CS272240B2 - Method of 3-(3-pyridyle)-1h,3h-pyrrolo (1,2-0)-thiazole-7-carboxylic dextrorotary acid production - Google Patents

Method of 3-(3-pyridyle)-1h,3h-pyrrolo (1,2-0)-thiazole-7-carboxylic dextrorotary acid production Download PDF

Info

Publication number: CS272240B2
Authority: CS; Czechoslovakia
Prior art keywords: acid; formula; ester; pyridyl; carboxylic acid
Prior art date: 1987-07-02

Application number

CS884762A

Other languages

Czech (cs)

English (en)

Other versions

CS476288A2 (en

Inventor

Harivelo G Rajoharison

Original Assignee

Rhone Poulenc Sante

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.)

1987-07-02

Filing date

1988-07-01

Publication date

1991-01-15

1988-07-01 Application filed by Rhone Poulenc Sante filed Critical Rhone Poulenc Sante

1990-03-14 Publication of CS476288A2 publication Critical patent/CS476288A2/cs

1991-01-15 Publication of CS272240B2 publication Critical patent/CS272240B2/cs

Links

239000002253 acid Substances 0.000 title claims description 35
238000000034 method Methods 0.000 title claims description 15
238000004519 manufacturing process Methods 0.000 title description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 28
150000002148 esters Chemical class 0.000 claims description 24
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 16
UAKRDYSCFUPEQV-UHFFFAOYSA-N 3-formyl-2-pyridin-3-yl-1,3-thiazolidine-4-carboxylic acid Chemical compound O=CN1C(C(=O)O)CSC1C1=CC=CN=C1 UAKRDYSCFUPEQV-UHFFFAOYSA-N 0.000 claims description 12
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
-1 2-chloroacrylic acid ester Chemical class 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
CVUNPKSKGHPMSY-UHFFFAOYSA-N ethyl 2-chloroprop-2-enoate Chemical group CCOC(=O)C(Cl)=C CVUNPKSKGHPMSY-UHFFFAOYSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
JODXKZAUFHEYGO-UHFFFAOYSA-N 2,3-dihydroxybutanedioyl dichloride Chemical compound ClC(=O)C(O)C(O)C(Cl)=O JODXKZAUFHEYGO-UHFFFAOYSA-N 0.000 claims 1
229940098779 methanesulfonic acid Drugs 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
239000000203 mixture Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 11
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000012153 distilled water Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
RZUMSHFSPJRQIU-UHFFFAOYSA-N 3-pyridin-3-yl-1,3-dihydropyrrolo[1,2-c][1,3]thiazole-7-carboxylic acid Chemical compound S1CC2=C(C(=O)O)C=CN2C1C1=CC=CN=C1 RZUMSHFSPJRQIU-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
230000006340 racemization Effects 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 2
GBJCWBWQIQXFLH-UHFFFAOYSA-N 2h-pyrrolo[2,3-d][1,3]thiazole Chemical class C1=NC2=NCSC2=C1 GBJCWBWQIQXFLH-UHFFFAOYSA-N 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000007815 allergy Effects 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
RNZPQAZETZXKCQ-UHFFFAOYSA-N ethyl 2,3-dichloropropanoate Chemical compound CCOC(=O)C(Cl)CCl RNZPQAZETZXKCQ-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000010183 spectrum analysis Methods 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
LINWZBWAZOPJKT-UHFFFAOYSA-N 1,3-dihydropyrrolo[1,2-c][1,3]thiazole-7-carboxylic acid Chemical compound C1C=2N(CS1)C=CC=2C(=O)O LINWZBWAZOPJKT-UHFFFAOYSA-N 0.000 description 1
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 1
RXNOYRCWKRFNIM-UHFFFAOYSA-N 2-carbonochloridoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(Cl)=O RXNOYRCWKRFNIM-UHFFFAOYSA-N 0.000 description 1
VXSBJHJXJYZMAH-UHFFFAOYSA-N 3-formyl-1,3-thiazolidine-4-carboxylic acid Chemical compound OC(=O)C1CSCN1C=O VXSBJHJXJYZMAH-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
108010003541 Platelet Activating Factor Proteins 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241000534944 Thia Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000010779 crude oil Substances 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
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
DYJCLJLGWQIAHV-UHFFFAOYSA-N ethyl 3-pyridin-3-yl-1,3-dihydropyrrolo[1,2-c][1,3]thiazole-1-carboxylate Chemical compound N12C=CC=C2C(C(=O)OCC)SC1C1=CC=CN=C1 DYJCLJLGWQIAHV-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000009987 spinning Methods 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- 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)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Immunology (AREA)
Hematology (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS884762A 1987-07-02 1988-07-01 Method of 3-(3-pyridyle)-1h,3h-pyrrolo (1,2-0)-thiazole-7-carboxylic dextrorotary acid production CS272240B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8709376A FR2617484B1 (fr)	1987-07-02	1987-07-02	Procede de preparation de l'acide (pyridyl-3)-3 1h-3h-pyrrolo (1,2-c) thiazolecarboxylique-7 dextrogyre

Publications (2)

Publication Number	Publication Date
CS476288A2 CS476288A2 (en)	1990-03-14
CS272240B2 true CS272240B2 (en)	1991-01-15

Family

ID=9352790

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS884762A CS272240B2 (en)	1987-07-02	1988-07-01	Method of 3-(3-pyridyle)-1h,3h-pyrrolo (1,2-0)-thiazole-7-carboxylic dextrorotary acid production

Country Status (24)

Country	Link
US (1)	US4906757A (da)
EP (1)	EP0297987A1 (da)
JP (1)	JP2571828B2 (da)
KR (1)	KR890002193A (da)
AU (1)	AU600838B2 (da)
BG (1)	BG48810A3 (da)
CA (1)	CA1298839C (da)
CS (1)	CS272240B2 (da)
DD (1)	DD271330A5 (da)
DK (1)	DK367388A (da)
FI (1)	FI95801C (da)
FR (1)	FR2617484B1 (da)
HU (1)	HU198073B (da)
IE (1)	IE65279B1 (da)
IL (1)	IL86919A (da)
MA (1)	MA21305A1 (da)
MX (1)	MX168612B (da)
NO (1)	NO882959L (da)
NZ (1)	NZ225261A (da)
PL (1)	PL157527B1 (da)
PT (1)	PT87907B (da)
SU (1)	SU1579463A3 (da)
TN (1)	TNSN88070A1 (da)
ZA (1)	ZA884746B (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5260451A (en) *	1989-05-11	1993-11-09	Merckle Gmbh	Substituted pyrrole compounds and use thereof in pharmaceutical compositions
DE3915450A1 (de) *	1989-05-11	1990-11-15	Gerd Prof Dr Dannhardt	Substituierte pyrrolverbindungen und deren anwendung in der pharmazie
WO1993001813A1 (en) *	1991-07-17	1993-02-04	Abbott Laboratories	Platelet activating factor antagonists
DE10004157A1 (de)	2000-02-01	2001-08-02	Merckle Gmbh Chem Pharm Fabrik	4-Pyridyl-und 2,4-Pyrimidinyl-substituierte Pyrrolderivate und ihre Anwendung in der Pharmazie
CN106543204A (zh) *	2016-11-08	2017-03-29	清华大学	一种合成多取代吡咯并[1,2‑c]噻唑衍生物的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2541280B1 (fr) *	1983-01-13	1985-06-21	Rhone Poulenc Sante	Nouveaux derives du 1h, 3h-pyrrolo (1,2c) thiazolecarboxamide-7, leur preparation et les medicaments qui les contiennent
FR2601016B1 (fr) *	1986-07-04	1988-10-07	Rhone Poulenc Sante	Nouveaux derives du 1h,3h-pyrrolo (1,2-c) thiazole, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2601015B1 (fr) *	1986-07-04	1988-08-05	Rhone Poulenc Sante	Nouveaux derives du 1h,3h-pyrrolo (1,2-c) thiazole, leur preparation et les compositions pharmaceutiques qui les contiennent

1987
- 1987-07-02 FR FR8709376A patent/FR2617484B1/fr not_active Expired
1988
- 1988-06-22 MA MA21548A patent/MA21305A1/fr unknown
- 1988-06-29 CA CA000570717A patent/CA1298839C/fr not_active Expired - Lifetime
- 1988-06-29 IL IL86919A patent/IL86919A/xx unknown
- 1988-06-29 PL PL1988273372A patent/PL157527B1/pl unknown
- 1988-06-30 EP EP88401685A patent/EP0297987A1/fr not_active Withdrawn
- 1988-06-30 MX MX012118A patent/MX168612B/es unknown
- 1988-06-30 US US07/213,764 patent/US4906757A/en not_active Expired - Fee Related
- 1988-07-01 FI FI883167A patent/FI95801C/fi not_active IP Right Cessation
- 1988-07-01 DK DK367388A patent/DK367388A/da not_active Application Discontinuation
- 1988-07-01 JP JP63162734A patent/JP2571828B2/ja not_active Expired - Lifetime
- 1988-07-01 ZA ZA884746A patent/ZA884746B/xx unknown
- 1988-07-01 SU SU884355994A patent/SU1579463A3/ru active
- 1988-07-01 NZ NZ225261A patent/NZ225261A/xx unknown
- 1988-07-01 BG BG084731A patent/BG48810A3/xx unknown
- 1988-07-01 NO NO88882959A patent/NO882959L/no unknown
- 1988-07-01 IE IE201588A patent/IE65279B1/en not_active IP Right Cessation
- 1988-07-01 HU HU883469A patent/HU198073B/hu not_active IP Right Cessation
- 1988-07-01 DD DD88317458A patent/DD271330A5/de not_active IP Right Cessation
- 1988-07-01 KR KR1019880008253A patent/KR890002193A/ko not_active Withdrawn
- 1988-07-01 AU AU18512/88A patent/AU600838B2/en not_active Ceased
- 1988-07-01 CS CS884762A patent/CS272240B2/cs unknown
- 1988-07-01 PT PT87907A patent/PT87907B/pt not_active IP Right Cessation
- 1988-07-04 TN TNTNSN88070A patent/TNSN88070A1/fr unknown

Also Published As

Publication number	Publication date
PL273372A1 (en)	1989-03-06
FI883167A0 (fi)	1988-07-01
HU198073B (en)	1989-07-28
IE65279B1 (en)	1995-10-18
CS476288A2 (en)	1990-03-14
NZ225261A (en)	1989-12-21
IL86919A (en)	1992-02-16
JPS6429382A (en)	1989-01-31
DD271330A5 (de)	1989-08-30
ZA884746B (en)	1989-03-29
AU600838B2 (en)	1990-08-23
BG48810A3 (bg)	1991-05-15
TNSN88070A1 (fr)	1990-07-10
NO882959L (no)	1989-01-03
PT87907A (pt)	1989-06-30
FI883167L (fi)	1989-01-03
MA21305A1 (fr)	1988-12-31
FI95801B (fi)	1995-12-15
PT87907B (pt)	1995-06-30
JP2571828B2 (ja)	1997-01-16
IE882015L (en)	1989-01-02
HUT47588A (en)	1989-03-28
DK367388A (da)	1989-01-03
KR890002193A (ko)	1989-04-08
DK367388D0 (da)	1988-07-01
AU1851288A (en)	1989-01-05
IL86919A0 (en)	1988-11-30
FR2617484B1 (fr)	1989-10-20
MX168612B (es)	1993-06-01
PL157527B1 (pl)	1992-06-30
FI95801C (fi)	1996-03-25
NO882959D0 (no)	1988-07-01
EP0297987A1 (fr)	1989-01-04
FR2617484A1 (fr)	1989-01-06
CA1298839C (fr)	1992-04-14
SU1579463A3 (ru)	1990-07-15
US4906757A (en)	1990-03-06

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