AU2013240842B2 - Process of preparing solifenacin or salt thereof, and novel intermediate used in the process - Google Patents
Process of preparing solifenacin or salt thereof, and novel intermediate used in the process Download PDFInfo
- Publication number
- AU2013240842B2 AU2013240842B2 AU2013240842A AU2013240842A AU2013240842B2 AU 2013240842 B2 AU2013240842 B2 AU 2013240842B2 AU 2013240842 A AU2013240842 A AU 2013240842A AU 2013240842 A AU2013240842 A AU 2013240842A AU 2013240842 B2 AU2013240842 B2 AU 2013240842B2
- Authority
- AU
- Australia
- Prior art keywords
- formula
- reaction solution
- reaction
- solifenacin
- added
- 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.)
- Ceased
Links
- FBOUYBDGKBSUES-VXKWHMMOSA-N solifenacin Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(O[C@@H]2C3CCN(CC3)C2)=O)=CC=CC=C1 FBOUYBDGKBSUES-VXKWHMMOSA-N 0.000 title claims abstract description 86
- 229960003855 solifenacin Drugs 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 50
- 150000003839 salts Chemical class 0.000 title claims abstract description 29
- IOVVFSGCNWQFQT-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenyl) carbonate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OC(=O)OC1=C(F)C(F)=C(F)C(F)=C1F IOVVFSGCNWQFQT-UHFFFAOYSA-N 0.000 claims abstract description 25
- FSNYTEYOTCTPSO-SSDOTTSWSA-N (2r)-1-azabicyclo[2.2.2]octan-2-ol Chemical compound C1CN2[C@H](O)CC1CC2 FSNYTEYOTCTPSO-SSDOTTSWSA-N 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 19
- PRTRSEDVLBBFJZ-HNNXBMFYSA-N (1s)-1-phenyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C1([C@H]2C3=CC=CC=C3CCN2)=CC=CC=C1 PRTRSEDVLBBFJZ-HNNXBMFYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 329
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 134
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 72
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 53
- FBOUYBDGKBSUES-KEKNWZKVSA-N 1-azabicyclo[2.2.2]octan-3-yl (1s)-1-phenyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(OC2C3CCN(CC3)C2)=O)=CC=CC=C1 FBOUYBDGKBSUES-KEKNWZKVSA-N 0.000 claims description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 229960001368 solifenacin succinate Drugs 0.000 claims description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 239000010410 layer Substances 0.000 description 26
- 239000007795 chemical reaction product Substances 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 19
- 230000037361 pathway Effects 0.000 description 18
- 238000004809 thin layer chromatography Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000006227 byproduct Substances 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 16
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
- 239000000908 ammonium hydroxide Substances 0.000 description 16
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 13
- 230000003595 spectral effect Effects 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- SVJROEXONLYKSH-ZETCQYMHSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] (2,3,4,5,6-pentafluorophenyl) carbonate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OC(=O)O[C@@H]1C(CC2)CCN2C1 SVJROEXONLYKSH-ZETCQYMHSA-N 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 229940093499 ethyl acetate Drugs 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000001384 succinic acid Substances 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- -1 2,5 -dioxopyrrolidine- 1 -yloxy Chemical group 0.000 description 2
- YBKLSFINFYXARJ-UHFFFAOYSA-N C(C)O.C(C)(=O)OCC.C(CCC(=O)O)(=O)O Chemical compound C(C)O.C(C)(=O)OCC.C(CCC(=O)O)(=O)O YBKLSFINFYXARJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- KPHBZYZBLGSCFH-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-2-yl carbonochloridate;hydrochloride Chemical compound Cl.C1CN2C(OC(=O)Cl)CC1CC2 KPHBZYZBLGSCFH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 206010020853 Hypertonic bladder Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 206010027566 Micturition urgency Diseases 0.000 description 1
- UQOFGTXDASPNLL-XHNCKOQMSA-N Muscarine Chemical compound C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O UQOFGTXDASPNLL-XHNCKOQMSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000009722 Overactive Urinary Bladder Diseases 0.000 description 1
- 206010036018 Pollakiuria Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- DMIPRIGMQXBATL-UHFFFAOYSA-N octan-3-yl 1-phenyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound CCCCCC(CC)OC(=O)N1CCC2=CC=CC=C2C1C1=CC=CC=C1 DMIPRIGMQXBATL-UHFFFAOYSA-N 0.000 description 1
- 208000020629 overactive bladder Diseases 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 208000022934 urinary frequency Diseases 0.000 description 1
- 230000036318 urination frequency Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/49—Cinchonan derivatives, e.g. quinine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Urology & Nephrology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20120031492A KR101365849B1 (ko) | 2012-03-28 | 2012-03-28 | 솔리페나신 또는 그의 염의 제조방법 및 이에 사용되는 신규 중간체 |
| KR10-2012-0031492 | 2012-03-28 | ||
| PCT/KR2013/002358 WO2013147458A1 (en) | 2012-03-28 | 2013-03-21 | Process of preparing solifenacin or salt thereof, and novel intermediate used in the process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2013240842A1 AU2013240842A1 (en) | 2014-08-28 |
| AU2013240842B2 true AU2013240842B2 (en) | 2015-09-03 |
Family
ID=49260649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013240842A Ceased AU2013240842B2 (en) | 2012-03-28 | 2013-03-21 | Process of preparing solifenacin or salt thereof, and novel intermediate used in the process |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9018379B1 (https=) |
| EP (1) | EP2831070A4 (https=) |
| JP (1) | JP5891334B2 (https=) |
| KR (1) | KR101365849B1 (https=) |
| CN (1) | CN104169280A (https=) |
| AU (1) | AU2013240842B2 (https=) |
| BR (1) | BR112014021223A2 (https=) |
| IN (1) | IN2014DN07762A (https=) |
| WO (1) | WO2013147458A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116986986A (zh) * | 2023-07-19 | 2023-11-03 | 杭州国瑞生物科技有限公司 | 一种3-氧代-1-环丁烷羧酸中间体的合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010103529A1 (en) * | 2009-03-09 | 2010-09-16 | Megafine Pharma(P) Ltd. | A new method for the preparation of solifenacin and new intermediate thereof |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO2005012I1 (no) | 1994-12-28 | 2005-06-06 | Debio Rech Pharma Sa | Triptorelin og farmasoytisk akseptable salter derav |
| EP0888543A4 (en) * | 1996-03-20 | 2004-04-07 | Scripps Research Inst | CHANNEL ESTIMATION DEVICE |
| KR100669823B1 (ko) | 2001-02-20 | 2007-01-17 | 경동제약 주식회사 | 2-(4-클로로벤조일아미노)-3-[2(1ｈ)-퀴놀리논-4-일]프로피온산의 제조방법 및 그 중간체 |
| US20040157804A1 (en) * | 2002-10-16 | 2004-08-12 | Gilead Sciences, Inc. | Pre-organized tricyclic integrase inhibitor compounds |
| GB0312426D0 (en) * | 2003-05-30 | 2003-07-09 | Albachem Ltd | Purification means |
| CA2558877A1 (en) | 2004-02-09 | 2005-08-18 | Astellas Pharma Inc. | Solifenacin succinate-containing composition |
| JPWO2005087231A1 (ja) | 2004-03-16 | 2008-01-24 | アステラス製薬株式会社 | ソリフェナシン含有組成物 |
| EP1742642B1 (en) * | 2004-04-14 | 2008-10-15 | Gilead Sciences, Inc. | Phosphonate analogs of hiv integrase inhibitor compounds |
| JP4803352B2 (ja) * | 2005-07-13 | 2011-10-26 | Ｊｓｒ株式会社 | アミノ酸−ｎ−カルボキシ無水物の製造方法 |
| CA2630846A1 (en) | 2005-12-21 | 2007-07-05 | Teva Pharmaceutical Industries Ltd. | Intermediates for preparing solifenacin |
| EP2102200A2 (en) | 2006-11-22 | 2009-09-23 | Medichem, S.A. | An improved process for the synthesis of solifenacin |
| CN101711248A (zh) * | 2007-03-30 | 2010-05-19 | 医药化学公司 | 一种改进的素非那新合成工艺 |
| JP2009538362A (ja) * | 2007-07-13 | 2009-11-05 | テバ ファーマシューティカル インダストリーズ リミティド | ソリフェナシンの調製方法 |
| HRP20161040T1 (hr) * | 2008-04-29 | 2016-12-16 | Ascendis Pharma Growth Disorders Division A/S | Pegilirani rekombinantni spojevi ljudskog hormona rasta |
| US8178700B2 (en) * | 2009-05-04 | 2012-05-15 | International Business Machines Corporation | Method of preparing cyclic carbonates, cyclic carbamates, cyclic ureas, cyclic thiocarbonates, cyclic thiocarbamates, and cyclic dithiocarbonates |
| WO2011030139A1 (en) * | 2009-09-11 | 2011-03-17 | Astrazeneca Ab | 4- (pyrimidin-2-yl) -piperazine and 4- (pyrimidin-2-yl) -piperidine derivatives as gpr119 modulators |
-
2012
- 2012-03-28 KR KR20120031492A patent/KR101365849B1/ko active Active
-
2013
- 2013-03-21 CN CN201380016063.XA patent/CN104169280A/zh active Pending
- 2013-03-21 US US14/382,529 patent/US9018379B1/en not_active Expired - Fee Related
- 2013-03-21 EP EP13768214.2A patent/EP2831070A4/en not_active Withdrawn
- 2013-03-21 JP JP2015501582A patent/JP5891334B2/ja active Active
- 2013-03-21 BR BR112014021223-6A patent/BR112014021223A2/pt not_active IP Right Cessation
- 2013-03-21 AU AU2013240842A patent/AU2013240842B2/en not_active Ceased
- 2013-03-21 WO PCT/KR2013/002358 patent/WO2013147458A1/en not_active Ceased
- 2013-03-21 IN IN7762DEN2014 patent/IN2014DN07762A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010103529A1 (en) * | 2009-03-09 | 2010-09-16 | Megafine Pharma(P) Ltd. | A new method for the preparation of solifenacin and new intermediate thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5891334B2 (ja) | 2016-03-22 |
| JP2015510927A (ja) | 2015-04-13 |
| US20150112072A1 (en) | 2015-04-23 |
| US9018379B1 (en) | 2015-04-28 |
| EP2831070A1 (en) | 2015-02-04 |
| AU2013240842A1 (en) | 2014-08-28 |
| WO2013147458A1 (en) | 2013-10-03 |
| KR20130109609A (ko) | 2013-10-08 |
| KR101365849B1 (ko) | 2014-02-24 |
| EP2831070A4 (en) | 2015-08-19 |
| CN104169280A (zh) | 2014-11-26 |
| IN2014DN07762A (https=) | 2015-05-15 |
| BR112014021223A2 (pt) | 2020-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7394785B2 (ja) | ジアステレオマー酒石酸エステルによるラセミ体分割による（４ｓ）－４－（４－シアノ－２－メトキシフェニル）－５－エトキシ－２，８－ジメチル－１，４－ジヒドロ－１，６－ナフチリジン－３－カルボキサミドを調製する方法 | |
| SK282865B6 (sk) | Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej a medziprodukty | |
| CA2914381A1 (en) | An efficient process for separation of diastereomers of 9-[(r)-2-[[(r,s)-[[(s)-1-(isopropoxycarbonyl)ethyl]amino]-phenoxyphosphinyl] methoxy]propyl]adenine | |
| HRP20040606A2 (en) | A process for producing phenserine and its analog | |
| WO2007147374A2 (en) | Process for the preparation of solifenacin | |
| WO2009010987A1 (en) | An improved process for the preparation of pure palonosetron hydrochloride | |
| CN111072633A (zh) | 一种埃索美拉唑镁三水合物的制备方法 | |
| AU2013240842B2 (en) | Process of preparing solifenacin or salt thereof, and novel intermediate used in the process | |
| JP7837559B2 (ja) | （ｒ）－４－（１－（６－（４－（トリフルオロメチル）ベンジル）－６－アザスピロ［２．５］オクタン－５－カルボキサミド）－シクロプロピル）安息香酸又はその塩の調製方法 | |
| CN116496214B (zh) | 一种手性3-(n-甲基-1,2,3,4-四氢异喹啉)丙酸酯苯磺酸盐的制备方法 | |
| EP1698615B1 (en) | Method of obtaining tolterodine | |
| KR101304640B1 (ko) | 신규의 로수바스타틴 엔-메틸벤질아민 염 및 그의 제조방법 | |
| KR100990046B1 (ko) | 신규한 몬테루카스트 4-할로 벤질아민염 및 이를 이용한 몬테루카스트 나트륨염의 제조방법 | |
| WO2001025236A2 (en) | A stereoselective process for the preparation of endo-3-aminoazabicycloalkanes | |
| US8242276B2 (en) | Methods for the preparation of N-(S)-1-azabicyclo[2.2.2]oct-3-yl-1H-indazole-3-carboxamide hydrochloride salt | |
| US20170233334A1 (en) | Method for preparing d-arginine | |
| KR100929414B1 (ko) | 트로스피움 클로라이드의 제조방법 | |
| EP4438598A1 (en) | Method for preparing arylethene compound | |
| CN117586177A (zh) | 一种阿维巴坦中间体的制备方法 | |
| KR101298046B1 (ko) | 솔리페나신과 이의 염의 효율적 제조방법 | |
| EP2855421B1 (en) | Process for the preparation of optically active 3,3-diphenylpropylamines | |
| WO2019098551A1 (ko) | 의약품 합성용 중간체 화합물의 제조 방법 | |
| CN111138333A (zh) | 一种(r)-2-(2,5-二氟苯基)-吡咯烷的制备方法 | |
| JP2012500251A (ja) | ４−［トランス−４−［（フェニルメチル）アミノ］シクロヘキシル］安息香酸のエチルエステルおよびこのヘミフマル酸塩の調製方法 | |
| HK1022300B (en) | Optical resolution of narwedine-type compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |