SK42299A3 - N-(benzothiazol-2-yl) piperidine-1-ethanamine derivatives, their preparation and application in therapeutics - Google Patents

N-(benzothiazol-2-yl) piperidine-1-ethanamine derivatives, their preparation and application in therapeutics Download PDF

Info

Publication number: SK42299A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; methyl; mixture; piperidine
Prior art date: 1996-10-01

Application number

SK422-99A

Other languages

English (en)

Slovak (sk)

Inventor

Gihad Dargazanli

Pascal George

Patrick Lardenois

Jonathan Frost

Johannes Schoemaker

Maria-Carmen Renones

Pascale Magat

Original Assignee

Synthelabo

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.)

1996-10-01

Filing date

1997-09-26

Publication date

1999-12-10

1997-09-26 Application filed by Synthelabo filed Critical Synthelabo

1999-12-10 Publication of SK42299A3 publication Critical patent/SK42299A3/sk

Links

239000003814 drug Substances 0.000 title claims abstract description 4
238000002360 preparation method Methods 0.000 title claims description 5
SLDOBMOFHWAPFE-UHFFFAOYSA-N n-(2-piperidin-1-ylethyl)-1,3-benzothiazol-2-amine Chemical class N=1C2=CC=CC=C2SC=1NCCN1CCCCC1 SLDOBMOFHWAPFE-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 47
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
239000000203 mixture Substances 0.000 claims description 30
-1 2-benzothiazolyl Chemical group 0.000 claims description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
QVKPPRYUGJFISN-UHFFFAOYSA-N n-methyl-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(NC)=NC2=C1 QVKPPRYUGJFISN-UHFFFAOYSA-N 0.000 claims description 6
IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 claims description 4
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
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CXLNKIFVGQZLQR-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-2-chloroacetamide;hydrochloride Chemical compound Cl.C1=CC=C2SC(NC(=O)CCl)=NC2=C1 CXLNKIFVGQZLQR-UHFFFAOYSA-N 0.000 description 3
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238000001953 recrystallisation Methods 0.000 description 3
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 3
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 2
BBDCCXMBOJDLMO-UHFFFAOYSA-N 4-benzyl-1-(2-chloroethyl)piperidine Chemical compound C1CN(CCCl)CCC1CC1=CC=CC=C1 BBDCCXMBOJDLMO-UHFFFAOYSA-N 0.000 description 2
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QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
208000010496 Heart Arrest Diseases 0.000 description 2
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208000018737 Parkinson disease Diseases 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
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MVPUGXJYDXAIOD-UHFFFAOYSA-N n-[2-(4-phenylpiperidin-1-yl)ethyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NCCN(CC1)CCC1C1=CC=CC=C1 MVPUGXJYDXAIOD-UHFFFAOYSA-N 0.000 description 2
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230000000324 neuroprotective effect Effects 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
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239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
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HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
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238000000921 elemental analysis Methods 0.000 description 1
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238000002474 experimental method Methods 0.000 description 1
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Classifications

- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Neurosurgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)

SK422-99A 1996-10-01 1997-09-26 N-(benzothiazol-2-yl) piperidine-1-ethanamine derivatives, their preparation and application in therapeutics SK42299A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9611925A FR2753970B1 (fr)	1996-10-01	1996-10-01	Derives de n-(benzothiazol-2-yl) piperidine-1-ethanamine, leur preparation et leur application en therapeutique
PCT/FR1997/001692 WO1998014444A1 (fr)	1996-10-01	1997-09-26	Derives de n-(benzothiazol-2-yl)piperidine-1-ethanamine, leur preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
SK42299A3 true SK42299A3 (en)	1999-12-10

Family

ID=9496217

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK422-99A SK42299A3 (en)	1996-10-01	1997-09-26	N-(benzothiazol-2-yl) piperidine-1-ethanamine derivatives, their preparation and application in therapeutics

Country Status (23)

Country	Link
EP (1)	EP0929550A1 (cs)
JP (1)	JP2001501217A (cs)
KR (1)	KR20000048767A (cs)
CN (1)	CN1230959A (cs)
AR (1)	AR009105A1 (cs)
AU (1)	AU722147B2 (cs)
BG (1)	BG103271A (cs)
BR (1)	BR9711842A (cs)
CA (1)	CA2266510A1 (cs)
CO (1)	CO4650030A1 (cs)
CZ (1)	CZ112699A3 (cs)
EE (1)	EE9900135A (cs)
FR (1)	FR2753970B1 (cs)
HU (1)	HUP9904091A3 (cs)
IL (1)	IL128902A (cs)
NO (1)	NO991581L (cs)
NZ (1)	NZ334553A (cs)
PL (1)	PL332648A1 (cs)
SK (1)	SK42299A3 (cs)
TR (1)	TR199900634T2 (cs)
TW (1)	TW438800B (cs)
WO (1)	WO1998014444A1 (cs)
ZA (1)	ZA978772B (cs)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9725541D0 (en) *	1997-12-02	1998-02-04	Pharmacia & Upjohn Spa	Amino-benzothiazole derivatives
US6107313A (en) *	1998-10-02	2000-08-22	Combichem, Inc.	Dopamine receptor antagonists
AU2001281817B2 (en) *	2000-06-21	2005-11-24	F. Hoffmann-La Roche Ag	Benzothiazole derivatives
US7087761B2 (en)	2003-01-07	2006-08-08	Hoffmann-La Roche Inc.	Cyclization process for substituted benzothiazole derivatives
EP1680408A2 (en) *	2003-10-24	2006-07-19	F. Hoffmann-La Roche Ag	Ccr3 receptor antagonists
RS50574B (sr)	2004-05-24	2010-05-07	F. Hoffmann-La Roche Ag.	(4-metoksi-7-morfolin-4-il-benzotiazol-2-il)-amid 4-hidroksi-4-metil-piperidin-1-karboksilne kiseline
ES2309814T3 (es)	2004-11-05	2008-12-16	F. Hoffmann-La Roche Ag	Proceso para la obtencion de derivados del acido isonicotinico.
WO2006099972A1 (en)	2005-03-23	2006-09-28	F. Hoffmann-La Roche Ag	Acetylenyl-pyrazolo-pvrimidine derivatives as mglur2 antagonists
JP5048675B2 (ja)	2005-09-27	2012-10-17	エフ．ホフマン−ラロシュアーゲー	ｍＧｌｕＲ２アンタゴニストとしてのオキサジアゾリルピラゾロ−ピリミジン類

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1260474A (en) *	1984-12-03	1989-09-26	Raymond A. Stokbroekx	Benzoxazol- and benzothiazolamine derivatives
KR930005004B1 (ko) *	1985-04-15	1993-06-11	쟈안센 파아마슈우티카 엔. 부이.	치환된 n-[(4-피페리디닐)알킬]이환 축합 옥사졸아민 및 티아졸아민의 제조방법

1996
- 1996-10-01 FR FR9611925A patent/FR2753970B1/fr not_active Expired - Fee Related
1997
- 1997-09-26 SK SK422-99A patent/SK42299A3/sk unknown
- 1997-09-26 CN CN97198112A patent/CN1230959A/zh active Pending
- 1997-09-26 BR BR9711842A patent/BR9711842A/pt not_active Application Discontinuation
- 1997-09-26 CO CO97056315A patent/CO4650030A1/es unknown
- 1997-09-26 IL IL12890297A patent/IL128902A/en not_active IP Right Cessation
- 1997-09-26 WO PCT/FR1997/001692 patent/WO1998014444A1/fr not_active Ceased
- 1997-09-26 TR TR1999/00634T patent/TR199900634T2/xx unknown
- 1997-09-26 NZ NZ334553A patent/NZ334553A/xx unknown
- 1997-09-26 CZ CZ991126A patent/CZ112699A3/cs unknown
- 1997-09-26 HU HU9904091A patent/HUP9904091A3/hu unknown
- 1997-09-26 JP JP10516272A patent/JP2001501217A/ja active Pending
- 1997-09-26 PL PL97332648A patent/PL332648A1/xx unknown
- 1997-09-26 EP EP97943001A patent/EP0929550A1/fr not_active Ceased
- 1997-09-26 KR KR1019990702753A patent/KR20000048767A/ko not_active Withdrawn
- 1997-09-26 AU AU44638/97A patent/AU722147B2/en not_active Ceased
- 1997-09-26 CA CA002266510A patent/CA2266510A1/en not_active Abandoned
- 1997-09-26 EE EEP199900135A patent/EE9900135A/xx unknown
- 1997-09-30 TW TW086114229A patent/TW438800B/zh active
- 1997-09-30 ZA ZA9708772A patent/ZA978772B/xx unknown
- 1997-09-30 AR ARP970104493A patent/AR009105A1/es not_active Application Discontinuation
1999
- 1999-03-22 BG BG103271A patent/BG103271A/xx unknown
- 1999-03-30 NO NO991581A patent/NO991581L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
TR199900634T2 (xx)	1999-06-21
TW438800B (en)	2001-06-07
IL128902A0 (en)	2000-02-17
EP0929550A1 (fr)	1999-07-21
FR2753970A1 (fr)	1998-04-03
HUP9904091A3 (en)	2000-07-28
KR20000048767A (ko)	2000-07-25
NZ334553A (en)	2000-11-24
EE9900135A (et)	1999-12-15
JP2001501217A (ja)	2001-01-30
FR2753970B1 (fr)	1998-10-30
IL128902A (en)	2001-07-24
ZA978772B (en)	1998-03-27
HUP9904091A2 (hu)	2000-05-28
AU4463897A (en)	1998-04-24
NO991581D0 (no)	1999-03-30
BR9711842A (pt)	1999-08-24
CN1230959A (zh)	1999-10-06
CA2266510A1 (en)	1998-04-09
WO1998014444A1 (fr)	1998-04-09
CO4650030A1 (es)	1998-09-03
NO991581L (no)	1999-06-01
CZ112699A3 (cs)	1999-06-16
AU722147B2 (en)	2000-07-20
BG103271A (en)	2000-05-31
PL332648A1 (en)	1999-09-27
AR009105A1 (es)	2000-03-08

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