IL95213A - Quinine salt of R3-) 3-carboxybenzyl (-6-) 5-fluoro-2-benzothiazolyl (methoxy-R4-chromanol and method for its preparation - Google Patents

Quinine salt of R3-) 3-carboxybenzyl (-6-) 5-fluoro-2-benzothiazolyl (methoxy-R4-chromanol and method for its preparation

Info

Publication number: IL95213A
Authority: IL; Israel
Prior art keywords: quinine; salt; methoxy; fluoro; chromanol
Prior art date: 1989-08-04

Application number

IL9521390A

Other languages

English (en)

Hebrew (he)

Other versions

IL95213A0 (en

Original Assignee

Pfizer

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.)

1989-08-04

Filing date

1990-07-27

Publication date

1995-01-24

1990-07-27 Application filed by Pfizer filed Critical Pfizer

1991-06-10 Publication of IL95213A0 publication Critical patent/IL95213A0/xx

1995-01-24 Publication of IL95213A publication Critical patent/IL95213A/en

Links

LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 title claims abstract description 41
238000002360 preparation method Methods 0.000 title claims abstract description 5
238000000034 method Methods 0.000 title claims description 16
WUKGGHOTJYRJBS-LHIURRSHSA-N (2R)-2-methoxy-3,4-dihydro-2H-chromen-4-ol Chemical compound CO[C@@H]1OC2=CC=CC=C2C(C1)O WUKGGHOTJYRJBS-LHIURRSHSA-N 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 13
235000001258 Cinchona calisaya Nutrition 0.000 claims abstract description 8
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims abstract description 8
229960000948 quinine Drugs 0.000 claims abstract description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 8
239000012442 inert solvent Substances 0.000 claims description 4
239000000047 product Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000004064 recycling Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
-1 3-CARBOXYBENZYL Chemical class 0.000 description 3
238000011084 recovery Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000003810 Jones reagent Substances 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003828 vacuum filtration Methods 0.000 description 2
JWPIRZSVGXXDRV-UHFFFAOYSA-N 3-[[6-[(5-fluoro-1,3-benzothiazol-2-yl)methoxy]-4-oxo-2,3-dihydrochromen-3-yl]methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CC2C(C3=CC(OCC=4SC5=CC=C(F)C=C5N=4)=CC=C3OC2)=O)=C1 JWPIRZSVGXXDRV-UHFFFAOYSA-N 0.000 description 1
VGKZBAMIYUHSMU-UHFFFAOYSA-N 4-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(NC(=O)N(CCCl)N=O)CC1 VGKZBAMIYUHSMU-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000005352 clarification Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000029087 digestion Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001640 fractional crystallisation Methods 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
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
102000003835 leukotriene receptors Human genes 0.000 description 1
108090000146 leukotriene receptors Proteins 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000006340 racemization Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL9521390A 1989-08-04 1990-07-27 Quinine salt of R3-) 3-carboxybenzyl (-6-) 5-fluoro-2-benzothiazolyl (methoxy-R4-chromanol and method for its preparation IL95213A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/389,715 US4987231A (en)	1989-08-04	1989-08-04	Optical resolution method for 3R-(3-carboxybenzyl)-6-(5-fluoro-2-benzothiazolyl)methoxy-4R-chromanol

Publications (2)

Publication Number	Publication Date
IL95213A0 IL95213A0 (en)	1991-06-10
IL95213A true IL95213A (en)	1995-01-24

Family

ID=23539421

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9521390A IL95213A (en)	1989-08-04	1990-07-27	Quinine salt of R3-) 3-carboxybenzyl (-6-) 5-fluoro-2-benzothiazolyl (methoxy-R4-chromanol and method for its preparation

Country Status (23)

Country	Link
US (1)	US4987231A (de)
EP (1)	EP0411813A1 (de)
JP (1)	JPH0374384A (de)
KR (1)	KR920011021B1 (de)
CN (1)	CN1024550C (de)
AU (1)	AU613838B2 (de)
CA (1)	CA2022611C (de)
CZ (1)	CZ279737B6 (de)
DD (1)	DD296924A5 (de)
EG (1)	EG19125A (de)
FI (1)	FI92826C (de)
HU (1)	HUT58734A (de)
IE (1)	IE902805A1 (de)
IL (1)	IL95213A (de)
MY (1)	MY105933A (de)
NO (1)	NO903420L (de)
NZ (1)	NZ234761A (de)
PH (1)	PH26568A (de)
PL (1)	PL164164B1 (de)
PT (1)	PT94888A (de)
RU (1)	RU1834889C (de)
YU (1)	YU47369B (de)
ZA (1)	ZA916126B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59198471A (ja) *	1983-04-26	1984-11-10	Canon Inc	複写装置
US5059609A (en) *	1987-10-19	1991-10-22	Pfizer Inc.	Substituted tetralins, chromans and related compounds in the treatment of asthma, arthritis and related diseases
US5539128A (en) *	1994-11-30	1996-07-23	Pfizer Inc.	Processes and intermediates for preparing cis(+)3-[4,6-dihydroxy chroman-3-ylmethyl]-4-methoxyaniline
DE102014010979B3 (de)	2014-07-29	2015-11-05	Sew-Eurodrive Gmbh & Co Kg	Verwendung eines Anzeigemittels eines Umrichters, Verfahren zum Betreiben eines Umrichters und Umrichter

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA739471B (en) *	1972-12-22	1974-08-28	Hoffmann La Roche	Chromane derivatives
JPS5745185A (en) *	1980-07-21	1982-03-13	Eisai Co Ltd	Hydantoin derivative and its preparation
MX13485A (es) *	1987-10-19	1993-05-01	Pfizer	Procedimiento para obtener tetralinas, cromados y compuestos relacionados, sustituidos

1989
- 1989-08-04 US US07/389,715 patent/US4987231A/en not_active Expired - Lifetime
1990
- 1990-07-20 PH PH40874A patent/PH26568A/en unknown
- 1990-07-25 EP EP90308122A patent/EP0411813A1/de not_active Withdrawn
- 1990-07-27 IL IL9521390A patent/IL95213A/en not_active IP Right Cessation
- 1990-08-01 JP JP2204937A patent/JPH0374384A/ja active Pending
- 1990-08-01 CZ CS903817A patent/CZ279737B6/cs unknown
- 1990-08-02 MY MYPI90001295A patent/MY105933A/en unknown
- 1990-08-02 DD DD90343216A patent/DD296924A5/de not_active IP Right Cessation
- 1990-08-02 PL PL90286327A patent/PL164164B1/pl unknown
- 1990-08-02 NZ NZ234761A patent/NZ234761A/xx unknown
- 1990-08-02 PT PT94888A patent/PT94888A/pt not_active Application Discontinuation
- 1990-08-02 CA CA002022611A patent/CA2022611C/en not_active Expired - Fee Related
- 1990-08-03 CN CN90106753A patent/CN1024550C/zh not_active Expired - Fee Related
- 1990-08-03 HU HU904892A patent/HUT58734A/hu unknown
- 1990-08-03 RU SU904830536A patent/RU1834889C/ru active
- 1990-08-03 IE IE280590A patent/IE902805A1/en unknown
- 1990-08-03 FI FI903861A patent/FI92826C/fi not_active IP Right Cessation
- 1990-08-03 NO NO90903420A patent/NO903420L/no unknown
- 1990-08-03 ZA ZA916126A patent/ZA916126B/xx unknown
- 1990-08-03 KR KR1019900011921A patent/KR920011021B1/ko not_active Expired
- 1990-08-03 AU AU60191/90A patent/AU613838B2/en not_active Ceased
- 1990-08-04 EG EG46390A patent/EG19125A/xx active
- 1990-08-06 YU YU152290A patent/YU47369B/sh unknown

Also Published As

Publication number	Publication date
IE902805A1 (en)	1991-02-27
HU904892D0 (en)	1991-01-28
NO903420L (no)	1991-02-05
ZA916126B (en)	1992-03-25
RU1834889C (ru)	1993-08-15
YU47369B (sh)	1995-01-31
KR910004610A (ko)	1991-03-29
CN1049160A (zh)	1991-02-13
KR920011021B1 (ko)	1992-12-26
FI92826B (fi)	1994-09-30
PH26568A (en)	1992-08-19
CZ279737B6 (cs)	1995-06-14
JPH0374384A (ja)	1991-03-28
CA2022611C (en)	1999-03-23
FI903861A0 (fi)	1990-08-03
NZ234761A (en)	1991-09-25
PT94888A (pt)	1991-04-18
CN1024550C (zh)	1994-05-18
PL164164B1 (pl)	1994-06-30
FI92826C (fi)	1995-01-10
PL286327A1 (en)	1991-03-25
YU152290A (sh)	1992-09-07
AU613838B2 (en)	1991-08-08
US4987231A (en)	1991-01-22
DD296924A5 (de)	1991-12-19
MY105933A (en)	1995-02-28
CA2022611A1 (en)	1991-02-05
NO903420D0 (no)	1990-08-03
EG19125A (en)	1994-07-30
HUT58734A (en)	1992-03-30
IL95213A0 (en)	1991-06-10
EP0411813A1 (de)	1991-02-06
AU6019190A (en)	1991-02-07

Legal Events

Date	Code	Title	Description
1997-04-15	RH	Patent void

Publication	Publication Date	Title
WO2001040159A1 (en)	2001-06-07	New process
EP2066638B1 (de)	2011-02-23	Verfahren zur aufreinigung von montelukast
US4987231A (en)	1991-01-22	Optical resolution method for 3R-(3-carboxybenzyl)-6-(5-fluoro-2-benzothiazolyl)methoxy-4R-chromanol
CN86101512A (zh)	1988-01-13	维生素b6中间体4-甲基-5-烷氧基唑的合成工艺
US20080293965A1 (en)	2008-11-27	Process for the Dynamic Resolution of (Substituted) (R)- or (S)- Mandelic Acid
JP2000327603A (ja)	2000-11-28	プロピオン酸誘導体の製造方法
US4916226A (en)	1990-04-10	Optical resolution method for 3S-(3-pyridylmethyl)-6-(2-quinolyl)-methoxy-4S-chromanol
EP0823907B1 (de)	1999-05-26	Verfahren zur herstellung von (-)-trans-n-p-fluorbenzoylmethyl-4-(p-fluorphenyl)-3-[[3,4-(methylendioxy)phenoxy]methyl]-piperidin
RU2015953C1 (ru)	1994-07-15	Способ расщепления рацемата 2,2-диметилциклопропанкарбоновой кислоты
WO2009053424A9 (en)	2009-08-06	Crystalline salt of montelukast
EP0970952B1 (de)	2006-08-09	Verfahren zur herstellung von 2-(omega-alkoxycarbonylalkanoyl)-4-butanoliden,omega-hydroxy-(omega-3)-keto-fettsäureestern und ihrer derivate
JP3084577B2 (ja)	2000-09-04	光学活性なアトロラクチン酸の製造方法および製造の中間体
JP3032987B2 (ja)	2000-04-17	非ラセミの３―オキソシクロペンタンカルボン酸若しくは３―オキソシクロヘキサンカルボン酸又はそれらのｃ１―ｃ６アルコールとのエステルのラセミ化のための方法
JPH0940621A (ja)	1997-02-10	光学活性インダニルメチルアミン誘導体及びその製造法
JP2002167381A (ja)	2002-06-11	（±）−６−ヒドロキシ−２，５，７，８−テトラメチルクロマン−２−カルボン酸の光学分割法
JPS6363546B2 (de)	1988-12-07
JPH02300154A (ja)	1990-12-12	安息香酸誘導体の製造法
JPS61183238A (ja)	1986-08-15	（ｓ）−ラバンジユロ−ルの製造方法
HU218467B (hu)	2000-09-28	Eljárás homokirális alkoholok előállítására
AU4793600A (en)	2000-11-21	New process
JPH10291980A (ja)	1998-11-04	光学活性な４，５−ジフェニル−２−イミダゾリジノン誘導体及びこれを用いた光学活性なα−アミノリン酸の製造方法