BR112014021223A2 - processo de preparar solifenacina ou sal deste, e intermediário inédito usado no processo - Google Patents
processo de preparar solifenacina ou sal deste, e intermediário inédito usado no processo Download PDFInfo
- Publication number
- BR112014021223A2 BR112014021223A2 BR112014021223-6A BR112014021223A BR112014021223A2 BR 112014021223 A2 BR112014021223 A2 BR 112014021223A2 BR 112014021223 A BR112014021223 A BR 112014021223A BR 112014021223 A2 BR112014021223 A2 BR 112014021223A2
- Authority
- BR
- Brazil
- Prior art keywords
- formula
- reaction solution
- reaction
- solifenacin
- fact
- Prior art date
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 85
- 229960003855 solifenacin Drugs 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 53
- 150000003839 salts Chemical class 0.000 title claims abstract description 29
- 239000003960 organic solvent Substances 0.000 claims abstract description 19
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 17
- 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 7
- 238000006243 chemical reaction Methods 0.000 claims description 330
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 135
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 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 20
- 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 12
- -1 oct-3-yl Chemical group 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 5
- 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 description 4
- 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
- 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
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 18
- 238000004809 thin layer chromatography Methods 0.000 description 18
- 239000006227 byproduct Substances 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000908 ammonium hydroxide Substances 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
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 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
- 239000002253 acid Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 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
- 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
- 230000037361 pathway Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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
- 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
- 206010036018 Pollakiuria Diseases 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
- 208000022934 urinary frequency Diseases 0.000 description 2
- 230000036318 urination frequency Effects 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
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-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
- 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
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 206010021639 Incontinence 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
- 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
- 101100234604 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ace-8 gene Proteins 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
- 229910000831 Steel Inorganic materials 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
- 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
- 239000005557 antagonist Substances 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
- HUGJLQDIAQYJEV-UHFFFAOYSA-N carbonochloridic acid hydrate Chemical compound O.OC(Cl)=O HUGJLQDIAQYJEV-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 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
- 239000012141 concentrate Substances 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
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 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
- 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
- 230000000269 nucleophilic effect Effects 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
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229940016141 solfenacin Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 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
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 (1)
| Publication Number | Publication Date |
|---|---|
| BR112014021223A2 true BR112014021223A2 (pt) | 2020-10-27 |
Family
ID=49260649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112014021223-6A BR112014021223A2 (pt) | 2012-03-28 | 2013-03-21 | processo de preparar solifenacina ou sal deste, e intermediário inédito usado no processo |
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 |
Family Cites Families (17)
| 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 |
| PL2406257T3 (pl) * | 2009-03-09 | 2020-01-31 | Megafine Pharma (P) Ltd. | Nowy sposób wytwarzania solifenacyny i jej nowy produkt pośredni |
| 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
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 |
| AU2013240842B2 (en) | 2015-09-03 |
| IN2014DN07762A (https=) | 2015-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2548078T3 (es) | Método de síntesis asimétrica, material de partida relacionado y método de preparación de (S,S)-2,8-diazabiciclo[4,3,0]nonano | |
| KR20100016116A (ko) | 개선된 솔리페나신의 합성공정 | |
| US10464898B2 (en) | Process for the preparation of enantiomerically enriched 3-aminopiperidine | |
| EP3498695B1 (en) | Method for synthesizing 3-(difluoromethyl)-1-methyl-1h-pyrazole-4-carboxylic acid | |
| ES2456866T3 (es) | Procedimiento para la obtención de 3,3-difenilpropilaminas | |
| US9663518B1 (en) | Process for preparation of (2S, 5R)-1,6-diaza-bicyclo[3.2.1]octane-2-carbonitrile-7-oxo-6-(sulfooxy)-mono sodium salt | |
| BRPI0621832A2 (pt) | processo para a preparaÇço de enantiâmeros oticamente puros ou oticamente enriquecidos de compostos de sulfàxido | |
| BR112014021223A2 (pt) | processo de preparar solifenacina ou sal deste, e intermediário inédito usado no processo | |
| JP2546624B2 (ja) | 光学的に純粋なアミノアルコールの製造方法 | |
| BRPI0511095B1 (pt) | um processo para produção de enantiômero de anlodipino em alta pureza ótica | |
| KR20250166841A (ko) | 키랄 3-하이드록시-4-플루오로피페리딘 유도체의 합성 방법 및 분리 방법 | |
| EP3081554A1 (en) | Method for preparing silodosin and intermediate thereof | |
| PL236141B1 (pl) | Sposób otrzymywania chininy na drodze deprotonacji chlorowodoru lub siarczanu(VI) chininy w acetonitrylu | |
| EP2292594A1 (en) | Method for producing optically active aminoalcohol derivative | |
| US10207986B2 (en) | Method for preparing D-arginine | |
| Kodama et al. | Direct enantioseparation of 1-(2-hydroxyphenyl) ethylamines via diastereomeric salt formation: chiral recognition mechanism based on the crystal structure | |
| CA2873721C (en) | Process for the preparation of optically active 3,3-diphenylpropylamines | |
| KR101298046B1 (ko) | 솔리페나신과 이의 염의 효율적 제조방법 | |
| BR112020020829A2 (pt) | Processo para a preparação de um composto opticamente ativo, composto e uso | |
| JP2011057619A (ja) | 光学活性アミン化合物の製造方法、並びに、ジアステレオマー塩及びその製造方法 | |
| WO2018234962A1 (en) | Process for o-sulfonation of 1,6-diazabicyclo[3.2.1]octane compounds | |
| EP3178815B1 (en) | Method for producing optically active 2-methylpiperazine | |
| EP2855421B1 (en) | Process for the preparation of optically active 3,3-diphenylpropylamines | |
| CN121358709A (zh) | 用于制备5-{2-[苄基-(1-(4-羟基苯基)-1-甲基乙基)氨基]-1-羟基乙基}苯-1,3-二醇半富马酸盐的方法 | |
| JP2020138947A (ja) | 光学活性ベンズアザボロール誘導体およびその製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE A 7A ANUIDADE. |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: EM VIRTUDE DO ARQUIVAMENTO PUBLICADO NA RPI 2600 DE 03-11-2020 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDO O ARQUIVAMENTO DO PEDIDO DE PATENTE, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |
|
| B350 | Update of information on the portal [chapter 15.35 patent gazette] |