JP2007514769A - １−アルカン−２−オール置換ピペラジンおよびピペリジン化合物 - Google Patents
１−アルカン−２−オール置換ピペラジンおよびピペリジン化合物 Download PDFInfo
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- JP2007514769A JP2007514769A JP2006545566A JP2006545566A JP2007514769A JP 2007514769 A JP2007514769 A JP 2007514769A JP 2006545566 A JP2006545566 A JP 2006545566A JP 2006545566 A JP2006545566 A JP 2006545566A JP 2007514769 A JP2007514769 A JP 2007514769A
- Authority
- JP
- Japan
- Prior art keywords
- yloxy
- methylbenzothiazol
- piperazinyl
- propyl
- hydroxy
- 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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- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title description 5
- 150000004885 piperazines Chemical class 0.000 title description 3
- 150000003053 piperidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 271
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 29
- 208000019622 heart disease Diseases 0.000 claims abstract description 10
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 9
- 201000010099 disease Diseases 0.000 claims abstract description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 9
- 206010022562 Intermittent claudication Diseases 0.000 claims abstract description 6
- 208000021156 intermittent vascular claudication Diseases 0.000 claims abstract description 6
- 208000010125 myocardial infarction Diseases 0.000 claims abstract description 6
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims abstract description 5
- 208000007718 Stable Angina Diseases 0.000 claims abstract description 5
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims abstract description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 5
- 208000007814 Unstable Angina Diseases 0.000 claims abstract description 4
- 206010002388 Angina unstable Diseases 0.000 claims abstract description 3
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims abstract description 3
- -1 2- [4- (4- {4-[(2R) -2-hydroxy-3- (2-methylbenzothiazol-5-yloxy) propyl] piperazinyl} butoxy) phenyl] ethyl Chemical group 0.000 claims description 202
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 111
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 150000001412 amines Chemical class 0.000 claims description 33
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- FCOVEHXMSLZUFC-LJQANCHMSA-N (2r)-1-[4-[2-(4-chlorophenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(Cl)C=C1 FCOVEHXMSLZUFC-LJQANCHMSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- USQYEHICAINAAI-HXUWFJFHSA-N (2r)-1-[4-(4-cyclopentyloxybutyl)piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1CCCC1 USQYEHICAINAAI-HXUWFJFHSA-N 0.000 claims description 5
- UWNDAXVJJYCJRM-JOCHJYFZSA-N 2-[4-[4-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]butoxy]phenoxy]-2-methylpropanoic acid Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1=CC=C(OC(C)(C)C(O)=O)C=C1 UWNDAXVJJYCJRM-JOCHJYFZSA-N 0.000 claims description 5
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- MWXVDZJCDVEGLN-OAQYLSRUSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-(4-phenoxybutyl)piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1=CC=CC=C1 MWXVDZJCDVEGLN-OAQYLSRUSA-N 0.000 claims description 4
- UUHMQYDKZGABNM-FYYLOGMGSA-N (3r)-1-(4-fluorophenyl)-3-[[1-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperidin-4-yl]amino]pyrrolidin-2-one Chemical compound C([C@H](C1=O)NC2CCN(CC2)C[C@@H](O)COC=2C=C3N=C(SC3=CC=2)C)CN1C1=CC=C(F)C=C1 UUHMQYDKZGABNM-FYYLOGMGSA-N 0.000 claims description 4
- LHOJERYLNWQTFM-FYYLOGMGSA-N (3r)-3-[[1-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperidin-4-yl]amino]-1-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C([C@H](C1=O)NC2CCN(CC2)C[C@@H](O)COC=2C=C3N=C(SC3=CC=2)C)CN1C1=CC=C(C(F)(F)F)C=C1 LHOJERYLNWQTFM-FYYLOGMGSA-N 0.000 claims description 4
- LWWCXHIXJNVTSN-VGAJERRHSA-N 3-[[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]-1-phenylpyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(C1=O)CC(=O)N1C1=CC=CC=C1 LWWCXHIXJNVTSN-VGAJERRHSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- YLRPALOQCRHPPQ-HXUWFJFHSA-N n-[2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]ethyl]-4-(trifluoromethyl)benzamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCNC(=O)C1=CC=C(C(F)(F)F)C=C1 YLRPALOQCRHPPQ-HXUWFJFHSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
- ZZYPAHYVBGCVGZ-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-(2-phenoxyethyl)piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=CC=C1 ZZYPAHYVBGCVGZ-LJQANCHMSA-N 0.000 claims description 3
- RJEDNSMPHIARKY-HXUWFJFHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-(3-phenoxypropyl)piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCOC1=CC=CC=C1 RJEDNSMPHIARKY-HXUWFJFHSA-N 0.000 claims description 3
- CAQVVOUVAFINPX-HXUWFJFHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[2-(2-methylphenoxy)ethyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=CC=C1C CAQVVOUVAFINPX-HXUWFJFHSA-N 0.000 claims description 3
- NLJDIJWXVUOJFD-RUZDIDTESA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[2-(4-phenylphenoxy)ethyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC(C=C1)=CC=C1C1=CC=CC=C1 NLJDIJWXVUOJFD-RUZDIDTESA-N 0.000 claims description 3
- XLTXRIHKLHVMHX-GOSISDBHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[2-[4-(trifluoromethoxy)phenoxy]ethyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(OC(F)(F)F)C=C1 XLTXRIHKLHVMHX-GOSISDBHSA-N 0.000 claims description 3
- PXXCLIPMCDDJJV-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[2-[4-(trifluoromethyl)phenoxy]ethyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(C(F)(F)F)C=C1 PXXCLIPMCDDJJV-LJQANCHMSA-N 0.000 claims description 3
- JCCWEXQYGWYMGT-HXUWFJFHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[3-[4-(trifluoromethyl)phenoxy]propyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCOC1=CC=C(C(F)(F)F)C=C1 JCCWEXQYGWYMGT-HXUWFJFHSA-N 0.000 claims description 3
- YTFYLKVQTIMNDL-RIBGEGAISA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)butyl]piperazin-1-yl]propan-2-ol Chemical compound C1CCC2=CC=CC=C2C1OCCCCN(CC1)CCN1C[C@@H](O)COC1=CC=C(SC(C)=N2)C2=C1 YTFYLKVQTIMNDL-RIBGEGAISA-N 0.000 claims description 3
- ZLUCCAXVBWMFNA-RUZDIDTESA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-(5,6,7,8-tetrahydronaphthalen-2-yloxy)butyl]piperazin-1-yl]propan-2-ol Chemical compound C1CCCC2=CC(OCCCCN3CCN(CC3)C[C@@H](O)COC=3C=C4N=C(SC4=CC=3)C)=CC=C21 ZLUCCAXVBWMFNA-RUZDIDTESA-N 0.000 claims description 3
- OCYNFJYVYJHILJ-DPUSYNFFSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-[(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)oxy]butyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1C(C2(C)C)(C)CCC2C1 OCYNFJYVYJHILJ-DPUSYNFFSA-N 0.000 claims description 3
- DRMDFXSPDNHEBO-GOSISDBHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxybutyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC=1C=C(C(F)(F)F)N(C)N=1 DRMDFXSPDNHEBO-GOSISDBHSA-N 0.000 claims description 3
- ATLPWOXYMCXYFK-OAQYLSRUSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-[4-(trifluoromethyl)phenoxy]butyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1=CC=C(C(F)(F)F)C=C1 ATLPWOXYMCXYFK-OAQYLSRUSA-N 0.000 claims description 3
- MYZKRQBPRIYHEA-HSZRJFAPSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[6-[4-(trifluoromethyl)phenoxy]hexyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCCCOC1=CC=C(C(F)(F)F)C=C1 MYZKRQBPRIYHEA-HSZRJFAPSA-N 0.000 claims description 3
- VRJPOOAFZYANCT-LJQANCHMSA-N (2r)-1-[4-(4-cyclobutyloxybutyl)piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1CCC1 VRJPOOAFZYANCT-LJQANCHMSA-N 0.000 claims description 3
- ZGQUGDSVCSKSRS-OAQYLSRUSA-N (2r)-1-[4-(4-cyclohexyloxybutyl)piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1CCCCC1 ZGQUGDSVCSKSRS-OAQYLSRUSA-N 0.000 claims description 3
- PFMDEVGDEAHHHN-LJQANCHMSA-N (2r)-1-[4-[2-(2-methoxyphenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound COC1=CC=CC=C1OCCN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 PFMDEVGDEAHHHN-LJQANCHMSA-N 0.000 claims description 3
- QHOSMFPDYSEGQO-LJQANCHMSA-N (2r)-1-[4-[2-(3,5-dichlorophenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC(Cl)=CC(Cl)=C1 QHOSMFPDYSEGQO-LJQANCHMSA-N 0.000 claims description 3
- QEHXJVZSNFOQKZ-QGZVFWFLSA-N (2r)-1-[4-[2-(3-chloro-4-fluorophenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(F)C(Cl)=C1 QEHXJVZSNFOQKZ-QGZVFWFLSA-N 0.000 claims description 3
- WEFOATARQOGEPR-QGZVFWFLSA-N (2r)-1-[4-[2-(4-bromo-3-chlorophenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(Br)C(Cl)=C1 WEFOATARQOGEPR-QGZVFWFLSA-N 0.000 claims description 3
- GCOVAPIXCFOKLY-LJQANCHMSA-N (2r)-1-[4-[2-(4-chloro-2-methoxyphenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound COC1=CC(Cl)=CC=C1OCCN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 GCOVAPIXCFOKLY-LJQANCHMSA-N 0.000 claims description 3
- BEVFHHAVOBHUMN-LJQANCHMSA-N (2r)-1-[4-[2-(4-fluorophenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(F)C=C1 BEVFHHAVOBHUMN-LJQANCHMSA-N 0.000 claims description 3
- CGBXLNUGMNCNTB-LJQANCHMSA-N (2r)-1-[4-[2-(4-methoxyphenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1=CC(OC)=CC=C1OCCN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 CGBXLNUGMNCNTB-LJQANCHMSA-N 0.000 claims description 3
- VKWFULSNZYOQFY-LJQANCHMSA-N (2r)-1-[4-[2-[3,5-bis(trifluoromethyl)phenoxy]ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VKWFULSNZYOQFY-LJQANCHMSA-N 0.000 claims description 3
- QYFGVPIQAZCOAF-HXUWFJFHSA-N (2r)-1-[4-[3-(4-fluorophenoxy)propyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCOC1=CC=C(F)C=C1 QYFGVPIQAZCOAF-HXUWFJFHSA-N 0.000 claims description 3
- XQVIZOXXEBNQFM-XMMPIXPASA-N (2r)-1-[4-[4-(2,3-dihydro-1h-inden-2-yloxy)butyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1C2=CC=CC=C2CC1OCCCCN(CC1)CCN1C[C@@H](O)COC1=CC=C(SC(C)=N2)C2=C1 XQVIZOXXEBNQFM-XMMPIXPASA-N 0.000 claims description 3
- UYTQMSKZRODTTA-XMMPIXPASA-N (2r)-1-[4-[4-(2,3-dihydro-1h-inden-5-yloxy)butyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1=C2CCCC2=CC(OCCCCN2CCN(CC2)C[C@@H](O)COC=2C=C3N=C(SC3=CC=2)C)=C1 UYTQMSKZRODTTA-XMMPIXPASA-N 0.000 claims description 3
- WTZWFUJGWNPUIK-OAQYLSRUSA-N (2r)-1-[4-[4-(4-chlorophenoxy)butyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1=CC=C(Cl)C=C1 WTZWFUJGWNPUIK-OAQYLSRUSA-N 0.000 claims description 3
- POQATYDECVVVMK-OADZCNSWSA-N (2r)-1-[4-[4-(4-tert-butylcyclohexyl)oxybutyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1CCC(C(C)(C)C)CC1 POQATYDECVVVMK-OADZCNSWSA-N 0.000 claims description 3
- DDAGFIRXTVDUSB-FTPFQACPSA-N (2r)-1-[4-[4-[(1-methoxy-2,3-dihydro-1h-inden-2-yl)oxy]butyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1=C2SC(C)=NC2=CC(OC[C@H](O)CN2CCN(CC2)CCCCOC2C(C3=CC=CC=C3C2)OC)=C1 DDAGFIRXTVDUSB-FTPFQACPSA-N 0.000 claims description 3
- SJWJDFCBAIMPAS-DENIHFKCSA-N (3r)-1-(2-fluorophenyl)-3-[[1-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperidin-4-yl]amino]pyrrolidin-2-one Chemical compound C([C@H](C1=O)NC2CCN(CC2)C[C@@H](O)COC=2C=C3N=C(SC3=CC=2)C)CN1C1=CC=CC=C1F SJWJDFCBAIMPAS-DENIHFKCSA-N 0.000 claims description 3
- PXYXGDHQGRXQKT-GWQXNCQPSA-N (3r)-1-(4-chlorophenyl)-3-[4-[2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]pyrrolidin-2-one Chemical compound C([C@H](C1=O)N2CCN(CC2)CC(O)COC=2C=C3N=C(SC3=CC=2)C)CN1C1=CC=C(Cl)C=C1 PXYXGDHQGRXQKT-GWQXNCQPSA-N 0.000 claims description 3
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- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FMLPQHJYUZTHQS-QMMMGPOBSA-N tert-butyl (3s)-3-methylpiperazine-1-carboxylate Chemical compound C[C@H]1CN(C(=O)OC(C)(C)C)CCN1 FMLPQHJYUZTHQS-QMMMGPOBSA-N 0.000 description 1
- OMDNNSJLZYDXME-GOEBONIOSA-N tert-butyl (3s)-4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]-3-methylpiperazine-1-carboxylate Chemical compound C[C@H]1CN(C(=O)OC(C)(C)C)CCN1C[C@@H](O)COC1=CC=C(SC(C)=N2)C2=C1 OMDNNSJLZYDXME-GOEBONIOSA-N 0.000 description 1
- OPIJMDUMLNGKKE-UHFFFAOYSA-N tert-butyl 4-[2-[[4-(trifluoromethyl)benzoyl]amino]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CCNC(=O)C1=CC=C(C(F)(F)F)C=C1 OPIJMDUMLNGKKE-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53125303P | 2003-12-18 | 2003-12-18 | |
| PCT/US2004/042859 WO2005061470A1 (en) | 2003-12-18 | 2004-12-17 | 1-akan-2-ol substituted piperazine and piperidine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007514769A true JP2007514769A (ja) | 2007-06-07 |
| JP2007514769A5 JP2007514769A5 (enExample) | 2008-01-24 |
Family
ID=34710215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006545566A Pending JP2007514769A (ja) | 2003-12-18 | 2004-12-17 | １−アルカン−２−オール置換ピペラジンおよびピペリジン化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US7115610B2 (enExample) |
| EP (1) | EP1723129A1 (enExample) |
| JP (1) | JP2007514769A (enExample) |
| KR (1) | KR20060124646A (enExample) |
| AU (1) | AU2004303882A1 (enExample) |
| CA (1) | CA2550257A1 (enExample) |
| WO (1) | WO2005061470A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2024515895A (ja) * | 2021-05-07 | 2024-04-10 | メルク・シャープ・アンド・ドーム・エルエルシー | Ｎａｖ１．８阻害薬としてのシクロアルキル ３－オキソピペラジンカルボキサミド類及びシクロヘテロアルキル ３－オキソピペラジンカルボキサミド類 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005061470A1 (en) * | 2003-12-18 | 2005-07-07 | Cv Therapeutics, Inc. | 1-akan-2-ol substituted piperazine and piperidine compounds |
| EP1829866A1 (en) * | 2006-03-02 | 2007-09-05 | Laboratorios Del Dr. Esteve, S.A. | Sigma receptor inhibitors |
| JP5566288B2 (ja) | 2008-05-30 | 2014-08-06 | 武田薬品工業株式会社 | 複素環化合物 |
| CN105175401A (zh) * | 2015-10-16 | 2015-12-23 | 北京康立生医药技术开发有限公司 | 一种依匹哌唑的制备方法 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04264078A (ja) * | 1990-10-31 | 1992-09-18 | Richter Gedeon V G Rt | ピペラジン誘導体の製造方法 |
| WO2001060348A2 (en) * | 2000-02-18 | 2001-08-23 | Cv Therapeutics, Inc. | Partial fatty acid oxidation inhibitors in the treatment of congestive heart failure |
| WO2002064576A1 (en) * | 2000-10-23 | 2002-08-22 | Cv Therapeutics, Inc. | Heteroaryl alkyl piperazine derivatives as fatty acid oxidation inhibitors |
| WO2003008411A1 (en) * | 2001-07-19 | 2003-01-30 | Cv Therapeutics, Inc. | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
| WO2003049680A2 (en) * | 2001-12-05 | 2003-06-19 | Peirce Management, Llc | Compositions containing both sedative and non-sedative antihistamines |
| WO2003075091A1 (en) * | 2002-03-05 | 2003-09-12 | Ciba Specialty Chemicals Holding Inc. | Colour photographic recording material |
| JP2003531116A (ja) * | 2000-02-22 | 2003-10-21 | スィーヴィー セラピューティクス インコーポレイテッド | 置換ピペラジン化合物 |
| WO2003086401A1 (en) * | 2002-04-04 | 2003-10-23 | Cv Therapeutics, Inc. | Use of ranolazine for the preparation of a medicament for the treatment of arrhythmias |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2034305B (en) | 1978-10-24 | 1982-12-22 | Wyeth John & Brother Ltd | Preparation of piperidine derivatives |
| DE3118881A1 (de) | 1980-09-29 | 1982-06-24 | Oltmanns Ziegel Und Kunststoffe Gmbh, 2905 Edewecht | "ziegel" |
| US4766125A (en) | 1981-06-23 | 1988-08-23 | Janssen Pharmaceutica N.V. | N-aryl-piperazinealkanamides useful for protecting hearts from myocardial injury caused by ischaemia, anoxia or hypoxia |
| US4558129A (en) | 1983-05-18 | 1985-12-10 | Syntex (U.S.A.) Inc. | Benzodioxanyl-hydroxyethylene-piperazinyl acetanilides which effect calcium entry and β-blockade |
| US4567264A (en) | 1983-05-18 | 1986-01-28 | Syntex (U.S.A.) Inc. | Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry |
| NZ247044A (en) | 1989-06-23 | 1997-04-24 | Syntex Usa Inc Substituted For | Use of ranolazine and related piperazine derivatives to treat tissue affected by muscle and neuronal damage, including transplant tissue |
| US5455045A (en) | 1993-05-13 | 1995-10-03 | Syntex (U.S.A.) Inc. | High dose formulations |
| US6552023B2 (en) | 2000-02-22 | 2003-04-22 | Cv Therapeutics, Inc. | Aralkyl substituted piperazine compounds |
| US6677336B2 (en) | 2000-02-22 | 2004-01-13 | Cv Therapeutics, Inc. | Substituted piperazine compounds |
| US6451798B2 (en) | 2000-02-22 | 2002-09-17 | Cv Therapeutics, Inc. | Substituted alkyl piperazine derivatives |
| AU2001238590A1 (en) | 2000-02-22 | 2001-09-03 | Cv Therapeutics, Inc. | Substituted piperazine compounds |
| CN1240688C (zh) * | 2000-04-07 | 2006-02-08 | 阿斯特拉曾尼卡有限公司 | 喹唑啉化合物 |
| US7001909B2 (en) | 2001-07-19 | 2006-02-21 | Cv Therapeutics, Inc. | Substituted heterocyclic compounds |
| WO2005061470A1 (en) * | 2003-12-18 | 2005-07-07 | Cv Therapeutics, Inc. | 1-akan-2-ol substituted piperazine and piperidine compounds |
-
2004
- 2004-12-17 WO PCT/US2004/042859 patent/WO2005061470A1/en not_active Ceased
- 2004-12-17 AU AU2004303882A patent/AU2004303882A1/en not_active Abandoned
- 2004-12-17 JP JP2006545566A patent/JP2007514769A/ja active Pending
- 2004-12-17 CA CA002550257A patent/CA2550257A1/en not_active Abandoned
- 2004-12-17 US US11/015,915 patent/US7115610B2/en not_active Expired - Lifetime
- 2004-12-17 EP EP04814988A patent/EP1723129A1/en not_active Withdrawn
- 2004-12-17 KR KR1020067011920A patent/KR20060124646A/ko not_active Ceased
-
2006
- 2006-06-13 US US11/452,479 patent/US7262198B2/en not_active Expired - Lifetime
-
2007
- 2007-08-27 US US11/845,720 patent/US7452889B2/en not_active Expired - Lifetime
-
2008
- 2008-10-27 US US12/259,085 patent/US20090054457A1/en not_active Abandoned
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04264078A (ja) * | 1990-10-31 | 1992-09-18 | Richter Gedeon V G Rt | ピペラジン誘導体の製造方法 |
| WO2001060348A2 (en) * | 2000-02-18 | 2001-08-23 | Cv Therapeutics, Inc. | Partial fatty acid oxidation inhibitors in the treatment of congestive heart failure |
| JP2003531116A (ja) * | 2000-02-22 | 2003-10-21 | スィーヴィー セラピューティクス インコーポレイテッド | 置換ピペラジン化合物 |
| WO2002064576A1 (en) * | 2000-10-23 | 2002-08-22 | Cv Therapeutics, Inc. | Heteroaryl alkyl piperazine derivatives as fatty acid oxidation inhibitors |
| WO2003008411A1 (en) * | 2001-07-19 | 2003-01-30 | Cv Therapeutics, Inc. | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
| WO2003049680A2 (en) * | 2001-12-05 | 2003-06-19 | Peirce Management, Llc | Compositions containing both sedative and non-sedative antihistamines |
| WO2003075091A1 (en) * | 2002-03-05 | 2003-09-12 | Ciba Specialty Chemicals Holding Inc. | Colour photographic recording material |
| WO2003086401A1 (en) * | 2002-04-04 | 2003-10-23 | Cv Therapeutics, Inc. | Use of ranolazine for the preparation of a medicament for the treatment of arrhythmias |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2024515895A (ja) * | 2021-05-07 | 2024-04-10 | メルク・シャープ・アンド・ドーム・エルエルシー | Ｎａｖ１．８阻害薬としてのシクロアルキル ３－オキソピペラジンカルボキサミド類及びシクロヘテロアルキル ３－オキソピペラジンカルボキサミド類 |
| JP7522943B2 (ja) | 2021-05-07 | 2024-07-25 | メルク・シャープ・アンド・ドーム・エルエルシー | Ｎａｖ１．８阻害薬としてのシクロアルキル ３－オキソピペラジンカルボキサミド類及びシクロヘテロアルキル ３－オキソピペラジンカルボキサミド類 |
Also Published As
| Publication number | Publication date |
|---|---|
| US7452889B2 (en) | 2008-11-18 |
| US7115610B2 (en) | 2006-10-03 |
| US20050197346A1 (en) | 2005-09-08 |
| KR20060124646A (ko) | 2006-12-05 |
| EP1723129A1 (en) | 2006-11-22 |
| US20090054457A1 (en) | 2009-02-26 |
| AU2004303882A1 (en) | 2005-07-07 |
| US20080032993A1 (en) | 2008-02-07 |
| WO2005061470A1 (en) | 2005-07-07 |
| US20060229317A1 (en) | 2006-10-12 |
| CA2550257A1 (en) | 2005-07-07 |
| US7262198B2 (en) | 2007-08-28 |
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