JP2004507442A5

JP2004507442A5 -

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Publication number: JP2004507442A5
Authority: JP; Japan
Prior art keywords: dihydro; dichlorophenyl; carbonyl; pyrimidin; methylpyrazolo
Prior art date: 2000-12-04
Legal status : Pending

Application number

JP2001540986A

Other languages

English (en)

Japanese (ja)

Other versions

JP2004507442A (ja

Filing date

2000-12-04

Publication date

2008-02-14

2000-12-04 Application filed filed Critical

2000-12-04 Priority claimed from PCT/US2000/032785 external-priority patent/WO2001040231A1/en

2004-03-11 Publication of JP2004507442A publication Critical patent/JP2004507442A/ja

2008-02-14 Publication of JP2004507442A5 publication Critical patent/JP2004507442A5/ja

Status Pending legal-status Critical Current

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125000000623 heterocyclic group Chemical group 0.000 description 54
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 50
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 44
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 40
-1 5-butyl-1,3,4-oxadiazol-2-yl Chemical group 0.000 description 39
125000000217 alkyl group Chemical group 0.000 description 38
150000001875 compounds Chemical class 0.000 description 32
125000003118 aryl group Chemical group 0.000 description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
125000002837 carbocyclic group Chemical group 0.000 description 19
125000003107 substituted aryl group Chemical group 0.000 description 18
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
125000003342 alkenyl group Chemical group 0.000 description 14
125000000547 substituted alkyl group Chemical group 0.000 description 13
125000004432 carbon atom Chemical group C* 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
125000000392 cycloalkenyl group Chemical group 0.000 description 10
125000000753 cycloalkyl group Chemical group 0.000 description 10
125000005843 halogen group Chemical group 0.000 description 10
239000012453 solvate Substances 0.000 description 10
125000003545 alkoxy group Chemical group 0.000 description 9
239000001257 hydrogen Substances 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
IVTZRJKKXSKXKO-UHFFFAOYSA-N 1-(2-fluorophenyl)piperazine Chemical compound FC1=CC=CC=C1N1CCNCC1 IVTZRJKKXSKXKO-UHFFFAOYSA-N 0.000 description 7
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
125000005907 alkyl ester group Chemical group 0.000 description 7
125000000304 alkynyl group Chemical group 0.000 description 7
125000003435 aroyl group Chemical group 0.000 description 7
125000004104 aryloxy group Chemical group 0.000 description 7
239000004202 carbamide Substances 0.000 description 7
125000001589 carboacyl group Chemical group 0.000 description 7
CISNNLXXANUBPI-UHFFFAOYSA-N cyano(nitro)azanide Chemical compound [O-][N+](=O)[N-]C#N CISNNLXXANUBPI-UHFFFAOYSA-N 0.000 description 7
125000004356 hydroxy functional group Chemical group O* 0.000 description 7
150000003951 lactams Chemical class 0.000 description 7
125000004043 oxo group Chemical group O=* 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
QMXROZWVTNXAOQ-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-6-carboxamide Chemical compound C1=C(C(=O)N)C=NC2=CC=NN21 QMXROZWVTNXAOQ-UHFFFAOYSA-N 0.000 description 7
125000005017 substituted alkenyl group Chemical group 0.000 description 7
125000004426 substituted alkynyl group Chemical group 0.000 description 7
239000003146 anticoagulant agent Substances 0.000 description 6
125000001183 hydrocarbyl group Chemical group 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000008194 pharmaceutical composition Substances 0.000 description 6
150000007860 aryl ester derivatives Chemical class 0.000 description 5
239000003814 drug Substances 0.000 description 5
MGDOQOMUDZRGPH-UHFFFAOYSA-N [7-(2,3-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical class N12N=C(C)C=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)C1C1=CC=CC(Cl)=C1Cl MGDOQOMUDZRGPH-UHFFFAOYSA-N 0.000 description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
150000003235 pyrrolidines Chemical class 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
101150096316 5 gene Proteins 0.000 description 3
206010003130 Arrhythmia supraventricular Diseases 0.000 description 3
PWIFGWFJTNBDFU-UHFFFAOYSA-N C(=O)=C1NCCN(C1)C1=CC=C(C=C1)F Chemical compound C(=O)=C1NCCN(C1)C1=CC=C(C=C1)F PWIFGWFJTNBDFU-UHFFFAOYSA-N 0.000 description 3
229940127291 Calcium channel antagonist Drugs 0.000 description 3
229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
206010042600 Supraventricular arrhythmias Diseases 0.000 description 3
NQKBNEUPKZMERR-UHFFFAOYSA-N [3-chloro-7-(2,3-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-(4-phenylpiperazin-1-yl)methanone Chemical compound N12N=CC(Cl)=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC=CC=2)C1C1=CC=CC(Cl)=C1Cl NQKBNEUPKZMERR-UHFFFAOYSA-N 0.000 description 3
QSWJCZNFQVNLOL-UHFFFAOYSA-N [3-chloro-7-(2,3-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical compound N12N=CC(Cl)=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)C1C1=CC=CC(Cl)=C1Cl QSWJCZNFQVNLOL-UHFFFAOYSA-N 0.000 description 3
YFRZAKRYBDUZRD-UHFFFAOYSA-N [7-(2,3-dichlorophenyl)-4,5-dimethyl-7h-pyrazolo[1,5-a]pyrimidin-6-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical compound CC=1N(C)C2=CC=NN2C(C=2C(=C(Cl)C=CC=2)Cl)C=1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 YFRZAKRYBDUZRD-UHFFFAOYSA-N 0.000 description 3
KBSRWRHNLKEKBS-UHFFFAOYSA-N [7-(2,3-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-(4-phenylpiperazin-1-yl)methanone Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC=CC=2)C1C1=CC=CC(Cl)=C1Cl KBSRWRHNLKEKBS-UHFFFAOYSA-N 0.000 description 3
SAIPWQFDGYDMPD-YTJLLHSVSA-N [7-(3,4-dichlorophenyl)-5-methyl-2-(trifluoromethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methanone Chemical compound COC[C@@H]1CCCN1C(=O)C1=C(C)NC2=CC(C(F)(F)F)=NN2C1C1=CC=C(Cl)C(Cl)=C1 SAIPWQFDGYDMPD-YTJLLHSVSA-N 0.000 description 3
DXRSMDOJZUNZNC-VEXWJQHLSA-N [7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-[(2S)-2-(phenoxymethyl)pyrrolidin-1-yl]methanone Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2[C@@H](CCC2)COC=2C=CC=CC=2)C1C1=CC=C(Cl)C(Cl)=C1 DXRSMDOJZUNZNC-VEXWJQHLSA-N 0.000 description 3
AVLWAWGUQFZEIA-UHFFFAOYSA-N [7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-[2-(3-methyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound CC1=NOC(C2N(CCCC2)C(=O)C=2C(N3N=CC=C3NC=2C)C=2C=C(Cl)C(Cl)=CC=2)=N1 AVLWAWGUQFZEIA-UHFFFAOYSA-N 0.000 description 3
229940083712 aldosterone antagonist Drugs 0.000 description 3
239000003416 antiarrhythmic agent Substances 0.000 description 3
229940127219 anticoagulant drug Drugs 0.000 description 3
239000003472 antidiabetic agent Substances 0.000 description 3
239000002220 antihypertensive agent Substances 0.000 description 3
229940127218 antiplatelet drug Drugs 0.000 description 3
230000001746 atrial effect Effects 0.000 description 3
239000000480 calcium channel blocker Substances 0.000 description 3
229940097217 cardiac glycoside Drugs 0.000 description 3
239000002368 cardiac glycoside Substances 0.000 description 3
FLNCEWAOBJCYIB-UHFFFAOYSA-N chembl464066 Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)C1C1=CC=CC(Cl)=C1Cl FLNCEWAOBJCYIB-UHFFFAOYSA-N 0.000 description 3
QAYJFCBUVMMOKG-UHFFFAOYSA-N chembl464077 Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)C1C1=CC=C(Cl)C(Cl)=C1 QAYJFCBUVMMOKG-UHFFFAOYSA-N 0.000 description 3
GSXVIOPVSCTVSK-UHFFFAOYSA-N chembl571976 Chemical compound N12N=CC=C2NC(C)=C(C=2N(C3=CC=C(F)C=C3N=2)C)C1C1=CC=C(Cl)C(Cl)=C1 GSXVIOPVSCTVSK-UHFFFAOYSA-N 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
230000014509 gene expression Effects 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000002265 prevention Effects 0.000 description 3
229930002534 steroid glycoside Natural products 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
LKCWOHZKJWUSRE-UHFFFAOYSA-N [3-chloro-7-(2,3-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical class CC=1NC2=C(Cl)C(C)=NN2C(C=2C(=C(Cl)C=CC=2)Cl)C=1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 LKCWOHZKJWUSRE-UHFFFAOYSA-N 0.000 description 2
KGRQZMATLLUIIJ-UHFFFAOYSA-N [3-chloro-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical class CC=1NC2=C(Cl)C(C)=NN2C(C=2C=C(Cl)C(Cl)=CC=2)C=1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 KGRQZMATLLUIIJ-UHFFFAOYSA-N 0.000 description 2
JUBGJEHEUMOXAA-UHFFFAOYSA-N [4-(4-fluorophenyl)piperazin-1-yl]-[5-methyl-7-(4-pyrrolidin-1-ylphenyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methanone Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)C1C(C=C1)=CC=C1N1CCCC1 JUBGJEHEUMOXAA-UHFFFAOYSA-N 0.000 description 2
BTUDAVUFAYBOJI-UHFFFAOYSA-N [7-(2,3-dichlorophenyl)-5-methyl-2-(trifluoromethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical compound N12N=C(C(F)(F)F)C=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)C1C1=CC=CC(Cl)=C1Cl BTUDAVUFAYBOJI-UHFFFAOYSA-N 0.000 description 2
XBFDHFWAHRILTC-UHFFFAOYSA-N [7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-(1,3-thiazolidin-3-yl)methanone Chemical class N12N=CC=C2NC(C)=C(C(=O)N2CSCC2)C1C1=CC=C(Cl)C(Cl)=C1 XBFDHFWAHRILTC-UHFFFAOYSA-N 0.000 description 2
PLVCUUOXALRMIC-XNUZUHMRSA-N [7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-[(3S)-3-phenoxypyrrolidin-1-yl]methanone Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2C[C@H](CC2)OC=2C=CC=CC=2)C1C1=CC=C(Cl)C(Cl)=C1 PLVCUUOXALRMIC-XNUZUHMRSA-N 0.000 description 2
SZDYHYPZQDUKLX-UHFFFAOYSA-N [7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]-[4-(3,4-dimethylphenyl)piperazin-1-yl]methanone Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=C(C)C(C)=CC=2)C1C1=CC=C(Cl)C(Cl)=C1 SZDYHYPZQDUKLX-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002785 anti-thrombosis Effects 0.000 description 2
229940125708 antidiabetic agent Drugs 0.000 description 2
229940030600 antihypertensive agent Drugs 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
WGRHMMVTMBRCRW-UHFFFAOYSA-N chembl2042147 Chemical class N12N=C(C)C=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)C1C1=CC=C(Cl)C(Cl)=C1 WGRHMMVTMBRCRW-UHFFFAOYSA-N 0.000 description 2
DEGANGVBJANIHO-UHFFFAOYSA-N chembl567671 Chemical compound N12N=CC=C2NC(COC)=C(C=2N(C3=CC=C(F)C=C3N=2)C)C1C1=CC=C(Cl)C(Cl)=C1 DEGANGVBJANIHO-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000004438 haloalkoxy group Chemical group 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000002394 mineralocorticoid antagonist Substances 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
125000003386 piperidinyl group Chemical group 0.000 description 2
LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 2
150000003230 pyrimidines Chemical class 0.000 description 2
125000000719 pyrrolidinyl group Chemical group 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
125000006413 ring segment Chemical group 0.000 description 2
150000008143 steroidal glycosides Chemical class 0.000 description 2
UMWWLTHUHGUKDT-UHFFFAOYSA-N (2-benzylpyrrolidin-1-yl)-[7-(3,4-dichlorophenyl)-5-methyl-2-(trifluoromethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methanone Chemical compound N12N=C(C(F)(F)F)C=C2NC(C)=C(C(=O)N2C(CCC2)CC=2C=CC=CC=2)C1C1=CC=C(Cl)C(Cl)=C1 UMWWLTHUHGUKDT-UHFFFAOYSA-N 0.000 description 1
GHXBZTUCVOUCOU-UHFFFAOYSA-N (2-benzylpyrrolidin-1-yl)-[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methanone Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2C(CCC2)CC=2C=CC=CC=2)C1C1=CC=C(Cl)C(Cl)=C1 GHXBZTUCVOUCOU-UHFFFAOYSA-N 0.000 description 1
CHWMQQSPLQAQRP-XPCCGILXSA-N (2R)-1-[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]pyrrolidine-2-carboxamide Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2[C@H](CCC2)C(N)=O)C1C1=CC=C(Cl)C(Cl)=C1 CHWMQQSPLQAQRP-XPCCGILXSA-N 0.000 description 1
XAAXYBCMEIWHDZ-UHFFFAOYSA-N (4-benzylpiperazin-1-yl)-[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methanone Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2CCN(CC=3C=CC=CC=3)CC2)C1C1=CC=C(Cl)C(Cl)=C1 XAAXYBCMEIWHDZ-UHFFFAOYSA-N 0.000 description 1
IEGOBRNQDWWXMP-UHFFFAOYSA-N (4-benzylpiperidin-1-yl)-[7-(3,4-dichlorophenyl)-5-methyl-2-(trifluoromethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methanone Chemical compound N12N=C(C(F)(F)F)C=C2NC(C)=C(C(=O)N2CCC(CC=3C=CC=CC=3)CC2)C1C1=CC=C(Cl)C(Cl)=C1 IEGOBRNQDWWXMP-UHFFFAOYSA-N 0.000 description 1
XMCCBSZEKUZGHJ-UHFFFAOYSA-N (4-benzylpiperidin-1-yl)-[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methanone Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2CCC(CC=3C=CC=CC=3)CC2)C1C1=CC=C(Cl)C(Cl)=C1 XMCCBSZEKUZGHJ-UHFFFAOYSA-N 0.000 description 1
XZBQIMCGRJDQOB-UHFFFAOYSA-N (5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)-(4-phenylpiperazin-1-yl)methanone Chemical compound C1N2N=CC=C2NC(C)=C1C(=O)N(CC1)CCN1C1=CC=CC=C1 XZBQIMCGRJDQOB-UHFFFAOYSA-N 0.000 description 1
YXXUQGHLMBVVPY-UHFFFAOYSA-N (7-cyclohexyl-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)-(4-phenylpiperazin-1-yl)methanone Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC=CC=2)C1C1CCCCC1 YXXUQGHLMBVVPY-UHFFFAOYSA-N 0.000 description 1
RZDVJFXRWHEVMI-UHFFFAOYSA-N (7-cyclopropyl-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)C1C1CC1 RZDVJFXRWHEVMI-UHFFFAOYSA-N 0.000 description 1
VDXVPAQGESOUCY-UHFFFAOYSA-N 1-(cyclobutanecarbonyl)-7-(3,4-dichlorophenyl)-6-[4-(4-fluorophenyl)piperazine-1-carbonyl]-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-2-one Chemical compound C=1C(=O)N(C(=O)C2CCC2)N2C=1NC(C)=C(C(=O)N1CCN(CC1)C=1C=CC(F)=CC=1)C2C1=CC=C(Cl)C(Cl)=C1 VDXVPAQGESOUCY-UHFFFAOYSA-N 0.000 description 1
MWVAOAGUOXBPQP-UHFFFAOYSA-N 1-(cyclopropanecarbonyl)-7-(2,3-dichlorophenyl)-6-[4-(4-fluorophenyl)piperazine-1-carbonyl]-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-2-one Chemical compound C=1C(=O)N(C(=O)C2CC2)N2C=1NC(C)=C(C(=O)N1CCN(CC1)C=1C=CC(F)=CC=1)C2C1=CC=CC(Cl)=C1Cl MWVAOAGUOXBPQP-UHFFFAOYSA-N 0.000 description 1
RWIAWTJKNLTGMK-UHFFFAOYSA-N 1-(cyclopropanecarbonyl)-7-(3,4-dichlorophenyl)-5-methyl-6-(4-phenylpiperazine-1-carbonyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-2-one Chemical compound C=1C(=O)N(C(=O)C2CC2)N2C=1NC(C)=C(C(=O)N1CCN(CC1)C=1C=CC=CC=1)C2C1=CC=C(Cl)C(Cl)=C1 RWIAWTJKNLTGMK-UHFFFAOYSA-N 0.000 description 1
MMSLEEQONNTURD-UHFFFAOYSA-N 1-(cyclopropanecarbonyl)-7-(3,4-dichlorophenyl)-6-[4-(4-fluorophenyl)piperazine-1-carbonyl]-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-2-one Chemical compound C=1C(=O)N(C(=O)C2CC2)N2C=1NC(C)=C(C(=O)N1CCN(CC1)C=1C=CC(F)=CC=1)C2C1=CC=C(Cl)C(Cl)=C1 MMSLEEQONNTURD-UHFFFAOYSA-N 0.000 description 1
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ACEZCEGHKCIGHU-UHFFFAOYSA-N chembl601456 Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2C(CCC2)C=2N=CC=CC=2)C1C1=CC=C(Cl)C(Cl)=C1 ACEZCEGHKCIGHU-UHFFFAOYSA-N 0.000 description 1
MQXWFRZMYXNNRF-UHFFFAOYSA-N chembl605992 Chemical compound N12N=CC=C2NC(C)=C(C(=O)N2C(CCC2)C=2C=CC=CC=2)C1C1=CC=C(Cl)C(Cl)=C1 MQXWFRZMYXNNRF-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
ABFCPRWYBWWOEF-UHFFFAOYSA-N ethyl 1-[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C1=C(C)NC2=CC=NN2C1C1=CC=C(Cl)C(Cl)=C1 ABFCPRWYBWWOEF-UHFFFAOYSA-N 0.000 description 1
WPBPKSJFDGVKJU-UHFFFAOYSA-N ethyl 1-[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)C1=C(C)NC2=CC=NN2C1C1=CC=C(Cl)C(Cl)=C1 WPBPKSJFDGVKJU-UHFFFAOYSA-N 0.000 description 1
NMHDMNMDKGWUGQ-UHFFFAOYSA-N ethyl 1-[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)C1=C(C)NC2=CC=NN2C1C1=CC=C(Cl)C(Cl)=C1 NMHDMNMDKGWUGQ-UHFFFAOYSA-N 0.000 description 1
MIPVIXCAVJNVIK-UHFFFAOYSA-N ethyl 2-[[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]-(2-ethoxy-2-oxoethyl)amino]acetate Chemical compound CCOC(=O)CN(CC(=O)OCC)C(=O)C1=C(C)NC2=CC=NN2C1C1=CC=C(Cl)C(Cl)=C1 MIPVIXCAVJNVIK-UHFFFAOYSA-N 0.000 description 1
RKWSSSNLJQIFEJ-UHFFFAOYSA-N ethyl 2-[[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]-methylamino]acetate Chemical compound CCOC(=O)CN(C)C(=O)C1=C(C)NC2=CC=NN2C1C1=CC=C(Cl)C(Cl)=C1 RKWSSSNLJQIFEJ-UHFFFAOYSA-N 0.000 description 1
OVWCAVAHOZQTRP-UHFFFAOYSA-N ethyl 2-[benzyl-[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]amino]acetate Chemical compound CC=1NC2=CC=NN2C(C=2C=C(Cl)C(Cl)=CC=2)C=1C(=O)N(CC(=O)OCC)CC1=CC=CC=C1 OVWCAVAHOZQTRP-UHFFFAOYSA-N 0.000 description 1
MUVNQVKUCQPXSO-UHFFFAOYSA-N ethyl 4-[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)C1=C(C)NC2=CC=NN2C1C1=CC=C(Cl)C(Cl)=C1 MUVNQVKUCQPXSO-UHFFFAOYSA-N 0.000 description 1
HAGBOZVHRSIILF-UHFFFAOYSA-N ethyl 7-(2,3-dichlorophenyl)-5-methyl-6-(4-phenylpiperazine-1-carbonyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound N12N=C(C(=O)OCC)C=C2NC(C)=C(C(=O)N2CCN(CC2)C=2C=CC=CC=2)C1C1=CC=CC(Cl)=C1Cl HAGBOZVHRSIILF-UHFFFAOYSA-N 0.000 description 1
DTWQWQNBPVMAAZ-UHFFFAOYSA-N ethyl 7-(2,3-dichlorophenyl)-5-methyl-6-(4-phenylpiperazine-1-carbonyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CC=1NC2=C(C(=O)OCC)C=NN2C(C=2C(=C(Cl)C=CC=2)Cl)C=1C(=O)N(CC1)CCN1C1=CC=CC=C1 DTWQWQNBPVMAAZ-UHFFFAOYSA-N 0.000 description 1
WPKPYKQEQUKZMM-UHFFFAOYSA-N ethyl 7-(3,4-dichlorophenyl)-5-methyl-6-(3-phenylpropylcarbamoyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CC=1NC2=C(C(=O)OCC)C=NN2C(C=2C=C(Cl)C(Cl)=CC=2)C=1C(=O)NCCCC1=CC=CC=C1 WPKPYKQEQUKZMM-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229960002591 hydroxyproline Drugs 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
BYMVUUKGSFNOHC-ZZWBGTBQSA-N methyl (2R)-2-[[7-(3,4-dichlorophenyl)-5-methyl-2-(trifluoromethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]amino]-3-phenylpropanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C(N2N=C(C=C2NC=1C)C(F)(F)F)C=1C=C(Cl)C(Cl)=CC=1)C1=CC=CC=C1 BYMVUUKGSFNOHC-ZZWBGTBQSA-N 0.000 description 1
NNGKSMVWYPCCHQ-UHFFFAOYSA-N methyl 3-[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]-1,3-thiazolidine-2-carboxylate Chemical compound COC(=O)C1SCCN1C(=O)C1=C(C)NC2=CC=NN2C1C1=CC=C(Cl)C(Cl)=C1 NNGKSMVWYPCCHQ-UHFFFAOYSA-N 0.000 description 1
ZDKPCSQIWVXKJN-UHFFFAOYSA-N methyl 4-[6-[4-(4-fluorophenyl)piperazine-1-carbonyl]-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-7-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1N2N=CC=C2NC(C)=C1C(=O)N1CCN(C=2C=CC(F)=CC=2)CC1 ZDKPCSQIWVXKJN-UHFFFAOYSA-N 0.000 description 1
TXLJSXYHUDUPSF-UHFFFAOYSA-N methyl 7-(3,4-dichlorophenyl)-6-[4-(4-fluorophenyl)piperazine-1-carbonyl]-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound COC(=O)c1cc2NC(C)=C(C(c3ccc(Cl)c(Cl)c3)n2n1)C(=O)N1CCN(CC1)c1ccc(F)cc1 TXLJSXYHUDUPSF-UHFFFAOYSA-N 0.000 description 1
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
239000000106 platelet aggregation inhibitor Substances 0.000 description 1
YIBBMDDEXKBIAM-UHFFFAOYSA-M potassium;pentoxymethanedithioate Chemical compound [K+].CCCCCOC([S-])=S YIBBMDDEXKBIAM-UHFFFAOYSA-M 0.000 description 1
229960002429 proline Drugs 0.000 description 1
GPBFNNFHZWDUIS-UHFFFAOYSA-N propan-2-yl 7-(3,4-dichlorophenyl)-6-[4-(4-fluorophenyl)piperazine-1-carbonyl]-5-methyl-2-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-1-carboxylate Chemical compound CC=1NC2=CC(=O)N(C(=O)OC(C)C)N2C(C=2C=C(Cl)C(Cl)=CC=2)C=1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 GPBFNNFHZWDUIS-UHFFFAOYSA-N 0.000 description 1
230000001110 prostacyclinlike Effects 0.000 description 1
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
SWMKDESQCDTENU-UHFFFAOYSA-N tert-butyl 2-[[7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carbonyl]-methylamino]acetate Chemical compound CC(C)(C)OC(=O)CN(C)C(=O)C1=C(C)NC2=CC=NN2C1C1=CC=C(Cl)C(Cl)=C1 SWMKDESQCDTENU-UHFFFAOYSA-N 0.000 description 1
239000002396 thromboxane receptor blocking agent Substances 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1

JP2001540986A 1999-12-06 2000-12-04 複素環式ジヒドロピリミジン化合物 Pending JP2004507442A (ja)