EA018989B1 - Производные 2,4-диоксотиазолидинилиденметана - Google Patents

Info

Publication number

EA018989B1

EA018989B1 EA201100119A EA201100119A EA018989B1 EA 018989 B1 EA018989 B1 EA 018989B1 EA 201100119 A EA201100119 A EA 201100119A EA 201100119 A EA201100119 A EA 201100119A EA 018989 B1 EA018989 B1 EA 018989B1

Authority

EA

Eurasian Patent Office

Prior art keywords

dione

thiazolidine

benzylidene

thiazolidin

chloro

Prior art date

2008-07-02

Links

• Espacenet
• Global Dossier
• Discuss

• GXITUSCERRRNDI-UHFFFAOYSA-N 5-methylidene-1,3-thiazolidine-2,4-dione Chemical class C=C1SC(=O)NC1=O GXITUSCERRRNDI-UHFFFAOYSA-N 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 134
• 150000003839 salts Chemical class 0.000 claims abstract description 25
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
• 201000011510 cancer Diseases 0.000 claims abstract description 13
• 238000011282 treatment Methods 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• -1 [1,3] dioxol-5-ylmethyl Chemical group 0.000 claims description 291
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 108
• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 57
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 50
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 40
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 30
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 14
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 14
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 12
• 108091000080 Phosphotransferase Proteins 0.000 claims description 11
• 102000020233 phosphotransferase Human genes 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 6
• VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• GAHMOOOPIAAIJZ-UHFFFAOYSA-N 5-[[2-(3-aminopropoxy)-5-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=C(OCCCN)C(C=C2C(NC(=O)S2)=O)=C1 GAHMOOOPIAAIJZ-UHFFFAOYSA-N 0.000 claims description 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
• 125000005605 benzo group Chemical group 0.000 claims description 2
• IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
• QMQYGDZSNITFMM-UHFFFAOYSA-N 5-[[2-(4-butyl-1,4-diazepan-1-yl)-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCCC)CCCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 QMQYGDZSNITFMM-UHFFFAOYSA-N 0.000 claims 1
• RLUWZNJWIKLKCP-UHFFFAOYSA-N 5-[[3-chloro-2-[4-(2-hydroxyethyl)-1,4-diazepan-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCO)CCCN1C1=C(Cl)C=C(C(F)(F)F)C=C1C=C1C(=O)NC(=O)S1 RLUWZNJWIKLKCP-UHFFFAOYSA-N 0.000 claims 1
• MZMOEKLRSIIVAX-UHFFFAOYSA-N 5-[[5-methoxy-2-[3-(propan-2-ylamino)propoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=C(OCCCNC(C)C)C(C=C2C(NC(=O)S2)=O)=C1 MZMOEKLRSIIVAX-UHFFFAOYSA-N 0.000 claims 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
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• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 27
• 239000007858 starting material Substances 0.000 description 27
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 24
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
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• JXHFHOSKMYEEHT-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione;hydrochloride Chemical compound Cl.O=C1CSC(=O)N1 JXHFHOSKMYEEHT-UHFFFAOYSA-N 0.000 description 20
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• 238000006243 chemical reaction Methods 0.000 description 18
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 18
• GMCGYLIRFCDMPS-UHFFFAOYSA-N piperidin-3-ylcarbamic acid Chemical compound OC(=O)NC1CCCNC1 GMCGYLIRFCDMPS-UHFFFAOYSA-N 0.000 description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 17
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• QCCWVNLOJADEAV-UHFFFAOYSA-N n,n-dimethyl-1h-pyrrol-3-amine Chemical compound CN(C)C=1C=CNC=1 QCCWVNLOJADEAV-UHFFFAOYSA-N 0.000 description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
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• YWSPWKXREVSQCA-UHFFFAOYSA-N 4,5-dimethoxy-2-nitrobenzaldehyde Chemical compound COC1=CC(C=O)=C([N+]([O-])=O)C=C1OC YWSPWKXREVSQCA-UHFFFAOYSA-N 0.000 description 9
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