NL194274C - - Google Patents

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Info

Publication number: NL194274C
Authority: NL; Netherlands
Prior art keywords: enantiomer; mixture; methoxyphenyl; methanol; hydroxy
Prior art date: 1989-07-12

Application number

NL9001515A

Other languages

English (en)

Dutch (nl)

Other versions

NL194274B (it

NL9001515A (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.)

1989-07-12

Filing date

1990-07-03

Publication date

2001-11-05

1990-07-03 Application filed by Zambon Spa filed Critical Zambon Spa

1991-02-01 Publication of NL9001515A publication Critical patent/NL9001515A/nl

2001-07-02 Publication of NL194274B publication Critical patent/NL194274B/xx

2001-11-05 Application granted granted Critical

2001-11-05 Publication of NL194274C publication Critical patent/NL194274C/nl

Links

239000000203 mixture Substances 0.000 claims description 15
238000000034 method Methods 0.000 claims description 9
238000002425 crystallisation Methods 0.000 claims description 7
230000008025 crystallization Effects 0.000 claims description 7
239000000010 aprotic solvent Substances 0.000 claims 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 claims 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 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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 6
239000000047 product Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229960004166 diltiazem Drugs 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000008096 xylene Substances 0.000 description 4
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 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
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 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-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
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
230000002213 calciumantagonistic effect Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
-1 paratoluene sulfonic acid monohydrate Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
WNAHEVXTGAEKIY-ZDUSSCGKSA-N tert-butyl n-[(2r)-1-phenylbut-3-en-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](C=C)CC1=CC=CC=C1 WNAHEVXTGAEKIY-ZDUSSCGKSA-N 0.000 description 1
YTWOHSWDLJUCRK-UHFFFAOYSA-N thiolane 1,1-dioxide Chemical compound O=S1(=O)CCCC1.O=S1(=O)CCCC1 YTWOHSWDLJUCRK-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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL9001515A 1989-07-12 1990-07-03 Werkwijze voor de zuivering van tussenprodukten. NL9001515A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2116689		1989-07-12
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
NL9001515A NL9001515A (nl)	1991-02-01
NL194274B NL194274B (it)	2001-07-02
NL194274C true NL194274C (it)	2001-11-05

Family

ID=11177746

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL9001515A NL9001515A (nl)	1989-07-12	1990-07-03	Werkwijze voor de zuivering van tussenprodukten.

Country Status (13)

Country	Link
US (1)	US5315005A (it)
JP (1)	JP2979240B2 (it)
AT (1)	AT401649B (it)
BE (1)	BE1003313A3 (it)
CA (1)	CA2020158C (it)
CH (1)	CH680219A5 (it)
DE (1)	DE4021999C2 (it)
ES (1)	ES2020722A6 (it)
FR (1)	FR2649706B1 (it)
GB (1)	GB2233646B (it)
IT (1)	IT1234387B (it)
NL (1)	NL9001515A (it)
SE (1)	SE509636C2 (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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)

* 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
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 (en) *	1981-02-27	1985-05-15	Tanabe Seiyaku Co., Ltd.	Novel process for preparing threo-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)-propionic ester
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/en 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 (it)	2001-07-02
BE1003313A3 (fr)	1992-02-25
CA2020158C (en)	1997-03-04
JP2979240B2 (ja)	1999-11-15
SE509636C2 (sv)	1999-02-15
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 (en)	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
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 (it)	1992-07-15
SE9002410L (sv)	1991-01-13

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

Publication	Publication Date	Title
NL194274C (it)	2001-11-05
DE69102462T2 (de)	1994-10-06	Verfahren zur Herstellung von 1,5-Benzothiazepin-Derivaten.
RU2055073C1 (ru)	1996-02-27	Производные тиазолидинона или оксазолидинона и способ их получения
FR2646423A1 (fr)	1990-11-02	Procede de preparation de derives de la 1,5-benzothiazepine
NL9100854A (nl)	1991-12-16	Werkwijze voor de bereiding van tussenprodukten bruikbaar voor de synthese van benzodiazepinen.
EP0669327B1 (en)	1999-10-06	Process for the preparation of 1,5-benzothiazepines by ring closure of amino esters
NL194275C (nl)	2001-11-05	Werkwijze voor de bereiding van benzothiazepinen door cyclisatie met fosfonzuren.
FR2646424A1 (fr)	1990-11-02	Procede de preparation de derives de la 1,5-benzothiazepine
AU728090B2 (en)	2001-01-04	Intermediates for the preparation of 2-imidazoline-5-ones
FR2662161A1 (fr)	1991-11-22	Procede pour le dedoublement de derives d'acide 3-(phenyl 4-substitue)-glycidique.
CA1145760A (en)	1983-05-03	Benzylidene derivatives, their preparation and compositions containing them
NL9001710A (nl)	1991-02-18	Resolutiewerkwijze van tussenprodukten, bruikbaar in de bereiding van diltiazem.
WO1999020603A1 (en)	1999-04-29	Process for the recycle of a waste product of diltiazem synthesis
KR0143805B1 (ko)	1998-07-15	(+)-(2s,3s)-3-히드록시-2-(4-메톡시페닐)-2,3-디히드로-5h-1,5-벤조티아제핀-4-온 및 그의 염소화 유도체
FI93213B (fi)	1994-11-30	Menetelmä (+)-(2S,3S)-3-hydroksi-2-(4-metoksifenyyli)-2,3-dihydro-5H-1,5-bentsotiatsepiini-4-onin ja sen kloorattujen johdannaisten valmistamiseksi
JP4040719B2 (ja)	2008-01-30	５−アルコキシヒダントイン化合物の製造方法
KR100404965B1 (ko)	2003-11-10	조합화학(combinatorial chemistry)에서 특징적으로 고체상과 고리화반응 단계에 트리에틸아민과 ＴＨＦ를 이용하여 신규 히덴토인 유도체의 합성법
KR20240154548A (ko)	2024-10-25	페닐테트라히드로푸란 화합물의 제조 공정
FR2642425A1 (fr)	1990-08-03	Procede de preparation de derives de benzothiazepine-1,5 one-4
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
HUT75713A (en)	1997-05-28	Process for producing 5-aryl-2,4-dialkyl-3h-1,2,4-triazol-3-thion derivatives
MXPA00003820A (en)	2001-06-26	Process for the recycle of a waste product of diltiazem synthesis
JPH06298751A (ja)	1994-10-25	塩酸ジルチアゼムの製造法
BE862480A (fr)	1978-06-29	Dithiolannes-1,3 substitues et leur procede de preparation