AT401650B - Verfahren zur herstellung eines zwischenproduktes von diltiazem - Google Patents
Verfahren zur herstellung eines zwischenproduktes von diltiazem Download PDFInfo
- Publication number
- AT401650B AT401650B AT0240890A AT240890A AT401650B AT 401650 B AT401650 B AT 401650B AT 0240890 A AT0240890 A AT 0240890A AT 240890 A AT240890 A AT 240890A AT 401650 B AT401650 B AT 401650B
- Authority
- AT
- Austria
- Prior art keywords
- compound
- mixture
- cis
- dihydro
- hydroxy
- Prior art date
Links
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 title description 11
- 229960004166 diltiazem Drugs 0.000 title description 11
- 239000013067 intermediate product Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 7
- 239000012965 benzophenone Substances 0.000 claims description 7
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 7
- 150000004678 hydrides Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 229910000085 borane Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- 239000000243 solution Substances 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- 239000007853 buffer solution Substances 0.000 claims 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 2
- 239000012279 sodium borohydride Substances 0.000 claims 2
- LHBHZALHFIQJGJ-UHFFFAOYSA-N 3-hydroxy-2-(4-methoxyphenyl)-3,5-dihydro-2h-1,5-benzothiazepin-4-one Chemical compound C1=CC(OC)=CC=C1C1C(O)C(=O)NC2=CC=CC=C2S1 LHBHZALHFIQJGJ-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 1
- 229910000105 potassium hydride Inorganic materials 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000000926 separation method Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- KHQWPNQLSKDWAR-LSDHHAIUSA-N (2r,3r)-3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1[C@H]([C@H](O)C(O)=O)SC1=CC=CC=C1N KHQWPNQLSKDWAR-LSDHHAIUSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- GTFMIJNXNMDHAB-UHFFFAOYSA-N 4h-1,4-benzothiazin-3-one Chemical class C1=CC=C2NC(=O)CSC2=C1 GTFMIJNXNMDHAB-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000007657 benzothiazepines Chemical class 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940111685 dibasic potassium phosphate Drugs 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT02263789A IT1237526B (it) | 1989-12-06 | 1989-12-06 | Processo di preparazione di un intermedio per il diltiazem |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA240890A ATA240890A (de) | 1996-03-15 |
| AT401650B true AT401650B (de) | 1996-10-25 |
Family
ID=11198703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0240890A AT401650B (de) | 1989-12-06 | 1990-11-27 | Verfahren zur herstellung eines zwischenproduktes von diltiazem |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5102999A (en, 2012) |
| JP (1) | JP2987714B2 (en, 2012) |
| AT (1) | AT401650B (en, 2012) |
| BE (1) | BE1003317A3 (en, 2012) |
| CA (1) | CA2030866C (en, 2012) |
| CH (1) | CH680443A5 (en, 2012) |
| DE (1) | DE4038676C2 (en, 2012) |
| ES (1) | ES2023774A6 (en, 2012) |
| FR (1) | FR2655340B1 (en, 2012) |
| GB (1) | GB2239014B (en, 2012) |
| IT (1) | IT1237526B (en, 2012) |
| NL (1) | NL194204C (en, 2012) |
| SE (1) | SE509634C2 (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0711157A4 (en) * | 1993-08-06 | 1996-07-31 | Smithkline Beecham Corp | ENDOTHELIN RECEPTOR ANTAGONISTS |
| US5817653A (en) * | 1993-08-06 | 1998-10-06 | Smithkline Beecham Corporation | Endothelin receptor antagonists |
| IL121525A0 (en) * | 1996-08-26 | 1998-02-08 | Tanabe Seiyaku Co | Process for preparing optically active benzothiazepine compound and intermediate therefor |
| IT1295376B1 (it) * | 1997-10-22 | 1999-05-12 | Zambon Spa | Processo per il riciclo di un sottoprodotto della sintesi del diltiazem |
| CN100364540C (zh) * | 2006-03-14 | 2008-01-30 | 北京大学 | (2s-顺)-(+)-2,3-二氢-3-羟基-2-(4-甲氧苯基)-1,5-苯并硫氮杂䓬-4(5h)-酮在制备治疗肝炎的药物中的用途 |
| CN100463904C (zh) * | 2006-08-15 | 2009-02-25 | 宁波工程学院 | 地尔硫卓中间体的制备方法 |
| CN103755663B (zh) * | 2014-01-26 | 2016-02-24 | 武汉工程大学 | 地尔硫卓中间体副产物L-cis-内酰胺的回收工艺 |
| CN110284181A (zh) * | 2019-08-07 | 2019-09-27 | 山东新华制药股份有限公司 | 地尔硫卓ab异构体的单晶制备方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3562257A (en) * | 1967-10-28 | 1971-02-09 | Tanabe Seiyaku Co | Benzothiazepine derivatives |
| US4416819A (en) * | 1982-07-09 | 1983-11-22 | Tanabe Seiyaku Co., Ltd. | Process for preparing 1,5-benzothiazephine derivatives |
| US4420628A (en) * | 1981-02-27 | 1983-12-13 | Tanabe Seiyaku Co., Ltd. | Process for preparing threo-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)-propionic ester |
| US4533748A (en) * | 1982-10-15 | 1985-08-06 | Istituto Luso Farmaco D'italia S.P.A. | Process for the optical resolution of the dl-α-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionic acid |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5920273A (ja) * | 1982-07-27 | 1984-02-01 | Tanabe Seiyaku Co Ltd | ベンゾチアゼピン誘導体の新規製造法 |
| JPS6025982A (ja) * | 1983-07-22 | 1985-02-08 | Tanabe Seiyaku Co Ltd | ベンゾチアゼピン誘導体の製法 |
| JPS6032779A (ja) * | 1983-08-01 | 1985-02-19 | Hamari Yakuhin Kogyo Kk | ベンゾチアゼピン誘導体の新規製造法 |
| DE602004001576T2 (de) | 2004-04-08 | 2007-07-05 | Mitsubishi Electric Information Technology Centre Europe B.V. | Verfahren zum Übertragen von Daten in einem Telekommunikationssystem mit wenigstens einem Sender |
-
1989
- 1989-12-06 IT IT02263789A patent/IT1237526B/it active IP Right Grant
-
1990
- 1990-10-31 CH CH3455/90A patent/CH680443A5/it not_active IP Right Cessation
- 1990-11-15 US US07/612,954 patent/US5102999A/en not_active Expired - Lifetime
- 1990-11-20 NL NL9002529A patent/NL194204C/nl not_active IP Right Cessation
- 1990-11-26 CA CA002030866A patent/CA2030866C/en not_active Expired - Lifetime
- 1990-11-27 AT AT0240890A patent/AT401650B/de not_active IP Right Cessation
- 1990-11-27 FR FR909014781A patent/FR2655340B1/fr not_active Expired - Lifetime
- 1990-11-28 GB GB9025887A patent/GB2239014B/en not_active Expired - Lifetime
- 1990-11-28 JP JP2333510A patent/JP2987714B2/ja not_active Expired - Lifetime
- 1990-11-28 BE BE9001134A patent/BE1003317A3/fr not_active IP Right Cessation
- 1990-12-04 DE DE4038676A patent/DE4038676C2/de not_active Expired - Lifetime
- 1990-12-05 SE SE9003860A patent/SE509634C2/sv not_active IP Right Cessation
- 1990-12-05 ES ES9003121A patent/ES2023774A6/es not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3562257A (en) * | 1967-10-28 | 1971-02-09 | Tanabe Seiyaku Co | Benzothiazepine derivatives |
| US4420628A (en) * | 1981-02-27 | 1983-12-13 | Tanabe Seiyaku Co., Ltd. | Process for preparing threo-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)-propionic ester |
| US4416819A (en) * | 1982-07-09 | 1983-11-22 | Tanabe Seiyaku Co., Ltd. | Process for preparing 1,5-benzothiazephine derivatives |
| US4533748A (en) * | 1982-10-15 | 1985-08-06 | Istituto Luso Farmaco D'italia S.P.A. | Process for the optical resolution of the dl-α-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| US5102999A (en) | 1992-04-07 |
| FR2655340B1 (fr) | 1994-10-14 |
| IT8922637A0 (it) | 1989-12-06 |
| ES2023774A6 (es) | 1992-02-01 |
| CH680443A5 (en, 2012) | 1992-08-31 |
| IT1237526B (it) | 1993-06-08 |
| SE9003860D0 (sv) | 1990-12-05 |
| CA2030866A1 (en) | 1991-06-07 |
| NL9002529A (nl) | 1991-07-01 |
| NL194204B (nl) | 2001-05-01 |
| GB9025887D0 (en) | 1991-01-09 |
| CA2030866C (en) | 2001-03-13 |
| GB2239014B (en) | 1993-09-22 |
| DE4038676A1 (de) | 1991-06-13 |
| SE9003860L (sv) | 1991-06-07 |
| NL194204C (nl) | 2001-09-04 |
| DE4038676C2 (de) | 1999-06-02 |
| JPH03193770A (ja) | 1991-08-23 |
| FR2655340A1 (fr) | 1991-06-07 |
| ATA240890A (de) | 1996-03-15 |
| JP2987714B2 (ja) | 1999-12-06 |
| GB2239014A (en) | 1991-06-19 |
| BE1003317A3 (fr) | 1992-02-25 |
| IT8922637A1 (it) | 1991-06-06 |
| SE509634C2 (sv) | 1999-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69226822T2 (de) | Diastereomeres Salz von optisch aktiver Chinolinmevalonsäure | |
| DE3415035A1 (de) | Verfahren zur stereospezifischen herstellung von diltiazemhydrochlorid | |
| SK128494A3 (en) | Method of production of indanylamine compounds | |
| AT401650B (de) | Verfahren zur herstellung eines zwischenproduktes von diltiazem | |
| DE69204840T2 (de) | Verfahren zur Herstellung von Sertralin. | |
| US4002632A (en) | Tetracyclic piperidino derivatives | |
| CH640212A5 (en) | Process for the preparation of 1-amino-3-aryloxy-2-propanol derivatives | |
| DD279013A5 (de) | Verfahren zum herstellen von sertralin-zwischenverbindungen | |
| EP0285681B1 (de) | Verfahren zur Herstellung von Nitroethenderivaten | |
| DE69031187T2 (de) | Verfahren für die Racemattrennung von Zwischenprodukten, die bei der Herstellung von 1,5-Benzothiazepinen verwendbar sind | |
| DE69308222T2 (de) | Katalysator zur asymmetrischen Induktion | |
| EP0222163A1 (de) | Verfahren zur Herstellung von gamma-Butyrolactamen | |
| DE4115698C2 (de) | Verfahren zur Trennung von Derivativen der 3-(4-substituierten-Phenyl)glycidsäure | |
| CH510688A (de) | Verfahren zur Herstellung neuer Derivate des 6,11-Dihydro-dibenz(b,e)oxepins | |
| DE69623117T2 (de) | Verfahren zur herstellung von 4-hydroxy-2-pyrrolidon | |
| DE2332707A1 (de) | Tricyclische tetrahydronaphthalinderivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE69409001T2 (de) | Chirale nitrile, ihre herstellung und ihre verwendung in der herstellung von verapamil und dessen analogen | |
| US4515977A (en) | Process for preparing optically active [S]-2-acetyl-7-(2-hydroxy-3-isopropylaminopropoxy)benzofuran and salts thereof | |
| DE69810653T2 (de) | Verfahren zur wiederverwertung eines nebenproduktes aus der diltiazem-synthese | |
| EP0180890B1 (de) | Verfahren zur diastereoselektiven Reduktion von 3-Amino-1-benzoxepin-5(2H)-onen | |
| DE69411387T2 (de) | Verfahren zur Herstellung von pharmazeutisch aktiven Benzothiazepinderivaten. | |
| DE68908812T2 (de) | Verfahren zur Spaltung racemischer Spirohydantoine. | |
| EP0385423B1 (de) | Verfahren zur Herstellung der optischen Isomeren von 1,4-Dihydro-5-isopropoxy-2-methyl-4-(2-trifluormethylphenyl)-1,6-naphthyridin-3-carbonsäure-ethyl-ester und 1,4-Dihydro-5-isopropoxy-2-methyl-4-(2-trifluormethylphenyl)-1,6-naphthyridin-3-carbonsäure- 2-(N-methyl-N-phenylmethylamino)ethyl ester | |
| DE69127846T2 (de) | Stereoselektives Verfahren zur Herstellung von 2-Amino-Ethanol-Derivaten mit zentralanalgetischer Aktivität und Zwischenprodukten | |
| DE69002500T2 (de) | Verfahren zur Synthese von N-Methyl-3,4-dimethoxyphenylethylamin. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELA | Expired due to lapse of time |