JP2005538134A5 - - Google Patents
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- JP2005538134A5 JP2005538134A5 JP2004527913A JP2004527913A JP2005538134A5 JP 2005538134 A5 JP2005538134 A5 JP 2005538134A5 JP 2004527913 A JP2004527913 A JP 2004527913A JP 2004527913 A JP2004527913 A JP 2004527913A JP 2005538134 A5 JP2005538134 A5 JP 2005538134A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethylpurine
- alkyl
- methylamino
- pharmaceutical composition
- cyclopropylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 62
- 239000008194 pharmaceutical composition Substances 0.000 claims 61
- -1 Nitro, methylenedioxy, ethylenedioxy Chemical group 0.000 claims 57
- 150000001875 compounds Chemical class 0.000 claims 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims 26
- 125000004432 carbon atom Chemical group C* 0.000 claims 25
- 125000003545 alkoxy group Chemical group 0.000 claims 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 21
- 125000006413 ring segment Chemical group 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 17
- 239000002253 acid Substances 0.000 claims 16
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 16
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000002757 morpholinyl group Chemical group 0.000 claims 15
- 125000004193 piperazinyl group Chemical group 0.000 claims 15
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims 14
- 230000007074 memory dysfunction Effects 0.000 claims 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 10
- 125000003282 alkyl amino group Chemical group 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 10
- 208000024827 Alzheimer disease Diseases 0.000 claims 9
- 208000028017 Psychotic disease Diseases 0.000 claims 9
- 208000010877 cognitive disease Diseases 0.000 claims 9
- 201000000980 schizophrenia Diseases 0.000 claims 9
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 208000027418 Wounds and injury Diseases 0.000 claims 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 7
- 230000006378 damage Effects 0.000 claims 7
- 208000014674 injury Diseases 0.000 claims 7
- 208000020925 Bipolar disease Diseases 0.000 claims 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims 6
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 6
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 6
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 6
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims 6
- 102000004190 Enzymes Human genes 0.000 claims 6
- 108090000790 Enzymes Proteins 0.000 claims 6
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 6
- 208000023105 Huntington disease Diseases 0.000 claims 6
- 208000001089 Multiple system atrophy Diseases 0.000 claims 6
- 208000018737 Parkinson disease Diseases 0.000 claims 6
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 6
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims 6
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 6
- 208000028683 bipolar I disease Diseases 0.000 claims 6
- 230000006999 cognitive decline Effects 0.000 claims 6
- 230000005764 inhibitory process Effects 0.000 claims 6
- 230000009529 traumatic brain injury Effects 0.000 claims 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- 208000031886 HIV Infections Diseases 0.000 claims 3
- 206010021143 Hypoxia Diseases 0.000 claims 3
- 208000012902 Nervous system disease Diseases 0.000 claims 3
- 208000025966 Neurological disease Diseases 0.000 claims 3
- 201000004810 Vascular dementia Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 230000032683 aging Effects 0.000 claims 3
- 208000026935 allergic disease Diseases 0.000 claims 3
- 230000000172 allergic effect Effects 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 208000025307 bipolar depression Diseases 0.000 claims 3
- 230000037396 body weight Effects 0.000 claims 3
- 210000004556 brain Anatomy 0.000 claims 3
- 210000003169 central nervous system Anatomy 0.000 claims 3
- 230000002490 cerebral effect Effects 0.000 claims 3
- 239000002552 dosage form Substances 0.000 claims 3
- 206010013663 drug dependence Diseases 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 230000007954 hypoxia Effects 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 208000024714 major depressive disease Diseases 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 208000008013 morphine dependence Diseases 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 208000020431 spinal cord injury Diseases 0.000 claims 3
- 208000011117 substance-related disease Diseases 0.000 claims 3
- CRVPLYPHXZQKII-UHFFFAOYSA-N 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-methylsulfonylbenzamide Chemical compound CS(=O)(=O)NC(=O)C1=CC=CC(N2C3=NC(=NC(NC4CC4)=C3N=C2)C(F)(F)F)=C1 CRVPLYPHXZQKII-UHFFFAOYSA-N 0.000 claims 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000006378 chloropyridyl group Chemical group 0.000 claims 2
- 230000019771 cognition Effects 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004212 difluorophenyl group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- WXHMEXHMKGNROM-UHFFFAOYSA-N methyl 3-[6-(methylamino)-2-(trifluoromethyl)purin-9-yl]benzoate Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC(C(=O)OC)=C1 WXHMEXHMKGNROM-UHFFFAOYSA-N 0.000 claims 2
- 125000006384 methylpyridyl group Chemical group 0.000 claims 2
- NPALSBVCCSTITO-UHFFFAOYSA-N n-methyl-9-(2-methylsulfinylphenyl)-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC=C1S(C)=O NPALSBVCCSTITO-UHFFFAOYSA-N 0.000 claims 2
- JZWMMKBJISBKPY-UHFFFAOYSA-N n-methyl-9-(2-methylsulfinylpyrimidin-4-yl)-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=NC(S(C)=O)=N1 JZWMMKBJISBKPY-UHFFFAOYSA-N 0.000 claims 2
- ORWXBLBRENXXHA-UHFFFAOYSA-N n-methyl-9-(3-methylsulfonylphenyl)-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC(S(C)(=O)=O)=C1 ORWXBLBRENXXHA-UHFFFAOYSA-N 0.000 claims 2
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- NOORXQVKQJQVNW-UHFFFAOYSA-N 2-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1C2=NC(C(F)(F)F)=NC(NC3CC3)=C2N=C1 NOORXQVKQJQVNW-UHFFFAOYSA-N 0.000 claims 1
- WXIBBDHMCUAWAG-UHFFFAOYSA-N 2-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]phenol Chemical compound OC1=CC=CC=C1N1C2=NC(C(F)(F)F)=NC(NC3CC3)=C2N=C1 WXIBBDHMCUAWAG-UHFFFAOYSA-N 0.000 claims 1
- QFMAZXCBTNIYTN-UHFFFAOYSA-N 2-[6-(methylamino)-2-(trifluoromethyl)purin-9-yl]phenol Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC=C1O QFMAZXCBTNIYTN-UHFFFAOYSA-N 0.000 claims 1
- KSNKQSPJFRQSEI-UHFFFAOYSA-M 3,3,3-trifluoropropanoate Chemical compound [O-]C(=O)CC(F)(F)F KSNKQSPJFRQSEI-UHFFFAOYSA-M 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- CZTGVGRZKNHNQQ-UHFFFAOYSA-N 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-(2,4-difluorophenyl)sulfonylbenzamide Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC(N2C3=NC(=NC(NC4CC4)=C3N=C2)C(F)(F)F)=C1 CZTGVGRZKNHNQQ-UHFFFAOYSA-N 0.000 claims 1
- VYOMMURRJYWRSN-UHFFFAOYSA-N 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-(2,6-difluorophenyl)sulfonylbenzamide Chemical compound FC1=CC=CC(F)=C1S(=O)(=O)NC(=O)C1=CC=CC(N2C3=NC(=NC(NC4CC4)=C3N=C2)C(F)(F)F)=C1 VYOMMURRJYWRSN-UHFFFAOYSA-N 0.000 claims 1
- TWSGUSHLSSFAII-UHFFFAOYSA-N 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-(4-fluorophenyl)sulfonylbenzamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC(N2C3=NC(=NC(NC4CC4)=C3N=C2)C(F)(F)F)=C1 TWSGUSHLSSFAII-UHFFFAOYSA-N 0.000 claims 1
- MRDYLPNERBVJNW-UHFFFAOYSA-N 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-(5-methylpyridin-2-yl)sulfonylbenzamide Chemical compound N1=CC(C)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC(N2C3=NC(=NC(NC4CC4)=C3N=C2)C(F)(F)F)=C1 MRDYLPNERBVJNW-UHFFFAOYSA-N 0.000 claims 1
- XLDHAVUHBPMPNJ-UHFFFAOYSA-N 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfonyl]benzamide Chemical compound S1C2=CC(OCC)=CC=C2N=C1S(=O)(=O)NC(=O)C(C=1)=CC=CC=1N(C1=NC(=N2)C(F)(F)F)C=NC1=C2NC1CC1 XLDHAVUHBPMPNJ-UHFFFAOYSA-N 0.000 claims 1
- KJEDLAOJYJUZCK-UHFFFAOYSA-N 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-ethylsulfonylbenzamide Chemical compound CCS(=O)(=O)NC(=O)C1=CC=CC(N2C3=NC(=NC(NC4CC4)=C3N=C2)C(F)(F)F)=C1 KJEDLAOJYJUZCK-UHFFFAOYSA-N 0.000 claims 1
- RRXWGSKNIDDRMP-UHFFFAOYSA-N 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-thiophen-2-ylsulfonylbenzamide Chemical compound C=12N=CN(C=3C=C(C=CC=3)C(=O)NS(=O)(=O)C=3SC=CC=3)C2=NC(C(F)(F)F)=NC=1NC1CC1 RRXWGSKNIDDRMP-UHFFFAOYSA-N 0.000 claims 1
- QVZKIFDPBKDGJA-UHFFFAOYSA-N 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(N2C3=NC(=NC(NC4CC4)=C3N=C2)C(F)(F)F)=C1 QVZKIFDPBKDGJA-UHFFFAOYSA-N 0.000 claims 1
- BJPNWVVDYIDTHK-UHFFFAOYSA-N 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]phenol Chemical compound OC1=CC=CC(N2C3=NC(=NC(NC4CC4)=C3N=C2)C(F)(F)F)=C1 BJPNWVVDYIDTHK-UHFFFAOYSA-N 0.000 claims 1
- JSFADFFXZGJHTL-UHFFFAOYSA-N 3-[6-(methylamino)-2-(trifluoromethyl)purin-9-yl]-n-methylsulfonylbenzamide Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC(C(=O)NS(C)(=O)=O)=C1 JSFADFFXZGJHTL-UHFFFAOYSA-N 0.000 claims 1
- PMMNMEAJHCEWAR-UHFFFAOYSA-N 3-[6-(methylamino)-2-(trifluoromethyl)purin-9-yl]benzoic acid Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC(C(O)=O)=C1 PMMNMEAJHCEWAR-UHFFFAOYSA-N 0.000 claims 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims 1
- BYSACIRLGZTHRV-UHFFFAOYSA-N 4-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-(4-fluorophenyl)sulfonylbenzamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2C3=NC(=NC(NC4CC4)=C3N=C2)C(F)(F)F)C=C1 BYSACIRLGZTHRV-UHFFFAOYSA-N 0.000 claims 1
- SZVYTDYZSICKAS-UHFFFAOYSA-N 4-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-ethylsulfonylbenzamide Chemical compound C1=CC(C(=O)NS(=O)(=O)CC)=CC=C1N1C2=NC(C(F)(F)F)=NC(NC3CC3)=C2N=C1 SZVYTDYZSICKAS-UHFFFAOYSA-N 0.000 claims 1
- CDLKSWAZUAPSEC-UHFFFAOYSA-N 4-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]-n-methylsulfonylbenzamide Chemical compound C1=CC(C(=O)NS(=O)(=O)C)=CC=C1N1C2=NC(C(F)(F)F)=NC(NC3CC3)=C2N=C1 CDLKSWAZUAPSEC-UHFFFAOYSA-N 0.000 claims 1
- QSQXVRJSGGZOPY-UHFFFAOYSA-N 4-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C2=NC(C(F)(F)F)=NC(NC3CC3)=C2N=C1 QSQXVRJSGGZOPY-UHFFFAOYSA-N 0.000 claims 1
- RPLPBDARRYLIAY-UHFFFAOYSA-N 4-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]phenol Chemical compound C1=CC(O)=CC=C1N1C2=NC(C(F)(F)F)=NC(NC3CC3)=C2N=C1 RPLPBDARRYLIAY-UHFFFAOYSA-N 0.000 claims 1
- QIUBCDZHJLOBLD-UHFFFAOYSA-N 4-[6-(methylamino)-2-(trifluoromethyl)purin-9-yl]-n-methylsulfonylbenzamide Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=C(C(=O)NS(C)(=O)=O)C=C1 QIUBCDZHJLOBLD-UHFFFAOYSA-N 0.000 claims 1
- SECCDGFHUBRHRY-UHFFFAOYSA-N 4-[6-(methylamino)-2-(trifluoromethyl)purin-9-yl]benzoic acid Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=C(C(O)=O)C=C1 SECCDGFHUBRHRY-UHFFFAOYSA-N 0.000 claims 1
- FVMMQNJQAFFMGN-UHFFFAOYSA-N 9-(2,3-dimethoxyphenyl)-n-methyl-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC(OC)=C1OC FVMMQNJQAFFMGN-UHFFFAOYSA-N 0.000 claims 1
- JDXPAPAFHNGWCK-UHFFFAOYSA-N 9-(2-aminopyrimidin-4-yl)-n-methyl-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=NC(N)=N1 JDXPAPAFHNGWCK-UHFFFAOYSA-N 0.000 claims 1
- QSNUQUGVLOKEOR-UHFFFAOYSA-N 9-(2-chloropyridin-4-yl)-n-cyclopropyl-2-(trifluoromethyl)purin-6-amine Chemical compound C=12N=CN(C=3C=C(Cl)N=CC=3)C2=NC(C(F)(F)F)=NC=1NC1CC1 QSNUQUGVLOKEOR-UHFFFAOYSA-N 0.000 claims 1
- ZMMCBJXOCQAOSI-UHFFFAOYSA-N 9-(2-chloropyrimidin-4-yl)-n-ethyl-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NCC)=NC(C(F)(F)F)=NC=2N1C1=CC=NC(Cl)=N1 ZMMCBJXOCQAOSI-UHFFFAOYSA-N 0.000 claims 1
- UZNGUNKFOXNYIW-UHFFFAOYSA-N 9-(2-fluoro-3-methoxyphenyl)-n-methyl-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC(OC)=C1F UZNGUNKFOXNYIW-UHFFFAOYSA-N 0.000 claims 1
- VDQLGPMWSILBSR-UHFFFAOYSA-N 9-(2-methoxypyrimidin-4-yl)-n-methyl-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=NC(OC)=N1 VDQLGPMWSILBSR-UHFFFAOYSA-N 0.000 claims 1
- CEFGQJBABYWKTG-UHFFFAOYSA-N 9-(3-aminophenyl)-n-methyl-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC(N)=C1 CEFGQJBABYWKTG-UHFFFAOYSA-N 0.000 claims 1
- ZFOSGOAXYJUXER-UHFFFAOYSA-N 9-(3-chloropyridin-4-yl)-n-cyclopropyl-2-(trifluoromethyl)purin-6-amine Chemical compound C=12N=CN(C=3C(=CN=CC=3)Cl)C2=NC(C(F)(F)F)=NC=1NC1CC1 ZFOSGOAXYJUXER-UHFFFAOYSA-N 0.000 claims 1
- RKXTWZWONLVNIM-UHFFFAOYSA-N 9-(3-ethylsulfonylphenyl)-n-methyl-2-(trifluoromethyl)purin-6-amine Chemical compound CCS(=O)(=O)C1=CC=CC(N2C3=NC(=NC(NC)=C3N=C2)C(F)(F)F)=C1 RKXTWZWONLVNIM-UHFFFAOYSA-N 0.000 claims 1
- KMKGJPAUHYBNIF-UHFFFAOYSA-N 9-(3-iodophenyl)-n-methyl-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC(I)=C1 KMKGJPAUHYBNIF-UHFFFAOYSA-N 0.000 claims 1
- ZRRYSWSWNIGGOA-UHFFFAOYSA-N 9-(5-chloropyridin-3-yl)-n-cyclopropyl-2-(trifluoromethyl)purin-6-amine Chemical compound C=12N=CN(C=3C=C(Cl)C=NC=3)C2=NC(C(F)(F)F)=NC=1NC1CC1 ZRRYSWSWNIGGOA-UHFFFAOYSA-N 0.000 claims 1
- AUQRBGALEBSZLC-UHFFFAOYSA-N 9-cyclopentyl-n-ethyl-2-(trifluoromethyl)purin-6-amine Chemical compound C1=NC=2C(NCC)=NC(C(F)(F)F)=NC=2N1C1CCCC1 AUQRBGALEBSZLC-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- DTPWOYNXPUBEPC-UHFFFAOYSA-N methyl 2-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]benzoate Chemical compound COC(=O)C1=CC=CC=C1N1C2=NC(C(F)(F)F)=NC(NC3CC3)=C2N=C1 DTPWOYNXPUBEPC-UHFFFAOYSA-N 0.000 claims 1
- ITCCIISXKGSABT-UHFFFAOYSA-N methyl 2-[6-(methylamino)-2-(trifluoromethyl)purin-9-yl]benzoate Chemical compound C1=NC=2C(NC)=NC(C(F)(F)F)=NC=2N1C1=CC=CC=C1C(=O)OC ITCCIISXKGSABT-UHFFFAOYSA-N 0.000 claims 1
- BXDARZXQWSSUAJ-UHFFFAOYSA-N methyl 3-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]benzoate Chemical compound COC(=O)C1=CC=CC(N2C3=NC(=NC(NC4CC4)=C3N=C2)C(F)(F)F)=C1 BXDARZXQWSSUAJ-UHFFFAOYSA-N 0.000 claims 1
- NBOUIDWLNULGNK-UHFFFAOYSA-N methyl 4-[6-(cyclopropylamino)-2-(trifluoromethyl)purin-9-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N1C2=NC(C(F)(F)F)=NC(NC3CC3)=C2N=C1 NBOUIDWLNULGNK-UHFFFAOYSA-N 0.000 claims 1
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| CA2602257A1 (en) | 2005-03-30 | 2006-10-05 | Conforma Therapeutics Corporation | Alkynyl pyrrolopyrimidines and related analogs as hsp90-inhibitors |
| WO2006123639A1 (ja) * | 2005-05-18 | 2006-11-23 | Asahi Kasei Pharma Corporation | ピリミジン誘導体 |
| ES2462240T3 (es) | 2006-02-28 | 2014-05-22 | Dart Neuroscience (Cayman) Ltd | Piperazinas terapéuticas como inhibidores de PDE4 |
| FR2898057B1 (fr) * | 2006-03-06 | 2008-07-04 | Centre Nat Rech Scient | Utilisation de composes derives de l'adenine pour le traitement de lupus |
| CL2007002994A1 (es) * | 2006-10-19 | 2008-02-08 | Wyeth Corp | Compuestos derivados heterociclicos que contienen sulfamoilo, inhibidores de hsp90; composicion farmaceutica; y uso para el tratamiento del cancer, tal como cancer de mama, de colon y prostata, entre otros. |
| PL2511264T3 (pl) | 2009-01-19 | 2015-08-31 | Abbvie Inc | Środki indukujące apoptozę do leczenia raka oraz chorób immunologicznych i autoimmunologicznych |
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| EP2308866A1 (de) | 2009-10-09 | 2011-04-13 | Bayer CropScience AG | Phenylpyri(mi)dinylpyrazole und ihre Verwendung als Fungizide |
| CN102762551A (zh) | 2009-12-21 | 2012-10-31 | 拜尔农作物科学股份公司 | 噻吩基吡(嘧)啶基吡唑及其用于防治植物致病菌的用途 |
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| CA2855019A1 (en) | 2011-10-31 | 2013-05-10 | Xenon Pharmaceuticals Inc. | Biaryl ether sulfonamides and their use as therapeutic agents |
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| WO2013177224A1 (en) * | 2012-05-22 | 2013-11-28 | Genentech, Inc. | N-substituted benzamides and their use in the treatment of pain |
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| EP3166939B1 (en) | 2014-07-07 | 2019-06-05 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| KR102412146B1 (ko) * | 2015-02-11 | 2022-06-22 | 주식회사 아이엔테라퓨틱스 | 소디움 채널 차단제 |
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| US5525606A (en) * | 1994-08-01 | 1996-06-11 | The United States Of America As Represented By The Department Of Health And Human Services | Substituted 06-benzylguanines and 6(4)-benzyloxypyrimidines |
| US5864037A (en) * | 1996-06-06 | 1999-01-26 | Euro-Celtique, S.A. | Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity |
| US5744473A (en) * | 1996-09-16 | 1998-04-28 | Euro-Celtique, S.A. | PDE IV inhibitors: "bis-compounds" |
| DE19702785A1 (de) | 1997-01-27 | 1998-07-30 | Bayer Ag | Neue cyclische Harnstoffderivate |
| WO1998058901A1 (en) | 1997-06-24 | 1998-12-30 | Nikken Chemicals Co., Ltd. | 3-anilino-2-cycloalkenone derivates |
| WO1999024432A1 (fr) | 1997-11-12 | 1999-05-20 | Mitsubishi Chemical Corporation | Derives de purine et medicament les renfermant en tant qu'ingredient actif |
| KR100349385B1 (ko) * | 1997-12-12 | 2002-08-24 | 유로-셀티크 소시에떼 아노뉨 | 2-티오크산틴으로부터 얻어진 3-치환 아데닌 |
| JP3542482B2 (ja) | 1997-12-25 | 2004-07-14 | 日研化学株式会社 | ３−アニリノ−２−シクロアルケノン誘導体 |
| US6319928B1 (en) * | 1998-11-30 | 2001-11-20 | Euro-Celtique, S.A. | Purine derivatives having phosphodiesterase IV inhibition activity |
| DE19935209A1 (de) | 1999-07-27 | 2001-02-08 | Truss Michael C | Verwendung von Substanzen, die den intrazellulären Gehalt von zyklischem Adenosinmonophosphat (cAMP) erhöhen oder die Aktivität cAMP-bindender Proteine stimulieren, zur Behandlung von Erkrankungen der Harnblase |
| GB0011802D0 (en) | 2000-05-16 | 2000-07-05 | Smithkline Beecham | Method for enhancing cognitive function |
| WO2002098878A1 (en) * | 2001-02-08 | 2002-12-12 | Memory Pharmaceuticals Corporation | Trifluoromethylpurines as phosphodiesterase 4 inhibitors |
| US7335654B2 (en) * | 2002-08-08 | 2008-02-26 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
| JP2005538134A (ja) * | 2002-08-08 | 2005-12-15 | メモリー・ファーマシューティカルズ・コーポレイション | ホスホジエステラーゼ４阻害剤 |
-
2003
- 2003-08-08 JP JP2004527913A patent/JP2005538134A/ja active Pending
- 2003-08-08 AT AT03785075T patent/ATE449099T1/de not_active IP Right Cessation
- 2003-08-08 CN CNA038239779A patent/CN1688580A/zh active Pending
- 2003-08-08 WO PCT/US2003/024914 patent/WO2004014913A2/en not_active Ceased
- 2003-08-08 US US10/636,979 patent/US7332486B2/en not_active Expired - Fee Related
- 2003-08-08 DE DE60330150T patent/DE60330150D1/de not_active Expired - Lifetime
- 2003-08-08 AU AU2003264017A patent/AU2003264017B2/en not_active Expired - Fee Related
- 2003-08-08 EP EP03785075A patent/EP1529049B1/en not_active Expired - Lifetime
- 2003-08-08 CA CA002494028A patent/CA2494028A1/en not_active Abandoned
-
2008
- 2008-02-05 US US12/026,198 patent/US20080139583A1/en not_active Abandoned
-
2009
- 2009-02-26 US US12/393,634 patent/US20100004236A1/en not_active Abandoned
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