CA2241633A1 - Vitronectin receptor antagonists - Google Patents
Vitronectin receptor antagonists Download PDFInfo
- Publication number
- CA2241633A1 CA2241633A1 CA002241633A CA2241633A CA2241633A1 CA 2241633 A1 CA2241633 A1 CA 2241633A1 CA 002241633 A CA002241633 A CA 002241633A CA 2241633 A CA2241633 A CA 2241633A CA 2241633 A1 CA2241633 A1 CA 2241633A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- oxo
- carbonyl
- tetrahydro
- benzodiazepine
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 102100022337 Integrin alpha-V Human genes 0.000 title claims abstract description 39
- 108010048673 Vitronectin Receptors Proteins 0.000 title claims abstract description 39
- 229940044551 receptor antagonist Drugs 0.000 title abstract description 5
- 239000002464 receptor antagonist Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 328
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 331
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 176
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 171
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 140
- -1 methylenedioxy Chemical group 0.000 claims description 123
- 238000000034 method Methods 0.000 claims description 109
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 67
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 66
- 239000002253 acid Substances 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 35
- 239000002319 fibrinogen receptor antagonist Substances 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 108010012088 Fibrinogen Receptors Proteins 0.000 claims description 23
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000006239 protecting group Chemical group 0.000 claims description 19
- 208000006386 Bone Resorption Diseases 0.000 claims description 18
- 230000024279 bone resorption Effects 0.000 claims description 18
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 201000001320 Atherosclerosis Diseases 0.000 claims description 11
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 208000037803 restenosis Diseases 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
- 102100025248 C-X-C motif chemokine 10 Human genes 0.000 claims description 8
- 101000858088 Homo sapiens C-X-C motif chemokine 10 Proteins 0.000 claims description 8
- 235000001014 amino acid Nutrition 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 150000003536 tetrazoles Chemical class 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 235000003704 aspartic acid Nutrition 0.000 claims description 4
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 4
- 229960002449 glycine Drugs 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 4
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims description 3
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- JSOMTIGKDWXVCJ-DEOSSOPVSA-N 2-[(2s)-7-[bis(1h-benzimidazol-2-ylmethyl)carbamoyl]-4-methyl-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)N(C)CC2=CC(C(=O)N(CC=3NC4=CC=CC=C4N=3)CC=3NC4=CC=CC=C4N=3)=CC=C21 JSOMTIGKDWXVCJ-DEOSSOPVSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- 125000001475 halogen functional group Chemical group 0.000 claims 7
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 claims 4
- 206010061218 Inflammation Diseases 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 230000004054 inflammatory process Effects 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims 2
- 101150113676 chr1 gene Proteins 0.000 claims 2
- UYIYDFHRFNTPBR-SFHVURJKSA-N (2s)-2-(2-amino-2-oxoethyl)-n-(1h-benzimidazol-2-ylmethyl)-n,4-dimethyl-3-oxo-2,5-dihydro-1h-1,4-benzodiazepine-7-carboxamide Chemical compound N1[C@@H](CC(N)=O)C(=O)N(C)CC2=CC(C(=O)N(CC=3NC4=CC=CC=C4N=3)C)=CC=C21 UYIYDFHRFNTPBR-SFHVURJKSA-N 0.000 claims 1
- FWZQYRSTSNFMQB-INIZCTEOSA-N 2-[(2s)-4-methyl-7-[(5-methyl-1h-imidazo[4,5-b]pyridin-2-yl)methylcarbamoyl]-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)N(C)CC2=CC(C(=O)NCC=3N=C4NC(C)=CC=C4N=3)=CC=C21 FWZQYRSTSNFMQB-INIZCTEOSA-N 0.000 claims 1
- NJVVLFTVLHGRKR-INIZCTEOSA-N 2-[(2s)-4-methyl-7-[methyl-[(4-nitro-1h-benzimidazol-2-yl)methyl]carbamoyl]-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)N(C)CC2=CC(C(=O)N(CC=3NC4=CC=CC(=C4N=3)[N+]([O-])=O)C)=CC=C21 NJVVLFTVLHGRKR-INIZCTEOSA-N 0.000 claims 1
- QWMJWEFRSJDVCR-SFHVURJKSA-N 2-[(2s)-4-methyl-7-[methyl-[[6-(trifluoromethyl)-1h-benzimidazol-2-yl]methyl]carbamoyl]-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)N(C)CC2=CC(C(=O)N(CC=3NC4=CC=C(C=C4N=3)C(F)(F)F)C)=CC=C21 QWMJWEFRSJDVCR-SFHVURJKSA-N 0.000 claims 1
- OORKISXHRJDTFL-INIZCTEOSA-N 2-[(2s)-7-(1h-benzimidazol-2-ylmethylcarbamoyl)-3-oxo-1,2,4,5-tetrahydro-1,4-benzodiazepin-2-yl]acetic acid Chemical compound C1NC(=O)[C@H](CC(=O)O)NC2=CC=C(C(=O)NCC=3NC4=CC=CC=C4N=3)C=C21 OORKISXHRJDTFL-INIZCTEOSA-N 0.000 claims 1
- WWUFFAAECGTHCS-QHCPKHFHSA-N 2-[(2s)-7-(1h-benzimidazol-2-ylmethylcarbamoyl)-3-oxo-4-(2-pyridin-3-ylethyl)-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N([C@H](C1=O)CC(=O)O)C2=CC=C(C(=O)NCC=3NC4=CC=CC=C4N=3)C=C2CN1CCC1=CC=CN=C1 WWUFFAAECGTHCS-QHCPKHFHSA-N 0.000 claims 1
- KNHICCKAVCYGSI-SANMLTNESA-N 2-[(2s)-7-(1h-benzimidazol-2-ylmethylcarbamoyl)-4-[4-(1,3-dioxoisoindol-2-yl)butyl]-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound O=C1[C@H](CC(=O)O)NC2=CC=C(C(=O)NCC=3NC4=CC=CC=C4N=3)C=C2CN1CCCCN1C(=O)C2=CC=CC=C2C1=O KNHICCKAVCYGSI-SANMLTNESA-N 0.000 claims 1
- NLZPVKJFFHYJNR-INIZCTEOSA-N 2-[(2s)-7-[(4,7-dimethoxy-1h-benzimidazol-2-yl)methyl-methylcarbamoyl]-4-methyl-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)N(C)CC2=CC(C(=O)N(C)CC=3NC=4C(OC)=CC=C(C=4N=3)OC)=CC=C21 NLZPVKJFFHYJNR-INIZCTEOSA-N 0.000 claims 1
- JQYCFEBYEBNEHP-KRWDZBQOSA-N 2-[(2s)-7-[(4-amino-1h-benzimidazol-2-yl)methyl-methylcarbamoyl]-4-methyl-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)N(C)CC2=CC(C(=O)N(CC=3NC4=CC=CC(N)=C4N=3)C)=CC=C21 JQYCFEBYEBNEHP-KRWDZBQOSA-N 0.000 claims 1
- RZMDOCONQPJDQB-SFHVURJKSA-N 2-[(2s)-7-[(5,6-difluoro-1h-benzimidazol-2-yl)methyl-methylcarbamoyl]-4-methyl-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)N(C)CC2=CC(C(=O)N(CC=3NC4=CC(F)=C(F)C=C4N=3)C)=CC=C21 RZMDOCONQPJDQB-SFHVURJKSA-N 0.000 claims 1
- PMIIVEPMDAQGST-HNNXBMFYSA-N 2-[(2s)-7-[(5-methyl-1h-imidazo[4,5-b]pyridin-2-yl)methylcarbamoyl]-3-oxo-1,2,4,5-tetrahydro-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)NCC2=CC(C(=O)NCC=3NC4=CC=C(N=C4N=3)C)=CC=C21 PMIIVEPMDAQGST-HNNXBMFYSA-N 0.000 claims 1
- JQCFTWVYYDQFDG-KRWDZBQOSA-N 2-[(2s)-7-[1h-benzimidazol-2-ylmethyl(methyl)carbamoyl]-3-oxo-1,2,4,5-tetrahydro-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)NCC2=CC(C(=O)N(CC=3NC4=CC=CC=C4N=3)C)=CC=C21 JQCFTWVYYDQFDG-KRWDZBQOSA-N 0.000 claims 1
- PVNQAXDNDZYXIW-SFHVURJKSA-N 2-[(2s)-7-[1h-benzimidazol-2-ylmethyl(methyl)carbamoyl]-4-methyl-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)N(C)CC2=CC(C(=O)N(CC=3NC4=CC=CC=C4N=3)C)=CC=C21 PVNQAXDNDZYXIW-SFHVURJKSA-N 0.000 claims 1
- WRDBYQHKNUONRD-SFHVURJKSA-N 2-[(2s)-7-[[1-(2-hydroxyethyl)benzimidazol-2-yl]methylcarbamoyl]-4-methyl-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)N(C)CC2=CC(C(=O)NCC=3N(C4=CC=CC=C4N=3)CCO)=CC=C21 WRDBYQHKNUONRD-SFHVURJKSA-N 0.000 claims 1
- JZOGWRODMVGPSY-INIZCTEOSA-N 2-[(2s)-7-[methyl-[(5-methyl-1h-imidazo[4,5-b]pyridin-2-yl)methyl]carbamoyl]-3-oxo-1,2,4,5-tetrahydro-1,4-benzodiazepin-2-yl]acetic acid Chemical compound N1[C@@H](CC(O)=O)C(=O)NCC2=CC(C(=O)N(CC=3NC4=CC=C(C)N=C4N=3)C)=CC=C21 JZOGWRODMVGPSY-INIZCTEOSA-N 0.000 claims 1
- UBTOLZYCPKOIKR-AWEZNQCLSA-N 2-[(3s)-4-[2-[[2-(1h-benzimidazol-2-yl)acetyl]amino]acetyl]-3-(2-methoxy-2-oxoethyl)-2-oxopiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)C(=O)[C@H](CC(=O)OC)N1C(=O)CNC(=O)CC1=NC2=CC=CC=C2N1 UBTOLZYCPKOIKR-AWEZNQCLSA-N 0.000 claims 1
- KGFKLEDRUITHPR-GJZGRUSLSA-N 2-[(3s,5s)-5-[[4-(1h-benzimidazol-2-ylmethyl)phenoxy]methyl]-2-oxopyrrolidin-3-yl]acetic acid Chemical compound N1C(=O)[C@H](CC(=O)O)C[C@H]1COC(C=C1)=CC=C1CC1=NC2=CC=CC=C2N1 KGFKLEDRUITHPR-GJZGRUSLSA-N 0.000 claims 1
- YXCHRCMLGGTXJG-NRFANRHFSA-N 2-[1-[(2s)-2-[[2-(1h-benzimidazol-2-yl)acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]piperidin-4-yl]oxyacetic acid Chemical compound C1CC(OCC(=O)O)CCN1C(=O)[C@@H](NC(=O)CC=1NC2=CC=CC=C2N=1)CC1=CC=C(O)C=C1 YXCHRCMLGGTXJG-NRFANRHFSA-N 0.000 claims 1
- YFMGNBYTMLQZLA-UHFFFAOYSA-N 2-[4-[3-(1h-benzimidazol-2-yl)propylcarbamoyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C(=O)NCCCC1=NC2=CC=CC=C2N1 YFMGNBYTMLQZLA-UHFFFAOYSA-N 0.000 claims 1
- CTQVDYDFANJQQB-UHFFFAOYSA-N 2-[4-[3-(1h-benzimidazol-2-yl)propylcarbamoyl]piperidin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCC1C(=O)NCCCC1=NC2=CC=CC=C2N1 CTQVDYDFANJQQB-UHFFFAOYSA-N 0.000 claims 1
- YBXSLIGNKJBGPW-UHFFFAOYSA-N 2-[4-[4-[2-(1h-benzimidazol-2-yl)ethyl]piperazin-1-yl]piperidin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCC1N1CCN(CCC=2NC3=CC=CC=C3N=2)CC1 YBXSLIGNKJBGPW-UHFFFAOYSA-N 0.000 claims 1
- GGPDFISGQNVCKX-UHFFFAOYSA-N 2-[4-[4-[3-(1h-benzimidazol-2-yl)propyl]piperazin-1-yl]-1-hydroxycyclohexyl]acetic acid Chemical compound C1CC(CC(=O)O)(O)CCC1N1CCN(CCCC=2NC3=CC=CC=C3N=2)CC1 GGPDFISGQNVCKX-UHFFFAOYSA-N 0.000 claims 1
- NJANIMVBGSTFGY-UHFFFAOYSA-N 2-[7-(1h-benzimidazol-2-ylmethylcarbamoyl)-3-oxo-4-(2,2,2-trifluoroethyl)-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound C1N(CC(F)(F)F)C(=O)C(CC(=O)O)NC2=CC=C(C(=O)NCC=3NC4=CC=CC=C4N=3)C=C21 NJANIMVBGSTFGY-UHFFFAOYSA-N 0.000 claims 1
- IARLEJBSBMLSJK-UHFFFAOYSA-N 2-[7-[[2-(1h-benzimidazol-2-yl)acetyl]amino]-5-oxo-4-(2-phenylethyl)-2,3-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound O=C1C2=CC(NC(=O)CC=3NC4=CC=CC=C4N=3)=CC=C2NC(CC(=O)O)CN1CCC1=CC=CC=C1 IARLEJBSBMLSJK-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- KQVPGGIEXXFLDO-UHFFFAOYSA-N 3-[4-[1-(1h-benzimidazol-2-ylmethyl)-3-methoxy-5-oxo-2h-pyrrol-4-yl]phenyl]propanoic acid Chemical compound O=C1N(CC=2NC3=CC=CC=C3N=2)CC(OC)=C1C1=CC=C(CCC(O)=O)C=C1 KQVPGGIEXXFLDO-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- JTKNHRAMQHGOFE-SFHVURJKSA-N ethyl 2-[(2S)-4-methyl-7-[(5-methyl-1H-imidazo[4,5-b]pyridin-2-yl)methylcarbamoyl]-3-oxo-2,5-dihydro-1H-1,4-benzodiazepin-2-yl]acetate Chemical compound CC1=NC2=C(N=C(N2)CNC(=O)C=2C=CC3=C(CN(C([C@@H](N3)CC(=O)OCC)=O)C)C=2)C=C1 JTKNHRAMQHGOFE-SFHVURJKSA-N 0.000 claims 1
- MLDBIVBJPDCGRL-FQEVSTJZSA-N ethyl 2-[(2s)-7-[1h-benzimidazol-2-ylmethyl(methyl)carbamoyl]-4-methyl-3-oxo-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetate Chemical compound C1N(C)C(=O)[C@H](CC(=O)OCC)NC2=CC=C(C(=O)N(C)CC=3NC4=CC=CC=C4N=3)C=C21 MLDBIVBJPDCGRL-FQEVSTJZSA-N 0.000 claims 1
- MLBYLEUJXUBIJJ-UHFFFAOYSA-N pent-4-ynoic acid Chemical compound OC(=O)CCC#C MLBYLEUJXUBIJJ-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 318
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- 239000000243 solution Substances 0.000 description 169
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REDSKZBUUUQMSK-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC REDSKZBUUUQMSK-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical class [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 150000003667 tyrosine derivatives Chemical class 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000002435 venom Substances 0.000 description 1
- 210000001048 venom Anatomy 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/36—Antigestagens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/16—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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- C07D413/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US936695P | 1995-12-29 | 1995-12-29 | |
| US60/009,366 | 1995-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2241633A1 true CA2241633A1 (en) | 1997-07-10 |
Family
ID=21737205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002241633A Abandoned CA2241633A1 (en) | 1995-12-29 | 1996-12-20 | Vitronectin receptor antagonists |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0869787A4 (cs) |
| JP (1) | JP2000502354A (cs) |
| KR (1) | KR19990076878A (cs) |
| CN (1) | CN1209744A (cs) |
| AU (1) | AU1354097A (cs) |
| BR (1) | BR9612327A (cs) |
| CA (1) | CA2241633A1 (cs) |
| CZ (1) | CZ203698A3 (cs) |
| HU (1) | HUP9900754A3 (cs) |
| IL (1) | IL125033A0 (cs) |
| MX (1) | MX9805255A (cs) |
| NO (1) | NO983003L (cs) |
| PL (1) | PL327694A1 (cs) |
| TR (1) | TR199801253T2 (cs) |
| WO (1) | WO1997024119A1 (cs) |
| ZA (1) | ZA9610859B (cs) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030125317A1 (en) | 1996-10-02 | 2003-07-03 | Smithkline Beecham Corporation | Vitronectin receptor antagonists |
| DE19653645A1 (de) * | 1996-12-20 | 1998-06-25 | Hoechst Ag | Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung |
| US6218387B1 (en) * | 1996-12-20 | 2001-04-17 | Hoechst Aktiengesellschaft | Vitronectin receptor anatagonists, their preparation and their use |
| US6482821B2 (en) | 1996-12-20 | 2002-11-19 | Hoechst Aktiengellschaft | Vitronectin receptor antagonists, their preparation and their use |
| DE19653647A1 (de) | 1996-12-20 | 1998-06-25 | Hoechst Ag | Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung |
| JP2001511452A (ja) * | 1997-08-04 | 2001-08-14 | スミスクライン・ビーチャム・コーポレイション | インテグリン受容体アンタゴニスト |
| EP1047425A4 (en) * | 1997-12-17 | 2009-04-22 | Merck & Co Inc | INTEGRIN RECEPTOR ANTAGONISTS |
| ES2381591T3 (es) | 1998-04-09 | 2012-05-29 | Meiji Seika Pharma Co., Ltd. | Derivados de aminopiperidina como antagonistas de integrina alfa v beta 3 |
| AU746963B2 (en) | 1998-06-12 | 2002-05-09 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Imidazolyl derivatives |
| SE9803518D0 (sv) * | 1998-10-15 | 1998-10-15 | Astra Pharma Prod | Novel compounds |
| US6339083B1 (en) * | 1998-12-14 | 2002-01-15 | Bayer Aktiengesellschaft | Multiheterocyclic pharmAceuticals |
| JP2002536370A (ja) | 1999-02-03 | 2002-10-29 | メルク エンド カムパニー インコーポレーテッド | α−Vインテグリン受容体拮抗薬としてのベンゾアゼピン誘導体 |
| US6271241B1 (en) | 1999-04-02 | 2001-08-07 | Neurogen Corporation | Cycloalkyl and aryl fused aminoalkyl-imidazole derivatives: modulators and GLP-1 receptors |
| US6358949B1 (en) | 1999-04-02 | 2002-03-19 | Neurogen Corporation | Aryl and hetroaryl fused aminoalkyl-imidazole derivatives: selective modulators of bradykinin B2 receptors |
| US6380210B1 (en) | 1999-04-02 | 2002-04-30 | Neurogen Corporation | Heteroaryl fused aminoalkyl-imidazole derivatives: selective modulators of GABAa receptors |
| JP2002541151A (ja) * | 1999-04-02 | 2002-12-03 | ニューロゲン コーポレイション | アリールおよびヘテロアリール縮合アミノアルキル−イミダゾール誘導体:GABAa受容体の選択的修飾物質 |
| US6627624B1 (en) | 1999-04-02 | 2003-09-30 | Neurogen Corporation | Aryl fused aminoalkyl-imidazole derivatives: selective modulators of GABAa receptors |
| US6281237B1 (en) | 1999-04-02 | 2001-08-28 | Neurogen Corporation | N-phenyl benzimidazolecarboxamide and N-phenyl indolecarboxamide derivatives |
| GB9908355D0 (en) * | 1999-04-12 | 1999-06-09 | Rhone Poulenc Rorer Ltd | Chemical compounds |
| AU5826100A (en) * | 1999-07-13 | 2001-01-30 | F. Hoffmann-La Roche Ag | Benzazepinones and quinazolines |
| BR0012683A (pt) | 1999-07-21 | 2002-04-16 | American Home Prod | Antagonistas bicìclicos seletivos para a integrina alfavbeta3 |
| EP1209152A4 (en) | 1999-08-05 | 2003-03-12 | Meiji Seika Kaisha | OMEGA-AMINO-ALPHA-HYDROXY-CARBONIC ACID DERIVATIVES WITH AN INTEGRIN ALPHA V BETA ANTAGONISM |
| JP2003506452A (ja) * | 1999-08-06 | 2003-02-18 | スミスクライン・ビーチャム・コーポレイション | 発作の治療に有用なビトロネクチン受容体アンタゴニスト |
| AU2001229580A1 (en) | 2000-01-18 | 2001-08-14 | Nuerogen Corporation | Substituted imidazoles as selective modulators of bradykinin b2 receptors |
| US6545029B2 (en) | 2000-06-12 | 2003-04-08 | Bayer Aktiengesellschaft | Phenylserine derivatives as integrin antagonists |
| DE60128102T2 (de) | 2000-08-01 | 2008-01-03 | Societe De Conseils De Recherches Et D`Applications Scientifiques (S.C.R.A.S.) | Imidazolderivate |
| EP2292251A1 (en) | 2001-04-24 | 2011-03-09 | Merck Patent GmbH | Combination therapy using anti-angiogenic agents and TNF-alpha |
| US7030150B2 (en) | 2001-05-11 | 2006-04-18 | Trimeris, Inc. | Benzimidazole compounds and antiviral uses thereof |
| GB0112348D0 (en) | 2001-05-19 | 2001-07-11 | Smithkline Beecham Plc | Compounds |
| JP4750360B2 (ja) | 2001-10-22 | 2011-08-17 | ザ スクリプス リサーチ インスティチュート | 抗体ターゲッティング化合物 |
| WO2004113330A1 (en) * | 2003-05-19 | 2004-12-29 | Irm Llc | Immunosuppressant compounds and compositions |
| MY150088A (en) | 2003-05-19 | 2013-11-29 | Irm Llc | Immunosuppressant compounds and compositions |
| US7179827B2 (en) | 2004-03-31 | 2007-02-20 | Lexicon Genetics Incorporated | Thiazoles and methods of their use |
| UA87854C2 (en) | 2004-06-07 | 2009-08-25 | Мерк Энд Ко., Инк. | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators |
| JP2008509923A (ja) | 2004-08-13 | 2008-04-03 | ジェネンテック・インコーポレーテッド | Atp利用酵素のチアゾールベースのインヒビター |
| KR20080089489A (ko) | 2006-01-18 | 2008-10-06 | 메르크 파텐트 게엠베하 | 인테그린 리간드를 사용하는 암치료용 특이적 요법 |
| KR20090108713A (ko) | 2007-01-18 | 2009-10-16 | 메르크 파텐트 게엠베하 | 인테그린 리간드를 사용하는 암치료용 특이적 요법 및 의약 |
| CA2685860A1 (en) | 2007-05-10 | 2008-11-20 | Amr Technology, Inc. | Aryl- and heteroaryl-substituted tetrahydrobenzo-1,4-diazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US8518927B2 (en) | 2009-02-10 | 2013-08-27 | The Scripps Research Institute | Chemically programmed vaccination |
| JP2012528079A (ja) | 2009-05-25 | 2012-11-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 癌を治療するためのインテグリンリガンドの連続投与 |
| CA2950390C (en) | 2014-05-30 | 2020-09-22 | Pfizer Inc. | Carbonitrile derivatives as selective androgen receptor modulators |
| DK3684767T3 (da) | 2017-09-22 | 2024-07-15 | Jubilant Epipad LLC | Heterocykliske forbindelser som pad-inhibitorer |
| RS64104B1 (sr) | 2017-10-18 | 2023-04-28 | Jubilant Epipad LLC | Jedinjenja imidazo-piridina kao inhibitori pad |
| KR20200085836A (ko) | 2017-11-06 | 2020-07-15 | 주빌런트 프로델 엘엘씨 | Pd1/pd-l1 활성화 억제제로서의 피리미딘 유도체 |
| IL274762B2 (en) | 2017-11-24 | 2023-10-01 | Jubilant Episcribe Llc | Novel heterocyclic compounds as prmt5 inhibitors |
| EP3765453A1 (en) | 2018-03-13 | 2021-01-20 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| WO2023275715A1 (en) | 2021-06-30 | 2023-01-05 | Pfizer Inc. | Metabolites of selective androgen receptor modulators |
Family Cites Families (2)
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| US3627754A (en) * | 1970-05-13 | 1971-12-14 | Hoffmann La Roche | Process for preparing 7-lower alkanoyl benzodiazepines utilizing ceric salts |
| US5250679A (en) * | 1991-10-18 | 1993-10-05 | Genentech, Inc. | Nonpeptidyl platelet aggregation inhibitors having specificity for the GPIIb III.sub. receptor |
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1996
- 1996-12-20 AU AU13540/97A patent/AU1354097A/en not_active Abandoned
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- 1996-12-20 CA CA002241633A patent/CA2241633A1/en not_active Abandoned
- 1996-12-20 EP EP96945087A patent/EP0869787A4/en not_active Withdrawn
- 1996-12-20 BR BR9612327A patent/BR9612327A/pt unknown
- 1996-12-20 KR KR1019980705005A patent/KR19990076878A/ko not_active Withdrawn
- 1996-12-20 HU HU9900754A patent/HUP9900754A3/hu unknown
- 1996-12-20 TR TR1998/01253T patent/TR199801253T2/xx unknown
- 1996-12-20 PL PL96327694A patent/PL327694A1/xx unknown
- 1996-12-20 CN CN96180113A patent/CN1209744A/zh active Pending
- 1996-12-20 WO PCT/US1996/020748 patent/WO1997024119A1/en not_active Ceased
- 1996-12-20 IL IL12503396A patent/IL125033A0/xx unknown
- 1996-12-23 ZA ZA9610859A patent/ZA9610859B/xx unknown
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1998
- 1998-06-26 NO NO983003A patent/NO983003L/no not_active Application Discontinuation
- 1998-06-26 MX MX9805255A patent/MX9805255A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9900754A3 (en) | 1999-11-29 |
| JP2000502354A (ja) | 2000-02-29 |
| NO983003D0 (no) | 1998-06-26 |
| TR199801253T2 (xx) | 1998-12-21 |
| ZA9610859B (en) | 1997-10-24 |
| HUP9900754A2 (hu) | 1999-07-28 |
| KR19990076878A (ko) | 1999-10-25 |
| AU1354097A (en) | 1997-07-28 |
| WO1997024119A1 (en) | 1997-07-10 |
| MX9805255A (es) | 1998-11-29 |
| CN1209744A (zh) | 1999-03-03 |
| BR9612327A (pt) | 1999-07-13 |
| EP0869787A1 (en) | 1998-10-14 |
| EP0869787A4 (en) | 1999-03-24 |
| CZ203698A3 (cs) | 1999-05-12 |
| PL327694A1 (en) | 1998-12-21 |
| IL125033A0 (en) | 1999-01-26 |
| NO983003L (no) | 1998-08-26 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |