MX2010014066A - Compuestos para el tratamiento del cancer. - Google Patents
Compuestos para el tratamiento del cancer.Info
- Publication number
- MX2010014066A MX2010014066A MX2010014066A MX2010014066A MX2010014066A MX 2010014066 A MX2010014066 A MX 2010014066A MX 2010014066 A MX2010014066 A MX 2010014066A MX 2010014066 A MX2010014066 A MX 2010014066A MX 2010014066 A MX2010014066 A MX 2010014066A
- Authority
- MX
- Mexico
- Prior art keywords
- methanone
- trimethoxyphenyl
- compound
- compound according
- thiazol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 221
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 70
- 201000011510 cancer Diseases 0.000 title claims abstract description 60
- 238000011282 treatment Methods 0.000 title description 13
- -1 C20 hydrocarbon Chemical class 0.000 claims abstract description 133
- 238000000034 method Methods 0.000 claims abstract description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 33
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 11
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 claims description 74
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 41
- 206010060862 Prostate cancer Diseases 0.000 claims description 29
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 29
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 26
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 22
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 21
- 125000005647 linker group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 150000001408 amides Chemical group 0.000 claims description 17
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 239000003153 chemical reaction reagent Substances 0.000 claims description 14
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 13
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- LNESSNOGBADQPV-UHFFFAOYSA-N [2-(4-fluorophenyl)-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(F)=CC=2)=C1 LNESSNOGBADQPV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 8
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
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- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- GMFZHRIKXBZXPE-UHFFFAOYSA-N (2-thiophen-2-yl-1,3-thiazol-4-yl)-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2SC=CC=2)=C1 GMFZHRIKXBZXPE-UHFFFAOYSA-N 0.000 claims description 6
- ZVEYCXZZSZYVNG-UHFFFAOYSA-N 4-[4-(3,4,5-trimethoxybenzoyl)-1,3-thiazol-2-yl]benzonitrile Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(=CC=2)C#N)=C1 ZVEYCXZZSZYVNG-UHFFFAOYSA-N 0.000 claims description 6
- OGHQVBIGARGOHC-UHFFFAOYSA-N [2-(4-ethylphenyl)-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C1=NC(C(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=CS1 OGHQVBIGARGOHC-UHFFFAOYSA-N 0.000 claims description 6
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
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- 125000002541 furyl group Chemical group 0.000 claims description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- FNFDWGCEPDFHHD-UHFFFAOYSA-N [2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 FNFDWGCEPDFHHD-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
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- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- ROYIPIXFQBIZPN-UHFFFAOYSA-N [2-(4-methylphenyl)-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(C)=CC=2)=C1 ROYIPIXFQBIZPN-UHFFFAOYSA-N 0.000 claims description 4
- CRCDSSNETKMUKH-UHFFFAOYSA-N [2-(4-nitrophenyl)-1,3-thiazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 CRCDSSNETKMUKH-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 4
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- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
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- 125000003368 amide group Chemical group 0.000 claims description 3
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- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
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- 125000004982 dihaloalkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
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- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- PSANBEISSGPKMF-UHFFFAOYSA-N (2-indol-1-yl-1,3-thiazol-4-yl)-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)N2C3=CC=CC=C3C=C2)=C1 PSANBEISSGPKMF-UHFFFAOYSA-N 0.000 claims description 2
- WZEMDWPKLKAUOH-UHFFFAOYSA-N (2-phenyl-1,3-thiazol-4-yl)-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2N=C(SC=2)C=2C=CC=CC=2)=C1 WZEMDWPKLKAUOH-UHFFFAOYSA-N 0.000 claims description 2
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- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- 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
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 2009-06-16 DK DK15168526.0T patent/DK2959900T3/en active
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