NL194371C - Resolutiewerkwijze van een mengsel van enantiomeren van een threo-2-hydroxy-3-(2-aminofenylthio)-3-(4-methoxyfenyl)- propionzuurester. - Google Patents

Resolutiewerkwijze van een mengsel van enantiomeren van een threo-2-hydroxy-3-(2-aminofenylthio)-3-(4-methoxyfenyl)- propionzuurester. Download PDF

Info

Publication number: NL194371C
Authority: NL; Netherlands
Prior art keywords: mixture; enantiomers; methoxyphenyl; hydroxy; enantiomer
Prior art date: 1989-07-27

Application number

NL9001710A

Other languages

English (en)

Dutch (nl)

Other versions

NL194371B (nl

NL9001710A (nl

Original Assignee

Zambon Spa

Priority date (The priority date 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 date listed.)

1989-07-27

Filing date

1990-07-27

Publication date

2002-02-04

1990-07-27 Application filed by Zambon Spa filed Critical Zambon Spa

1991-02-18 Publication of NL9001710A publication Critical patent/NL9001710A/nl

2001-10-01 Publication of NL194371B publication Critical patent/NL194371B/xx

2002-02-04 Application granted granted Critical

2002-02-04 Publication of NL194371C publication Critical patent/NL194371C/nl

Links

239000000203 mixture Substances 0.000 title claims description 33
238000000034 method Methods 0.000 title claims description 28
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 title claims description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
230000002269 spontaneous effect Effects 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 13
230000003287 optical effect Effects 0.000 claims description 12
238000002425 crystallisation Methods 0.000 claims description 7
230000008025 crystallization Effects 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000000010 aprotic solvent Substances 0.000 claims description 4
150000004702 methyl esters Chemical class 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 3
125000005907 alkyl ester group Chemical group 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 2
240000008042 Zea mays Species 0.000 claims 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims 1
235000002017 Zea mays subsp mays Nutrition 0.000 claims 1
235000009973 maize Nutrition 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 17
-1 diltiazem Chemical class 0.000 description 13
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 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
229960004166 diltiazem Drugs 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
MPWGGMIUPWSNEV-UHFFFAOYSA-N methyl 3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoate Chemical compound C=1C=C(OC)C=CC=1C(C(O)C(=O)OC)SC1=CC=CC=C1N MPWGGMIUPWSNEV-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 3
239000004593 Epoxy Substances 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
MPWGGMIUPWSNEV-JKSUJKDBSA-N methyl (2r,3r)-3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoate Chemical compound S([C@@H]([C@H](O)C(=O)OC)C=1C=CC(OC)=CC=1)C1=CC=CC=C1N MPWGGMIUPWSNEV-JKSUJKDBSA-N 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 3
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
MPWGGMIUPWSNEV-CVEARBPZSA-N methyl (2s,3s)-3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoate Chemical compound S([C@H]([C@@H](O)C(=O)OC)C=1C=CC(OC)=CC=1)C1=CC=CC=C1N MPWGGMIUPWSNEV-CVEARBPZSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
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 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
LHBHZALHFIQJGJ-CABCVRRESA-N (2s,3s)-3-hydroxy-2-(4-methoxyphenyl)-3,5-dihydro-2h-1,5-benzothiazepin-4-one Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](O)C(=O)NC2=CC=CC=C2S1 LHBHZALHFIQJGJ-CABCVRRESA-N 0.000 description 1
KJFRSZASZNLCDF-UHFFFAOYSA-N 1,5-benzothiazepine Chemical class S1C=CC=NC2=CC=CC=C12 KJFRSZASZNLCDF-UHFFFAOYSA-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
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
BKPLREMAGZISSP-UHFFFAOYSA-N 3-(2-acetamidophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1C(C(O)C(O)=O)SC1=CC=CC=C1NC(C)=O BKPLREMAGZISSP-UHFFFAOYSA-N 0.000 description 1
KHQWPNQLSKDWAR-UHFFFAOYSA-N 3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1C(C(O)C(O)=O)SC1=CC=CC=C1N KHQWPNQLSKDWAR-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
235000019766 L-Lysine Nutrition 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000012345 acetylating agent Substances 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000002213 calciumantagonistic effect Effects 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
ARQVRCKIVSELCG-UHFFFAOYSA-N methyl 2-(4-methoxyphenyl)propanoate Chemical compound COC(=O)C(C)C1=CC=C(OC)C=C1 ARQVRCKIVSELCG-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000006340 racemization Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification

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)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NL9001710A 1989-07-27 1990-07-27 Resolutiewerkwijze van een mengsel van enantiomeren van een threo-2-hydroxy-3-(2-aminofenylthio)-3-(4-methoxyfenyl)- propionzuurester. NL194371C (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT8921338A IT1232306B (it)	1989-07-27	1989-07-27	Processo di risoluzione di intermedi utili per la preparazione del diltiazem
IT2133889		1989-07-27

Publications (3)

Publication Number	Publication Date
NL9001710A NL9001710A (nl)	1991-02-18
NL194371B NL194371B (nl)	2001-10-01
NL194371C true NL194371C (nl)	2002-02-04

Family

ID=11180324

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL9001710A NL194371C (nl)	1989-07-27	1990-07-27	Resolutiewerkwijze van een mengsel van enantiomeren van een threo-2-hydroxy-3-(2-aminofenylthio)-3-(4-methoxyfenyl)- propionzuurester.

Country Status (13)

Country	Link
US (1)	US5097059A (fr)
JP (1)	JP2873609B2 (fr)
AT (1)	AT400143B (fr)
BE (1)	BE1003314A3 (fr)
CA (1)	CA2021342C (fr)
CH (1)	CH680855A5 (fr)
DE (1)	DE4023773B4 (fr)
ES (1)	ES2020789A6 (fr)
FR (1)	FR2650272B1 (fr)
GB (1)	GB2234243B (fr)
IT (1)	IT1232306B (fr)
NL (1)	NL194371C (fr)
SE (1)	SE509635C2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL102592A (en) *	1992-07-21	1996-09-12	Teva Pharma	Optical resolution of threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid
FI93741C (fi) *	1993-03-24	1995-05-26	Orion Yhtymae Oy	Menetelmä optisesti puhtaitten (2S,3S)- ja (2R,3R)-threo-alkyyli-2-hydroksi-3-(4-metoksifenyyli)-3-(2-X-fenyylitio)propionaattien tai vastaavien asyloitujen yhdisteiden valmistamiseksi
IT1295376B1 (it) *	1997-10-22	1999-05-12	Zambon Spa	Processo per il riciclo di un sottoprodotto della sintesi del diltiazem

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE449611B (sv) *	1982-07-09	1987-05-11	Tanabe Seiyaku Co	Sett att framstella 1,5-bensotiazepinderivat
IT1152721B (it) *	1982-10-15	1987-01-07	Luso Farmaco Inst	Risoluzione ottica dell'acido dl-alfa-2-idrossi-3-(4-metossifenil)-3-(2-amminofeniltio)propionico
JPS59110668A (ja) *	1982-12-17	1984-06-26	Tokawa Tetsuo	２−置換−３−（ｐ−メトキシフエニル）−３−〔（２−置換）フエニルチオ〕プロピオン酸の光学分割法
US4552695A (en) *	1983-04-21	1985-11-12	Shionogi & Co., Ltd.	Process for production of diltiazem hydrochloride
EP0320532A1 (fr) *	1986-07-15	1989-06-21	Nihon Iyakuhin Kogyo Co., Ltd.	Dérivé optiquement actif d'un sel de l-lysine d'un acide carboxylique et son procédé de préparation
IT1217988B (it) *	1988-01-28	1990-03-30	Ind Chimica Profarmaco Spa	Procedimento per la risoluzione ottica di un pacemo
US4908469A (en) *	1988-05-18	1990-03-13	Marion Laboratories, Inc.	2-Hydroxy-propanoic acid acyclic alkyl esters for benzothiazepines
IT1226300B (it) *	1988-07-26	1990-12-27	Zambon Spa	Processo per la preparazione di intermedi per la sintesi del diltiazem.

1989
- 1989-07-27 IT IT8921338A patent/IT1232306B/it active
1990
- 1990-07-05 CH CH2245/90A patent/CH680855A5/it not_active IP Right Cessation
- 1990-07-12 GB GB9015302A patent/GB2234243B/en not_active Expired - Fee Related
- 1990-07-16 JP JP2189251A patent/JP2873609B2/ja not_active Expired - Lifetime
- 1990-07-17 CA CA002021342A patent/CA2021342C/fr not_active Expired - Lifetime
- 1990-07-25 FR FR909009492A patent/FR2650272B1/fr not_active Expired - Fee Related
- 1990-07-26 ES ES909002010A patent/ES2020789A6/es not_active Expired - Fee Related
- 1990-07-26 BE BE9000745A patent/BE1003314A3/fr not_active IP Right Cessation
- 1990-07-26 DE DE4023773A patent/DE4023773B4/de not_active Expired - Fee Related
- 1990-07-26 SE SE9002499A patent/SE509635C2/sv not_active IP Right Cessation
- 1990-07-26 US US07/557,808 patent/US5097059A/en not_active Expired - Lifetime
- 1990-07-26 AT AT0156790A patent/AT400143B/de not_active IP Right Cessation
- 1990-07-27 NL NL9001710A patent/NL194371C/nl not_active IP Right Cessation

Also Published As

Publication number	Publication date
NL194371B (nl)	2001-10-01
JPH03188059A (ja)	1991-08-16
BE1003314A3 (fr)	1992-02-25
ES2020789A6 (es)	1991-09-16
FR2650272A1 (fr)	1991-02-01
GB2234243A (en)	1991-01-30
SE509635C2 (sv)	1999-02-15
FR2650272B1 (fr)	1992-08-28
CA2021342C (fr)	2002-01-29
AT400143B (de)	1995-10-25
ATA156790A (de)	1995-02-15
SE9002499D0 (sv)	1990-07-26
GB9015302D0 (en)	1990-08-29
NL9001710A (nl)	1991-02-18
IT8921338A0 (it)	1989-07-27
DE4023773B4 (de)	2004-01-08
IT1232306B (it)	1992-01-28
GB2234243B (en)	1992-11-25
US5097059A (en)	1992-03-17
CA2021342A1 (fr)	1991-01-28
DE4023773A1 (de)	1991-01-31
CH680855A5 (fr)	1992-11-30
SE9002499L (sv)	1991-01-28
JP2873609B2 (ja)	1999-03-24

Legal Events

Date	Code	Title	Description
1995-10-02	BB	A search report has been drawn up
1996-02-01	BC	A request for examination has been filed
2006-04-03	V1	Lapsed because of non-payment of the annual fee	Effective date: 20060201

Publication	Publication Date	Title
US5013834A (en)	1991-05-07	Process for the preparation of an optically active benzothiazepinone
US4963671A (en)	1990-10-16	Process for resolving chiral intermediates used in making calcium channel blockers
JP2004511476A (ja)	2004-04-15	Ｒ（＋）α−リポ酸の製造方法
US5144025A (en)	1992-09-01	Process for the resolution of intermediates useful in the preparation of 1,5-benzothiazepines
US4939295A (en)	1990-07-03	Process for the preparation of intermediates for the synthesis of diltiazem
EP0998470B1 (fr)	2003-05-07	Procede de preparation de derives amines d'alkyloxyfuranone, composes issus de ce procede et utilisation de ces composes
US4908469A (en)	1990-03-13	2-Hydroxy-propanoic acid acyclic alkyl esters for benzothiazepines
US5097059A (en)	1992-03-17	Resolution process of intermediates useful for the preparation of diltiazem
EP0174358A1 (fr)	1986-03-19	Nouveaux sels diastereomeres de phenylalanine et ses derives n-acyliques et procede de separation de phenylalanine optiquement actives et de ses derives n-acyliques
US5183922A (en)	1993-02-02	Process for the optical resolution of threo-2-hydroxy-3-(2'-aminophenylthio)-3-(4"-methoxyphenyl)-propionic acid
US20080214833A1 (en)	2008-09-04	Process For Manufacture of Racemic Carvedilol
JP2714315B2 (ja)	1998-02-16	光学活性エポキシプロピオン酸誘導体およびその製法
US5705638A (en)	1998-01-06	Process for preparing optically active 3-hydroxy-1,5-benzothiazepine derivative and intermediate therefor
US5929068A (en)	1999-07-27	Optically active benzothiazepine compounds and process for preparing the same
AU2005212390A1 (en)	2005-08-25	Resolution of racemates of methyl alpha-5-(4,5,6,7-tetrahydro(3,2-c)thienopyridyl)-(2-chlorophenil)acetate
KR910002879B1 (ko)	1991-05-09	1,5-벤조티아제핀 유도체의 제조방법
US6495694B2 (en)	2002-12-17	Efficient separation of enantiomers of piperidone derivatives by precipitation of the desired eantiomer during in situ racemization of the unwanted enantiomer
EP0370366A2 (fr)	1990-05-30	Procédé de résolution d'intermediaires de benzazépines
FR2642425A1 (fr)	1990-08-03	Procede de preparation de derives de benzothiazepine-1,5 one-4
JPS59231065A (ja)	1984-12-25	プロピオン酸誘導体の光学分割方法
JPH01128974A (ja)	1989-05-22	１，５−ベンゾチアゼピン誘導体の製法
JPH09216874A (ja)	1997-08-19	光学活性ベンゾチアゼピン誘導体およびその製法
BE896927A (fr)	1983-12-02	Derives d'isoquinoleine, leur procede de preparation et medicament les contenant
JPH09216875A (ja)	1997-08-19	光学活性ベンゾチアゼピン誘導体およびその製法
IL153085A (en)	2008-11-26	Enantiomer separation of piperidone derivatives with simultaneous in situ racemization of the unwanted enantiomer