JP2008521805A5 - - Google Patents
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- JP2008521805A5 JP2008521805A5 JP2007543114A JP2007543114A JP2008521805A5 JP 2008521805 A5 JP2008521805 A5 JP 2008521805A5 JP 2007543114 A JP2007543114 A JP 2007543114A JP 2007543114 A JP2007543114 A JP 2007543114A JP 2008521805 A5 JP2008521805 A5 JP 2008521805A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- chloro
- phenyl
- propylamino
- dihydro
- 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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- 150000001875 compounds Chemical class 0.000 claims 54
- 125000002947 alkylene group Chemical group 0.000 claims 20
- 125000004450 alkenylene group Chemical group 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000004419 alkynylene group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- -1 trifluoromethoxy, amino 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
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- XTYQURXDUQYQBR-UHFFFAOYSA-N 3-[4-[3-[[3-(9h-carbazol-4-yloxy)-2-hydroxypropyl]amino]propoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=2NC3=CC=CC=C3C=2C=1OCC(O)CNCCCOC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 XTYQURXDUQYQBR-UHFFFAOYSA-N 0.000 claims 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 206010019280 Heart failures Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- LNKPCRZEPZDETA-UHFFFAOYSA-N 3-[3-chloro-4-[2-[4-[[2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(CCOC)=CC=C1OCC(O)CNC1CCN(C(=O)COC=2C(=CC(=CC=2)C=2CCC(=O)NN=2)Cl)CC1 LNKPCRZEPZDETA-UHFFFAOYSA-N 0.000 claims 2
- DYTDRSWKTNPDHL-UHFFFAOYSA-N 3-[4-[2-[3-[[3-(9h-carbazol-4-yloxy)-2-hydroxypropyl]amino]pyrrolidin-1-yl]-2-oxoethoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=2NC3=CC=CC=C3C=2C=1OCC(O)CNC(C1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 DYTDRSWKTNPDHL-UHFFFAOYSA-N 0.000 claims 2
- PQESBQUNXWBSOO-UHFFFAOYSA-N 3-[4-[2-[4-[[3-(9h-carbazol-4-yloxy)-2-hydroxypropyl]amino]piperidin-1-yl]-2-oxoethoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=2NC3=CC=CC=C3C=2C=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 PQESBQUNXWBSOO-UHFFFAOYSA-N 0.000 claims 2
- ZXUVYXVQFKIQRW-UHFFFAOYSA-N 3-[4-[2-[[3-(9h-carbazol-4-yloxy)-2-hydroxypropyl]amino]ethoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=2NC3=CC=CC=C3C=2C=1OCC(O)CNCCOC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 ZXUVYXVQFKIQRW-UHFFFAOYSA-N 0.000 claims 2
- LSFSNENFVRUQPD-UHFFFAOYSA-N 3-[4-[3-[[3-(9h-carbazol-4-yloxy)-2-hydroxypentyl]amino]propoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=2NC3=CC=CC=C3C=2C=1OC(CC)C(O)CNCCCOC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 LSFSNENFVRUQPD-UHFFFAOYSA-N 0.000 claims 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 230000004094 calcium homeostasis Effects 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 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 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052760 oxygen Inorganic materials 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
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- GGZCHUNYPHPIPZ-NRFANRHFSA-N 2-[2-chloro-4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenoxy]-n-[2-[[(2s)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]-2-methylpropyl]acetamide Chemical compound C1=CC(CCOC)=CC=C1OC[C@@H](O)CNC(C)(C)CNC(=O)COC1=CC=C(C=2CCC(=O)NN=2)C=C1Cl GGZCHUNYPHPIPZ-NRFANRHFSA-N 0.000 claims 1
- UNRXPIIBEBLZNY-UHFFFAOYSA-N 2-[2-chloro-4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenoxy]-n-[2-[[2-hydroxy-3-[9-(2-hydroxyethyl)carbazol-4-yl]oxypropyl]amino]-2-methylpropyl]acetamide Chemical compound C=1C=CC=2N(CCO)C3=CC=CC=C3C=2C=1OCC(O)CNC(C)(C)CNC(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 UNRXPIIBEBLZNY-UHFFFAOYSA-N 0.000 claims 1
- WRTBSWAEOPAEPD-UHFFFAOYSA-N 2-[2-chloro-4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenoxy]-n-[2-[[2-hydroxy-3-[9-(2-methoxyethyl)carbazol-4-yl]oxypropyl]amino]-2-methylpropyl]acetamide Chemical compound C1=CC=C2N(CCOC)C3=CC=CC=C3C2=C1OCC(O)CNC(C)(C)CNC(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 WRTBSWAEOPAEPD-UHFFFAOYSA-N 0.000 claims 1
- IMXKYUZPYNEPPS-UHFFFAOYSA-N 2-[3-[[1-[2-[2-chloro-4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenoxy]acetyl]piperidin-4-yl]amino]-2-hydroxypropoxy]benzonitrile Chemical compound C=1C=CC=C(C#N)C=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 IMXKYUZPYNEPPS-UHFFFAOYSA-N 0.000 claims 1
- VJDNUQLZSIVKGX-UHFFFAOYSA-N 2-[4-(5-cyano-2-methyl-6-oxo-1h-pyridin-3-yl)phenoxy]acetic acid Chemical compound N1C(=O)C(C#N)=CC(C=2C=CC(OCC(O)=O)=CC=2)=C1C VJDNUQLZSIVKGX-UHFFFAOYSA-N 0.000 claims 1
- RLIVYVRULOVIHD-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)carbazol-9-yl]ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCN(C1=CC=C2)C3=CC=CC=C3C1=C2OCC1CO1 RLIVYVRULOVIHD-UHFFFAOYSA-N 0.000 claims 1
- UEHRSHCVECOSHW-UHFFFAOYSA-N 3-[3-[[1-[2-[2-chloro-4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenoxy]acetyl]piperidin-4-yl]amino]-2-hydroxypropoxy]benzonitrile Chemical compound C=1C=CC(C#N)=CC=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 UEHRSHCVECOSHW-UHFFFAOYSA-N 0.000 claims 1
- NYDDJHKXUHNLDP-NRFANRHFSA-N 3-[3-chloro-4-[2-[3-[[(2s)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]azetidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(CCOC)=CC=C1OC[C@@H](O)CNC1CN(C(=O)COC=2C(=CC(=CC=2)C=2CCC(=O)NN=2)Cl)C1 NYDDJHKXUHNLDP-NRFANRHFSA-N 0.000 claims 1
- LXGFXTAZLACYER-KEKNWZKVSA-N 3-[3-chloro-4-[2-[3-[[(2s)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]pyrrolidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(CCOC)=CC=C1OC[C@@H](O)CNC1CN(C(=O)COC=2C(=CC(=CC=2)C=2CCC(=O)NN=2)Cl)CC1 LXGFXTAZLACYER-KEKNWZKVSA-N 0.000 claims 1
- SFWVFXYXVOWMPL-UHFFFAOYSA-N 3-[3-chloro-4-[2-[4-[(2-hydroxy-3-phenoxypropyl)amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=CC=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 SFWVFXYXVOWMPL-UHFFFAOYSA-N 0.000 claims 1
- RHKBTFPPYBKHSE-UHFFFAOYSA-N 3-[3-chloro-4-[2-[4-[[2-hydroxy-3-(2-methoxyphenoxy)propyl]amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound COC1=CC=CC=C1OCC(O)CNC1CCN(C(=O)COC=2C(=CC(=CC=2)C=2CCC(=O)NN=2)Cl)CC1 RHKBTFPPYBKHSE-UHFFFAOYSA-N 0.000 claims 1
- ADSLLZRYFWZCMP-UHFFFAOYSA-N 3-[3-chloro-4-[2-[4-[[2-hydroxy-3-(2-methylphenoxy)propyl]amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1=CC=CC=C1OCC(O)CNC1CCN(C(=O)COC=2C(=CC(=CC=2)C=2CCC(=O)NN=2)Cl)CC1 ADSLLZRYFWZCMP-UHFFFAOYSA-N 0.000 claims 1
- NJZLHMXSEXTXBG-UHFFFAOYSA-N 3-[3-chloro-4-[2-[4-[[2-hydroxy-3-(4-methoxyphenoxy)propyl]amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(OC)=CC=C1OCC(O)CNC1CCN(C(=O)COC=2C(=CC(=CC=2)C=2CCC(=O)NN=2)Cl)CC1 NJZLHMXSEXTXBG-UHFFFAOYSA-N 0.000 claims 1
- HNHCFEKUPQQOTN-UHFFFAOYSA-N 3-[3-chloro-4-[2-[4-[[2-hydroxy-3-(4-methylphenoxy)propyl]amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(C)=CC=C1OCC(O)CNC1CCN(C(=O)COC=2C(=CC(=CC=2)C=2CCC(=O)NN=2)Cl)CC1 HNHCFEKUPQQOTN-UHFFFAOYSA-N 0.000 claims 1
- IJQKUTAXSQXDMZ-UHFFFAOYSA-N 3-[3-chloro-4-[2-[4-[[2-hydroxy-3-[2-(trifluoromethoxy)phenoxy]propyl]amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=C(OC(F)(F)F)C=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 IJQKUTAXSQXDMZ-UHFFFAOYSA-N 0.000 claims 1
- DCDJQDAGMCTDES-UHFFFAOYSA-N 3-[3-chloro-4-[2-[4-[[2-hydroxy-3-[2-(trifluoromethyl)phenoxy]propyl]amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=C(C(F)(F)F)C=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 DCDJQDAGMCTDES-UHFFFAOYSA-N 0.000 claims 1
- JCFIOMKSKIJMGM-UHFFFAOYSA-N 3-[3-chloro-4-[2-[4-[[3-(2-chlorophenoxy)-2-hydroxypropyl]amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=C(Cl)C=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 JCFIOMKSKIJMGM-UHFFFAOYSA-N 0.000 claims 1
- XRQNMDFZKGSUHV-UHFFFAOYSA-N 3-[3-chloro-4-[2-[4-[[3-(2-fluorophenoxy)-2-hydroxypropyl]amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=C(F)C=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 XRQNMDFZKGSUHV-UHFFFAOYSA-N 0.000 claims 1
- OGYAAULTDWUXKD-UHFFFAOYSA-N 3-[4-[2-[3-[[3-(9h-carbazol-4-yloxy)-2-hydroxypropyl]amino]azetidin-1-yl]-2-oxoethoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=2NC3=CC=CC=C3C=2C=1OCC(O)CNC(C1)CN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 OGYAAULTDWUXKD-UHFFFAOYSA-N 0.000 claims 1
- JLOWGNPLCGHMCF-QFIPXVFZSA-N 3-[4-[2-[4-[[(2s)-3-(9h-carbazol-2-yloxy)-2-hydroxypropyl]amino]piperidin-1-yl]-2-oxoethoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C([C@H](O)COC=1C=C2C(C3=CC=CC=C3N2)=CC=1)NC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 JLOWGNPLCGHMCF-QFIPXVFZSA-N 0.000 claims 1
- UJMRNGINERHZLW-UHFFFAOYSA-N 3-[4-[2-[4-[[3-(2-acetylphenoxy)-2-hydroxypropyl]amino]piperidin-1-yl]-2-oxoethoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CNC1CCN(C(=O)COC=2C(=CC(=CC=2)C=2CCC(=O)NN=2)Cl)CC1 UJMRNGINERHZLW-UHFFFAOYSA-N 0.000 claims 1
- ICCFVGVBCXEGPP-UHFFFAOYSA-N 3-[4-[2-[4-[[3-(2-bromophenoxy)-2-hydroxypropyl]amino]piperidin-1-yl]-2-oxoethoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=C(Br)C=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 ICCFVGVBCXEGPP-UHFFFAOYSA-N 0.000 claims 1
- ODFNVJYYKXJEKK-UHFFFAOYSA-N 3-[4-[2-[4-[[3-(3-bromophenoxy)-2-hydroxypropyl]amino]piperidin-1-yl]-2-oxoethoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC(Br)=CC=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 ODFNVJYYKXJEKK-UHFFFAOYSA-N 0.000 claims 1
- VEQBMLQPDDRMDK-UHFFFAOYSA-N 3-[4-[2-[4-[[3-(4-bromophenoxy)-2-hydroxypropyl]amino]piperidin-1-yl]-2-oxoethoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=C(Br)C=CC=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 VEQBMLQPDDRMDK-UHFFFAOYSA-N 0.000 claims 1
- DIPGSVXIUCPYLS-UHFFFAOYSA-N 3-[4-[2-[[3-(9h-carbazol-2-yloxy)-2-hydroxypropyl]amino]ethoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCC(O)CNCCOC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 DIPGSVXIUCPYLS-UHFFFAOYSA-N 0.000 claims 1
- FKSFQFKRDDXVIO-IBGZPJMESA-N 3-[4-[3-[[(2s)-3-(9h-carbazol-2-yloxy)-2-hydroxypropyl]amino]propoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C([C@H](O)COC=1C=C2C(C3=CC=CC=C3N2)=CC=1)NCCCOC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 FKSFQFKRDDXVIO-IBGZPJMESA-N 0.000 claims 1
- XQIKCVKAUVHAKT-UHFFFAOYSA-N 3-[4-[3-[[3-(9h-carbazol-4-yloxy)-2-hydroxybutyl]amino]propoxy]-3-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=CC=2NC3=CC=CC=C3C=2C=1OC(C)C(O)CNCCCOC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 XQIKCVKAUVHAKT-UHFFFAOYSA-N 0.000 claims 1
- INKKMAXJWAPYPL-UHFFFAOYSA-N 4-[3-[[1-[2-[2-chloro-4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenoxy]acetyl]piperidin-4-yl]amino]-2-hydroxypropoxy]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1OCC(O)CNC(CC1)CCN1C(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 INKKMAXJWAPYPL-UHFFFAOYSA-N 0.000 claims 1
- IZNYWMGPZZHGFP-UHFFFAOYSA-N 5-[4-(3-aminopropoxy)phenyl]-6-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound N1C(=O)C(C#N)=CC(C=2C=CC(OCCCN)=CC=2)=C1C IZNYWMGPZZHGFP-UHFFFAOYSA-N 0.000 claims 1
- UZNZYSVRWSCHHT-UHFFFAOYSA-N 5-[4-(4-aminobutoxy)-3-chlorophenyl]-6-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound N1C(=O)C(C#N)=CC(C=2C=C(Cl)C(OCCCCN)=CC=2)=C1C UZNZYSVRWSCHHT-UHFFFAOYSA-N 0.000 claims 1
- MYWLCMYTVHESSV-UHFFFAOYSA-N 5-[4-(5-aminopentoxy)-3-chlorophenyl]-6-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound N1C(=O)C(C#N)=CC(C=2C=C(Cl)C(OCCCCCN)=CC=2)=C1C MYWLCMYTVHESSV-UHFFFAOYSA-N 0.000 claims 1
- YGBSTPZNNHZYDA-UHFFFAOYSA-N 5-[4-[2-[4-[[3-(9h-carbazol-4-yloxy)-2-hydroxypropyl]amino]piperidin-1-yl]-2-oxoethoxy]phenyl]-6-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound N1C(=O)C(C#N)=CC(C=2C=CC(OCC(=O)N3CCC(CC3)NCC(O)COC=3C=4C5=CC=CC=C5NC=4C=CC=3)=CC=2)=C1C YGBSTPZNNHZYDA-UHFFFAOYSA-N 0.000 claims 1
- OHXNTMISGYCGNR-UHFFFAOYSA-N 5-[4-[3-[[3-(9h-carbazol-4-yloxy)-2-hydroxypropyl]amino]propoxy]phenyl]-6-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound N1C(=O)C(C#N)=CC(C=2C=CC(OCCCNCC(O)COC=3C=4C5=CC=CC=C5NC=4C=CC=3)=CC=2)=C1C OHXNTMISGYCGNR-UHFFFAOYSA-N 0.000 claims 1
- RZMKXWPQQJQVKD-UHFFFAOYSA-N 5-[4-[5-[[3-(9h-carbazol-4-yloxy)-2-hydroxypropyl]amino]pentoxy]-3-chlorophenyl]-6-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound N1C(=O)C(C#N)=CC(C=2C=C(Cl)C(OCCCCCNCC(O)COC=3C=4C5=CC=CC=C5NC=4C=CC=3)=CC=2)=C1C RZMKXWPQQJQVKD-UHFFFAOYSA-N 0.000 claims 1
- LAYRMAGSLDYUGW-UHFFFAOYSA-N 9-(2-methoxyethyl)-4-(oxiran-2-ylmethoxy)carbazole Chemical compound C1=CC=C2N(CCOC)C3=CC=CC=C3C2=C1OCC1CO1 LAYRMAGSLDYUGW-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000031481 Pathologic Constriction Diseases 0.000 claims 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 210000001992 atrioventricular node Anatomy 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 230000001969 hypertrophic effect Effects 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 239000002207 metabolite Substances 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- LHVVHGAAFBTQJS-UHFFFAOYSA-N n-[2-[[3-[(1-bromo-9h-carbazol-4-yl)oxy]-2-hydroxypropyl]amino]-2-methylpropyl]-2-[2-chloro-4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenoxy]acetamide Chemical compound C=1C=C(Br)C=2NC3=CC=CC=C3C=2C=1OCC(O)CNC(C)(C)CNC(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 LHVVHGAAFBTQJS-UHFFFAOYSA-N 0.000 claims 1
- ZEHDCPKEWNTGFG-UHFFFAOYSA-N n-[2-[[3-[(3-bromo-9h-carbazol-4-yl)oxy]-2-hydroxypropyl]amino]-2-methylpropyl]-2-[2-chloro-4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenoxy]acetamide Chemical compound BrC=1C=CC=2NC3=CC=CC=C3C=2C=1OCC(O)CNC(C)(C)CNC(=O)COC(C(=C1)Cl)=CC=C1C1=NNC(=O)CC1 ZEHDCPKEWNTGFG-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 230000036262 stenosis Effects 0.000 claims 1
- 208000037804 stenosis Diseases 0.000 claims 1
- GWBONLFYENOTBK-UHFFFAOYSA-N Cc(ccc(C(CC1)=NNC1=O)c1)c1Cl Chemical compound Cc(ccc(C(CC1)=NNC1=O)c1)c1Cl GWBONLFYENOTBK-UHFFFAOYSA-N 0.000 description 1
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| DE102004011512B4 (de) | 2004-03-08 | 2022-01-13 | Boehringer Ingelheim Vetmedica Gmbh | Pharmazeutische Zubereitung enthaltend Pimobendan |
| EP1579862A1 (en) | 2004-03-25 | 2005-09-28 | Boehringer Ingelheim Vetmedica Gmbh | Use of PDE III inhibitors for the reduction of heart size in mammals suffering from heart failure |
| US8980894B2 (en) | 2004-03-25 | 2015-03-17 | Boehringer Ingelheim Vetmedica Gmbh | Use of PDE III inhibitors for the treatment of asymptomatic (occult) heart failure |
| GB0415746D0 (en) * | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
| ES2524922T3 (es) | 2005-05-10 | 2014-12-15 | Intermune, Inc. | Derivados de piridona para modular el sistema de proteína cinasa activada por estrés |
| NZ567266A (en) | 2005-10-13 | 2010-09-30 | Orchid Res Lab Ltd | Carbazole derivatives as pSTAT3/IL-6 inhibitors (carvedilol) |
| UA95644C2 (ru) | 2006-07-25 | 2011-08-25 | Сефалон, Инк. | Пиридазиноновые производные, фармацевтическая композиция и способ лечения заболеваний |
| WO2008058198A1 (en) * | 2006-11-07 | 2008-05-15 | Cardiome Pharma Corp. | Methods of making compounds having a beta-adrenergic inhibitor and a linker and methods of making compounds having a beta-adrenergic inhibitor, a linker and a phosphodiesterase inhibitor |
| EP1920785A1 (en) | 2006-11-07 | 2008-05-14 | Boehringer Ingelheim Vetmedica Gmbh | Liquid preparation comprising a complex of pimobendan and cyclodextrin |
| CA2726588C (en) | 2008-06-03 | 2019-04-16 | Karl Kossen | Compounds and methods for treating inflammatory and fibrotic disorders |
| CN102223882B (zh) * | 2008-11-25 | 2016-02-03 | 贝林格尔.英格海姆维特梅迪卡有限公司 | 用于治疗肥厚型心肌病的III 型磷酸二酯酶(PPE III)抑制剂或Ca2+敏化剂 |
| EP3167876B1 (en) | 2012-03-15 | 2021-09-08 | Boehringer Ingelheim Vetmedica GmbH | Pharmaceutical tablet formulation for the veterinary medical sector, method of production and use thereof |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| EP3021832B9 (en) | 2013-07-19 | 2023-03-15 | Boehringer Ingelheim Vetmedica GmbH | Preserved etherified cyclodextrin derivatives containing liquid aqueous pharmaceutical composition |
| WO2015031914A1 (en) * | 2013-08-30 | 2015-03-05 | Uti Limited Partnership | Store overload-induced calcium release inhibitors and methods for producing and using the same |
| CA2930033C (en) | 2013-12-04 | 2022-12-13 | Boehringer Ingelheim Vetmedica Gmbh | Improved pharmaceutical compositions of pimobendan |
| WO2015104602A2 (en) | 2014-01-08 | 2015-07-16 | Wockhardt Limited | A process for the preparation of anagliptin and its intermediates thereof |
| IN2014MU01191A (https=) | 2014-03-29 | 2015-10-02 | Wockhardt Ltd | |
| MX382781B (es) | 2014-04-02 | 2025-03-13 | Intermune Inc | Piridinonas anti-fibroticas. |
| US10919249B2 (en) | 2016-02-19 | 2021-02-16 | Albert Mardikian | Apparatus for pressing and dehydrating of waste |
| US10537570B2 (en) | 2016-04-06 | 2020-01-21 | Boehringer Ingelheim Vetmedica Gmbh | Use of pimobendan for the reduction of heart size and/or the delay of onset of clinical symptoms in patients with asymptomatic heart failure due to mitral valve disease |
| AU2017263657A1 (en) * | 2016-05-13 | 2018-11-29 | The Board Of Trustees Of The Leland Stanford Junior University | Adrenergic receptor modulating compounds and methods of using the same |
| MA44037B1 (fr) * | 2016-06-06 | 2020-03-31 | Arena Pharm Inc | Modulateurs du récepteur adrénergique bêta 3 utile dans le traitement ou la prévention de troubles associés à ceux-ci |
| ES2747768T3 (es) | 2017-03-20 | 2020-03-11 | Forma Therapeutics Inc | Composiciones de pirrolopirrol como activadores de quinasa de piruvato (PKR) |
| CN111699189B (zh) * | 2017-12-06 | 2025-02-18 | 艾尼纳制药公司 | 可用于治疗或预防与其相关的心力衰竭和障碍的β-3肾上腺素能受体的调节剂 |
| US12053458B2 (en) | 2018-09-19 | 2024-08-06 | Novo Nordisk Health Care Ag | Treating sickle cell disease with a pyruvate kinase R activating compound |
| ES2989438T3 (es) | 2018-09-19 | 2024-11-26 | Novo Nordisk Healthcare Ag | Activación de la piruvato cinasa R |
| US20220378756A1 (en) | 2019-09-19 | 2022-12-01 | Forma Therapeutics, Inc. | Activating pyruvate kinase r |
| CN111170997A (zh) * | 2019-12-31 | 2020-05-19 | 广州医科大学 | 咔唑类化合物及其制备方法和应用 |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
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| DE2815926A1 (de) * | 1978-04-13 | 1979-10-18 | Boehringer Mannheim Gmbh | Neue carbazolyl-(4)-oxy-propanolamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| GB1488330A (en) * | 1973-12-19 | 1977-10-12 | Smith Kline French Lab | Dihydropyridazinones |
| US4111935A (en) * | 1975-01-02 | 1978-09-05 | Smith Kline & French Laboratories Limited | 3-chloro-6-phenylpyridazine compounds |
| JPS5283382A (en) * | 1975-12-27 | 1977-07-12 | Otsuka Pharmaceut Co Ltd | Synthesis of carbostyril derivatives |
| DE2609645A1 (de) * | 1976-03-09 | 1977-09-15 | Boehringer Sohn Ingelheim | Aminoalkylheterocyclen |
| DE2644833A1 (de) * | 1976-10-05 | 1978-04-20 | Boehringer Sohn Ingelheim | Neue 1-aryloxy-2-hydroxy-3-alkylenaminopropane und verfahren zu ihrer herstellung |
| DE3023369A1 (de) * | 1980-06-23 | 1982-01-14 | Boehringer Mannheim Gmbh, 6800 Mannheim | Aryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| GB8323553D0 (en) * | 1983-09-02 | 1983-10-05 | Smith Kline French Lab | Pharmaceutical compositions |
| JPS6193169A (ja) * | 1984-10-12 | 1986-05-12 | Sankyo Co Ltd | ピリダジノン誘導体及びその製法 |
| GB8503424D0 (en) * | 1985-02-11 | 1985-03-13 | Ici Plc | Heterocyclic derivatives |
| JPH0629254B2 (ja) * | 1986-09-08 | 1994-04-20 | 帝国臓器製薬株式会社 | ピリダジノン誘導体 |
| DE3934436A1 (de) * | 1989-06-01 | 1991-04-18 | Thomae Gmbh Dr K | 2-hydroxy-n-propylamine, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| JP2799186B2 (ja) * | 1989-06-02 | 1998-09-17 | 帝国臓器製薬株式会社 | 光学活性ピリダジノン誘導体 |
| NZ234087A (en) * | 1989-06-19 | 1991-08-27 | Teikoku Hormone Mfg Co Ltd | 2-(3-aryloxy(2-hydroxy-propylamino))-2-methylpropyl- aminophenyl pyridazine derivatives |
| JP2931635B2 (ja) * | 1989-06-19 | 1999-08-09 | 帝国臓器製薬株式会社 | ピリダジノン化合物 |
| PT94954A (pt) * | 1989-08-10 | 1991-04-18 | Glaxo Inc., | Processo para a preparacao de derivados de piridazinona |
| US5051431A (en) * | 1989-09-22 | 1991-09-24 | Glaxo Inc. | Pyridone nitriles useful in treating cardiovascular disease |
| US5641783A (en) * | 1993-11-12 | 1997-06-24 | Cell Therapeutics, Inc. | Substituted amino alcohol compounds |
| US5827893A (en) * | 1996-03-29 | 1998-10-27 | Lurie; Keith G. | Mechanical and pharmacological therapies to treat cardiac arrest |
| US5905078A (en) * | 1998-06-19 | 1999-05-18 | Orion Corporation | Use of a pyridazinone derivative |
| WO2004050657A2 (en) * | 2002-11-27 | 2004-06-17 | Artesian Therapeutics, Inc. | COMPOUNDS WITH MIXED PDE-INHIBITORY AND β-ADRENERGIC ANTAGONIST OR PARTIAL AGONIST ACTIVITY FOR TREATMENT OF HEART FAILURE |
| US20070117978A1 (en) * | 2002-12-23 | 2007-05-24 | Artesian Therapecutics, Inc | Cardiotonic compounds with inhibitory activity against beta-adrenergic receptors and phosphodiesterase |
| JP5258763B2 (ja) * | 2007-06-20 | 2013-08-07 | 興和株式会社 | ５−フェニル−３−ピリダジノン誘導体 |
| RU2010121763A (ru) * | 2007-10-31 | 2011-12-10 | Ниссан Кемикал Индастриз, Лтд. (Jp) | Производные пиридазинона и ингибиторы р2х7 рецептора |
| EP2204366A1 (de) * | 2008-12-19 | 2010-07-07 | Bayer CropScience AG | Herbizid und insektizid wirksame phenylsubstituierte Pyridazinone |
-
2005
- 2005-11-08 US US11/791,894 patent/US20080255134A1/en not_active Abandoned
- 2005-11-08 CA CA002588947A patent/CA2588947A1/en not_active Abandoned
- 2005-11-08 EP EP05848640A patent/EP1833480A2/en not_active Withdrawn
- 2005-11-08 JP JP2007543114A patent/JP2008521805A/ja active Pending
- 2005-11-08 WO PCT/US2005/040409 patent/WO2006060122A2/en not_active Ceased
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