JP2007522200A5 - - Google Patents
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- JP2007522200A5 JP2007522200A5 JP2006552710A JP2006552710A JP2007522200A5 JP 2007522200 A5 JP2007522200 A5 JP 2007522200A5 JP 2006552710 A JP2006552710 A JP 2006552710A JP 2006552710 A JP2006552710 A JP 2006552710A JP 2007522200 A5 JP2007522200 A5 JP 2007522200A5
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- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- ethyl
- dimethyl
- phenyl
- 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.)
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- -1 benzoisothiazolyl Chemical group 0.000 claims 55
- 125000000217 alkyl group Chemical group 0.000 claims 40
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000001153 fluoro group Chemical group F* 0.000 claims 16
- 229910052760 oxygen Inorganic materials 0.000 claims 15
- 239000003693 atypical antipsychotic agent Substances 0.000 claims 14
- 229940002612 prodrug Drugs 0.000 claims 14
- 239000000651 prodrug Substances 0.000 claims 14
- 229940122010 Corticotropin releasing factor antagonist Drugs 0.000 claims 13
- 239000002769 corticotropin releasing factor antagonist Substances 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 9
- 229940127236 atypical antipsychotics Drugs 0.000 claims 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 239000001301 oxygen Substances 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 150000003891 oxalate salts Chemical class 0.000 claims 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 239000011593 sulfur Chemical group 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- GATYVUUKXLTIJT-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenoxy)-3,6-dimethyl-n-pentan-3-ylpyridin-4-amine Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2C)C)=C1C GATYVUUKXLTIJT-UHFFFAOYSA-N 0.000 claims 4
- VIZBSVDBNLAVAW-UHFFFAOYSA-N 3,6-dimethyl-n-pentan-3-yl-2-(2,4,6-trimethylphenoxy)pyridin-4-amine Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C VIZBSVDBNLAVAW-UHFFFAOYSA-N 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- VSWBSWWIRNCQIJ-GJZGRUSLSA-N (R,R)-asenapine Chemical compound O1C2=CC=CC=C2[C@@H]2CN(C)C[C@H]2C2=CC(Cl)=CC=C21 VSWBSWWIRNCQIJ-GJZGRUSLSA-N 0.000 claims 3
- ZSEJGVQTBLJRCQ-UHFFFAOYSA-N 3,6-dimethyl-4-pentan-3-yloxy-2-(2,4,6-trimethylphenoxy)pyridine Chemical group CCC(CC)OC1=CC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C ZSEJGVQTBLJRCQ-UHFFFAOYSA-N 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 229960005245 asenapine Drugs 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 3
- 125000005493 quinolyl group Chemical group 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 229960000607 ziprasidone Drugs 0.000 claims 3
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- GVSYRLGZIBEHOU-UHFFFAOYSA-N 1-(4-chloro-2,6-dimethylphenyl)-7-methyl-5-pentan-3-yloxy-2,4-dihydropyrido[2,3-d][1,3]oxazine Chemical compound C1OCC=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(Cl)C=C1C GVSYRLGZIBEHOU-UHFFFAOYSA-N 0.000 claims 2
- OBYABPUZVBFQAU-UHFFFAOYSA-N 2-methyl-n-pentan-3-yl-8-(2,4,6-trimethylphenyl)quinolin-4-amine Chemical compound C1=CC=C2C(NC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C OBYABPUZVBFQAU-UHFFFAOYSA-N 0.000 claims 2
- CJERNBGBGBNILW-UHFFFAOYSA-N 4,7-dimethyl-1-pentan-3-yl-5-(2,4,6-trimethylphenoxy)-2h-pyrido[3,4-b]pyrazin-3-one Chemical compound N1=C(C)C=C2N(C(CC)CC)CC(=O)N(C)C2=C1OC1=C(C)C=C(C)C=C1C CJERNBGBGBNILW-UHFFFAOYSA-N 0.000 claims 2
- DHFGAVHKEJQQAZ-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenyl)-n-(6-methoxyisoquinolin-5-yl)-5-methyl-n-propyl-1,3-thiazol-2-amine Chemical compound COC=1C=CC2=CN=CC=C2C=1N(CCC)C(SC=1C)=NC=1C1=CC=C(OC)C=C1Cl DHFGAVHKEJQQAZ-UHFFFAOYSA-N 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- HNMZXNKERMVFCH-UHFFFAOYSA-N 1,6-dimethyl-8-pentan-3-yloxy-4-(2,4,6-trimethylphenyl)-2,3-dihydropyrido[2,3-b]pyrazine Chemical compound C1CN(C)C=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C HNMZXNKERMVFCH-UHFFFAOYSA-N 0.000 claims 1
- GYPQSNBMZWFUDI-UHFFFAOYSA-N 1-(4-bromo-2,6-dimethylphenyl)-7-methyl-5-pentan-3-yloxy-2h-pyrido[2,3-d][1,3]oxazin-4-one Chemical compound C1OC(=O)C=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(Br)C=C1C GYPQSNBMZWFUDI-UHFFFAOYSA-N 0.000 claims 1
- HJYVOLRRIABQTI-UHFFFAOYSA-N 1-(4-chloro-2,6-dimethylphenyl)-7-methyl-5-pentan-3-yloxy-2h-pyrido[2,3-d][1,3]oxazin-4-one Chemical compound C1OC(=O)C=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(Cl)C=C1C HJYVOLRRIABQTI-UHFFFAOYSA-N 0.000 claims 1
- XUZPQHMFBHDLGQ-UHFFFAOYSA-N 2,5,6-trimethyl-4-pentan-3-yl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidine Chemical compound CC1=C(C)C=2C(C(CC)CC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C XUZPQHMFBHDLGQ-UHFFFAOYSA-N 0.000 claims 1
- KRMRXASLDQJAJD-UHFFFAOYSA-N 2,5,6-trimethyl-4-pentan-3-yloxy-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-b]pyridine Chemical compound C12=NC(C)=CC2=C(OC(CC)CC)C(C)=C(C)N1C1=C(C)C=C(C)C=C1C KRMRXASLDQJAJD-UHFFFAOYSA-N 0.000 claims 1
- LKCLYCBOCLUPQG-UHFFFAOYSA-N 2,5-dimethyl-4-(oxolan-3-yloxy)-7-(2,4,6-trimethylphenyl)pyrrolo[3,2-d]pyrimidine Chemical compound CC1=CC(C)=CC(C)=C1C(C1=NC(C)=N2)=CN(C)C1=C2OC1COCC1 LKCLYCBOCLUPQG-UHFFFAOYSA-N 0.000 claims 1
- QUANHMWAGRHYSS-UHFFFAOYSA-N 2,5-dimethyl-4-pentan-3-yloxy-6-(2,4,6-trimethylphenoxy)pyrimidine Chemical compound CCC(CC)OC1=NC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C QUANHMWAGRHYSS-UHFFFAOYSA-N 0.000 claims 1
- UCFKSOVFXKRDMS-UHFFFAOYSA-N 2,5-dimethyl-4-pentan-3-yloxy-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-b]pyridine Chemical compound C12=NC(C)=CC2=C(OC(CC)CC)C(C)=CN1C1=C(C)C=C(C)C=C1C UCFKSOVFXKRDMS-UHFFFAOYSA-N 0.000 claims 1
- VKKFIULENLDJRO-UHFFFAOYSA-N 2,5-dimethyl-4-pentan-3-yloxy-7-(2,4,6-trimethylphenyl)pyrrolo[3,2-d]pyrimidine Chemical compound C=1N(C)C=2C(OC(CC)CC)=NC(C)=NC=2C=1C1=C(C)C=C(C)C=C1C VKKFIULENLDJRO-UHFFFAOYSA-N 0.000 claims 1
- NIEKVPZHTADNKL-UHFFFAOYSA-N 2,5-dimethyl-7-pentan-3-yloxy-3-(2,4,6-trimethylphenyl)pyrazolo[1,5-a]pyrimidine Chemical compound CC1=NN2C(OC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C NIEKVPZHTADNKL-UHFFFAOYSA-N 0.000 claims 1
- WTWDXRZCFVEBIH-UHFFFAOYSA-N 2,5-dimethyl-n-pentan-3-yl-3-(2,4,6-trimethylphenyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(NC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C WTWDXRZCFVEBIH-UHFFFAOYSA-N 0.000 claims 1
- SXRVXRMLYNYENP-UHFFFAOYSA-N 2-[2-methyl-8-(2,4,6-trimethylphenyl)quinolin-4-yl]oxybutan-1-ol Chemical compound C1=CC=C2C(OC(CO)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C SXRVXRMLYNYENP-UHFFFAOYSA-N 0.000 claims 1
- MFGOIKCRAMOZST-UHFFFAOYSA-N 2-[[2-methyl-8-(2,4,6-trimethylphenyl)quinolin-4-yl]amino]butan-1-ol Chemical compound C1=CC=C2C(NC(CO)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C MFGOIKCRAMOZST-UHFFFAOYSA-N 0.000 claims 1
- BIKVAAJFQJWHEG-UHFFFAOYSA-N 2-[[6-methyl-4-(2,4,6-trimethylphenyl)-2,3-dihydro-1h-pyrido[2,3-b]pyrazin-8-yl]amino]butan-1-ol Chemical compound C1CNC=2C(NC(CO)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C BIKVAAJFQJWHEG-UHFFFAOYSA-N 0.000 claims 1
- BNKGKWTYNSBHDH-UHFFFAOYSA-N 2-[[6-methyl-4-(2,4,6-trimethylphenyl)-2,3-dihydro-1h-pyrido[2,3-b]pyrazin-8-yl]oxy]butan-1-ol Chemical compound C1CNC=2C(OC(CO)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C BNKGKWTYNSBHDH-UHFFFAOYSA-N 0.000 claims 1
- XDQCDBYXMDOGCG-UHFFFAOYSA-N 2-[[7-methyl-1-(2,4,6-trimethylphenyl)-2,4-dihydropyrido[2,3-d][1,3]oxazin-5-yl]amino]butan-1-ol Chemical compound C1OCC=2C(NC(CO)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C XDQCDBYXMDOGCG-UHFFFAOYSA-N 0.000 claims 1
- GNLLNLYTKYRGRA-UHFFFAOYSA-N 2-[[7-methyl-1-(2,4,6-trimethylphenyl)-2,4-dihydropyrido[2,3-d][1,3]oxazin-5-yl]oxy]butan-1-ol Chemical compound C1OCC=2C(OC(CO)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C GNLLNLYTKYRGRA-UHFFFAOYSA-N 0.000 claims 1
- HNJCZHSFAURGSI-UHFFFAOYSA-N 2-[butyl-[6-methyl-3-methylsulfanyl-1-(2,4,6-trichlorophenyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]ethanol Chemical compound N1=C(SC)C=2C(N(CCO)CCCC)=NC(C)=NC=2N1C1=C(Cl)C=C(Cl)C=C1Cl HNJCZHSFAURGSI-UHFFFAOYSA-N 0.000 claims 1
- WFNUPOXIJJGIAZ-UHFFFAOYSA-N 2-methyl-4-pentan-3-yloxy-8-(2,4,6-trimethylphenyl)-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1CCC=2C(OC(CC)CC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C WFNUPOXIJJGIAZ-UHFFFAOYSA-N 0.000 claims 1
- QIIZTANZQMETMP-UHFFFAOYSA-N 2-methyl-4-pentan-3-yloxy-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5h-pyrido[2,3-d]pyrimidine Chemical compound C1CCC=2C(OC(CC)CC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C QIIZTANZQMETMP-UHFFFAOYSA-N 0.000 claims 1
- SQVZUGHPSMFDBH-UHFFFAOYSA-N 2-methyl-4-pentan-3-yloxy-8-(2,4,6-trimethylphenyl)quinoline Chemical compound C1=CC=C2C(OC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C SQVZUGHPSMFDBH-UHFFFAOYSA-N 0.000 claims 1
- GUMZEWVVHDKXNG-UHFFFAOYSA-N 2-methyl-9-pentan-3-yl-6-(2,4,6-trimethylanilino)-7h-purin-8-one Chemical compound C=12NC(=O)N(C(CC)CC)C2=NC(C)=NC=1NC1=C(C)C=C(C)C=C1C GUMZEWVVHDKXNG-UHFFFAOYSA-N 0.000 claims 1
- JCGHMRBJFIIZCB-UHFFFAOYSA-N 2-methyl-n-pentan-2-yl-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5h-pyrido[2,3-d]pyrimidin-4-amine Chemical class C1CCC=2C(NC(C)CCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C JCGHMRBJFIIZCB-UHFFFAOYSA-N 0.000 claims 1
- QPAIYACHPNHYGO-UHFFFAOYSA-N 2-methyl-n-pentan-3-yl-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5h-pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1CCC=2C(NC(CC)CC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C QPAIYACHPNHYGO-UHFFFAOYSA-N 0.000 claims 1
- ZIHGOUCHARGSHH-UHFFFAOYSA-N 3,3,6-trimethyl-1-pentan-3-yl-4-(2,4,6-trimethylphenoxy)-2h-pyrrolo[3,2-c]pyridine Chemical compound CCC(CC)N1CC(C)(C)C2=C1C=C(C)N=C2OC1=C(C)C=C(C)C=C1C ZIHGOUCHARGSHH-UHFFFAOYSA-N 0.000 claims 1
- STVAQTHQBGWOKU-UHFFFAOYSA-N 3,5,6-trimethyl-n-pentan-3-yl-1-(2,4,6-trimethylphenyl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N1=C(C)C=2C(NC(CC)CC)=C(C)C(C)=NC=2N1C1=C(C)C=C(C)C=C1C STVAQTHQBGWOKU-UHFFFAOYSA-N 0.000 claims 1
- NAIUYSKGKROYQB-UHFFFAOYSA-N 3,6-dimethyl-1-pentan-3-yl-4-(2,4,6-trimethylanilino)imidazo[4,5-c]pyridin-2-one Chemical compound C=12N(C)C(=O)N(C(CC)CC)C2=CC(C)=NC=1NC1=C(C)C=C(C)C=C1C NAIUYSKGKROYQB-UHFFFAOYSA-N 0.000 claims 1
- DALHKUCEMJELGX-UHFFFAOYSA-N 3,6-dimethyl-1-pentan-3-yl-4-(2,4,6-trimethylphenoxy)imidazo[4,5-c]pyridin-2-one Chemical compound C=12N(C)C(=O)N(C(CC)CC)C2=CC(C)=NC=1OC1=C(C)C=C(C)C=C1C DALHKUCEMJELGX-UHFFFAOYSA-N 0.000 claims 1
- NOVMRCQAXSODAQ-UHFFFAOYSA-N 3,6-dimethyl-4-pentan-3-yloxy-n-(2,4,6-trimethylphenyl)pyridin-2-amine Chemical compound CCC(CC)OC1=CC(C)=NC(NC=2C(=CC(C)=CC=2C)C)=C1C NOVMRCQAXSODAQ-UHFFFAOYSA-N 0.000 claims 1
- SGQKMKKONKLFNB-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-2,5-dimethyl-n-pentan-3-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(NC(CC)CC)=CC(C)=NC2=C1C1=CC=C(Cl)C=C1Cl SGQKMKKONKLFNB-UHFFFAOYSA-N 0.000 claims 1
- AKFWXFDMKRSYRD-UHFFFAOYSA-N 3-(2,4-dimethoxyphenyl)-n-(2-methoxyethyl)-2,5-dimethyl-n-propylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(N(CCOC)CCC)=CC(C)=NC2=C1C1=CC=C(OC)C=C1OC AKFWXFDMKRSYRD-UHFFFAOYSA-N 0.000 claims 1
- MUXBHSAZFHTFEJ-UHFFFAOYSA-N 3-(2,4-dimethylphenyl)-2,5-dimethyl-n-pentan-3-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(NC(CC)CC)=CC(C)=NC2=C1C1=CC=C(C)C=C1C MUXBHSAZFHTFEJ-UHFFFAOYSA-N 0.000 claims 1
- BLKLUABHJBNQSU-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-2,5-dimethyl-n,n-dipropylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(N(CCC)CCC)=CC(C)=NC2=C1C1=CC=C(Cl)C=C1C BLKLUABHJBNQSU-UHFFFAOYSA-N 0.000 claims 1
- UQADAKVNVOCEIM-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-n-(cyclopropylmethyl)-2,5-dimethyl-n-propylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C(=CC(Cl)=CC=3)C)C(C)=NN2C=1N(CCC)CC1CC1 UQADAKVNVOCEIM-UHFFFAOYSA-N 0.000 claims 1
- DOPVGJROKFQOTD-UHFFFAOYSA-N 3-(4-chlorophenyl)-2,5-dimethyl-n,n-dipropylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(N(CCC)CCC)=CC(C)=NC2=C1C1=CC=C(Cl)C=C1 DOPVGJROKFQOTD-UHFFFAOYSA-N 0.000 claims 1
- ANNRUWYFVIGKHA-UHFFFAOYSA-N 3-[6-(dimethylamino)-4-methylpyridin-3-yl]-2,5-dimethyl-n,n-dipropylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(N(CCC)CCC)=CC(C)=NC2=C1C1=CN=C(N(C)C)C=C1C ANNRUWYFVIGKHA-UHFFFAOYSA-N 0.000 claims 1
- NSZSAPMQWCARQU-UHFFFAOYSA-N 3-[[3,6-dimethyl-1-(2,4,6-trimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]-[(4-methylphenyl)methyl]amino]propan-1-ol Chemical compound C12=NC(C)=NC(N(CCCO)CC=3C=CC(C)=CC=3)=C2C(C)=NN1C1=C(C)C=C(C)C=C1C NSZSAPMQWCARQU-UHFFFAOYSA-N 0.000 claims 1
- ZZNOWBFPUVEVCB-UHFFFAOYSA-N 4,7-dimethyl-1-pentan-3-yl-5-(2,4,6-trimethylphenoxy)-2,3-dihydropyrido[3,4-b]pyrazine Chemical compound N1=C(C)C=C2N(C(CC)CC)CCN(C)C2=C1OC1=C(C)C=C(C)C=C1C ZZNOWBFPUVEVCB-UHFFFAOYSA-N 0.000 claims 1
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| IL296683B2 (en) | 2014-01-21 | 2023-12-01 | Neurocrine Biosciences Inc | Preparations for the treatment of congenital adrenal hyperplasia |
| CN106132415A (zh) | 2014-03-20 | 2016-11-16 | 奥克梅斯制药爱尔兰有限公司 | 具有增加的注射速度的阿立哌唑制剂 |
| KR102571296B1 (ko) * | 2016-09-07 | 2023-08-28 | 더 리전트 오브 더 유니버시티 오브 캘리포니아 | P-tau를 감소시키고 인지를 개선하는 알로스테릭 코르티코트로핀-방출 인자 수용체 1 (crfr1) 길항제 |
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| EP3664806B1 (en) * | 2017-08-09 | 2025-04-30 | Sanford Burnham Prebys Medical Discovery Institute | 3-PHENYL-PYRAZOLO[1,5-A]PYRIMIDINE-5-CARBOXILIC ACID DERIVATIVES AS APELIN (APJ) RECEPTOR AGONISTS FOR THE TREATMENT OF CARDIOVASCULAR, METABOLIC, CNS, OR INFECTIOUS DISEASES OR DISORDERS |
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| US11273158B2 (en) | 2018-03-05 | 2022-03-15 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
| US12329862B2 (en) | 2018-06-20 | 2025-06-17 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| NL7605526A (nl) * | 1976-05-24 | 1977-11-28 | Akzo Nv | Nieuwe tetracyclische derivaten. |
| TW530047B (en) * | 1994-06-08 | 2003-05-01 | Pfizer | Corticotropin releasing factor antagonists |
| TW477787B (en) * | 1996-08-27 | 2002-03-01 | Pfizer | Pyrido six-membered nitrogen-containing cyclic ring derivatives having corticotropin releasing factor antagonist activity and pharmaceutical composition containing same |
| IL127497A (en) * | 1997-12-18 | 2002-07-25 | Pfizer Prod Inc | Medicinal products containing piperazinyl-heterocyclic compounds for the treatment of psychiatric disorders |
| EP1040831A3 (en) * | 1999-04-02 | 2003-05-02 | Pfizer Products Inc. | Use of corticotropin releasing factor (CRF) antagonists to prevent sudden death |
| US6432989B1 (en) * | 1999-08-27 | 2002-08-13 | Pfizer Inc | Use of CRF antagonists to treat circadian rhythm disorders |
-
2005
- 2005-02-01 WO PCT/IB2005/000251 patent/WO2005079807A1/en not_active Ceased
- 2005-02-01 CN CNA2005800049430A patent/CN1917882A/zh active Pending
- 2005-02-01 BR BRPI0507609-9A patent/BRPI0507609A/pt not_active IP Right Cessation
- 2005-02-01 AU AU2005215257A patent/AU2005215257A1/en not_active Abandoned
- 2005-02-01 KR KR1020067018643A patent/KR20060110006A/ko not_active Ceased
- 2005-02-01 EP EP05702400A patent/EP1718311A1/en not_active Withdrawn
- 2005-02-01 RU RU2006129307/15A patent/RU2006129307A/ru not_active Application Discontinuation
- 2005-02-01 JP JP2006552710A patent/JP2007522200A/ja active Pending
- 2005-02-01 CA CA002556160A patent/CA2556160A1/en not_active Abandoned
- 2005-02-05 TW TW094103864A patent/TW200538128A/zh unknown
- 2005-02-14 US US11/058,329 patent/US20050209250A1/en not_active Abandoned
-
2006
- 2006-08-10 ZA ZA200606636A patent/ZA200606636B/en unknown
- 2006-08-10 IL IL177433A patent/IL177433A0/en unknown
- 2006-09-08 NO NO20064054A patent/NO20064054L/no not_active Application Discontinuation
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