAR-UHFFFAOYSA-N methyl 3-[(4-hydroxyphenyl)methyl]pent-4-enoate Chemical compound COC(=O)CC(C=C)CC1=CC=C(O)C=C1 OYVBPFWLDNQBAR-UHFFFAOYSA-N 0.000 description 1
BZHQJFZWSUVPBW-UHFFFAOYSA-N methyl 3-[[4-[2-[6-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]pyridin-2-yl]ethoxy]phenyl]methyl]pent-4-ynoate Chemical compound C1=CC(CC(CC(=O)OC)C#C)=CC=C1OCCC1=CC=CC(NCC(=O)OC(C)(C)C)=N1 BZHQJFZWSUVPBW-UHFFFAOYSA-N 0.000 description 1
NDRSMXIAHTZREZ-UHFFFAOYSA-N methyl 4-(4-hydroxyphenyl)-3-(1,3-oxazol-2-yl)butanoate Chemical compound N=1C=COC=1C(CC(=O)OC)CC1=CC=C(O)C=C1 NDRSMXIAHTZREZ-UHFFFAOYSA-N 0.000 description 1
JOTQJBDUSFHREU-UHFFFAOYSA-N methyl 4-(4-hydroxyphenyl)-3-(1,3-thiazol-2-yl)butanoate Chemical compound N=1C=CSC=1C(CC(=O)OC)CC1=CC=C(O)C=C1 JOTQJBDUSFHREU-UHFFFAOYSA-N 0.000 description 1
OROMDIVIXPINEM-UHFFFAOYSA-N methyl 4-(4-hydroxyphenyl)-3-thiophen-2-ylbutanoate Chemical compound C=1C=CSC=1C(CC(=O)OC)CC1=CC=C(O)C=C1 OROMDIVIXPINEM-UHFFFAOYSA-N 0.000 description 1
AQXAZEHBZZARKB-UHFFFAOYSA-N methyl 4-(4-methoxyphenyl)-3-thiophen-2-ylbutanoate Chemical compound C=1C=CSC=1C(CC(=O)OC)CC1=CC=C(OC)C=C1 AQXAZEHBZZARKB-UHFFFAOYSA-N 0.000 description 1
OHLMRVLMXWJMRL-UHFFFAOYSA-N methyl 4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]-3-(1,3-oxazol-2-yl)butanoate Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CC(=O)OC)C=3OC=CN=3)=CC=2)=N1 OHLMRVLMXWJMRL-UHFFFAOYSA-N 0.000 description 1
AWXLZTPQZOLSEX-UHFFFAOYSA-N methyl 4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]-3-(4-propan-2-ylphenyl)butanoate Chemical compound CNC1=CC=CC(CCOC=2C=CC(CC(CC(=O)OC)C=3C=CC(=CC=3)C(C)C)=CC=2)=N1 AWXLZTPQZOLSEX-UHFFFAOYSA-N 0.000 description 1
LEIAZRWQZSQFLF-UHFFFAOYSA-N methyl 4-[4-[2-[6-(methylamino)pyridin-2-yl]ethoxy]phenyl]butanoate Chemical compound CNC1=CC=CC(CCOC=2C=CC(CCCC(=O)OC)=CC=2)=N1 LEIAZRWQZSQFLF-UHFFFAOYSA-N 0.000 description 1
SKIIBFPBJNJTQS-UHFFFAOYSA-N methyl 4-[4-[3-[(4-methylpyridin-2-yl)amino]propoxy]phenyl]-3-(4-propan-2-ylphenyl)butanoate Chemical compound C=1C=C(C(C)C)C=CC=1C(CC(=O)OC)CC(C=C1)=CC=C1OCCCNC1=CC(C)=CC=N1 SKIIBFPBJNJTQS-UHFFFAOYSA-N 0.000 description 1
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YRRWNBMOJMMXQY-UHFFFAOYSA-N n,n-dimethylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=CN=C1 YRRWNBMOJMMXQY-UHFFFAOYSA-N 0.000 description 1
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SJADZVLGLQJTAO-UHFFFAOYSA-N n-[(2-methylpropan-2-yl)oxy]pyridin-2-amine Chemical compound CC(C)(C)ONC1=CC=CC=N1 SJADZVLGLQJTAO-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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239000001509 sodium citrate Substances 0.000 description 1
229960001790 sodium citrate Drugs 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
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BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
CHWMFCCGEWQABK-UHFFFAOYSA-N tert-butyl 7-methyl-3,4-dihydro-2h-1,8-naphthyridine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)(C)C)C2=NC(C)=CC=C21 CHWMFCCGEWQABK-UHFFFAOYSA-N 0.000 description 1
AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
TUUMNHGLJLFEDM-UHFFFAOYSA-N tert-butyl n-[4-(4-nitrophenyl)butyl]-n-pyridin-2-ylcarbamate Chemical compound C=1C=CC=NC=1N(C(=O)OC(C)(C)C)CCCCC1=CC=C([N+]([O-])=O)C=C1 TUUMNHGLJLFEDM-UHFFFAOYSA-N 0.000 description 1
ORUGTGTZBRUQIT-UHFFFAOYSA-N tert-butyl n-pyridin-2-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=N1 ORUGTGTZBRUQIT-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
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HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
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230000009466 transformation Effects 0.000 description 1
108091007466 transmembrane glycoproteins Proteins 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
LGSAOJLQTXCYHF-UHFFFAOYSA-N tri(propan-2-yl)-tri(propan-2-yl)silyloxysilane Chemical compound CC(C)[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)C(C)C LGSAOJLQTXCYHF-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
ITRBOGBMPGNZBO-AJRGADBESA-N undulifoline Chemical compound C1OCC[C@@H]2[C@H]3N(C)CC[C@@H]2[C@]1(C(=O)OC)C1=C3C2=CC=CC=C2N1 ITRBOGBMPGNZBO-AJRGADBESA-N 0.000 description 1
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Classifications

- 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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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- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
- 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
- C07D401/12—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
- 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
- C07D409/12—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 chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

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Heart & Thoracic Surgery (AREA)
Orthopedic Medicine & Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
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OA00000248A 1998-03-10 1999-03-10 Vitronectin receptor antagonists. OA12189A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7761098P	1998-03-10	1998-03-10
US9606398P	1998-08-11	1998-08-11

Publications (1)

Publication Number	Publication Date
OA12189A true OA12189A (en)	2006-05-09

Family

ID=26759473

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA00000248A OA12189A (en)	1998-03-10	1999-03-10	Vitronectin receptor antagonists.

Country Status (24)

Country	Link
EP (1)	EP1061921A4 (fr)
JP (1)	JP2002506033A (fr)
KR (1)	KR20010041812A (fr)
CN (1)	CN1299282A (fr)
AP (1)	AP2000001898A0 (fr)
AR (1)	AR015241A1 (fr)
AU (1)	AU758498B2 (fr)
BG (1)	BG104824A (fr)
BR (1)	BR9908636A (fr)
CA (1)	CA2323208A1 (fr)
CO (1)	CO5080762A1 (fr)
DZ (1)	DZ2741A1 (fr)
EA (1)	EA200000921A1 (fr)
HU (1)	HUP0101143A3 (fr)
ID (1)	ID26223A (fr)
IL (1)	IL138245A0 (fr)
NO (1)	NO20004503L (fr)
OA (1)	OA12189A (fr)
PE (1)	PE20000323A1 (fr)
PL (1)	PL342881A1 (fr)
SK (1)	SK13292000A3 (fr)
TR (1)	TR200002625T2 (fr)
UY (2)	UY25421A1 (fr)
WO (1)	WO1999045927A1 (fr)

Families Citing this family (19)

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DE19939981A1 (de) *	1999-08-24	2001-03-01	Merck Patent Gmbh	Neue Inhibitoren des Integrins alphavß3
DE19939980A1 (de)	1999-08-24	2001-03-01	Merck Patent Gmbh	Inhibitoren des Integrins alphavbeta¶3¶
US6881736B1 (en)	1999-09-07	2005-04-19	Smithkline Beecham Corporation	Vitronectin receptor antagonists
EG24179A (en) *	1999-09-07	2008-09-28	Smithkline Beecham Corp	Vitronectin receptor antagonists
US6448278B2 (en)	1999-12-23	2002-09-10	Pfizer Inc.	Procollagen C-proteinase inhibitors
GB9930570D0 (en) *	1999-12-23	2000-02-16	Pfizer Ltd	Therapy
FR2808798A1 (fr) *	2000-05-09	2001-11-16	Hoechst Marion Roussel Inc	Nouveaux derives antagonistes du recepteur de la vitronectine
PE20020665A1 (es)	2000-06-15	2002-08-14	Pharmacia Corp	ACIDO CICLOALQUIL FENIL ALCANOICO COMO ANTAGONISTA DE INTEGRINAS OVß3
US6531494B1 (en)	2001-08-29	2003-03-11	Pharmacia Corporation	Gem-substituted αvβ3 antagonists
US6645993B2 (en)	2001-03-30	2003-11-11	Warner-Lambert Company	3-heterocyclylpropanohydroxamic acid PCP inhibitors
US6716842B2 (en)	2002-04-05	2004-04-06	Warner-Lambert Company, Llc	Antidiabetic agents
US20070275956A1 (en) *	2003-10-14	2007-11-29	Lohray Braj B	Novel Heterocyclic Compounds
RU2367661C2 (ru) *	2004-03-05	2009-09-20	Тайсо Фармасьютикал Ко., Лтд.	Производные тиазола
UA87854C2 (en)	2004-06-07	2009-08-25	Мерк Энд Ко., Инк.	N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators
EP1879864A1 (fr)	2005-04-20	2008-01-23	Janssen Pharmaceutica N.V.	Modulateurs de la thrombine a base de pyridine n-oxyde fluoree et procede de n-oxydation d'heteroaryles azotes
DK3040329T3 (en) *	2013-08-29	2019-01-28	Kyoto Pharma Ind	AROMATIC RELATIONSHIP AND APPLICATION THEREOF IN THE TREATMENT OF DISEASES CONNECTED WITH BONE METABOLISM.
SI3050878T1 (sl)	2013-09-24	2022-01-31	Fujifilm Corporation	Nova dušik-vsebujoča spojina ali njena sol ali kovinski kompleks le-te
JP6649902B2 (ja)	2014-05-30	2020-02-19	ファイザー・インク	選択的アンドロゲン受容体モジュレーターとしてのカルボニトリル誘導体
WO2023275715A1 (fr)	2021-06-30	2023-01-05	Pfizer Inc.	Métabolites de modulateurs sélectifs du récepteur des androgènes

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2000502704A (ja) *	1995-12-29	2000-03-07	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拮抗物質
JP2000502708A (ja) *	1995-12-29	2000-03-07	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拮抗物質

1999
- 1999-03-10 AR ARP990101019A patent/AR015241A1/es not_active Application Discontinuation
- 1999-03-10 HU HU0101143A patent/HUP0101143A3/hu unknown
- 1999-03-10 BR BR9908636-0A patent/BR9908636A/pt not_active Application Discontinuation
- 1999-03-10 IL IL13824599A patent/IL138245A0/xx unknown
- 1999-03-10 TR TR2000/02625T patent/TR200002625T2/xx unknown
- 1999-03-10 EA EA200000921A patent/EA200000921A1/ru unknown
- 1999-03-10 EP EP99909952A patent/EP1061921A4/fr not_active Withdrawn
- 1999-03-10 SK SK1329-2000A patent/SK13292000A3/sk unknown
- 1999-03-10 AU AU29033/99A patent/AU758498B2/en not_active Ceased
- 1999-03-10 DZ DZ990042A patent/DZ2741A1/fr active
- 1999-03-10 AP APAP/P/2000/001898A patent/AP2000001898A0/en unknown
- 1999-03-10 PE PE1999000188A patent/PE20000323A1/es not_active Application Discontinuation
- 1999-03-10 CO CO99014712A patent/CO5080762A1/es unknown
- 1999-03-10 WO PCT/US1999/005232 patent/WO1999045927A1/fr not_active Ceased
- 1999-03-10 OA OA00000248A patent/OA12189A/en unknown
- 1999-03-10 PL PL99342881A patent/PL342881A1/xx unknown
- 1999-03-10 KR KR1020007010091A patent/KR20010041812A/ko not_active Withdrawn
- 1999-03-10 CN CN99805833A patent/CN1299282A/zh active Pending
- 1999-03-10 JP JP2000535342A patent/JP2002506033A/ja not_active Withdrawn
- 1999-03-10 CA CA002323208A patent/CA2323208A1/fr not_active Abandoned
- 1999-03-10 ID IDW20001737A patent/ID26223A/id unknown
- 1999-03-10 UY UY25421A patent/UY25421A1/es unknown
- 1999-05-19 UY UY25519A patent/UY25519A1/es unknown
2000
- 2000-09-08 NO NO20004503A patent/NO20004503L/no unknown
- 2000-10-03 BG BG104824A patent/BG104824A/xx unknown

Also Published As

Publication number	Publication date
AR015241A1 (es)	2001-04-18
TR200002625T2 (tr)	2000-12-21
UY25519A1 (es)	1999-12-13
ID26223A (id)	2000-12-07
PE20000323A1 (es)	2000-05-24
CN1299282A (zh)	2001-06-13
AU2903399A (en)	1999-09-27
BR9908636A (pt)	2002-01-08
AU758498B2 (en)	2003-03-20
HUP0101143A3 (en)	2002-12-28
CO5080762A1 (es)	2001-09-25
WO1999045927A1 (fr)	1999-09-16
UY25421A1 (es)	2001-07-31
HUP0101143A2 (hu)	2001-08-28
AP2000001898A0 (en)	2000-09-30
CA2323208A1 (fr)	1999-09-16
SK13292000A3 (sk)	2001-06-11
NO20004503D0 (no)	2000-09-08
BG104824A (en)	2001-05-31
EA200000921A1 (ru)	2001-04-23
KR20010041812A (ko)	2001-05-25
DZ2741A1 (fr)	2003-09-08
JP2002506033A (ja)	2002-02-26
PL342881A1 (en)	2001-07-16
IL138245A0 (en)	2001-10-31
EP1061921A1 (fr)	2000-12-27
NO20004503L (no)	2000-10-10
EP1061921A4 (fr)	2005-03-30

Publication	Publication Date	Title
OA12189A (en)	2006-05-09	Vitronectin receptor antagonists.
AU733417B2 (en)	2001-05-17	Vitronectin receptor antagonists
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MX2008014284A (es)	2008-11-18	Derivados biciclicos como inhibidores de cetp.
CN103562200A (zh)	2014-02-05	用于治疗关节炎的新咪唑衍生物
JPWO1999046232A1 (ja)	2002-10-15	カルボン酸誘導体およびその誘導体を有効成分として含有する薬剤
TW201823208A (zh)	2018-07-01	N－醯基胺基酸化合物及其使用方法
JP2012525390A (ja)	2012-10-22	置換イミダゾ［１，２−ａ］ピリジン誘導体、医薬組成物、及びβ−セクレターゼ阻害剤としての使用方法
CN101213184A (zh)	2008-07-02	包含不饱和或环状连接基团的杂芳基取代的酰胺及其作为药物的用途
AU738433B2 (en)	2001-09-20	Vitronectin receptor antagonists
US6610701B2 (en)	2003-08-26	Thrombin inhibitors
CA2758961A1 (fr)	2010-11-04	Derives d'isoquinoline substitues, compositions pharmaceutiques et leurs methodes d'utilisation en tant qu'inhibiteurs de .beta.-secretase
EP1218005B1 (fr)	2004-12-15	Antagonistes du recepteur de la vitronectine
JP4647726B2 (ja)	2011-03-09	新規なアニリド化合物及びこれを含有する医薬
US20020147334A1 (en)	2002-10-10	Vitronectin Receptor Antagonists
GB2264115A (en)	1993-08-18	1h-2-methylimidazo(4,5-c)pyridinyl derivatives as paf antagonists
US6881736B1 (en)	2005-04-19	Vitronectin receptor antagonists
EP1268429B1 (fr)	2004-08-18	Composes bicycliques antagonistes des recepteurs de la vitronectine, leur procede de preparation et les compositions qui les contiennent
JPH06128257A (ja)	1994-05-10	ピリドジアゼピン化合物
MXPA00008847A (en)	2001-09-07	Vitronectin receptor antagonists
CZ20003289A3 (cs)	2001-03-14	Antagonisté receptoru vitronektinu
HK1241881B (zh)	2021-01-29	作为mglur4的调节剂的3-(4-乙炔基苯基)六氢嘧啶-2，4-二酮衍生物