JP2009544709A5 - - Google Patents
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- JP2009544709A5 JP2009544709A5 JP2009521813A JP2009521813A JP2009544709A5 JP 2009544709 A5 JP2009544709 A5 JP 2009544709A5 JP 2009521813 A JP2009521813 A JP 2009521813A JP 2009521813 A JP2009521813 A JP 2009521813A JP 2009544709 A5 JP2009544709 A5 JP 2009544709A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyridazin
- methyl
- propoxy
- pyrrolidin
- 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 57
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 6
- 230000019771 cognition Effects 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- -1 6- [4- (2-diethylaminoethoxy) -phenyl] -3 (2H) pyridazinone Chemical compound 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 230000037007 arousal Effects 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 230000015654 memory Effects 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims 28
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 11
- 239000000203 mixture Substances 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 125000000524 functional group Chemical group 0.000 claims 5
- XUKROCVZGZNGSI-CQSZACIVSA-N irdabisant Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NNC(=O)C=C2)C=C1 XUKROCVZGZNGSI-CQSZACIVSA-N 0.000 claims 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 4
- 206010062519 Poor quality sleep Diseases 0.000 claims 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims 4
- 201000003631 narcolepsy Diseases 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- MQLBMCXXBLJWQO-LSDHHAIUSA-N 3-[4-[(2s)-2-methyl-3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-1h-pyridazin-6-one Chemical compound C([C@@H](C)CN1[C@@H](CCC1)C)OC(C=C1)=CC=C1C=1C=CC(=O)NN=1 MQLBMCXXBLJWQO-LSDHHAIUSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims 3
- XODBQZUDZRJGQM-UHFFFAOYSA-N 2-methyl-6-(4-piperidin-4-yloxyphenyl)pyridazin-3-one Chemical compound C1=CC(=O)N(C)N=C1C(C=C1)=CC=C1OC1CCNCC1 XODBQZUDZRJGQM-UHFFFAOYSA-N 0.000 claims 2
- IMHDBSPIICNYKZ-UHFFFAOYSA-N 3-[4-(3-piperidin-1-ylpropoxy)phenyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(C=2C=CC(OCCCN3CCCCC3)=CC=2)=N1 IMHDBSPIICNYKZ-UHFFFAOYSA-N 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 208000020401 Depressive disease Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 230000020595 eating behavior Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 230000036651 mood Effects 0.000 claims 2
- 201000003152 motion sickness Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 150000003053 piperidines Chemical class 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- PJIJHCWXHMXSCU-KRWDZBQOSA-N 1-[3-[3-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]propoxy]phenyl]-3-methyl-6,7-dihydro-5h-cyclopenta[d]pyridazin-4-one Chemical compound C1=2CCCC=2C(=O)N(C)N=C1C(C=1)=CC=CC=1OCCCN1CCC[C@H]1CO PJIJHCWXHMXSCU-KRWDZBQOSA-N 0.000 claims 1
- ZGTJSKKWYJBRSU-UHFFFAOYSA-N 2,4-dimethyl-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazin-3-one Chemical compound CN1C(=O)C(C)=CC(C=2C=CC(OCCCN3CCCCC3)=CC=2)=N1 ZGTJSKKWYJBRSU-UHFFFAOYSA-N 0.000 claims 1
- LBRODLJSFLEILM-MRXNPFEDSA-N 2-(2-fluoroethyl)-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NN(CCF)C(=O)C=C2)C=C1 LBRODLJSFLEILM-MRXNPFEDSA-N 0.000 claims 1
- QBWTYVZNFJLATQ-MRXNPFEDSA-N 2-(2-hydroxyethyl)-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NN(CCO)C(=O)C=C2)C=C1 QBWTYVZNFJLATQ-MRXNPFEDSA-N 0.000 claims 1
- MRVOMMIRMGIKGE-QGZVFWFLSA-N 2-(3,5-dichlorophenyl)-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NN(C(=O)C=C2)C=2C=C(Cl)C=C(Cl)C=2)C=C1 MRVOMMIRMGIKGE-QGZVFWFLSA-N 0.000 claims 1
- ZYVKPPAFYWDVQZ-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-4-[4-(3-piperidin-1-ylpropoxy)phenyl]phthalazin-1-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C2=CC=CC=C2C(C=2C=CC(OCCCN3CCCCC3)=CC=2)=N1 ZYVKPPAFYWDVQZ-UHFFFAOYSA-N 0.000 claims 1
- ZKRWZYLBGGTSEL-OAQYLSRUSA-N 2-[(4-chlorophenyl)methyl]-4-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]phthalazin-1-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2C3=CC=CC=C3C(=O)N(CC=3C=CC(Cl)=CC=3)N=2)C=C1 ZKRWZYLBGGTSEL-OAQYLSRUSA-N 0.000 claims 1
- AFEMXVRMEKINAU-CQSZACIVSA-N 2-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]-5-(6-oxo-1h-pyridazin-3-yl)benzonitrile Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NNC(=O)C=C2)C=C1C#N AFEMXVRMEKINAU-CQSZACIVSA-N 0.000 claims 1
- CGFJVIVMWFTPIS-UHFFFAOYSA-N 2-benzyl-4-methyl-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazin-3-one Chemical compound O=C1C(C)=CC(C=2C=CC(OCCCN3CCCCC3)=CC=2)=NN1CC1=CC=CC=C1 CGFJVIVMWFTPIS-UHFFFAOYSA-N 0.000 claims 1
- QBQUERHUCHEPPQ-OAQYLSRUSA-N 2-benzyl-4-methyl-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NN(CC=3C=CC=CC=3)C(=O)C(C)=C2)C=C1 QBQUERHUCHEPPQ-OAQYLSRUSA-N 0.000 claims 1
- RHWZUOYNWFIKDR-HXUWFJFHSA-N 2-benzyl-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NN(CC=3C=CC=CC=3)C(=O)C=C2)C=C1 RHWZUOYNWFIKDR-HXUWFJFHSA-N 0.000 claims 1
- YYQHFNTWPUXHOE-MRXNPFEDSA-N 2-ethyl-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-one Chemical compound C1=CC(=O)N(CC)N=C1C(C=C1)=CC=C1OCCCN1[C@H](C)CCC1 YYQHFNTWPUXHOE-MRXNPFEDSA-N 0.000 claims 1
- PRQBLTDWNZALRX-UHFFFAOYSA-N 2-methyl-4-[4-(2-piperidin-1-ylethoxy)phenyl]phthalazin-1-one Chemical compound C12=CC=CC=C2C(=O)N(C)N=C1C(C=C1)=CC=C1OCCN1CCCCC1 PRQBLTDWNZALRX-UHFFFAOYSA-N 0.000 claims 1
- UQECZBVIJKOGTA-UHFFFAOYSA-N 2-methyl-4-[4-(3-piperidin-1-ylpropoxy)phenyl]phthalazin-1-one Chemical compound C12=CC=CC=C2C(=O)N(C)N=C1C(C=C1)=CC=C1OCCCN1CCCCC1 UQECZBVIJKOGTA-UHFFFAOYSA-N 0.000 claims 1
- JOYSLGOQDKSDOB-UHFFFAOYSA-N 2-methyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]phthalazin-1-one Chemical compound C12=CC=CC=C2C(=O)N(C)N=C1C(C=C1)=CC=C1OCCCN1CCCC1 JOYSLGOQDKSDOB-UHFFFAOYSA-N 0.000 claims 1
- JQAPBTNWOFQUQP-UHFFFAOYSA-N 2-methyl-4-[4-(piperidin-4-ylmethoxy)phenyl]phthalazin-1-one Chemical compound C12=CC=CC=C2C(=O)N(C)N=C1C(C=C1)=CC=C1OCC1CCNCC1 JQAPBTNWOFQUQP-UHFFFAOYSA-N 0.000 claims 1
- YVEZLENKSRCDCK-QGZVFWFLSA-N 2-methyl-4-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-5,6,7,8-tetrahydrophthalazin-1-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2C=3CCCCC=3C(=O)N(C)N=2)C=C1 YVEZLENKSRCDCK-QGZVFWFLSA-N 0.000 claims 1
- FPBNXYHEHLCUGS-QGZVFWFLSA-N 2-methyl-4-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]phthalazin-1-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2C3=CC=CC=C3C(=O)N(C)N=2)C=C1 FPBNXYHEHLCUGS-QGZVFWFLSA-N 0.000 claims 1
- YVRKTWNIYHVZHZ-UHFFFAOYSA-N 2-methyl-5-phenyl-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazin-3-one Chemical compound C=1C=CC=CC=1C1=CC(=O)N(C)N=C1C(C=C1)=CC=C1OCCCN1CCCCC1 YVRKTWNIYHVZHZ-UHFFFAOYSA-N 0.000 claims 1
- DWVFWHRZYFWUSW-UHFFFAOYSA-N 2-methyl-6-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]pyridazin-3-one Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2=NN(C)C(=O)C=C2)C=C1 DWVFWHRZYFWUSW-UHFFFAOYSA-N 0.000 claims 1
- RLFMOUXTFPMOEA-UHFFFAOYSA-N 2-methyl-6-[4-(3-piperidin-1-ylpropoxy)phenyl]pyridazin-3-one Chemical compound C1=CC(=O)N(C)N=C1C(C=C1)=CC=C1OCCCN1CCCCC1 RLFMOUXTFPMOEA-UHFFFAOYSA-N 0.000 claims 1
- YCQPJNQRAFWMQN-UHFFFAOYSA-N 2-methyl-6-[4-(piperidin-4-ylmethoxy)phenyl]pyridazin-3-one Chemical compound C1=CC(=O)N(C)N=C1C(C=C1)=CC=C1OCC1CCNCC1 YCQPJNQRAFWMQN-UHFFFAOYSA-N 0.000 claims 1
- MGLMJVPIRXKQMU-UHFFFAOYSA-N 2-methyl-6-[4-[(1-methylpiperidin-4-yl)methoxy]phenyl]pyridazin-3-one Chemical compound C1CN(C)CCC1COC1=CC=C(C2=NN(C)C(=O)C=C2)C=C1 MGLMJVPIRXKQMU-UHFFFAOYSA-N 0.000 claims 1
- LAOMKYBOVFZAIJ-UHFFFAOYSA-N 2-methyl-6-[4-[(1-propan-2-ylpiperidin-4-yl)methoxy]phenyl]pyridazin-3-one Chemical compound C1CN(C(C)C)CCC1COC1=CC=C(C2=NN(C)C(=O)C=C2)C=C1 LAOMKYBOVFZAIJ-UHFFFAOYSA-N 0.000 claims 1
- VHKZHZYOGPESQF-HZPDHXFCSA-N 2-methyl-6-[4-[(2r)-2-methyl-3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-one Chemical compound C([C@H](C)CN1[C@@H](CCC1)C)OC(C=C1)=CC=C1C=1C=CC(=O)N(C)N=1 VHKZHZYOGPESQF-HZPDHXFCSA-N 0.000 claims 1
- VHKZHZYOGPESQF-JKSUJKDBSA-N 2-methyl-6-[4-[(2s)-2-methyl-3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-one Chemical compound C([C@@H](C)CN1[C@@H](CCC1)C)OC(C=C1)=CC=C1C=1C=CC(=O)N(C)N=1 VHKZHZYOGPESQF-JKSUJKDBSA-N 0.000 claims 1
- DGEXIBFXOHSEDQ-LJQANCHMSA-N 2-methyl-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-5-phenylpyridazin-3-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C=2C(=CC(=O)N(C)N=2)C=2C=CC=CC=2)C=C1 DGEXIBFXOHSEDQ-LJQANCHMSA-N 0.000 claims 1
- LWTPHINMYBPWKW-OAHLLOKOSA-N 2-methyl-6-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyridazin-3-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NN(C)C(=O)C=C2)C=C1 LWTPHINMYBPWKW-OAHLLOKOSA-N 0.000 claims 1
- WGBQXIANYLTAHQ-CYBMUJFWSA-N 3-[2-fluoro-4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-1h-pyridazin-6-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NNC(=O)C=C2)C(F)=C1 WGBQXIANYLTAHQ-CYBMUJFWSA-N 0.000 claims 1
- VSCYFWPBZANBSJ-CQSZACIVSA-N 3-[2-methoxy-4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-1h-pyridazin-6-one Chemical compound C=1C=C(C2=NNC(=O)C=C2)C(OC)=CC=1OCCCN1CCC[C@H]1C VSCYFWPBZANBSJ-CQSZACIVSA-N 0.000 claims 1
- JYXBHHZLGGRIPE-UHFFFAOYSA-N 3-[2-methyl-4-(3-piperidin-1-ylpropoxy)phenyl]-1h-pyridazin-6-one Chemical compound C=1C=C(C2=NNC(=O)C=C2)C(C)=CC=1OCCCN1CCCCC1 JYXBHHZLGGRIPE-UHFFFAOYSA-N 0.000 claims 1
- WPIHJKLZPYZLQY-GFCCVEGCSA-N 3-[3,5-dibromo-4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-1h-pyridazin-6-one Chemical compound C[C@@H]1CCCN1CCCOC1=C(Br)C=C(C2=NNC(=O)C=C2)C=C1Br WPIHJKLZPYZLQY-GFCCVEGCSA-N 0.000 claims 1
- CVWBBUYUSWNUBE-GFCCVEGCSA-N 3-[3,5-difluoro-4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-1h-pyridazin-6-one Chemical compound C[C@@H]1CCCN1CCCOC1=C(F)C=C(C2=NNC(=O)C=C2)C=C1F CVWBBUYUSWNUBE-GFCCVEGCSA-N 0.000 claims 1
- OYNNRYALGOXEHS-UHFFFAOYSA-N 3-[3-fluoro-4-(3-piperidin-1-ylpropoxy)phenyl]-1h-pyridazin-6-one Chemical compound FC1=CC(C2=NNC(=O)C=C2)=CC=C1OCCCN1CCCCC1 OYNNRYALGOXEHS-UHFFFAOYSA-N 0.000 claims 1
- PRRSHLNBJKWQGK-CYBMUJFWSA-N 3-[3-fluoro-4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-1h-pyridazin-6-one Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NNC(=O)C=C2)C=C1F PRRSHLNBJKWQGK-CYBMUJFWSA-N 0.000 claims 1
- ITXUDFUDTRVRBH-UHFFFAOYSA-N 3-[3-methoxy-4-(3-piperidin-1-ylpropoxy)phenyl]-1h-pyridazin-6-one Chemical compound COC1=CC(C2=NNC(=O)C=C2)=CC=C1OCCCN1CCCCC1 ITXUDFUDTRVRBH-UHFFFAOYSA-N 0.000 claims 1
- CNZWZBXBLOLCGI-CQSZACIVSA-N 3-[3-methoxy-4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-1h-pyridazin-6-one Chemical compound COC1=CC(C2=NNC(=O)C=C2)=CC=C1OCCCN1CCC[C@H]1C CNZWZBXBLOLCGI-CQSZACIVSA-N 0.000 claims 1
- ZZZBDMIUIQFWKY-UHFFFAOYSA-N 3-[4-(1-cyclobutylpiperidin-4-yl)oxy-2-fluorophenyl]-1h-pyridazin-6-one Chemical compound C=1C=C(C2=NNC(=O)C=C2)C(F)=CC=1OC(CC1)CCN1C1CCC1 ZZZBDMIUIQFWKY-UHFFFAOYSA-N 0.000 claims 1
- XIMLRDRBYJSNCN-UHFFFAOYSA-N 3-[4-(1-cyclobutylpiperidin-4-yl)oxy-3,5-difluorophenyl]-1h-pyridazin-6-one Chemical compound FC1=CC(C2=NNC(=O)C=C2)=CC(F)=C1OC(CC1)CCN1C1CCC1 XIMLRDRBYJSNCN-UHFFFAOYSA-N 0.000 claims 1
- QDKAUNLMBLQUMI-UHFFFAOYSA-N 3-[4-(1-cyclobutylpiperidin-4-yl)oxy-3-fluorophenyl]-1h-pyridazin-6-one Chemical compound FC1=CC(C2=NNC(=O)C=C2)=CC=C1OC(CC1)CCN1C1CCC1 QDKAUNLMBLQUMI-UHFFFAOYSA-N 0.000 claims 1
- IAUVZRBJEZBOFA-UHFFFAOYSA-N 3-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(C=2C=CC(OC3CCN(CC3)C3CCC3)=CC=2)=N1 IAUVZRBJEZBOFA-UHFFFAOYSA-N 0.000 claims 1
- UINCAURBECEZLK-UHFFFAOYSA-N 3-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]-4-methyl-1h-pyridazin-6-one Chemical compound CC1=CC(=O)NN=C1C(C=C1)=CC=C1OC1CCN(C2CCC2)CC1 UINCAURBECEZLK-UHFFFAOYSA-N 0.000 claims 1
- IDUGVQRRVIAOKF-UHFFFAOYSA-N 3-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]-4-pyridin-2-yl-1h-pyridazin-6-one Chemical compound C=1C=C(OC2CCN(CC2)C2CCC2)C=CC=1C1=NNC(=O)C=C1C1=CC=CC=N1 IDUGVQRRVIAOKF-UHFFFAOYSA-N 0.000 claims 1
- DQUAQBPYBUZQTK-UHFFFAOYSA-N 3-[4-(1-cyclopentylpiperidin-4-yl)oxyphenyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(C=2C=CC(OC3CCN(CC3)C3CCCC3)=CC=2)=N1 DQUAQBPYBUZQTK-UHFFFAOYSA-N 0.000 claims 1
- VYIVGISQXJJLJF-UHFFFAOYSA-N 3-[4-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-1h-pyridazin-6-one Chemical compound C1CCCCN1CC(O)COC(C=C1)=CC=C1C=1C=CC(=O)NN=1 VYIVGISQXJJLJF-UHFFFAOYSA-N 0.000 claims 1
- SPIUWADXBWWZRR-UHFFFAOYSA-N 3-[4-(3-morpholin-4-ylpropoxy)phenyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(C=2C=CC(OCCCN3CCOCC3)=CC=2)=N1 SPIUWADXBWWZRR-UHFFFAOYSA-N 0.000 claims 1
- ZOYICIUZAKWQLX-UHFFFAOYSA-N 3-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(C=2C=CC(OCCCN3CCCC3)=CC=2)=N1 ZOYICIUZAKWQLX-UHFFFAOYSA-N 0.000 claims 1
- SZIITWTXIFGKTM-UKRRQHHQSA-N 3-[4-[(2r)-2-hydroxy-3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]-1h-pyridazin-6-one Chemical compound C[C@@H]1CCCN1C[C@@H](O)COC1=CC=C(C2=NNC(=O)C=C2)C=C1 SZIITWTXIFGKTM-UKRRQHHQSA-N 0.000 claims 1
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- 2007-07-25 UA UAA200901612A patent/UA95644C2/ru unknown
- 2007-07-25 KR KR1020147004736A patent/KR20140037967A/ko not_active Ceased
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- 2007-07-25 EP EP11194125.8A patent/EP2502918B1/en active Active
- 2007-07-25 EP EP11194158A patent/EP2492263A1/en not_active Withdrawn
- 2007-07-25 DK DK07810758.8T patent/DK2069312T3/da active
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- 2009-02-10 NO NO20090628A patent/NO20090628L/no not_active Application Discontinuation
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- 2010-06-15 US US12/815,813 patent/US8586588B2/en active Active
- 2010-06-15 US US12/815,800 patent/US8207168B2/en active Active - Reinstated
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