HUE025663T2 - Eljárás szolifenacin elõállítására - Google Patents
Eljárás szolifenacin elõállítására Download PDFInfo
- Publication number
- HUE025663T2 HUE025663T2 HUE07764312A HUE07764312A HUE025663T2 HU E025663 T2 HUE025663 T2 HU E025663T2 HU E07764312 A HUE07764312 A HU E07764312A HU E07764312 A HUE07764312 A HU E07764312A HU E025663 T2 HUE025663 T2 HU E025663T2
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- carboxylate
- phenyl
- tetrahydro
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 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 description 7
- 229960003855 solifenacin Drugs 0.000 title description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 150000007942 carboxylates Chemical class 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- IVLICPVPXWEGCA-ZETCQYMHSA-N (3r)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1CC2[C@@H](O)CN1CC2 IVLICPVPXWEGCA-ZETCQYMHSA-N 0.000 abstract description 16
- 125000000217 alkyl group Chemical group 0.000 abstract description 12
- 230000000269 nucleophilic effect Effects 0.000 abstract description 10
- 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 abstract description 5
- 125000005907 alkyl ester group Chemical group 0.000 abstract description 3
- 239000012442 inert solvent Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- DKKVDRQVNMALLN-KRWDZBQOSA-N ethyl (1s)-1-phenyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(=O)OCC)=CC=CC=C1 DKKVDRQVNMALLN-KRWDZBQOSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- -1 sodium alkoxide Chemical class 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- PRTRSEDVLBBFJZ-UHFFFAOYSA-N 1-phenyl-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC=CC=C2C1C1=CC=CC=C1 PRTRSEDVLBBFJZ-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PUPKPAZSFZOLOR-UHFFFAOYSA-N n,n-dimethylformamide;toluene Chemical compound CN(C)C=O.CC1=CC=CC=C1 PUPKPAZSFZOLOR-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (4)
1 Eljárás {1S}-(3R)~1-a2abiCJN.lQ-|2;2,2ÍOkt“3“ííi 3(4~dihk1rO“l4enil-2(1H}--izokjnDÍir?" karboxilát előállítására {lS>-afki 14enií~1 !2J,44atrah§drO“2”izokínoliri'-karboxílát és 3-(R)-kinukydinol ínért oldószerben való reagálfatásávai azzal jellemezve:, hogy a karboxllát 1 - 4 szénatomos primer aJkil-észterét használjuk és a reakciót egy nern-nukleofll bázissal katalizáljuk, ahol a nem-
2, Az1. Igénypont szerinti eljárás azzal jellemez ve, hogy a reagá Itatást tolóéiban végezzük el a reakdóelegy 90 ÜC ~ 129 ÖC közötti hőmérsékletén, a 3~{R)~kinukiidinoli [az (1S)-alkíl 1 -íenlht ^Aá-tetrahidro-S-izokínolln karboxllátra vonatkoztatott] 0% - 50% közötti moláris feleslegben használva és 0 - 50 moi% katalizátort használva az (IS)-aíkil 1 -fenlt-l ,2,3,4-tetrahidro~2"izoklnoíin karboxllátra vonatkoztatva.
3, A 2. igénypont szerinti eljárás azzal jellemeim, hogy a katalizátor moláris mennyisége kisebb, mint a 3~{R}~kínukiidinoi moláris feleslege az (1S)~alki! 1-fenik 1 >2s3i4-tefraliidro~2-'izokinolln karboxllátra vonatkoztatva.
4, Az 1. - 3. igénypontok szerinti eljárás azzal jellemezve, hegyez (1S}-alkil 1-fenihl ,2,3,4-!etrahidrö~2~ízökinö!in karboxllátok csoportjából az etilésztert alkalmazzuk.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20060407A CZ300699B6 (cs) | 2006-06-21 | 2006-06-21 | Zpusob prípravy solifenacinu |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE025663T2 true HUE025663T2 (hu) | 2016-04-28 |
Family
ID=38433757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE07764312A HUE025663T2 (hu) | 2006-06-21 | 2007-06-21 | Eljárás szolifenacin elõállítására |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8034942B2 (hu) |
| EP (1) | EP2029587B1 (hu) |
| CZ (1) | CZ300699B6 (hu) |
| EA (1) | EA015774B1 (hu) |
| HU (1) | HUE025663T2 (hu) |
| UA (1) | UA94614C2 (hu) |
| WO (1) | WO2007147374A2 (hu) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1726304A4 (en) * | 2004-03-16 | 2010-04-28 | Astellas Pharma Inc | COMPOSITION CONTAINING SOLIFENACIN |
| JP2011505416A (ja) * | 2007-12-04 | 2011-02-24 | カディラ ヘルスケア リミティド | 化学的及びキラル的に純粋なソリフェナシン塩基及びその塩を調製する方法 |
| ITMI20080195A1 (it) * | 2008-02-08 | 2009-08-09 | Dipharma Francis Srl | Procedimento per la preparazione di solifenacin |
| PL385265A1 (pl) | 2008-05-23 | 2009-12-07 | Zakłady Farmaceutyczne POLPHARMA Spółka Akcyjna | Sposób wytwarzania solifenacyny i/lub jej soli o wysokiej czystości farmaceutycznej |
| PL234208B1 (pl) | 2010-01-18 | 2020-01-31 | Zakl Farmaceutyczne Polpharma Spolka Akcyjna | Sposób wytwarzania bursztynianu solifenacyny |
| JP2015521635A (ja) * | 2012-07-02 | 2015-07-30 | ファーマシェン エス．エー． | ソリフェナシン又はその塩の調製方法 |
| CN103450183B (zh) * | 2013-08-16 | 2017-09-12 | 威海迪素制药有限公司 | 一种琥珀酸索利那新的制备方法 |
| CN104447734A (zh) * | 2014-12-11 | 2015-03-25 | 荆楚理工学院 | 一种琥珀酸索利那新的合成方法 |
Family Cites Families (3)
| 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 |
| EP1726304A4 (en) * | 2004-03-16 | 2010-04-28 | Astellas Pharma Inc | COMPOSITION CONTAINING SOLIFENACIN |
| WO2008011462A2 (en) * | 2006-07-19 | 2008-01-24 | Dr. Reddy's Laboratories Ltd. | Process for preparing solifenacin and its salts |
-
2006
- 2006-06-21 CZ CZ20060407A patent/CZ300699B6/cs not_active IP Right Cessation
-
2007
- 2007-06-21 US US12/305,452 patent/US8034942B2/en not_active Expired - Fee Related
- 2007-06-21 EP EP07764312.0A patent/EP2029587B1/en not_active Not-in-force
- 2007-06-21 EA EA200802388A patent/EA015774B1/ru not_active IP Right Cessation
- 2007-06-21 WO PCT/CZ2007/000061 patent/WO2007147374A2/en active Application Filing
- 2007-06-21 UA UAA200900442A patent/UA94614C2/ru unknown
- 2007-06-21 HU HUE07764312A patent/HUE025663T2/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2029587A2 (en) | 2009-03-04 |
| CZ2006407A3 (cs) | 2007-08-29 |
| EA015774B1 (ru) | 2011-12-30 |
| US8034942B2 (en) | 2011-10-11 |
| WO2007147374A2 (en) | 2007-12-27 |
| US20090203914A1 (en) | 2009-08-13 |
| UA94614C2 (en) | 2011-05-25 |
| WO2007147374A3 (en) | 2008-04-17 |
| CZ300699B6 (cs) | 2009-07-22 |
| EA200802388A1 (ru) | 2009-06-30 |
| EP2029587B1 (en) | 2015-09-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HUE025663T2 (hu) | Eljárás szolifenacin elõállítására | |
| JP2008514712A (ja) | ４，５−ジヒドロ−ピラゾロ［３，４−ｃ］ピリド−２−オン類を製造する方法 | |
| KR20210057032A (ko) | 메틸 6-(2,4-디클로로페닐)-5-[4-[(3s)-1-(3-플루오로프로필)피롤리딘-3-일]옥시페닐]-8,9-디히드로-7h-벤조[7]아눌렌-2-카르복실레이트의 염 및 이의 제조 방법 | |
| CN111170855A (zh) | 一种化合物及采用该化合物合成8-羟基-2,2,14,14-四甲基十五烷二酸的方法 | |
| WO2008009397A1 (en) | Process for manufacturing 3(r)-(2-hydroxy-2,2-dithien-2-ylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide | |
| HUE025985T2 (hu) | Eljárás 6-szubsztituált-1-(2H)-izokinolinonok elõállítására | |
| EP2978748B1 (en) | Process and intermediates for the preparation of pregabalin | |
| CN103183673B (zh) | (s,s)-2,8-二氮杂双环[4,3,0]壬烷的合成方法 | |
| CN110642790B (zh) | 瑞舒伐他汀钙及其中间体的制备方法 | |
| TWI445711B (zh) | 肝適能製備的改良方法 | |
| JP2015521635A (ja) | ソリフェナシン又はその塩の調製方法 | |
| US7544802B2 (en) | Process for the preparation of 2-(ethoxymethyl)-tropane derivatives | |
| CN101514201A (zh) | (4,7-顺)-八氢-吡咯并[3,4-b]吡啶和莫西沙星的制备方法 | |
| US6861525B2 (en) | Process for the preparation imidazo[1,2-A]pyridine-3-acetamides | |
| JP4057088B2 (ja) | ピロリジン誘導体の製造方法 | |
| KR20130021476A (ko) | 라미부딘 옥살레이트 및 이의 제조방법 | |
| US7446227B2 (en) | Process for preparation of 5H-dibenzo[a,d] cycloheptene derivatives | |
| EP2867214B1 (en) | Preparation process of carboxylic acid derivatives and intermediates thereof | |
| JP5247699B2 (ja) | キラルピペリジンアルコールの分割プロセスおよびピペリジンアルコールを用いるピラゾロ−［１，５］−ピリミジン誘導体の合成プロセス | |
| CZ74097A3 (en) | Process for preparing r-(+)-1,2,3,6-tetrahydro-4-phenyl-1-£(3-phenyl-3-cyclohexen-1-yl)methyl|py- ridine, intermediates for such process and process for preparing the intermediates | |
| CN101263128B (zh) | 1,2-苯并异噁唑-3-乙酸的磺化方法 | |
| WO2012000925A1 (en) | Preparation of n-(s)-1-azabicyclo[2.2.2]oct-3-yl-1h-indazole-3-carboxamide hydrochloride salt | |
| WO2011121598A1 (en) | Crystalline 7-[4-(4-fluorophenyl)-6-isopropyl-2-(methanesulfonyl-methyl-amino)-pyrimidin-5-yl]-3(r)-hydroxy-5-oxo-hept-6-enoic acid methyl ester and process thereof | |
| JP2007529569A (ja) | メシル酸フェノルドパムの調製方法 |