RU2318810C2 - Производные тетрагидрокарбазола и их фармацевтическое применение - Google Patents

Info

Publication number

RU2318810C2

RU2318810C2 RU2005138124/04A RU2005138124A RU2318810C2 RU 2318810 C2 RU2318810 C2 RU 2318810C2 RU 2005138124/04 A RU2005138124/04 A RU 2005138124/04A RU 2005138124 A RU2005138124 A RU 2005138124A RU 2318810 C2 RU2318810 C2 RU 2318810C2

Authority

RU

Russia

Prior art keywords

tetrahydro

amine

bromo

carbazole

carbazol

Prior art date

2003-06-10

Links

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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 claims abstract 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 144
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 34
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 32
• 150000002367 halogens Chemical class 0.000 claims abstract description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 29
• 150000003839 salts Chemical class 0.000 claims abstract description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 26
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 24
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 24
• 238000011282 treatment Methods 0.000 claims abstract description 24
• 125000003118 aryl group Chemical group 0.000 claims abstract description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 22
• 208000009608 Papillomavirus Infections Diseases 0.000 claims abstract description 20
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• 239000003814 drug Substances 0.000 claims abstract description 19
• 239000012453 solvate Substances 0.000 claims abstract description 16
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
• 230000000694 effects Effects 0.000 claims abstract description 6
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 4
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
• 150000001408 amides Chemical class 0.000 claims abstract description 3
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 3
• 150000002148 esters Chemical class 0.000 claims abstract description 3
• 125000004434 sulfur atom Chemical group 0.000 claims abstract 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
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• QODCQNSYEPOBKP-UHFFFAOYSA-N 6-bromo-9-(4-fluorophenoxy)-1,2,3,4-tetrahydrocarbazole Chemical compound C1=CC(F)=CC=C1ON1C2=CC=C(Br)C=C2C2=C1CCCC2 QODCQNSYEPOBKP-UHFFFAOYSA-N 0.000 claims description 8
• NNQBFVSAJHLPMW-UHFFFAOYSA-N 6-bromo-n-(3-fluorophenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound FC1=CC=CC(NC2C3=C(C4=CC(Br)=CC=C4N3)CCC2)=C1 NNQBFVSAJHLPMW-UHFFFAOYSA-N 0.000 claims description 8
• IXYPWFUDXMSOQR-UHFFFAOYSA-N 6-bromo-n-phenyl-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1CCC=2C3=CC(Br)=CC=C3NC=2C1NC1=CC=CC=C1 IXYPWFUDXMSOQR-UHFFFAOYSA-N 0.000 claims description 8
• YJAFEVJACSAADZ-UHFFFAOYSA-N methyl 8-anilino-6,7,8,9-tetrahydro-5h-carbazole-3-carboxylate Chemical compound C1CCC=2C3=CC(C(=O)OC)=CC=C3NC=2C1NC1=CC=CC=C1 YJAFEVJACSAADZ-UHFFFAOYSA-N 0.000 claims description 8
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• NZIDKQYZUMXIPG-UHFFFAOYSA-N 6-chloro-n-(4-methylphenyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1=CC(C)=CC=C1NC1C(NC=2C3=CC(Cl)=CC=2)=C3CCC1 NZIDKQYZUMXIPG-UHFFFAOYSA-N 0.000 claims description 7
• QNTJZKOUHMTCOZ-UHFFFAOYSA-N 6-chloro-n-phenyl-2,3,4,9-tetrahydro-1h-carbazol-1-amine Chemical compound C1CCC=2C3=CC(Cl)=CC=C3NC=2C1NC1=CC=CC=C1 QNTJZKOUHMTCOZ-UHFFFAOYSA-N 0.000 claims description 7
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• FYAPDWQVYMPJNT-UHFFFAOYSA-N n-phenyl-6-(trifluoromethyl)-2,3,4,9-tetrahydro-1h-carbazol-1-amine;hydrochloride Chemical compound Cl.C1CCC=2C3=CC(C(F)(F)F)=CC=C3NC=2C1NC1=CC=CC=C1 FYAPDWQVYMPJNT-UHFFFAOYSA-N 0.000 claims description 7
• 231100000590 oncogenic Toxicity 0.000 claims description 7
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• ZOFYAVWOFRSXCF-UHFFFAOYSA-N 2-bromo-n-pyrimidin-2-yl-5,6,7,8,9,10-hexahydrocyclohepta[b]indol-6-amine Chemical compound C1CCCC=2C3=CC(Br)=CC=C3NC=2C1NC1=NC=CC=N1 ZOFYAVWOFRSXCF-UHFFFAOYSA-N 0.000 claims description 6
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