JP2004530650A5 - - Google Patents
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- JP2004530650A5 JP2004530650A5 JP2002562717A JP2002562717A JP2004530650A5 JP 2004530650 A5 JP2004530650 A5 JP 2004530650A5 JP 2002562717 A JP2002562717 A JP 2002562717A JP 2002562717 A JP2002562717 A JP 2002562717A JP 2004530650 A5 JP2004530650 A5 JP 2004530650A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- dioxo
- cyclobuten
- pyridinylamino
- dimethylpropyl
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 25
- 125000000623 heterocyclic group Chemical group 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 21
- -1 Cycloalkenylalkyl Chemical group 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 18
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- AVADIIKNSMRDTA-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3,5-difluorobenzamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC(F)=CC(F)=C1 AVADIIKNSMRDTA-UHFFFAOYSA-N 0.000 claims 3
- WVIKUGZWKRRWCP-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3,5-dimethoxybenzamide Chemical compound COC1=CC(OC)=CC(C(=O)NC(NC=2C(C(=O)C=2NC=2C=NC=CC=2)=O)C(C)(C)C)=C1 WVIKUGZWKRRWCP-UHFFFAOYSA-N 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 2
- GIRHRIMHTIJFIY-UHFFFAOYSA-N n-[1-[[2-[(2-chloropyridin-3-yl)amino]-3,4-dioxocyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3,5-difluorobenzamide Chemical compound C=1C=CN=C(Cl)C=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC(F)=CC(F)=C1 GIRHRIMHTIJFIY-UHFFFAOYSA-N 0.000 claims 2
- YNIIXBAQLUVQIU-UHFFFAOYSA-N n-[1-[[2-[(2-chloropyridin-3-yl)amino]-3,4-dioxocyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC(NC=2C(C(=O)C=2NC=2C(=NC=CC=2)Cl)=O)C(C)(C)C)=C1 YNIIXBAQLUVQIU-UHFFFAOYSA-N 0.000 claims 2
- CWNKZXOLUZPIEC-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]-3,5-difluorobenzamide Chemical compound C=1C(F)=CC(F)=CC=1C(=O)NC(NC=1C(C(=O)C=1NC=1C=NC=CC=1)=O)C(C)(C)CC1=CC=CC=C1 CWNKZXOLUZPIEC-UHFFFAOYSA-N 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- UWNNLSQZFMTYMG-UHFFFAOYSA-N 2-benzyl-3-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-4,4-dimethylpentanamide Chemical compound C=1C=CC=CC=1CC(C(N)=O)C(C(C)(C)C)NC(C(C1=O)=O)=C1NC1=CC=CN=C1 UWNNLSQZFMTYMG-UHFFFAOYSA-N 0.000 claims 1
- NORDBEGPKCQCJS-UHFFFAOYSA-N 3,5-dichloro-n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]benzamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 NORDBEGPKCQCJS-UHFFFAOYSA-N 0.000 claims 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000008967 Enuresis Diseases 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 206010057671 Female sexual dysfunction Diseases 0.000 claims 1
- 208000014540 Functional gastrointestinal disease Diseases 0.000 claims 1
- 206010022562 Intermittent claudication Diseases 0.000 claims 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010036018 Pollakiuria Diseases 0.000 claims 1
- 208000005107 Premature Birth Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000003782 Raynaud disease Diseases 0.000 claims 1
- 208000012322 Raynaud phenomenon Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims 1
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims 1
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims 1
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims 1
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 231100000360 alopecia Toxicity 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000007637 bowel dysfunction Diseases 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims 1
- 125000000232 haloalkynyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 208000021156 intermittent vascular claudication Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 230000002175 menstrual effect Effects 0.000 claims 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims 1
- 229940095102 methyl benzoate Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 230000002107 myocardial effect Effects 0.000 claims 1
- CMHJEJTWGWBVMI-UHFFFAOYSA-N n-[1-[[2-[(2-chloropyridin-3-yl)amino]-3,4-dioxocyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC(NC=2C(C(=O)C=2NC=2C(=NC=CC=2)Cl)=O)C(C)(C)CC=2C=CC=CC=2)=C1 CMHJEJTWGWBVMI-UHFFFAOYSA-N 0.000 claims 1
- OBPDTNKUJRXEFK-UHFFFAOYSA-N n-[1-[[2-[(2-chloropyridin-3-yl)amino]-3,4-dioxocyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(NC=1C(C(=O)C=1NC=1C(=NC=CC=1)Cl)=O)C(C)(C)CC1=CC=CC=C1 OBPDTNKUJRXEFK-UHFFFAOYSA-N 0.000 claims 1
- CYMWUXVYHJYSES-UHFFFAOYSA-N n-[1-[[2-[(2-chloropyridin-3-yl)amino]-3,4-dioxocyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3-fluorobenzamide Chemical compound C=1C=CN=C(Cl)C=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC=CC(F)=C1 CYMWUXVYHJYSES-UHFFFAOYSA-N 0.000 claims 1
- CGPXXPVHBOONDH-UHFFFAOYSA-N n-[1-[[2-[(2-chloropyridin-3-yl)amino]-3,4-dioxocyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3-phenylpropanamide Chemical compound C=1C=CN=C(Cl)C=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)CCC1=CC=CC=C1 CGPXXPVHBOONDH-UHFFFAOYSA-N 0.000 claims 1
- BHISFXXROSIJTI-UHFFFAOYSA-N n-[1-[[2-[(2-chloropyridin-3-yl)amino]-3,4-dioxocyclobuten-1-yl]amino]-3,3-dimethylbutyl]benzamide Chemical compound C=1C=CN=C(Cl)C=1NC=1C(=O)C(=O)C=1NC(CC(C)(C)C)NC(=O)C1=CC=CC=C1 BHISFXXROSIJTI-UHFFFAOYSA-N 0.000 claims 1
- PQIQZRRWZBENHJ-UHFFFAOYSA-N n-[1-[[2-[(2-methoxypyridin-3-yl)amino]-3,4-dioxocyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]-3-methylbenzamide Chemical compound COC1=NC=CC=C1NC(C(C1=O)=O)=C1NC(C(C)(C)CC=1C=CC=CC=1)NC(=O)C1=CC=CC(C)=C1 PQIQZRRWZBENHJ-UHFFFAOYSA-N 0.000 claims 1
- FEDRDZNWTKCNES-UHFFFAOYSA-N n-[1-[[2-[(2-methoxypyridin-3-yl)amino]-3,4-dioxocyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3-methylbenzamide Chemical compound COC1=NC=CC=C1NC(C(C1=O)=O)=C1NC(C(C)(C)C)NC(=O)C1=CC=CC(C)=C1 FEDRDZNWTKCNES-UHFFFAOYSA-N 0.000 claims 1
- FUWAHLNNLYOXKJ-UHFFFAOYSA-N n-[1-[[2-[(5-bromo-6-fluoropyridin-3-yl)amino]-3,4-dioxocyclobuten-1-yl]amino]-2,2-dimethylpropyl]-4-chlorobenzamide Chemical compound C=1N=C(F)C(Br)=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1 FUWAHLNNLYOXKJ-UHFFFAOYSA-N 0.000 claims 1
- PYLYEJXULKREIQ-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]-2-methyl-2-phenylpropanamide Chemical compound C=1C=CC=CC=1C(C)(C)C(=O)NC(NC=1C(C(=O)C=1NC=1C=NC=CC=1)=O)C(C)(C)CC1=CC=CC=C1 PYLYEJXULKREIQ-UHFFFAOYSA-N 0.000 claims 1
- LVBONDMXRWMBRE-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]-2-phenoxyacetamide Chemical compound C=1C=CC=CC=1OCC(=O)NC(NC=1C(C(=O)C=1NC=1C=NC=CC=1)=O)C(C)(C)CC1=CC=CC=C1 LVBONDMXRWMBRE-UHFFFAOYSA-N 0.000 claims 1
- QZMGCYINAOANKX-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC(NC=2C(C(=O)C=2NC=2C=NC=CC=2)=O)C(C)(C)CC=2C=CC=CC=2)=C1 QZMGCYINAOANKX-UHFFFAOYSA-N 0.000 claims 1
- SCOKWAYIQIZEPG-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]-3-phenylpropanamide Chemical compound C=1C=CC=CC=1CCC(=O)NC(NC=1C(C(=O)C=1NC=1C=NC=CC=1)=O)C(C)(C)CC1=CC=CC=C1 SCOKWAYIQIZEPG-UHFFFAOYSA-N 0.000 claims 1
- UKLSGXQMQXACFA-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(NC=1C(C(=O)C=1NC=1C=NC=CC=1)=O)C(C)(C)CC1=CC=CC=C1 UKLSGXQMQXACFA-UHFFFAOYSA-N 0.000 claims 1
- WQRDZTZMPYHBNO-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(NC=1C(C(=O)C=1NC=1C=NC=CC=1)=O)C(C)(C)CC1=CC=CC=C1 WQRDZTZMPYHBNO-UHFFFAOYSA-N 0.000 claims 1
- LIWDAYMMNJWWSM-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethyl-3-phenylpropyl]pyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC(NC=1C(C(=O)C=1NC=1C=NC=CC=1)=O)C(C)(C)CC1=CC=CC=C1 LIWDAYMMNJWWSM-UHFFFAOYSA-N 0.000 claims 1
- IAZJQFOUXPJCJA-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethyl-3-pyridin-4-ylpropyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC(NC=2C(C(=O)C=2NC=2C=NC=CC=2)=O)C(C)(C)CC=2C=CN=CC=2)=C1 IAZJQFOUXPJCJA-UHFFFAOYSA-N 0.000 claims 1
- WMULVOGISFGJTB-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-2-methyl-2-phenylpropanamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C(C)(C)C1=CC=CC=C1 WMULVOGISFGJTB-UHFFFAOYSA-N 0.000 claims 1
- CBVNSGIKZXCIRC-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-2-phenoxyacetamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)COC1=CC=CC=C1 CBVNSGIKZXCIRC-UHFFFAOYSA-N 0.000 claims 1
- YJQSZBIWMNTSFM-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-2-phenylacetamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)CC1=CC=CC=C1 YJQSZBIWMNTSFM-UHFFFAOYSA-N 0.000 claims 1
- KXBLEAGQTAVNKW-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC(C(C)(C)C)NC(C(C1=O)=O)=C1NC1=CC=CN=C1 KXBLEAGQTAVNKW-UHFFFAOYSA-N 0.000 claims 1
- JKLZZMSROOEJOR-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3,4-dimethylbenzamide Chemical compound C1=C(C)C(C)=CC=C1C(=O)NC(C(C)(C)C)NC(C(C1=O)=O)=C1NC1=CC=CN=C1 JKLZZMSROOEJOR-UHFFFAOYSA-N 0.000 claims 1
- GAEBPUCZGQGNAP-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3-ethenylbenzamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC=CC(C=C)=C1 GAEBPUCZGQGNAP-UHFFFAOYSA-N 0.000 claims 1
- PUDZZYIFGNYJFL-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3-fluorobenzamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC=CC(F)=C1 PUDZZYIFGNYJFL-UHFFFAOYSA-N 0.000 claims 1
- UMPCKVXXOXZXNA-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3-iodobenzamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC=CC(I)=C1 UMPCKVXXOXZXNA-UHFFFAOYSA-N 0.000 claims 1
- IAVPCXLMCVLKGD-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC(NC=2C(C(=O)C=2NC=2C=NC=CC=2)=O)C(C)(C)C)=C1 IAVPCXLMCVLKGD-UHFFFAOYSA-N 0.000 claims 1
- KQECRAMFMDCLJJ-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-3-phenylprop-2-enamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C=CC1=CC=CC=C1 KQECRAMFMDCLJJ-UHFFFAOYSA-N 0.000 claims 1
- QGSCSAVARZHUCQ-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-4-iodobenzamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC=C(I)C=C1 QGSCSAVARZHUCQ-UHFFFAOYSA-N 0.000 claims 1
- WKPWSVUKDJVGPQ-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(C)(C)C)NC(C(C1=O)=O)=C1NC1=CC=CN=C1 WKPWSVUKDJVGPQ-UHFFFAOYSA-N 0.000 claims 1
- FRSPOIYNYKEESS-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]benzamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC=CC=C1 FRSPOIYNYKEESS-UHFFFAOYSA-N 0.000 claims 1
- QHSIIFRQMKTHFN-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]furan-2-carboxamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC=CO1 QHSIIFRQMKTHFN-UHFFFAOYSA-N 0.000 claims 1
- YDFYEQVCWFNCCE-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]naphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NC(C(C)(C)C)NC(C(C1=O)=O)=C1NC1=CC=CN=C1 YDFYEQVCWFNCCE-UHFFFAOYSA-N 0.000 claims 1
- FOYFSOBUMYGCEY-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC=CN=C1 FOYFSOBUMYGCEY-UHFFFAOYSA-N 0.000 claims 1
- PDBLVYDZDHNUQX-UHFFFAOYSA-N n-[1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]-2,2-dimethylpropyl]thiophene-2-carboxamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(C)(C)C)NC(=O)C1=CC=CS1 PDBLVYDZDHNUQX-UHFFFAOYSA-N 0.000 claims 1
- HHAMIEIUHHEYKJ-UHFFFAOYSA-N n-[2,2-dichloro-1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]propyl]-3,5-difluorobenzamide Chemical compound C=1C=CN=CC=1NC=1C(=O)C(=O)C=1NC(C(Cl)(Cl)C)NC(=O)C1=CC(F)=CC(F)=C1 HHAMIEIUHHEYKJ-UHFFFAOYSA-N 0.000 claims 1
- HJGAXZOXZCZTMR-UHFFFAOYSA-N n-[2,2-dimethyl-1-(pyridin-3-ylsulfamoylamino)propyl]-4-iodobenzamide Chemical compound C=1C=CN=CC=1NS(=O)(=O)NC(C(C)(C)C)NC(=O)C1=CC=C(I)C=C1 HJGAXZOXZCZTMR-UHFFFAOYSA-N 0.000 claims 1
- HWXBYJBDQLNCAP-UHFFFAOYSA-N n-[2-(1-adamantyl)-1-[[3,4-dioxo-2-(pyridin-3-ylamino)cyclobuten-1-yl]amino]ethyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC(NC=1C(C(=O)C=1NC=1C=NC=CC=1)=O)CC1(C2)CC(C3)CC2CC3C1 HWXBYJBDQLNCAP-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 206010029446 nocturia Diseases 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 206010036596 premature ejaculation Diseases 0.000 claims 1
- 230000011514 reflex Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/778,684 US20020147230A1 (en) | 2001-02-07 | 2001-02-07 | Aminal Diones as potassium channel openers |
| US10/046,465 US6495576B2 (en) | 2001-02-07 | 2002-01-14 | Aminal diones as potassium channel openers |
| PCT/US2002/002949 WO2002062761A1 (en) | 2001-02-07 | 2002-01-31 | Aminal diones as potassium channel openers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004530650A JP2004530650A (ja) | 2004-10-07 |
| JP2004530650A5 true JP2004530650A5 (enrdf_load_stackoverflow) | 2005-06-09 |
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| JP2002562717A Pending JP2004530650A (ja) | 2001-02-07 | 2002-01-31 | カリウムチャンネル開口薬としてのアミナールジオン |
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| EP (1) | EP1358160A1 (enrdf_load_stackoverflow) |
| JP (1) | JP2004530650A (enrdf_load_stackoverflow) |
| CA (1) | CA2437400A1 (enrdf_load_stackoverflow) |
| MX (1) | MXPA03007071A (enrdf_load_stackoverflow) |
| WO (1) | WO2002062761A1 (enrdf_load_stackoverflow) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7635694B2 (en) | 2004-02-27 | 2009-12-22 | Schering Corporation | Cyclobutenedione-containing compounds as inhibitors of hepatitis C virus NS3 serine protease |
| WO2005085197A1 (en) * | 2004-02-27 | 2005-09-15 | Schering Corporation | Cyclobutenedione groups-containing compounds as inhibitors of hepatitis c virus ns3 serine protease |
| ATE432921T1 (de) | 2004-12-23 | 2009-06-15 | Gpc Biotech Ag | Quadratsäurederivate mit antiproliferativer wirkung |
| JP5437061B2 (ja) * | 2006-05-26 | 2014-03-12 | アッヴィ・インコーポレイテッド | ポロ様キナーゼの阻害薬 |
| US8450348B2 (en) | 2007-02-21 | 2013-05-28 | Forma Tm, Llc | Derivatives of squaric acid with anti-proliferative activity |
| FR2918665B1 (fr) * | 2007-07-13 | 2009-10-02 | Sod Conseils Rech Applic | Derives de tri-amino-pyrimidine cyclobutenedione comme inhibiteurs de phosphatase cdc25 |
| JP5816082B2 (ja) | 2008-06-24 | 2015-11-17 | トポターゲット・アクティーゼルスカブＴｏｐｏＴａｒｇｅｔ Ａ／Ｓ | ニコチンアミドの阻害剤としてのスクアリン酸誘導体 |
| US8168795B2 (en) * | 2009-08-11 | 2012-05-01 | Allergan, Inc. | Selective sphingosine-1-phosphate receptor antagonists |
| PL2760821T3 (pl) | 2011-09-02 | 2018-04-30 | Novartis Ag | Sól cholinowa przeciwzapalnego związku podstawionego cyklobutenodionem |
| CN114835639B (zh) * | 2022-05-30 | 2023-12-15 | 南京红太阳生物化学有限责任公司 | 一种奈韦拉平中间体的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0741708B1 (en) * | 1994-01-28 | 1998-05-20 | PHARMACIA & UPJOHN COMPANY | Cyanoguanidines as k-channel blockers |
| MXPA02001207A (es) * | 1999-08-03 | 2002-07-30 | Abbott Lab | Abridores de canal de potasio. |
-
2002
- 2002-01-31 WO PCT/US2002/002949 patent/WO2002062761A1/en not_active Application Discontinuation
- 2002-01-31 MX MXPA03007071A patent/MXPA03007071A/es unknown
- 2002-01-31 JP JP2002562717A patent/JP2004530650A/ja active Pending
- 2002-01-31 EP EP02704321A patent/EP1358160A1/en not_active Withdrawn
- 2002-01-31 CA CA002437400A patent/CA2437400A1/en not_active Abandoned
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