SE509636C2 - Förfarande för optisk rening av (2S,3S)-2,3-diväte-3-hydroxi- 2-(4-metoxifenyl)-1,5-bensotiazepin-4(5H)-on - Google Patents
Förfarande för optisk rening av (2S,3S)-2,3-diväte-3-hydroxi- 2-(4-metoxifenyl)-1,5-bensotiazepin-4(5H)-onInfo
- Publication number
- SE509636C2 SE509636C2 SE9002410A SE9002410A SE509636C2 SE 509636 C2 SE509636 C2 SE 509636C2 SE 9002410 A SE9002410 A SE 9002410A SE 9002410 A SE9002410 A SE 9002410A SE 509636 C2 SE509636 C2 SE 509636C2
- Authority
- SE
- Sweden
- Prior art keywords
- mixture
- methoxyphenyl
- hydroxy
- benzothiazepine
- dewa
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000000746 purification Methods 0.000 title claims abstract description 8
- 230000003287 optical effect Effects 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 238000002425 crystallisation Methods 0.000 claims abstract description 10
- 230000008025 crystallization Effects 0.000 claims abstract description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 5
- 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 abstract description 4
- 229960004166 diltiazem Drugs 0.000 abstract description 4
- 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 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 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 2
- -1 dimethylformamide sulfoxide Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- GINQYTLDMNFGQP-UHFFFAOYSA-N n,n-dimethylformamide;methylsulfinylmethane Chemical compound CS(C)=O.CN(C)C=O GINQYTLDMNFGQP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000012502 risk assessment Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8921166A IT1234387B (it) | 1989-07-12 | 1989-07-12 | Processo di purificazione di intermedi utili nella preparazione del diltiazem |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9002410D0 SE9002410D0 (sv) | 1990-07-11 |
| SE9002410L SE9002410L (sv) | 1991-01-13 |
| SE509636C2 true SE509636C2 (sv) | 1999-02-15 |
Family
ID=11177746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9002410A SE509636C2 (sv) | 1989-07-12 | 1990-07-11 | Förfarande för optisk rening av (2S,3S)-2,3-diväte-3-hydroxi- 2-(4-metoxifenyl)-1,5-bensotiazepin-4(5H)-on |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5315005A (fr) |
| JP (1) | JP2979240B2 (fr) |
| AT (1) | AT401649B (fr) |
| BE (1) | BE1003313A3 (fr) |
| CA (1) | CA2020158C (fr) |
| CH (1) | CH680219A5 (fr) |
| DE (1) | DE4021999C2 (fr) |
| ES (1) | ES2020722A6 (fr) |
| FR (1) | FR2649706B1 (fr) |
| GB (1) | GB2233646B (fr) |
| IT (1) | IT1234387B (fr) |
| NL (1) | NL9001515A (fr) |
| SE (1) | SE509636C2 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5559229A (en) * | 1995-06-01 | 1996-09-24 | Acic (Canada) Inc. | Method for the manufacture of benzothiazepine |
| US7513937B2 (en) | 2005-07-08 | 2009-04-07 | Refined Global Solutions, Inc. | Oil reconditioning device and associated methods |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3562257A (en) * | 1967-10-28 | 1971-02-09 | Tanabe Seiyaku Co | Benzothiazepine derivatives |
| FR2360124A1 (fr) * | 1976-07-30 | 1978-02-24 | Amiens Const Electro Mecan | Procede de controle de commutation de la puissance de chauffage dans un appareil electrodomestique a programmateur et dispositif pour la mise en oeuvre dudit procede |
| EP0059335B1 (fr) * | 1981-02-27 | 1985-05-15 | Tanabe Seiyaku Co., Ltd. | Procédé pour la préparation des esters de l'acide thréo-hydroxy-2 (méthoxy-4 phényl)-3 (nitro-2 phénylthio)-3 propionique |
| 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 |
| IT1217988B (it) * | 1988-01-28 | 1990-03-30 | Ind Chimica Profarmaco Spa | Procedimento per la risoluzione ottica di un pacemo |
| ZA893392B (en) * | 1988-05-24 | 1990-01-31 | Hoffmann La Roche | Process for the manufacture of optically active naphthothiazepinones |
| FR2641535B1 (fr) * | 1989-01-11 | 1991-03-15 | Synthelabo | Procede de preparation de (+) - (2s, 3s)-hydroxy-3 (methoxy-4 phenyl)-2 dihydro-2,3 5h-benzothiazepine-1,5 one-4 |
| FR2642425A1 (fr) * | 1989-01-30 | 1990-08-03 | Sanofi Sa | Procede de preparation de derives de benzothiazepine-1,5 one-4 |
| IT1230057B (it) * | 1989-04-13 | 1991-09-27 | Zambon Spa | Processo di risoluzione di intermedi utili per la preparazione di 1,5-benzotiazepine |
| ATE116643T1 (de) * | 1989-04-28 | 1995-01-15 | Tanabe Seiyaku Co | Verfahren zur herstellung von 1,5- benzothiazepinderivaten. |
| JPH0798813B2 (ja) * | 1989-04-28 | 1995-10-25 | 田辺製薬株式会社 | １，５―ベンゾチアゼピン誘導体の製法 |
-
1989
- 1989-07-12 IT IT8921166A patent/IT1234387B/it active
-
1990
- 1990-06-22 CH CH2086/90A patent/CH680219A5/it not_active IP Right Cessation
- 1990-06-29 CA CA002020158A patent/CA2020158C/fr not_active Expired - Lifetime
- 1990-07-03 FR FR9008374A patent/FR2649706B1/fr not_active Expired - Fee Related
- 1990-07-03 NL NL9001515A patent/NL9001515A/nl active Search and Examination
- 1990-07-04 JP JP2178494A patent/JP2979240B2/ja not_active Expired - Lifetime
- 1990-07-04 GB GB9014799A patent/GB2233646B/en not_active Expired - Fee Related
- 1990-07-11 AT AT0147690A patent/AT401649B/de not_active IP Right Cessation
- 1990-07-11 DE DE4021999A patent/DE4021999C2/de not_active Expired - Fee Related
- 1990-07-11 SE SE9002410A patent/SE509636C2/sv not_active IP Right Cessation
- 1990-07-11 BE BE9000707A patent/BE1003313A3/fr not_active IP Right Cessation
- 1990-07-11 ES ES9001892A patent/ES2020722A6/es not_active Expired - Fee Related
-
1993
- 1993-01-25 US US08/008,892 patent/US5315005A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL194274B (fr) | 2001-07-02 |
| BE1003313A3 (fr) | 1992-02-25 |
| CA2020158C (fr) | 1997-03-04 |
| JP2979240B2 (ja) | 1999-11-15 |
| DE4021999A1 (de) | 1991-01-17 |
| GB2233646A (en) | 1991-01-16 |
| ES2020722A6 (es) | 1991-09-01 |
| AT401649B (de) | 1996-10-25 |
| DE4021999C2 (de) | 2002-08-29 |
| IT8921166A0 (it) | 1989-07-12 |
| CA2020158A1 (fr) | 1991-01-13 |
| GB9014799D0 (en) | 1990-08-22 |
| JPH0348671A (ja) | 1991-03-01 |
| IT1234387B (it) | 1992-05-18 |
| US5315005A (en) | 1994-05-24 |
| FR2649706B1 (fr) | 1994-10-07 |
| NL194274C (fr) | 2001-11-05 |
| GB2233646B (en) | 1993-01-27 |
| FR2649706A1 (fr) | 1991-01-18 |
| NL9001515A (nl) | 1991-02-01 |
| SE9002410D0 (sv) | 1990-07-11 |
| ATA147690A (de) | 1996-03-15 |
| CH680219A5 (fr) | 1992-07-15 |
| SE9002410L (sv) | 1991-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |