NO309423B1 - Fremgangsmåte ved fremstilling av lercanidipinhydroklorid - Google Patents
Fremgangsmåte ved fremstilling av lercanidipinhydroklorid Download PDFInfo
- Publication number
- NO309423B1 NO309423B1 NO975176A NO975176A NO309423B1 NO 309423 B1 NO309423 B1 NO 309423B1 NO 975176 A NO975176 A NO 975176A NO 975176 A NO975176 A NO 975176A NO 309423 B1 NO309423 B1 NO 309423B1
- Authority
- NO
- Norway
- Prior art keywords
- dimethyl
- lercanidipine
- propanol
- aprotic
- crystallization
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- WMFYOYKPJLRMJI-UHFFFAOYSA-N Lercanidipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WMFYOYKPJLRMJI-UHFFFAOYSA-N 0.000 title description 15
- 229960002162 lercanidipine hydrochloride Drugs 0.000 title description 11
- 238000002360 preparation method Methods 0.000 title description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000010 aprotic solvent Substances 0.000 claims description 10
- ZDXUKAKRHYTAKV-UHFFFAOYSA-N lercanidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZDXUKAKRHYTAKV-UHFFFAOYSA-N 0.000 claims description 10
- 229960004294 lercanidipine Drugs 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000026030 halogenation Effects 0.000 claims description 6
- 238000005658 halogenation reaction Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- MQWDISMNBYOLAB-UHFFFAOYSA-N 1-[3,3-diphenylpropyl(methyl)amino]-2-methylpropan-2-ol Chemical compound C=1C=CC=CC=1C(CCN(C)CC(C)(C)O)C1=CC=CC=C1 MQWDISMNBYOLAB-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- JPXPPUOCSLMCHK-UHFFFAOYSA-N 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims 4
- 230000008025 crystallization Effects 0.000 claims 4
- 239000000243 solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001414 amino alcohols Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- -1 1,1,N-trimethyl-N-(3,3- diphenylpropyl)-2-aminoethyl α-acetyl-3-nitrocinnamate Chemical compound 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 108090000312 Calcium Channels Proteins 0.000 description 1
- 102000003922 Calcium Channels Human genes 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012297 crystallization seed Substances 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type 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
- C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
- C07D211/84—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 two 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 directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (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)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI950957A IT1274480B (it) | 1995-05-12 | 1995-05-12 | Procedimento migliorato per la preparazione della lercanidipina cloridrato |
| PCT/EP1996/002122 WO1996035668A1 (fr) | 1995-05-12 | 1996-05-09 | Procede de preparation d'hydrochlorure de lercanidipine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO975176D0 NO975176D0 (no) | 1997-11-11 |
| NO975176L NO975176L (no) | 1997-11-11 |
| NO309423B1 true NO309423B1 (no) | 2001-01-29 |
Family
ID=11371581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO975176A NO309423B1 (no) | 1995-05-12 | 1997-11-11 | Fremgangsmåte ved fremstilling av lercanidipinhydroklorid |
Country Status (37)
| Country | Link |
|---|---|
| EP (1) | EP0824517B1 (fr) |
| JP (1) | JP4038622B2 (fr) |
| KR (1) | KR100395441B1 (fr) |
| CN (1) | CN1101810C (fr) |
| AR (1) | AR002739A1 (fr) |
| AT (1) | ATE221050T1 (fr) |
| AU (1) | AU694046B2 (fr) |
| BG (1) | BG62400B1 (fr) |
| BR (1) | BR9608374A (fr) |
| CA (1) | CA2217849C (fr) |
| CZ (1) | CZ288634B6 (fr) |
| DE (1) | DE69622552T2 (fr) |
| DK (1) | DK0824517T3 (fr) |
| DZ (1) | DZ2032A1 (fr) |
| EA (1) | EA000346B1 (fr) |
| EE (1) | EE03351B1 (fr) |
| EG (1) | EG21755A (fr) |
| ES (1) | ES2179942T3 (fr) |
| HU (1) | HU226709B1 (fr) |
| IL (1) | IL118143A (fr) |
| IN (1) | IN188486B (fr) |
| IT (1) | IT1274480B (fr) |
| MA (1) | MA23858A1 (fr) |
| MX (1) | MX9708662A (fr) |
| MY (1) | MY113802A (fr) |
| NO (1) | NO309423B1 (fr) |
| NZ (1) | NZ309059A (fr) |
| PL (1) | PL185260B1 (fr) |
| PT (1) | PT824517E (fr) |
| RO (1) | RO119616B1 (fr) |
| SA (1) | SA96170216B1 (fr) |
| SK (1) | SK283321B6 (fr) |
| TN (1) | TNSN96069A1 (fr) |
| TW (1) | TW404940B (fr) |
| UA (1) | UA46769C2 (fr) |
| WO (1) | WO1996035668A1 (fr) |
| ZA (1) | ZA963716B (fr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6852737B2 (en) | 2001-08-06 | 2005-02-08 | Recordati Ireland Limited | Crude and crystalline forms of lercanidipine hydrochloride |
| ITMI20011726A1 (it) * | 2001-08-06 | 2003-02-06 | Recordati Ind Chimica E Farma | Forme polimorfe della lercanidipina cloridrato |
| WO2004035051A1 (fr) * | 2002-10-16 | 2004-04-29 | Recordati Ireland Limited | Polytherapie a base de lisinopril/lercanidipine |
| AR052918A1 (es) | 2005-02-25 | 2007-04-11 | Recordati Ireland Ltd | Clorhidrato de lercanidipina amorfo |
| KR100713136B1 (ko) * | 2005-05-04 | 2007-05-02 | 주식회사 대희화학 | 무수 레르카니디핀 염화수소 결정다형의 개선된 신규결정화 방법 |
| PT1891009E (pt) * | 2005-06-15 | 2010-01-19 | Hetero Drugs Ltd | Processo inédito para a preparação de lercanidipina |
| KR20080048065A (ko) | 2005-09-16 | 2008-05-30 | 그렌마크 파머수티칼스 엘티디. | 다형 형태의 염산 레르카니디핀 및 이것의 제조방법 |
| KR100811497B1 (ko) * | 2005-10-19 | 2008-03-07 | 신풍제약주식회사 | 무수 염산 1,4-디하이드로피리딘 유도체의 제조 방법 |
| ATE415389T1 (de) * | 2006-05-24 | 2008-12-15 | Cf Pharma Ltd | Verfahren zur herstellung von lercanipidin |
| KR100808281B1 (ko) * | 2006-06-30 | 2008-03-03 | 주식회사 하원정밀화학 | 레르카니디핀 및 그 산부가염의 제조방법 |
| CN102020602B (zh) * | 2009-09-18 | 2013-12-25 | 深圳信立泰药业股份有限公司 | 盐酸乐卡地平晶型及其制备方法和含有该晶型的药物组合物 |
| WO2011161223A2 (fr) | 2010-06-23 | 2011-12-29 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Formes pharmaceutiques à usage oral comprenant de la lercanidipine et de l'énalapril et leurs sels pharmaceutiquement acceptables |
| SI2654729T1 (sl) | 2010-12-24 | 2016-08-31 | Krka, D.D., Novo Mesto | Homogene farmacevtske oralne dozirne oblike, ki obsegajo lerkanidipin in enalapril ali njune farmacevtsko sprejemljive soli skupaj z organsko kislino |
| CN102516160B (zh) * | 2011-12-16 | 2014-04-02 | 华润赛科药业有限责任公司 | 一种高纯盐酸乐卡地平的合成工艺 |
| CN102558032B (zh) * | 2011-12-16 | 2014-02-26 | 华润赛科药业有限责任公司 | 一种无定形盐酸乐卡地平及其制备方法 |
| CN102584682A (zh) * | 2011-12-31 | 2012-07-18 | 苏州二叶制药有限公司 | 盐酸乐卡地平的制备方法 |
| CN109956943B (zh) * | 2019-04-18 | 2021-07-20 | 合肥合源药业有限公司 | 一种二氢吡啶类药物中脱羧缩合杂质及其制备、控制方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8403866D0 (en) * | 1984-02-14 | 1984-03-21 | Recordati Chem Pharm | Diphenylalkylaminoalkyl esters |
-
1995
- 1995-05-12 IT ITMI950957A patent/IT1274480B/it active IP Right Grant
-
1996
- 1996-05-03 IL IL11814396A patent/IL118143A/en not_active IP Right Cessation
- 1996-05-06 IN IN822CA1996 patent/IN188486B/en unknown
- 1996-05-07 MA MA24223A patent/MA23858A1/fr unknown
- 1996-05-08 DZ DZ960075A patent/DZ2032A1/fr active
- 1996-05-09 HU HU9801913A patent/HU226709B1/hu unknown
- 1996-05-09 EA EA199700374A patent/EA000346B1/ru not_active IP Right Cessation
- 1996-05-09 JP JP53379796A patent/JP4038622B2/ja not_active Expired - Lifetime
- 1996-05-09 ES ES96916111T patent/ES2179942T3/es not_active Expired - Lifetime
- 1996-05-09 SK SK1514-97A patent/SK283321B6/sk not_active IP Right Cessation
- 1996-05-09 CA CA002217849A patent/CA2217849C/fr not_active Expired - Lifetime
- 1996-05-09 WO PCT/EP1996/002122 patent/WO1996035668A1/fr active IP Right Grant
- 1996-05-09 MY MYPI96001751A patent/MY113802A/en unknown
- 1996-05-09 UA UA97125981A patent/UA46769C2/uk unknown
- 1996-05-09 EP EP96916111A patent/EP0824517B1/fr not_active Expired - Lifetime
- 1996-05-09 CZ CZ19973567A patent/CZ288634B6/cs not_active IP Right Cessation
- 1996-05-09 DK DK96916111T patent/DK0824517T3/da active
- 1996-05-09 KR KR1019970707905A patent/KR100395441B1/ko not_active IP Right Cessation
- 1996-05-09 CN CN96193842A patent/CN1101810C/zh not_active Expired - Lifetime
- 1996-05-09 PL PL96323236A patent/PL185260B1/pl unknown
- 1996-05-09 DE DE69622552T patent/DE69622552T2/de not_active Expired - Lifetime
- 1996-05-09 BR BR9608374A patent/BR9608374A/pt not_active Application Discontinuation
- 1996-05-09 AT AT96916111T patent/ATE221050T1/de active
- 1996-05-09 EG EG40296A patent/EG21755A/xx active
- 1996-05-09 PT PT96916111T patent/PT824517E/pt unknown
- 1996-05-09 RO RO97-02101A patent/RO119616B1/ro unknown
- 1996-05-09 AU AU58985/96A patent/AU694046B2/en not_active Expired
- 1996-05-09 EE EE9700303A patent/EE03351B1/xx unknown
- 1996-05-09 NZ NZ309059A patent/NZ309059A/xx not_active IP Right Cessation
- 1996-05-10 ZA ZA963716A patent/ZA963716B/xx unknown
- 1996-05-10 TN TNTNSN96069A patent/TNSN96069A1/fr unknown
- 1996-05-10 AR ARP960102528A patent/AR002739A1/es unknown
- 1996-05-10 TW TW085105567A patent/TW404940B/zh not_active IP Right Cessation
- 1996-08-07 SA SA96170216A patent/SA96170216B1/ar unknown
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1997
- 1997-11-07 BG BG102034A patent/BG62400B1/bg unknown
- 1997-11-11 MX MX9708662A patent/MX9708662A/es unknown
- 1997-11-11 NO NO975176A patent/NO309423B1/no not_active IP Right Cessation
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