NL1002687C2 - Werkwijze voor de bereiding van een benzothiazepine. - Google Patents

Werkwijze voor de bereiding van een benzothiazepine. Download PDF

Info

Publication number: NL1002687C2
Authority: NL; Netherlands
Prior art keywords: carboxylic acid; amount; alkyl group; propanoic acid; acid
Prior art date: 1996-03-22

Application number

NL1002687A

Other languages

English (en)

Dutch (nl)

Inventor

Wilhelmus Hubertus Jos Boesten

Marcus Joseph Maria Plaum

Eric Cornelis Roos

Original Assignee

Dsm Nv

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.)

1996-03-22

Filing date

1996-03-22

Publication date

1997-09-23

1996-03-22 Application filed by Dsm Nv filed Critical Dsm Nv

1996-03-22 Priority to NL1002687A priority Critical patent/NL1002687C2/nl

1997-02-27 Priority to TW086102634A priority patent/TW360644B/zh

1997-03-17 Priority to JP9062592A priority patent/JPH107667A/ja

1997-03-17 Priority to EP97200797A priority patent/EP0796853B1/en

1997-03-17 Priority to PT97200797T priority patent/PT796853E/pt

1997-03-17 Priority to AT97200797T priority patent/ATE188963T1/de

1997-03-17 Priority to ES97200797T priority patent/ES2143282T3/es

1997-03-17 Priority to DK97200797T priority patent/DK0796853T3/da

1997-03-17 Priority to DE69701160T priority patent/DE69701160T2/de

1997-03-20 Priority to IL12050297A priority patent/IL120502A/xx

1997-03-20 Priority to CA002200537A priority patent/CA2200537A1/en

1997-03-20 Priority to KR1019970010775A priority patent/KR970065530A/ko

1997-03-21 Priority to US08/821,519 priority patent/US5859241A/en

1997-09-23 Application granted granted Critical

1997-09-23 Publication of NL1002687C2 publication Critical patent/NL1002687C2/nl

Links

238000000034 method Methods 0.000 title claims abstract description 25
FHGWEHGZBUBQKL-UHFFFAOYSA-N 1,2-benzothiazepine Chemical compound S1N=CC=CC2=CC=CC=C12 FHGWEHGZBUBQKL-UHFFFAOYSA-N 0.000 title claims abstract description 6
238000002360 preparation method Methods 0.000 title claims abstract description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims abstract description 12
150000001735 carboxylic acids Chemical class 0.000 claims abstract description 10
239000002904 solvent Substances 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims 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 claims abstract description 5
229960004166 diltiazem Drugs 0.000 claims abstract description 4
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
KJFRSZASZNLCDF-UHFFFAOYSA-N 1,5-benzothiazepine Chemical class S1C=CC=NC2=CC=CC=C12 KJFRSZASZNLCDF-UHFFFAOYSA-N 0.000 claims abstract description 3
238000005917 acylation reaction Methods 0.000 claims abstract description 3
238000005804 alkylation reaction Methods 0.000 claims abstract description 3
150000003839 salts Chemical class 0.000 claims abstract description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 22
238000007363 ring formation reaction Methods 0.000 claims description 11
229940078552 o-xylene Drugs 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 5
230000029936 alkylation Effects 0.000 claims description 2
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 4
238000006243 chemical reaction Methods 0.000 abstract 1
239000000825 pharmaceutical preparation Substances 0.000 abstract 1
229940127557 pharmaceutical product Drugs 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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 5
238000010533 azeotropic distillation Methods 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000005457 ice water Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
GKGVPDQNHDBNDR-UHFFFAOYSA-N 2,2-dichlorooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(Cl)(Cl)C(O)=O GKGVPDQNHDBNDR-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
238000010992 reflux Methods 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
-1 methoxyphenyl Chemical group 0.000 description 3
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 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
CVZUMGUZDAWOGA-VHSXEESVSA-N methyl (2r,3s)-3-(4-methoxyphenyl)oxirane-2-carboxylate Chemical compound COC(=O)[C@@H]1O[C@H]1C1=CC=C(OC)C=C1 CVZUMGUZDAWOGA-VHSXEESVSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
KHQWPNQLSKDWAR-CABCVRRESA-N (2s,3s)-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-CABCVRRESA-N 0.000 description 1
KJOJTPANXQIYQH-UHFFFAOYSA-N 2-phenyloxirane-2-carboxylic acid Chemical class C=1C=CC=CC=1C1(C(=O)O)CO1 KJOJTPANXQIYQH-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
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 1
150000004702 methyl esters Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL1002687A 1996-03-22 1996-03-22 Werkwijze voor de bereiding van een benzothiazepine. NL1002687C2 (nl)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
NL1002687A NL1002687C2 (nl)	1996-03-22	1996-03-22	Werkwijze voor de bereiding van een benzothiazepine.
TW086102634A TW360644B (en)	1996-03-22	1997-02-27	Process for the preparation of a benzothiazepine
EP97200797A EP0796853B1 (en)	1996-03-22	1997-03-17	Process for the preparation of a benzothiazepine
PT97200797T PT796853E (pt)	1996-03-22	1997-03-17	Processo para a preparacao de uma benzotiazepina
AT97200797T ATE188963T1 (de)	1996-03-22	1997-03-17	Verfahren zur herstellung eines benzothiazepinen
ES97200797T ES2143282T3 (es)	1996-03-22	1997-03-17	Procedimiento para la preparacion de una benzotiazepina.
JP9062592A JPH107667A (ja)	1996-03-22	1997-03-17	１，５−ベンゾチアゼピン誘導体の製法
DK97200797T DK0796853T3 (da)	1996-03-22	1997-03-17	Fremgangsmåde til fremstilling af en benzothiazepin
DE69701160T DE69701160T2 (de)	1996-03-22	1997-03-17	Verfahren zur Herstellung eines Benzothiazepinen
IL12050297A IL120502A (en)	1996-03-22	1997-03-20	Process for the preparation of benzothiazepines
CA002200537A CA2200537A1 (en)	1996-03-22	1997-03-20	Process for the preparation of a benzothiazepine
KR1019970010775A KR970065530A (ko)	1996-03-22	1997-03-20	벤조티아제핀의 제조방법
US08/821,519 US5859241A (en)	1996-03-22	1997-03-21	Process for the preparation of a benzothiazepine

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL1002687A NL1002687C2 (nl)	1996-03-22	1996-03-22	Werkwijze voor de bereiding van een benzothiazepine.
NL1002687		1996-03-22

Publications (1)

Publication Number	Publication Date
NL1002687C2 true NL1002687C2 (nl)	1997-09-23

Family

ID=19762546

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1002687A NL1002687C2 (nl)	1996-03-22	1996-03-22	Werkwijze voor de bereiding van een benzothiazepine.

Country Status (13)

Country	Link
US (1)	US5859241A (da)
EP (1)	EP0796853B1 (da)
JP (1)	JPH107667A (da)
KR (1)	KR970065530A (da)
AT (1)	ATE188963T1 (da)
CA (1)	CA2200537A1 (da)
DE (1)	DE69701160T2 (da)
DK (1)	DK0796853T3 (da)
ES (1)	ES2143282T3 (da)
IL (1)	IL120502A (da)
NL (1)	NL1002687C2 (da)
PT (1)	PT796853E (da)
TW (1)	TW360644B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2003252259A1 (en) *	2002-07-26	2004-02-16	Nihon Nohyaku Co., Ltd.	Novel haloalkylsulfonanilide derivatives, herbicides and usage thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57122065A (en) *	1981-01-23	1982-07-29	Ihara Chem Ind Co Ltd	Dichloromaleimide derivative and fungicide containing the same
EP0378455A1 (fr) *	1989-01-11	1990-07-18	Synthelabo	Procédé de préparation de dérivés de (+)-(2S,3S)-3-hydroxy-2-(4-méthoxyphényl)2,3-dihydro-5H-1,5-benzothiazépine-4-one
EP0395302A1 (en) *	1989-04-28	1990-10-31	Tanabe Seiyaku Co., Ltd.	Process for preparing 1,5-benzothiazepine derivatives
EP0395323A1 (en) *	1989-04-28	1990-10-31	Tanabe Seiyaku Co., Ltd.	Process for preparing 1,5-benzothiazepine derivatives
EP0447135A1 (en) *	1990-03-08	1991-09-18	Tanabe Seiyaku Co., Ltd.	Process for preparing 1,5-benzothiazepine derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3562257A (en) *	1967-10-28	1971-02-09	Tanabe Seiyaku Co	Benzothiazepine derivatives
USRE34935E (en) *	1989-01-11	1995-05-09	Synthelabo	Method for preparing (+)-(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-5H-1,5-benzothiazepine-4-one and chlorinated derivatives thereof
US5128469A (en) *	1989-04-28	1992-07-07	Tanabe Seiyaku Co., Ltd.	Process for preparing 1,5-benzothiazepine derivatives

1996
- 1996-03-22 NL NL1002687A patent/NL1002687C2/nl not_active IP Right Cessation
1997
- 1997-02-27 TW TW086102634A patent/TW360644B/zh active
- 1997-03-17 EP EP97200797A patent/EP0796853B1/en not_active Expired - Lifetime
- 1997-03-17 JP JP9062592A patent/JPH107667A/ja active Pending
- 1997-03-17 DE DE69701160T patent/DE69701160T2/de not_active Expired - Fee Related
- 1997-03-17 PT PT97200797T patent/PT796853E/pt unknown
- 1997-03-17 DK DK97200797T patent/DK0796853T3/da active
- 1997-03-17 AT AT97200797T patent/ATE188963T1/de not_active IP Right Cessation
- 1997-03-17 ES ES97200797T patent/ES2143282T3/es not_active Expired - Lifetime
- 1997-03-20 IL IL12050297A patent/IL120502A/xx not_active IP Right Cessation
- 1997-03-20 KR KR1019970010775A patent/KR970065530A/ko not_active Withdrawn
- 1997-03-20 CA CA002200537A patent/CA2200537A1/en not_active Abandoned
- 1997-03-21 US US08/821,519 patent/US5859241A/en not_active Expired - Fee Related

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57122065A (en) *	1981-01-23	1982-07-29	Ihara Chem Ind Co Ltd	Dichloromaleimide derivative and fungicide containing the same
EP0378455A1 (fr) *	1989-01-11	1990-07-18	Synthelabo	Procédé de préparation de dérivés de (+)-(2S,3S)-3-hydroxy-2-(4-méthoxyphényl)2,3-dihydro-5H-1,5-benzothiazépine-4-one
EP0395302A1 (en) *	1989-04-28	1990-10-31	Tanabe Seiyaku Co., Ltd.	Process for preparing 1,5-benzothiazepine derivatives
EP0395323A1 (en) *	1989-04-28	1990-10-31	Tanabe Seiyaku Co., Ltd.	Process for preparing 1,5-benzothiazepine derivatives
EP0447135A1 (en) *	1990-03-08	1991-09-18	Tanabe Seiyaku Co., Ltd.	Process for preparing 1,5-benzothiazepine derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Derwent World Patents Index; AN 82-75290E, XP002017000 *

Also Published As

Publication number	Publication date
PT796853E (pt)	2000-06-30
DE69701160T2 (de)	2000-09-14
US5859241A (en)	1999-01-12
EP0796853B1 (en)	2000-01-19
DK0796853T3 (da)	2000-06-26
KR970065530A (ko)	1997-10-13
CA2200537A1 (en)	1997-09-22
IL120502A0 (en)	1997-07-13
ATE188963T1 (de)	2000-02-15
ES2143282T3 (es)	2000-05-01
IL120502A (en)	2000-06-29
TW360644B (en)	1999-06-11
JPH107667A (ja)	1998-01-13
EP0796853A1 (en)	1997-09-24
DE69701160D1 (de)	2000-02-24

Legal Events

Date	Code	Title	Description
1997-11-03	PD2B	A search report has been drawn up
2000-12-01	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20001001

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EP0054951B1 (en)	1984-12-12	Dibenz(b,f)(1,4)oxazepine derivatives, process for preparing the same, and pharmaceutical compositions comprising the same
EP0626952B1 (en)	1999-04-14	Hypolipidaemic benzothiazepine compounds
NL1002687C2 (nl)	1997-09-23	Werkwijze voor de bereiding van een benzothiazepine.
FI93011B (fi)	1994-10-31	Menetelmä 1,5-bentsotiatsepiinijohdannaisten valmistamiseksi
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US5128469A (en)	1992-07-07	Process for preparing 1,5-benzothiazepine derivatives
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NL1005338C2 (nl)	1998-08-24	Werkwijze voor de bereiding van een optisch actief fenylglycidylzuurderivaat.
FR2524468A1 (fr)	1983-10-07	Nouveaux derives condenses du thiophene, leur preparation et leur utilisation comme azurants optiques
CZ279019B6 (en)	1994-11-16	Process of dilthiazemium chloride purification
JPS61260059A (ja)	1986-11-18	プロピオン酸誘導体のｄ体の製造方法