SK283413B6 - 2-Tioindoly, 2-indolíntióny a polysulfidy, ich selénové analógy a farmaceutické prostriedky na ich báze - Google Patents
2-Tioindoly, 2-indolíntióny a polysulfidy, ich selénové analógy a farmaceutické prostriedky na ich báze Download PDFInfo
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- SK283413B6 SK283413B6 SK135-95A SK13595A SK283413B6 SK 283413 B6 SK283413 B6 SK 283413B6 SK 13595 A SK13595 A SK 13595A SK 283413 B6 SK283413 B6 SK 283413B6
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- Slovakia
- Prior art keywords
- methyl
- formula
- bis
- disulfide
- arh
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- 239000005077 polysulfide Substances 0.000 title claims abstract description 35
- 229920001021 polysulfide Polymers 0.000 title claims abstract description 35
- 150000008117 polysulfides Polymers 0.000 title claims abstract description 35
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- IGJWTYFTQNHSEK-UHFFFAOYSA-N 1,3-dihydroindole-2-thione Chemical class C1=CC=C2NC(=S)CC2=C1 IGJWTYFTQNHSEK-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 150000003346 selenoethers Chemical class 0.000 title description 3
- IWPFCVWNSWZZFA-UHFFFAOYSA-N C1=CC=C2NC(=[Se])CC2=C1 Chemical compound C1=CC=C2NC(=[Se])CC2=C1 IWPFCVWNSWZZFA-UHFFFAOYSA-N 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 404
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 157
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 87
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 73
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 54
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 52
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 32
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 27
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229930192474 thiophene Natural products 0.000 claims abstract description 26
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 24
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical class [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 13
- 150000001875 compounds Chemical class 0.000 claims description 628
- 239000001257 hydrogen Substances 0.000 claims description 255
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 218
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 191
- 150000002431 hydrogen Chemical group 0.000 claims description 142
- 229910052799 carbon Inorganic materials 0.000 claims description 116
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 102
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 98
- -1 cyclic radical Chemical class 0.000 claims description 70
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 56
- OTYIADUBGFZFSV-UHFFFAOYSA-N n-[4-(acetylsulfamoyl)phenyl]-2-[[2-[[4-(acetylsulfamoyl)phenyl]carbamoyl]phenyl]disulfanyl]benzamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=C(S(=O)(=O)NC(C)=O)C=C1 OTYIADUBGFZFSV-UHFFFAOYSA-N 0.000 claims description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 15
- 239000011669 selenium Substances 0.000 claims description 11
- 230000001419 dependent effect Effects 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- 230000010261 cell growth Effects 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 150000003342 selenium Chemical class 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- HVRCLXXJIQTXHC-UHFFFAOYSA-N 1-methylindole-3-carboxylic acid Chemical compound C1=CC=C2N(C)C=C(C(O)=O)C2=C1 HVRCLXXJIQTXHC-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- KTIODNZPIYCZSR-UHFFFAOYSA-N 2-(2-sulfanylidene-1,3-dihydroindol-3-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)C(=S)NC2=C1 KTIODNZPIYCZSR-UHFFFAOYSA-N 0.000 claims description 3
- HNEORRPIDMAPCB-UHFFFAOYSA-N 2-[(3-carboxy-1-methylindol-2-yl)diselanyl]-1-methylindole-3-carboxylic acid Chemical compound C1=CC=C2N(C)C([Se][Se]C=3N(C4=CC=CC=C4C=3C(O)=O)C)=C(C(O)=O)C2=C1 HNEORRPIDMAPCB-UHFFFAOYSA-N 0.000 claims description 3
- XZFPVQIMSWHDCR-UHFFFAOYSA-N 3-(2-sulfanylidene-1,3-dihydroindol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)C(=S)NC2=C1 XZFPVQIMSWHDCR-UHFFFAOYSA-N 0.000 claims description 3
- XMTNWZBWWSPDPN-UHFFFAOYSA-N 3-butyl-1,5-dimethyl-3H-indole-2-thione Chemical compound C1=C(C)C=C2C(CCCC)C(=S)N(C)C2=C1 XMTNWZBWWSPDPN-UHFFFAOYSA-N 0.000 claims description 3
- HGQLOUYLTRSJRA-UHFFFAOYSA-N 3-butyl-2-[(3-butyl-1-methylindol-2-yl)disulfanyl]-1-methylindole Chemical compound CN1C2=CC=CC=C2C(CCCC)=C1SSC1=C(CCCC)C2=CC=CC=C2N1C HGQLOUYLTRSJRA-UHFFFAOYSA-N 0.000 claims description 3
- JRCARFUVXOJUCM-UHFFFAOYSA-N C1=CC=C2C(CCCC)C(=S)N(C)C2=C1 Chemical compound C1=CC=C2C(CCCC)C(=S)N(C)C2=C1 JRCARFUVXOJUCM-UHFFFAOYSA-N 0.000 claims description 3
- KKTAXCWCKSLCHF-UHFFFAOYSA-N n,1-dimethyl-2-[[1-methyl-3-(methylcarbamoyl)indol-2-yl]diselanyl]indole-3-carboxamide Chemical compound CN1C2=CC=CC=C2C(C(=O)NC)=C1[Se][Se]C1=C(C(=O)NC)C2=CC=CC=C2N1C KKTAXCWCKSLCHF-UHFFFAOYSA-N 0.000 claims description 3
- PMQPQXPWWRMDGF-UHFFFAOYSA-N 1-methyl-n-phenyl-2-sulfanylidene-3h-indole-3-carboxamide Chemical compound C12=CC=CC=C2N(C)C(=S)C1C(=O)NC1=CC=CC=C1 PMQPQXPWWRMDGF-UHFFFAOYSA-N 0.000 claims description 2
- MGQMNRPORBTSDW-UHFFFAOYSA-N 2-(1-methyl-2-sulfanylidene-3h-indol-3-yl)acetic acid Chemical compound C1=CC=C2N(C)C(=S)C(CC(O)=O)C2=C1 MGQMNRPORBTSDW-UHFFFAOYSA-N 0.000 claims description 2
- KUXZZVWLUDGVFK-UHFFFAOYSA-N 2-[[1-carboxy-1-(1-methylindol-3-yl)ethyl]disulfanyl]-2-(1-methylindol-3-yl)propanoic acid Chemical compound C1=CC=C2C(C(C)(C(O)=O)SSC(C)(C3=CN(C4=CC=CC=C43)C)C(O)=O)=CN(C)C2=C1 KUXZZVWLUDGVFK-UHFFFAOYSA-N 0.000 claims description 2
- YNAIRLXDPHCRHZ-UHFFFAOYSA-N 2-[[1-carboxy-2-(1-methylindol-3-yl)ethyl]disulfanyl]-3-(1-methylindol-3-yl)propanoic acid Chemical compound C12=CC=CC=C2N(C)C=C1CC(C(O)=O)SSC(C(O)=O)CC1=CN(C)C2=CC=CC=C12 YNAIRLXDPHCRHZ-UHFFFAOYSA-N 0.000 claims description 2
- LBALNCFWTZTSFW-UHFFFAOYSA-N 3-(1-methyl-2-sulfanylidene-3h-indol-3-yl)propanoic acid Chemical compound C1=CC=C2N(C)C(=S)C(CCC(O)=O)C2=C1 LBALNCFWTZTSFW-UHFFFAOYSA-N 0.000 claims description 2
- QHJCJUXULVYEKC-UHFFFAOYSA-N 4-(1-methyl-2-sulfanylidene-3h-indol-3-yl)butanoic acid Chemical compound C1=CC=C2N(C)C(=S)C(CCCC(O)=O)C2=C1 QHJCJUXULVYEKC-UHFFFAOYSA-N 0.000 claims description 2
- HDSHPZKIYJXQSA-UHFFFAOYSA-N 4-(1-methyl-2-sulfanylidene-3h-indole-3-carbonyl)benzoic acid Chemical compound C12=CC=CC=C2N(C)C(=S)C1C(=O)C1=CC=C(C(O)=O)C=C1 HDSHPZKIYJXQSA-UHFFFAOYSA-N 0.000 claims description 2
- 230000001594 aberrant effect Effects 0.000 claims description 2
- MMQRRPCTOSYLTB-UHFFFAOYSA-N n-benzyl-2-[[1-(benzylamino)-3-(1h-indol-3-yl)-1-oxopropan-2-yl]disulfanyl]-3-(1h-indol-3-yl)propanamide Chemical compound C=1NC2=CC=CC=C2C=1CC(SSC(CC=1C2=CC=CC=C2NC=1)C(=O)NCC=1C=CC=CC=1)C(=O)NCC1=CC=CC=C1 MMQRRPCTOSYLTB-UHFFFAOYSA-N 0.000 claims description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical group CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 4
- RHQWHANZNHLOIO-UHFFFAOYSA-N 1-[2-(diethylamino)ethyl]-2-[[1-[2-(diethylamino)ethyl]-3-(methylcarbamoyl)indol-2-yl]diselanyl]-n-methylindole-3-carboxamide Chemical compound C1=CC=C2N(CCN(CC)CC)C([Se][Se]C=3N(C4=CC=CC=C4C=3C(=O)NC)CCN(CC)CC)=C(C(=O)NC)C2=C1 RHQWHANZNHLOIO-UHFFFAOYSA-N 0.000 claims 2
- XQPHLDWWTAAPNR-UHFFFAOYSA-N CN1C(=C(C2=CC=CC=C12)S(=O)(=O)C1=CC=CC=C1)SSC=1N(C2=CC=CC=C2C1S(=O)(=O)C1=CC=CC=C1)C Chemical compound CN1C(=C(C2=CC=CC=C12)S(=O)(=O)C1=CC=CC=C1)SSC=1N(C2=CC=CC=C2C1S(=O)(=O)C1=CC=CC=C1)C XQPHLDWWTAAPNR-UHFFFAOYSA-N 0.000 claims 2
- ZKIIIDMIMRJWPR-UHFFFAOYSA-N N-benzyl-N-(2-sulfanylidene-1,3-dihydroindol-3-yl)acetamide Chemical compound CC(=O)N(Cc1ccccc1)C1C(=S)Nc2ccccc12 ZKIIIDMIMRJWPR-UHFFFAOYSA-N 0.000 claims 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 2
- DWORZCJMOCMSFP-UHFFFAOYSA-N methyl 2-(2-methylsulfanyl-1h-indol-3-yl)acetate Chemical compound C1=CC=C2C(CC(=O)OC)=C(SC)NC2=C1 DWORZCJMOCMSFP-UHFFFAOYSA-N 0.000 claims 2
- PJKWAKAPBOGIKH-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-[[3-[2-(diethylamino)ethyl-methylcarbamoyl]-1h-indol-2-yl]diselanyl]-n-methyl-1h-indole-3-carboxamide Chemical compound N1C2=CC=CC=C2C(C(=O)N(C)CCN(CC)CC)=C1[Se][Se]C1=C(C(=O)N(C)CCN(CC)CC)C2=CC=CC=C2N1 PJKWAKAPBOGIKH-UHFFFAOYSA-N 0.000 claims 2
- XZTHVVIRCUVGRE-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-[[3-[2-(diethylamino)ethylcarbamoyl]-1-methylindol-2-yl]diselanyl]-1-methylindole-3-carboxamide Chemical compound CN1C2=CC=CC=C2C(C(=O)NCCN(CC)CC)=C1[Se][Se]C1=C(C(=O)NCCN(CC)CC)C2=CC=CC=C2N1C XZTHVVIRCUVGRE-UHFFFAOYSA-N 0.000 claims 2
- DOBDKFHLOMDQHB-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-[[3-[2-(diethylamino)ethylcarbamoyl]-1h-indol-2-yl]diselanyl]-1h-indole-3-carboxamide Chemical compound N1C2=CC=CC=C2C(C(=O)NCCN(CC)CC)=C1[Se][Se]C1=C(C(=O)NCCN(CC)CC)C2=CC=CC=C2N1 DOBDKFHLOMDQHB-UHFFFAOYSA-N 0.000 claims 2
- LNRQRRCDPILCSE-UHFFFAOYSA-N 1-methyl-2-methylsulfanyl-n-phenyl-2,3-dihydroindole-3-carboxamide Chemical compound C12=CC=CC=C2N(C)C(SC)C1C(=O)NC1=CC=CC=C1 LNRQRRCDPILCSE-UHFFFAOYSA-N 0.000 claims 1
- SUTIISXRTZTQML-UHFFFAOYSA-N 2-[[1-carboxy-3-(1-methylindol-3-yl)propyl]disulfanyl]-4-(1-methylindol-3-yl)butanoic acid Chemical compound C12=CC=CC=C2N(C)C=C1CCC(C(O)=O)SSC(C(O)=O)CCC1=CN(C)C2=CC=CC=C12 SUTIISXRTZTQML-UHFFFAOYSA-N 0.000 claims 1
- HHPDUGVXIBPIEG-UHFFFAOYSA-N 2-[[2-carboxy-1-(1-methylindol-3-yl)propan-2-yl]disulfanyl]-2-methyl-3-(1-methylindol-3-yl)propanoic acid Chemical compound C12=CC=CC=C2N(C)C=C1CC(C)(C(O)=O)SSC(C)(C(O)=O)CC1=CN(C)C2=CC=CC=C12 HHPDUGVXIBPIEG-UHFFFAOYSA-N 0.000 claims 1
- OKZLZNFBUWVBMP-UHFFFAOYSA-N 4-(2-sulfanylidene-1,3-dihydroindol-3-yl)butanoic acid Chemical compound C1=CC=C2C(CCCC(=O)O)C(=S)NC2=C1 OKZLZNFBUWVBMP-UHFFFAOYSA-N 0.000 claims 1
- XFLYPZYKOUEZGL-UHFFFAOYSA-N methyl 4-(1-methyl-2-sulfanylidene-3h-indole-3-carbonyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)C1C2=CC=CC=C2N(C)C1=S XFLYPZYKOUEZGL-UHFFFAOYSA-N 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- YABONUOGDVBUJI-UHFFFAOYSA-N n-benzyl-2-[[2-(benzylamino)-1-(1h-indol-3-yl)-2-oxoethyl]disulfanyl]-2-(1h-indol-3-yl)acetamide Chemical compound C=1C=CC=CC=1CNC(=O)C(C=1C2=CC=CC=C2NC=1)SSC(C=1C2=CC=CC=C2NC=1)C(=O)NCC1=CC=CC=C1 YABONUOGDVBUJI-UHFFFAOYSA-N 0.000 claims 1
- SSIOMHJBYZEOEK-UHFFFAOYSA-N n-methyl-2-[[3-(methylcarbamoyl)-1h-indol-2-yl]diselanyl]-1h-indole-3-carboxamide Chemical compound N1C2=CC=CC=C2C(C(=O)NC)=C1[Se][Se]C1=C(C(=O)NC)C2=CC=CC=C2N1 SSIOMHJBYZEOEK-UHFFFAOYSA-N 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 15
- 239000003112 inhibitor Substances 0.000 abstract description 8
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 414
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- 239000000203 mixture Substances 0.000 description 185
- 238000004458 analytical method Methods 0.000 description 160
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
- 229910052717 sulfur Inorganic materials 0.000 description 79
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- 238000002425 crystallisation Methods 0.000 description 76
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- 239000003480 eluent Substances 0.000 description 19
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 19
- GOLXRNDWAUTYKT-UHFFFAOYSA-N 3-(1H-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—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
- 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
- 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
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US92601592A | 1992-08-06 | 1992-08-06 | |
PCT/US1993/007272 WO1994003427A1 (en) | 1992-08-06 | 1993-08-02 | 2-thioindoles (selenoindoles) and related disulfides (selenides) which inhibit protein tyrosine kinases and which have antitumor properties |
Publications (2)
Publication Number | Publication Date |
---|---|
SK13595A3 SK13595A3 (en) | 1995-09-13 |
SK283413B6 true SK283413B6 (sk) | 2003-07-01 |
Family
ID=25452614
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK135-95A SK283413B6 (sk) | 1992-08-06 | 1993-08-02 | 2-Tioindoly, 2-indolíntióny a polysulfidy, ich selénové analógy a farmaceutické prostriedky na ich báze |
Country Status (10)
Country | Link |
---|---|
US (1) | US5464861A (cs) |
EP (1) | EP0654024A1 (cs) |
JP (1) | JPH08503450A (cs) |
AU (1) | AU672224B2 (cs) |
CA (1) | CA2140440A1 (cs) |
CZ (1) | CZ283965B6 (cs) |
HU (1) | HUT71553A (cs) |
RU (1) | RU2155187C2 (cs) |
SK (1) | SK283413B6 (cs) |
WO (1) | WO1994003427A1 (cs) |
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US5981569A (en) * | 1992-11-13 | 1999-11-09 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Substituted phenylacrylonitrile compounds and compositions thereof for the treatment of disease |
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US5763441A (en) * | 1992-11-13 | 1998-06-09 | Sugen, Inc. | Compounds for the treatment of disorders related to vasculogenesis and/or angiogenesis |
US5712395A (en) * | 1992-11-13 | 1998-01-27 | Yissum Research Development Corp. | Compounds for the treatment of disorders related to vasculogenesis and/or angiogenesis |
GB9326136D0 (en) * | 1993-12-22 | 1994-02-23 | Erba Carlo Spa | Biologically active 3-substituted oxindole derivatives useful as anti-angiogenic agents |
US5847192A (en) * | 1994-01-28 | 1998-12-08 | Prolinx, Inc. | Boronic compound complexing reagents and complexes |
DE4415463C2 (de) * | 1994-05-03 | 1996-09-26 | Lutz F Prof Dr Tietze | Acetale und Glykoside von 6-Hydroxy-2,3-dihydro-1H-indolen und 5-Hydroxy-1,2-dihydro-3H-pyrrolo(3,2-e)indolen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
AU4301096A (en) * | 1994-12-13 | 1996-07-03 | F. Hoffmann-La Roche Ag | Imidazole derivatives as protein kinase inhibitors in particular egf-r tyrosine kinase |
US5650415A (en) * | 1995-06-07 | 1997-07-22 | Sugen, Inc. | Quinoline compounds |
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US6316635B1 (en) | 1995-06-07 | 2001-11-13 | Sugen, Inc. | 2-indolinone derivatives as modulators of protein kinase activity |
EP0832073B1 (en) * | 1995-06-07 | 2002-01-16 | Sugen, Inc. | Quinazolines and pharmaceutical compositions |
US5773459A (en) * | 1995-06-07 | 1998-06-30 | Sugen, Inc. | Urea- and thiourea-type compounds |
US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
US5763470A (en) * | 1995-06-07 | 1998-06-09 | Sugen Inc. | Benzopyran compounds and methods for their use |
WO1996040629A1 (en) * | 1995-06-07 | 1996-12-19 | Sugen, Inc. | Tyrphostin-like compounds for the treatment of cell proliferative disorders or cell differentiation disorders |
US5710173A (en) * | 1995-06-07 | 1998-01-20 | Sugen, Inc. | Thienyl compounds for inhibition of cell proliferative disorders |
US6147106A (en) | 1997-08-20 | 2000-11-14 | Sugen, Inc. | Indolinone combinatorial libraries and related products and methods for the treatment of disease |
GB9523999D0 (en) * | 1995-11-23 | 1996-01-24 | Lilly Co Eli | Indolyl neuropeptide y receptor antagonists |
FR2738818B1 (fr) * | 1995-09-18 | 1997-12-05 | Valentonine | Nouveaux derives d'oxydation d'indolylalkylamines, et leur utilisation a titre de medicament |
US7119174B2 (en) | 1995-12-18 | 2006-10-10 | Sugen, Inc. | Diagnosis and treatment of AUR1 and/or AUR2 related disorders |
US6716575B2 (en) | 1995-12-18 | 2004-04-06 | Sugen, Inc. | Diagnosis and treatment of AUR1 and/or AUR2 related disorders |
US6696448B2 (en) | 1996-06-05 | 2004-02-24 | Sugen, Inc. | 3-(piperazinylbenzylidenyl)-2-indolinone compounds and derivatives as protein tyrosine kinase inhibitors |
ATE338754T1 (de) * | 1996-07-19 | 2006-09-15 | Takeda Pharmaceutical | Heterocyclische verbindungen, ihre herstellung und verwendung |
US6075126A (en) * | 1996-08-05 | 2000-06-13 | Prolinx, Inc. | Phenyldiboronic acid reagents and complexes |
US6156884A (en) * | 1996-08-05 | 2000-12-05 | Prolinx, Inc. | Bifunctional boronic compound complexing reagents and complexes |
US6682921B1 (en) | 1996-08-21 | 2004-01-27 | New York University | Crystals of the tyrosine kinase domain of non-insulin receptor tyrosine kinases |
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AR012634A1 (es) | 1997-05-02 | 2000-11-08 | Sugen Inc | Compuesto basado en quinazolina, composicion famaceutica que lo comprende, metodo para sintetizarlo, su uso, metodos de modulacion de la funcion deserina/treonina proteinaquinasa con dicho compuesto y metodo in vitro para identificar compuestos que modulan dicha funcion |
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JPH07103105B2 (ja) * | 1989-05-12 | 1995-11-08 | 杏林製薬株式会社 | インドール誘導体及びその製造方法 |
GB9004483D0 (en) * | 1990-02-28 | 1990-04-25 | Erba Carlo Spa | New aryl-and heteroarylethenylene derivatives and process for their preparation |
US5196446A (en) * | 1990-04-16 | 1993-03-23 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Certain indole compounds which inhibit EGF receptor tyrosine kinase |
-
1993
- 1993-08-02 CZ CZ95288A patent/CZ283965B6/cs not_active IP Right Cessation
- 1993-08-02 WO PCT/US1993/007272 patent/WO1994003427A1/en not_active Application Discontinuation
- 1993-08-02 EP EP93918594A patent/EP0654024A1/en not_active Withdrawn
- 1993-08-02 AU AU47994/93A patent/AU672224B2/en not_active Ceased
- 1993-08-02 SK SK135-95A patent/SK283413B6/sk unknown
- 1993-08-02 RU RU95108332/04A patent/RU2155187C2/ru not_active IP Right Cessation
- 1993-08-02 CA CA002140440A patent/CA2140440A1/en not_active Abandoned
- 1993-08-02 HU HU9500341A patent/HUT71553A/hu unknown
- 1993-08-02 JP JP5519671A patent/JPH08503450A/ja not_active Ceased
- 1993-08-09 US US08/094,792 patent/US5464861A/en not_active Expired - Fee Related
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RU95108332A (ru) | 1996-12-20 |
JPH08503450A (ja) | 1996-04-16 |
CZ28895A3 (en) | 1996-06-12 |
RU2155187C2 (ru) | 2000-08-27 |
HU9500341D0 (en) | 1995-03-28 |
US5464861A (en) | 1995-11-07 |
AU4799493A (en) | 1994-03-03 |
HUT71553A (en) | 1995-12-28 |
CA2140440A1 (en) | 1994-02-17 |
SK13595A3 (en) | 1995-09-13 |
CZ283965B6 (cs) | 1998-07-15 |
EP0654024A1 (en) | 1995-05-24 |
WO1994003427A1 (en) | 1994-02-17 |
AU672224B2 (en) | 1996-09-26 |
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