ZA200509902B - Tetrahydrocarbazole derivatives and their pharmaceutical use - Google Patents

Info

Publication number

ZA200509902B

ZA200509902B ZA200509902A ZA200509902A ZA200509902B ZA 200509902 B ZA200509902 B ZA 200509902B ZA 200509902 A ZA200509902 A ZA 200509902A ZA 200509902 A ZA200509902 A ZA 200509902A ZA 200509902 B ZA200509902 B ZA 200509902B

Authority

ZA

South Africa

Prior art keywords

tetrahydro

carbazol

bromo

compound

chloro

Prior art date

2003-06-12

Links

• Espacenet
• Global Dossier
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• XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 152
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• 239000000203 mixture Substances 0.000 claims description 51
• 229910052736 halogen Inorganic materials 0.000 claims description 43
• 238000011282 treatment Methods 0.000 claims description 40
• 125000001188 haloalkyl group Chemical group 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 38
• 238000000034 method Methods 0.000 claims description 36
• -1 N-(6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl}-N-phenylurea Chemical compound 0.000 claims description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• 150000003839 salts Chemical class 0.000 claims description 27
• 238000011321 prophylaxis Methods 0.000 claims description 25
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
• 208000009608 Papillomavirus Infections Diseases 0.000 claims description 21
• 125000003342 alkenyl group Chemical group 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 125000000304 alkynyl group Chemical group 0.000 claims description 20
• 239000000126 substance Substances 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• 206010028980 Neoplasm Diseases 0.000 claims description 17
• 208000035475 disorder Diseases 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 239000012453 solvate Substances 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 15
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• 206010059313 Anogenital warts Diseases 0.000 claims description 13
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 13
• 208000000907 Condylomata Acuminata Diseases 0.000 claims description 12
• 208000025009 anogenital human papillomavirus infection Diseases 0.000 claims description 12
• 201000004201 anogenital venereal wart Diseases 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
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• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
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• 125000002947 alkylene group Chemical group 0.000 claims description 9
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• 208000014829 head and neck neoplasm Diseases 0.000 claims description 9
• WJQBOBGVBBZLJU-UHFFFAOYSA-N n-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-1-yl)pyridine-2-carboxamide Chemical compound C1CCC=2C3=CC(Cl)=CC=C3NC=2C1NC(=O)C1=CC=CC=N1 WJQBOBGVBBZLJU-UHFFFAOYSA-N 0.000 claims description 9
• 241001631646 Papillomaviridae Species 0.000 claims description 8
• 241001505332 Polyomavirus sp. Species 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
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• 125000004450 alkenylene group Chemical group 0.000 claims description 7
• YKHTXFXCBWSEFY-UHFFFAOYSA-N benzyl n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)carbamate Chemical compound C1CCC=2C3=CC(Br)=CC=C3NC=2C1NC(=O)OCC1=CC=CC=C1 YKHTXFXCBWSEFY-UHFFFAOYSA-N 0.000 claims description 7
• PZXSGDSLSXXHJD-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-2-fluorobenzenesulfonamide Chemical compound FC1=CC=CC=C1S(=O)(=O)NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 PZXSGDSLSXXHJD-UHFFFAOYSA-N 0.000 claims description 7
• OWFQYITVIASELA-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 OWFQYITVIASELA-UHFFFAOYSA-N 0.000 claims description 7
• OERQBJZPNQUMSB-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 OERQBJZPNQUMSB-UHFFFAOYSA-N 0.000 claims description 7
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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• UNZPBZMTHUBHJO-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)pyridine-2-carboxamide Chemical compound C1CCC=2C3=CC(Br)=CC=C3NC=2C1NC(=O)C1=CC=CC=N1 UNZPBZMTHUBHJO-UHFFFAOYSA-N 0.000 claims description 6
• XDNJBIOPNSPBOV-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)pyridine-4-carboxamide Chemical compound C1CCC=2C3=CC(Br)=CC=C3NC=2C1NC(=O)C1=CC=NC=C1 XDNJBIOPNSPBOV-UHFFFAOYSA-N 0.000 claims description 6
• ZIBUWHQYDKJMIQ-UHFFFAOYSA-N n-(6-methyl-2,3,4,9-tetrahydro-1h-carbazol-1-yl)benzamide Chemical compound C1CCC=2C3=CC(C)=CC=C3NC=2C1NC(=O)C1=CC=CC=C1 ZIBUWHQYDKJMIQ-UHFFFAOYSA-N 0.000 claims description 6
• 206010004146 Basal cell carcinoma Diseases 0.000 claims description 5
• 208000002471 Penile Neoplasms Diseases 0.000 claims description 5
• PWKNPBVWUHZZOA-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-2,6-difluorobenzenesulfonamide Chemical compound FC1=CC=CC(F)=C1S(=O)(=O)NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 PWKNPBVWUHZZOA-UHFFFAOYSA-N 0.000 claims description 5
• KXORNHGXMBLSKZ-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC2C3=C(C4=CC(Br)=CC=C4N3)CCC2)=C1 KXORNHGXMBLSKZ-UHFFFAOYSA-N 0.000 claims description 5
• MJVBNTSTNSJMIC-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 MJVBNTSTNSJMIC-UHFFFAOYSA-N 0.000 claims description 5
• NUMNOLWLEWXOHU-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 NUMNOLWLEWXOHU-UHFFFAOYSA-N 0.000 claims description 5
• RQJJJEPZUUJDOD-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 RQJJJEPZUUJDOD-UHFFFAOYSA-N 0.000 claims description 5
• CCKKWPZGJSTSDW-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-6-chloropyridine-3-carboxamide Chemical compound C1=NC(Cl)=CC=C1C(=O)NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 CCKKWPZGJSTSDW-UHFFFAOYSA-N 0.000 claims description 5
• TXFFKXTVYMUXME-UHFFFAOYSA-N n-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC1C(NC=2C3=CC(Cl)=CC=2)=C3CCC1 TXFFKXTVYMUXME-UHFFFAOYSA-N 0.000 claims description 5
• TXFFKXTVYMUXME-QGZVFWFLSA-N n-[(1r)-6-chloro-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)N[C@H]1C(NC=2C3=CC(Cl)=CC=2)=C3CCC1 TXFFKXTVYMUXME-QGZVFWFLSA-N 0.000 claims description 5
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 4
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• 125000005724 cycloalkenylene group Chemical group 0.000 claims description 4
• UPHLQROVIPDWPW-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1C(NC=2C3=CC(Br)=CC=2)=C3CCC1 UPHLQROVIPDWPW-UHFFFAOYSA-N 0.000 claims description 4
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• BBMRKYQFAGEGAY-UHFFFAOYSA-N n-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC2C3=C(C4=CC(Br)=CC=C4N3)CCC2)=C1 BBMRKYQFAGEGAY-UHFFFAOYSA-N 0.000 claims description 4
• CEGSYYPFMKTREE-UHFFFAOYSA-N n-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-1h-pyrazole-5-carboxamide Chemical compound C1CCC=2C3=CC(Cl)=CC=C3NC=2C1NC(=O)C=1C=CNN=1 CEGSYYPFMKTREE-UHFFFAOYSA-N 0.000 claims description 4
• BODYNFMOAHRAPN-UHFFFAOYSA-N n-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-2-methylpyrazole-3-carboxamide Chemical compound CN1N=CC=C1C(=O)NC1C(NC=2C3=CC(Cl)=CC=2)=C3CCC1 BODYNFMOAHRAPN-UHFFFAOYSA-N 0.000 claims description 4
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• RCYVVZGKRXFRPC-UHFFFAOYSA-N 1-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-1-yl)-3-phenylurea Chemical compound C1CCC=2C3=CC(Cl)=CC=C3NC=2C1NC(=O)NC1=CC=CC=C1 RCYVVZGKRXFRPC-UHFFFAOYSA-N 0.000 claims description 3
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