JP2004519454A5 - - Google Patents
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- JP2004519454A5 JP2004519454A5 JP2002554677A JP2002554677A JP2004519454A5 JP 2004519454 A5 JP2004519454 A5 JP 2004519454A5 JP 2002554677 A JP2002554677 A JP 2002554677A JP 2002554677 A JP2002554677 A JP 2002554677A JP 2004519454 A5 JP2004519454 A5 JP 2004519454A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethoxy
- dihydro
- quinazolin
- group
- lower alkyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 54
- -1 methylenedioxy Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052757 nitrogen Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- NWWDMEBFEXNAQY-UHFFFAOYSA-N 2-(3-cyclohexyl-3,5,6,7-tetrahydroimidazo[1,5-a]pyrazin-6-yl)-6,7-dimethoxy-3H-quinazolin-4-one Chemical compound COC1=C(C=C2C(=C1)C(=O)NC(=N2)C3CN4C(N=CC4=CN3)C5CCCCC5)OC NWWDMEBFEXNAQY-UHFFFAOYSA-N 0.000 claims description 5
- NSMYFMQCZREYGB-UHFFFAOYSA-N 6,7-dimethoxy-2-(3-phenyl-3,5,6,7-tetrahydroimidazo[1,5-a]pyrazin-6-yl)-3H-quinazolin-4-one Chemical compound COC1=C(C=C2C(=C1)C(=O)NC(=N2)C3CN4C(N=CC4=CN3)C5=CC=CC=C5)OC NSMYFMQCZREYGB-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- CFKFKGSYZNAKOS-UHFFFAOYSA-N 2-(6,7-dimethoxy-4-oxo-1h-quinazolin-2-yl)-6,7-dimethoxy-3,4-dihydro-1h-isoquinoline-5-carbonitrile Chemical compound C1CC(C(=C(OC)C(OC)=C2)C#N)=C2CN1C1=NC(C=C(C(=C2)OC)OC)=C2C(=O)N1 CFKFKGSYZNAKOS-UHFFFAOYSA-N 0.000 claims description 3
- XCHMRCYMRVDBSW-UHFFFAOYSA-N 2-[4-(benzylamino)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-6,7-dimethoxy-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1N=CN=C2NCC1=CC=CC=C1 XCHMRCYMRVDBSW-UHFFFAOYSA-N 0.000 claims description 3
- BKTPWLOJLYJMJI-UHFFFAOYSA-N 6,7-dimethoxy-2-(4-piperidin-1-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl)-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1N=CN=C2N1CCCCC1 BKTPWLOJLYJMJI-UHFFFAOYSA-N 0.000 claims description 3
- JQOSCBFBHIQXRR-UHFFFAOYSA-N 6,7-dimethoxy-2-(5-pyridin-4-yl-3,4-dihydro-1h-isoquinolin-2-yl)-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1C=CC=C2C1=CC=NC=C1 JQOSCBFBHIQXRR-UHFFFAOYSA-N 0.000 claims description 3
- ZSKWVHWKJVIBTJ-UHFFFAOYSA-N 6,7-dimethoxy-2-(5-pyrimidin-5-yl-3,4-dihydro-1h-isoquinolin-2-yl)-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1C=CC=C2C1=CN=CN=C1 ZSKWVHWKJVIBTJ-UHFFFAOYSA-N 0.000 claims description 3
- NONNATLFKKPMCH-UHFFFAOYSA-N 6,7-dimethoxy-2-(5-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinolin-2-yl)-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1C=CC=C2N1CCCC1 NONNATLFKKPMCH-UHFFFAOYSA-N 0.000 claims description 3
- VMAPZVYRBPLTBN-UHFFFAOYSA-N 6,7-dimethoxy-2-[4-[2-methoxyethyl(methyl)amino]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-1h-quinazolin-4-one Chemical compound COC1=C(OC)C=C2NC(N3CC=4N=CN=C(C=4CC3)N(C)CCOC)=NC(=O)C2=C1 VMAPZVYRBPLTBN-UHFFFAOYSA-N 0.000 claims description 3
- GABKFCIKDYWSQR-UHFFFAOYSA-N 6,7-dimethoxy-2-[5-(1h-pyrrol-2-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1C=CC=C2C1=CC=CN1 GABKFCIKDYWSQR-UHFFFAOYSA-N 0.000 claims description 3
- NJVDRVLBZQASQR-UHFFFAOYSA-N 6,7-dimethoxy-2-[5-(4-methoxyphenyl)-3,4-dihydro-1h-isoquinolin-2-yl]-1h-quinazolin-4-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC2=C1CCN(C=1NC(=O)C3=CC(OC)=C(OC)C=C3N=1)C2 NJVDRVLBZQASQR-UHFFFAOYSA-N 0.000 claims description 3
- IXLKNTSCBQHVRZ-UHFFFAOYSA-N 6,7-dimethoxy-2-[7-(4-methoxyphenyl)-3,4-dihydro-1h-isoquinolin-2-yl]-1h-quinazolin-4-one Chemical compound C1=CC(OC)=CC=C1C1=CC=C(CCN(C2)C=3NC(=O)C4=CC(OC)=C(OC)C=C4N=3)C2=C1 IXLKNTSCBQHVRZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- MYYKTZCWELANAY-UHFFFAOYSA-N 2-(3,4-dihydro-1h-pyrido[4,3-b][1,6]naphthyridin-2-yl)-6,7-dimethoxy-1h-quinazolin-4-one Chemical compound C1=NC=C2C=C(CN(C=3NC=4C=C(C(=CC=4C(=O)N=3)OC)OC)CC3)C3=NC2=C1 MYYKTZCWELANAY-UHFFFAOYSA-N 0.000 claims description 2
- NUVNTYDEDKGAPU-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-6,7-dihydro-4h-imidazo[4,5-c]pyridin-5-yl]-6,7-dimethoxy-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1N=CN2C1=CC=C(Cl)C=C1 NUVNTYDEDKGAPU-UHFFFAOYSA-N 0.000 claims description 2
- FSAGFYQBPWGVMA-UHFFFAOYSA-N 2-[5-(4,5-dihydro-1h-imidazol-2-ylamino)-3,4-dihydro-1h-isoquinolin-2-yl]-6,7-dimethoxy-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1C=CC=C2NC1=NCCN1 FSAGFYQBPWGVMA-UHFFFAOYSA-N 0.000 claims description 2
- ZZRHPMVACJGNBF-UHFFFAOYSA-N 3-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-6,7-dimethoxy-4h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound COC1=C(OC)C=C2S(=O)(=O)NC(N3CCC=4C=C(C(=CC=4C3)OC)OC)=NC2=C1 ZZRHPMVACJGNBF-UHFFFAOYSA-N 0.000 claims description 2
- BZSCPRDBSKPCNT-UHFFFAOYSA-N 6,7-dimethoxy-2-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)-1h-quinazolin-4-one Chemical compound N1C2=CC=CC=C2C(CC2)=C1CN2C1=NC(C=C(C(=C2)OC)OC)=C2C(=O)N1 BZSCPRDBSKPCNT-UHFFFAOYSA-N 0.000 claims description 2
- NCHIHXQFKMPELD-UHFFFAOYSA-N 6,7-dimethoxy-2-(1-naphthalen-2-yl-6,7-dihydro-4h-imidazo[4,5-c]pyridin-5-yl)-1h-quinazolin-4-one Chemical compound C1=CC=CC2=CC(N3C=NC4=C3CCN(C4)C3=NC=4C=C(C(=CC=4C(=O)N3)OC)OC)=CC=C21 NCHIHXQFKMPELD-UHFFFAOYSA-N 0.000 claims description 2
- ZXJDRUCKZNIUDB-UHFFFAOYSA-N 6,7-dimethoxy-2-(1-phenyl-6,7-dihydro-4h-imidazo[4,5-c]pyridin-5-yl)-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1N=CN2C1=CC=CC=C1 ZXJDRUCKZNIUDB-UHFFFAOYSA-N 0.000 claims description 2
- XUGNZQMRYTVJRN-UHFFFAOYSA-N 6,7-dimethoxy-2-(4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl)-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1N=CN=C2N1CCOCC1 XUGNZQMRYTVJRN-UHFFFAOYSA-N 0.000 claims description 2
- UVPXAIPQNSGMNS-UHFFFAOYSA-N 6,7-dimethoxy-2-(5-morpholin-4-ylsulfonyl-3,4-dihydro-1h-isoquinolin-2-yl)-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1C=CC=C2S(=O)(=O)N1CCOCC1 UVPXAIPQNSGMNS-UHFFFAOYSA-N 0.000 claims description 2
- FJFOFGNODBELRP-UHFFFAOYSA-N 6,7-dimethoxy-2-(5-pyridin-3-yl-3,4-dihydro-1h-isoquinolin-2-yl)-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1C=CC=C2C1=CC=CN=C1 FJFOFGNODBELRP-UHFFFAOYSA-N 0.000 claims description 2
- UAIZAGBMGMPSNL-UHFFFAOYSA-N 6,7-dimethoxy-2-(6-methoxy-1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)-1h-quinazolin-4-one Chemical compound COC1=C(OC)C=C2C(=O)NC(N3CC=4NC5=CC=C(C=C5C=4CC3)OC)=NC2=C1 UAIZAGBMGMPSNL-UHFFFAOYSA-N 0.000 claims description 2
- FVYPHLUZMORLDY-UHFFFAOYSA-N 6,7-dimethoxy-2-[1-(3-methylphenyl)-6,7-dihydro-4h-imidazo[4,5-c]pyridin-5-yl]-1h-quinazolin-4-one Chemical compound N=1C(=O)C=2C=C(OC)C(OC)=CC=2NC=1N(C1)CCC2=C1N=CN2C1=CC=CC(C)=C1 FVYPHLUZMORLDY-UHFFFAOYSA-N 0.000 claims description 2
- CPQOASVWAIUXGF-UHFFFAOYSA-N 6,7-dimethoxy-2-[1-(4-methoxyphenyl)-6,7-dihydro-4h-imidazo[4,5-c]pyridin-5-yl]-1h-quinazolin-4-one Chemical compound C1=CC(OC)=CC=C1N1C(CCN(C2)C=3NC(=O)C4=CC(OC)=C(OC)C=C4N=3)=C2N=C1 CPQOASVWAIUXGF-UHFFFAOYSA-N 0.000 claims description 2
- PXSIQYGEMWYZAO-UHFFFAOYSA-N 6,7-dimethoxy-2-[4-(4-methylpiperazin-1-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1N=CN=C2N1CCN(C)CC1 PXSIQYGEMWYZAO-UHFFFAOYSA-N 0.000 claims description 2
- KGCAQIWQLMNEJR-UHFFFAOYSA-N 6,7-dimethoxy-2-[5-(morpholin-4-ylmethyl)-3,4-dihydro-1h-isoquinolin-2-yl]-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(CC1=CC=C2)CCC1=C2CN1CCOCC1 KGCAQIWQLMNEJR-UHFFFAOYSA-N 0.000 claims description 2
- LOSUHUKJOXFUHY-UHFFFAOYSA-N 6,7-dimethoxy-2-[5-[(1-methylpyrrolidin-2-yl)amino]-3,4-dihydro-1h-isoquinolin-2-yl]-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1C=CC=C2NC1CCCN1C LOSUHUKJOXFUHY-UHFFFAOYSA-N 0.000 claims description 2
- JXCMPBSWEIGZIS-UHFFFAOYSA-N 6,7-dimethoxy-3-(4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl)-4h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound N1S(=O)(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1N=CN=C2N1CCOCC1 JXCMPBSWEIGZIS-UHFFFAOYSA-N 0.000 claims description 2
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 claims description 2
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 claims description 2
- UCTSSAKPFOKZHT-UHFFFAOYSA-N n'-[2-(6,7-dimethoxy-4-oxo-1h-quinazolin-2-yl)-3,4-dihydro-1h-isoquinolin-5-yl]cyclobutanecarboximidamide Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1C=CC=C2NC(=N)C1CCC1 UCTSSAKPFOKZHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 40
- 125000003545 alkoxy group Chemical group 0.000 claims 28
- 125000003118 aryl group Chemical group 0.000 claims 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 125000004414 alkyl thio group Chemical group 0.000 claims 12
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 8
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 8
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 8
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims 8
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 8
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- 239000000674 adrenergic antagonist Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004971 nitroalkyl group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- XSXTYCBJTRYMFL-UHFFFAOYSA-N COC1=CC2=CNC(N3CC4=CC=CC(NC5=NCCC5)=C4CC3)N=C2C=C1OC Chemical compound COC1=CC2=CNC(N3CC4=CC=CC(NC5=NCCC5)=C4CC3)N=C2C=C1OC XSXTYCBJTRYMFL-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 208000026723 Urinary tract disease Diseases 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 208000014001 urinary system disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CEIXWJHURKEBMQ-UHFFFAOYSA-N Heliamine Chemical compound C1CNCC2=C1C=C(OC)C(OC)=C2 CEIXWJHURKEBMQ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- QLTVPNPZNQEUJY-UHFFFAOYSA-N 2-[5-(1h-imidazol-2-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-6,7-dimethoxy-1h-quinazolin-4-one Chemical compound N1C(=O)C=2C=C(OC)C(OC)=CC=2N=C1N(C1)CCC2=C1C=CC=C2C1=NC=CN1 QLTVPNPZNQEUJY-UHFFFAOYSA-N 0.000 description 2
- DBOAGRILJPETJN-UHFFFAOYSA-N 2-chloro-6,7-dimethoxy-1h-quinazolin-4-one Chemical compound N1=C(Cl)NC(=O)C2=C1C=C(OC)C(OC)=C2 DBOAGRILJPETJN-UHFFFAOYSA-N 0.000 description 2
- OSYBRIQODOIRJL-UHFFFAOYSA-N N-cyclohexyl-6-(6,7-dimethoxy-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazin-3-yl)-3,5,6,7-tetrahydro-1H-imidazo[1,5-a]pyrazin-2-amine Chemical compound COC1=C(C=C2C(=C1)NC(=NS2(=O)=O)C3CN4CN(CC4=CN3)NC5CCCCC5)OC OSYBRIQODOIRJL-UHFFFAOYSA-N 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 1
- JXYOTTCEJSPHHY-UHFFFAOYSA-N 2-(3-butyl-3,5,6,7-tetrahydroimidazo[1,5-a]pyrazin-6-yl)-6,7-dimethoxy-3H-quinazolin-4-one Chemical compound CCCCC1N=CC2=CNC(CN12)C3=NC4=CC(=C(C=C4C(=O)N3)OC)OC JXYOTTCEJSPHHY-UHFFFAOYSA-N 0.000 description 1
- PMZGXSOONNHUAF-UHFFFAOYSA-N 2-(3-tert-butyl-3,5,6,7-tetrahydroimidazo[1,5-a]pyrazin-6-yl)-6,7-dimethoxy-3H-quinazolin-4-one Chemical compound CC(C)(C)C1N=CC2=CNC(CN12)C3=NC4=CC(=C(C=C4C(=O)N3)OC)OC PMZGXSOONNHUAF-UHFFFAOYSA-N 0.000 description 1
- YCLWUNHKRDNNND-UHFFFAOYSA-N 2-(5,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-6,7-dimethoxy-1h-quinazolin-4-one Chemical compound C1CC2=C(OC)C=CC(OC)=C2CN1C(N1)=NC(=O)C2=C1C=C(OC)C(OC)=C2 YCLWUNHKRDNNND-UHFFFAOYSA-N 0.000 description 1
- CRXRGGSYKXAZGP-UHFFFAOYSA-N 2-(5-amino-3,4-dihydro-1h-isoquinolin-2-yl)-6,7-dimethoxy-1h-quinazolin-4-one Chemical compound C1CC2=C(N)C=CC=C2CN1C1=NC(C=C(C(=C2)OC)OC)=C2C(=O)N1 CRXRGGSYKXAZGP-UHFFFAOYSA-N 0.000 description 1
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| GB0206033D0 (en) | 2002-03-14 | 2002-04-24 | Pfizer Ltd | Compounds useful in therapy |
| GB0225908D0 (en) * | 2002-11-06 | 2002-12-11 | Pfizer Ltd | Treatment of female sexual dysfunction |
| CN1845924A (zh) | 2003-07-02 | 2006-10-11 | 弗·哈夫曼-拉罗切有限公司 | 芳基胺取代的喹唑啉酮化合物 |
| ES2290726T3 (es) * | 2003-07-02 | 2008-02-16 | F. Hoffmann-La Roche Ag | Derivados de quinazolina 5-sustituidos. |
| TW200530235A (en) | 2003-12-24 | 2005-09-16 | Renovis Inc | Bicycloheteroarylamine compounds as ion channel ligands and uses thereof |
| US7793137B2 (en) | 2004-10-07 | 2010-09-07 | Cisco Technology, Inc. | Redundant power and data in a wired data telecommunincations network |
| FR2870846B1 (fr) | 2004-05-25 | 2006-08-04 | Sanofi Synthelabo | Derives de tetrahydroisoquinolylsulfonamides, leur preparation et leur utilisation en therapeutique |
| US20060128710A1 (en) * | 2004-12-09 | 2006-06-15 | Chih-Hung Lee | Antagonists to the vanilloid receptor subtype 1 (VR1) and uses thereof |
| US7402596B2 (en) | 2005-03-24 | 2008-07-22 | Renovis, Inc. | Bicycloheteroaryl compounds as P2X7 modulators and uses thereof |
| MX2007013595A (es) | 2005-05-04 | 2008-01-24 | Renovis Inc | Compuestos heterociclicos fusionados y composiciones y usos de estos. |
| WO2007028051A2 (en) | 2005-09-02 | 2007-03-08 | Abbott Laboratories | Novel imidazo based heterocycles |
| EA016008B1 (ru) * | 2005-11-24 | 2012-01-30 | Киссеи Фармасьютикал Ко., Лтд. | Применение силодозина для лечения уретеролитиаза |
| CA2682162C (en) | 2007-04-02 | 2016-05-10 | Renovis, Inc. | Pyrid-2-yl fused heterocyclic compounds, and compositions and uses thereof |
| HRP20130867T1 (hr) | 2007-04-17 | 2013-10-25 | Evotec Ag | Kondenzirani heterocikliäśki spojevi 2-cijanofenila, te njihovi pripravci i uporaba |
| EP2170350B1 (en) | 2007-06-21 | 2013-09-11 | Cara Therapeutics, Inc. | Substituted imidazoheterocycles |
| US8859538B2 (en) | 2007-06-21 | 2014-10-14 | Cara Therapeutics, Inc. | Uses of substituted imidazoheterocycles |
| CN101417999A (zh) * | 2007-10-25 | 2009-04-29 | 上海恒瑞医药有限公司 | 哌嗪类衍生物,其制备方法及其在医药上的应用 |
| JO3156B1 (ar) | 2009-07-09 | 2017-09-20 | Novartis Ag | ايميدازولات مدمجة والتركيبات التي تشملها لعلاج الأمراض الطفيلية على مثال الملاريا |
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| GB201321748D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| BR112016014295A2 (pt) * | 2013-12-20 | 2017-08-08 | Esteve Labor Dr | Composto; processo para a preparação de um composto; e composição farmacêutica compreendendo um composto |
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| CN107434786B (zh) * | 2016-05-27 | 2025-11-18 | 广东东阳光药业股份有限公司 | 苯并咪唑化合物及其制备方法 |
| WO2018198021A1 (en) | 2017-04-24 | 2018-11-01 | Novartis Ag | Therapeutic regimen of 2-amino-l-(2-(4-fluorophenyl)-3-(4-fluorophenylamino)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8h)-yl)ethanone and combinations thereof |
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| JP7592601B2 (ja) | 2019-01-10 | 2024-12-02 | ミラティ セラピューティクス， インコーポレイテッド | Ｋｒａｓ ｇ１２ｃ阻害剤 |
| KR20210146288A (ko) * | 2019-03-01 | 2021-12-03 | 레볼루션 메디슨즈, 인크. | 이환식 헤테로사이클릴 화합물 및 이의 용도 |
| JP7622043B2 (ja) | 2019-08-29 | 2025-01-27 | ミラティ セラピューティクス， インコーポレイテッド | Ｋｒａｓ ｇ１２ｄ阻害剤 |
| AU2020356455A1 (en) | 2019-09-24 | 2022-04-14 | Mirati Therapeutics, Inc. | Combination therapies |
| CN110950886A (zh) * | 2019-12-13 | 2020-04-03 | 苏州莱克施德药业有限公司 | 一种合成1-甲基-咪唑-2-甲酸甲酯衍生物的方法 |
| CN115135315B (zh) | 2019-12-20 | 2024-11-26 | 米拉蒂治疗股份有限公司 | Sos1抑制剂 |
| JP2023540809A (ja) | 2020-09-11 | 2023-09-26 | ミラティ セラピューティクス， インコーポレイテッド | Ｋｒａｓ ｇ１２ｃ阻害剤の結晶形態 |
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| GB1062357A (en) * | 1965-03-23 | 1967-03-22 | Pfizer & Co C | Quinazolone derivatives |
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| DE2757925A1 (de) * | 1977-12-24 | 1979-06-28 | Bayer Ag | Diazacyclo-1.2.4-benzothiadizine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| GB9526546D0 (en) * | 1995-12-23 | 1996-02-28 | Pfizer Ltd | Compounds useful in therapy |
| GB9700504D0 (en) * | 1997-01-11 | 1997-02-26 | Pfizer Ltd | Pharmaceutical compounds |
| AU3555200A (en) * | 1999-03-17 | 2000-10-04 | F. Hoffmann-La Roche Ag | Oxazolone derivatives and their use as alpha-1 adrenoreceptor modulators |
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- 2001-12-17 DE DE60110844T patent/DE60110844T2/de not_active Expired - Fee Related
- 2001-12-27 PA PA20018536001A patent/PA8536001A1/es unknown
- 2001-12-27 PE PE2001001308A patent/PE20020735A1/es not_active Application Discontinuation
- 2001-12-28 UY UY27109A patent/UY27109A1/es not_active Application Discontinuation
- 2001-12-28 AR ARP010106092A patent/AR035775A1/es unknown
-
2003
- 2003-06-28 ZA ZA200305038A patent/ZA200305038B/en unknown
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