NO890247L - Fremgangsmaate for fremstilling av 3-(3-pyridyl)-1h, 3h-pyrrolo-(1,2-c)tiazol-7-karbonitril. - Google Patents

Fremgangsmaate for fremstilling av 3-(3-pyridyl)-1h, 3h-pyrrolo-(1,2-c)tiazol-7-karbonitril.

Info

Publication number: NO890247L
Authority: NO; Norway
Prior art keywords: grams; pyridyl; acid; formula; chloride
Prior art date: 1988-01-20

Application number

NO89890247A

Other languages

English (en)

Norwegian (no)

Other versions

NO890247D0 (no

Inventor

Gerard Harivelo 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.)

1988-01-20

Filing date

1989-01-19

Publication date

1989-07-21

1989-01-19 Application filed by Rhone Poulenc Sante filed Critical Rhone Poulenc Sante

1989-01-19 Publication of NO890247D0 publication Critical patent/NO890247D0/no

1989-07-21 Publication of NO890247L publication Critical patent/NO890247L/no

Links

238000000034 method Methods 0.000 title claims description 13
-1 3-PYRIDYL Chemical class 0.000 title description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 8
OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 claims description 7
BHMGUWHKUWZTML-UHFFFAOYSA-N 3-pyridin-3-yl-1,3-dihydropyrrolo[1,2-c][1,3]thiazole-7-carbonitrile Chemical compound S1CC2=C(C#N)C=CN2C1C1=CC=CN=C1 BHMGUWHKUWZTML-UHFFFAOYSA-N 0.000 claims description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 5
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 5
238000006243 chemical reaction Methods 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
238000001816 cooling Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
239000008240 homogeneous mixture Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229940126601 medicinal product Drugs 0.000 description 2
238000003756 stirring Methods 0.000 description 2
ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
230000007815 allergy Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000007547 defect Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003786 synthesis reaction Methods 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
- 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)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO89890247A 1988-01-20 1989-01-19 Fremgangsmaate for fremstilling av 3-(3-pyridyl)-1h, 3h-pyrrolo-(1,2-c)tiazol-7-karbonitril. NO890247L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8800591A FR2626004B1 (fr)	1988-01-20	1988-01-20	Procede de preparation du (pyridyl-3)-3 1h, 3h-pyrrolo (1,2-c) thiazolecarbonitrile-7

Publications (2)

Publication Number	Publication Date
NO890247D0 NO890247D0 (no)	1989-01-19
NO890247L true NO890247L (no)	1989-07-21

Family

ID=9362456

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO89890247A NO890247L (no)	1988-01-20	1989-01-19	Fremgangsmaate for fremstilling av 3-(3-pyridyl)-1h, 3h-pyrrolo-(1,2-c)tiazol-7-karbonitril.

Country Status (15)

Country	Link
US (1)	US5124459A (cs)
EP (1)	EP0327417A1 (cs)
JP (1)	JPH01250387A (cs)
AU (1)	AU609929B2 (cs)
CS (1)	CS34789A2 (cs)
FR (1)	FR2626004B1 (cs)
HU (1)	HU201083B (cs)
IE (1)	IE61426B1 (cs)
IL (1)	IL89006A0 (cs)
NO (1)	NO890247L (cs)
NZ (1)	NZ227689A (cs)
PL (1)	PL277239A1 (cs)
PT (1)	PT89493A (cs)
SU (1)	SU1609454A3 (cs)
ZA (1)	ZA89409B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1993001813A1 (en) *	1991-07-17	1993-02-04	Abbott Laboratories	Platelet activating factor antagonists

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3270716D1 (en) *	1981-02-27	1986-05-28	Ici Plc	Guanidino-substituted heterocyclic derivatives having histamine h-2 antagonist activity
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

1988
- 1988-01-20 FR FR8800591A patent/FR2626004B1/fr not_active Expired - Lifetime
1989
- 1989-01-18 IE IE14589A patent/IE61426B1/en not_active IP Right Cessation
- 1989-01-18 ZA ZA89409A patent/ZA89409B/xx unknown
- 1989-01-18 EP EP89400139A patent/EP0327417A1/fr not_active Withdrawn
- 1989-01-18 AU AU28630/89A patent/AU609929B2/en not_active Withdrawn - After Issue
- 1989-01-18 CS CS89347A patent/CS34789A2/cs unknown
- 1989-01-18 PL PL27723989A patent/PL277239A1/xx unknown
- 1989-01-19 SU SU894613287A patent/SU1609454A3/ru active
- 1989-01-19 US US07/298,943 patent/US5124459A/en not_active Expired - Fee Related
- 1989-01-19 NO NO89890247A patent/NO890247L/no unknown
- 1989-01-19 IL IL89006A patent/IL89006A0/xx unknown
- 1989-01-20 JP JP1010058A patent/JPH01250387A/ja active Pending
- 1989-01-20 NZ NZ227689A patent/NZ227689A/xx unknown
- 1989-01-20 PT PT89493A patent/PT89493A/pt not_active Application Discontinuation
- 1989-01-20 HU HU89235A patent/HU201083B/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA89409B (en)	1989-10-25
JPH01250387A (ja)	1989-10-05
AU2863089A (en)	1989-07-20
IE61426B1 (en)	1994-11-02
NZ227689A (en)	1991-01-29
IE890145L (en)	1989-07-20
IL89006A0 (en)	1989-08-15
SU1609454A3 (ru)	1990-11-23
HUT50838A (en)	1990-03-28
AU609929B2 (en)	1991-05-09
US5124459A (en)	1992-06-23
PL277239A1 (en)	1989-08-21
PT89493A (pt)	1989-10-04
FR2626004B1 (fr)	1991-08-02
NO890247D0 (no)	1989-01-19
HU201083B (en)	1990-09-28
CS34789A2 (en)	1991-05-14
FR2626004A1 (fr)	1989-07-21
EP0327417A1 (fr)	1989-08-09

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