CA1098524A - Procede de preparation de nouveaux derives de l'acide piperazinecarbodithioique - Google Patents

Procede de preparation de nouveaux derives de l'acide piperazinecarbodithioique

Info

Publication number: CA1098524A
Authority: CA; Canada
Prior art keywords: acid; radical; sodium salt; piperazine; thiazolyl
Prior art date: 1977-06-10
Legal status (The legal status 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 status listed.): Expired

Application number

CA305,059A

Other languages

English (en)

French (fr)

Inventor

Gilbert Regnier

Roger Canevari

Xavier Pascaud

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Science Union et Cie

Original Assignee

Science Union et Cie

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.)

1977-06-10

Filing date

1978-06-08

Publication date

1981-03-31

1978-06-08 Application filed by Science Union et Cie filed Critical Science Union et Cie

1981-03-31 Application granted granted Critical

1981-03-31 Publication of CA1098524A publication Critical patent/CA1098524A/fr

Status Expired legal-status Critical Current

Links

IDIICHZCEIGXGB-UHFFFAOYSA-N 1-piperazinecarbodithioic acid Chemical class SC(=S)N1CCNCC1 IDIICHZCEIGXGB-UHFFFAOYSA-N 0.000 title claims abstract 4
238000000034 method Methods 0.000 title claims description 24
238000002360 preparation method Methods 0.000 title claims description 4
-1 monosubstituted piperazines Chemical class 0.000 claims abstract description 27
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 claims abstract description 25
229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 9
239000003795 chemical substances by application Substances 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
239000011593 sulfur Substances 0.000 claims abstract description 5
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 7
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 48
159000000000 sodium salts Chemical class 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 6
238000001311 chemical methods and process Methods 0.000 claims 6
AEJARLYXNFRVLK-UHFFFAOYSA-N 4H-1,2,3-triazole Chemical compound C1C=NN=N1 AEJARLYXNFRVLK-UHFFFAOYSA-N 0.000 claims 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 3
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
150000001875 compounds Chemical class 0.000 abstract description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
201000010099 disease Diseases 0.000 abstract description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
231100000334 hepatotoxic Toxicity 0.000 abstract description 2
230000003082 hepatotoxic effect Effects 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 abstract 3
239000001257 hydrogen Substances 0.000 abstract 3
229910052736 halogen Inorganic materials 0.000 abstract 2
150000002367 halogens Chemical group 0.000 abstract 2
150000002431 hydrogen Chemical class 0.000 abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
238000002560 therapeutic procedure Methods 0.000 abstract 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 19
239000011734 sodium Substances 0.000 description 19
229910052708 sodium Inorganic materials 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000000354 decomposition reaction Methods 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
239000000243 solution Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 4
231100000566 intoxication Toxicity 0.000 description 4
230000035987 intoxication Effects 0.000 description 4
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
230000002443 hepatoprotective effect Effects 0.000 description 3
231100000572 poisoning Toxicity 0.000 description 3
230000000607 poisoning effect Effects 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000001989 choleretic effect Effects 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
108010082126 Alanine transaminase Proteins 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010016654 Fibrosis Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
208000015924 Lithiasis Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000002690 anti-lithiasic effect Effects 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000000731 choleretic agent Substances 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
230000007882 cirrhosis Effects 0.000 description 1
208000019425 cirrhosis of liver Diseases 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000010463 virgin olive oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Hematology (AREA)
Diabetes (AREA)
Obesity (AREA)
Gastroenterology & Hepatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

CA305,059A 1977-06-10 1978-06-08 Procede de preparation de nouveaux derives de l'acide piperazinecarbodithioique Expired CA1098524A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB24,370		1977-06-10
GB2437077		1977-06-10
GB3085177		1977-07-22
GB30,851		1977-07-22

Publications (1)

Publication Number	Publication Date
CA1098524A true CA1098524A (fr)	1981-03-31

Family

ID=26257079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA305,059A Expired CA1098524A (fr)	1977-06-10	1978-06-08	Procede de preparation de nouveaux derives de l'acide piperazinecarbodithioique

Country Status (13)

Country	Link
JP (1)	JPS545987A (de)
AT (1)	AT360545B (de)
AU (1)	AU3692878A (de)
CA (1)	CA1098524A (de)
DE (1)	DE2825407C3 (de)
ES (1)	ES470679A1 (de)
FR (1)	FR2393802A1 (de)
GR (1)	GR63662B (de)
IT (1)	IT1104750B (de)
NL (1)	NL7806321A (de)
NZ (1)	NZ187474A (de)
PT (1)	PT68159A (de)
YU (1)	YU135378A (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2961406D1 (en) *	1978-04-13	1982-01-28	Science Union & Cie	Monosubstituted piperazines, processes for their preparation and pharmaceutical compositions containing them
WO2000000482A1 (en) *	1998-06-30	2000-01-06	Neurogen Corporation	1-(benzothiazol-2-yl)-4-(1-phenylmethyl)piperazines: dopamine receptor subtype specific ligands
NZ570524A (en) *	2006-03-28	2011-08-26	High Point Pharmaceuticals Llc	Benzothiazoles having histamine H3 receptor activity
EP2350067A2 (de) *	2008-10-16	2011-08-03	Schering Corporation	Pyrrolidin-, piperidin- und piperazinderivate und verfahren zu deren anwendung

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1307256A (en) *	1970-09-15	1973-02-14	Science Union & Cie	Piperazine derivatives and a process for their preparation
CH583232A5 (de) *	1973-02-02	1976-12-31	Wander Ag Dr A
GB1432660A (en)	1973-10-30	1976-04-22	Science Union & Cie	Piperazine derivatives processes for their preparation and and pharamacueitcal compositions containing them

1978
- 1978-06-06 NZ NZ187474A patent/NZ187474A/xx unknown
- 1978-06-06 YU YU01353/78A patent/YU135378A/xx unknown
- 1978-06-08 GR GR56478A patent/GR63662B/el unknown
- 1978-06-08 CA CA305,059A patent/CA1098524A/fr not_active Expired
- 1978-06-08 IT IT49764/78A patent/IT1104750B/it active
- 1978-06-08 AU AU36928/78A patent/AU3692878A/en active Pending
- 1978-06-09 FR FR787817256A patent/FR2393802A1/fr active Granted
- 1978-06-09 PT PT68159A patent/PT68159A/pt unknown
- 1978-06-09 JP JP6975378A patent/JPS545987A/ja active Pending
- 1978-06-09 AT AT420878A patent/AT360545B/de not_active IP Right Cessation
- 1978-06-09 ES ES470679A patent/ES470679A1/es not_active Expired
- 1978-06-09 DE DE2825407A patent/DE2825407C3/de not_active Expired
- 1978-06-09 NL NL7806321A patent/NL7806321A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE2825407C3 (de)	1981-04-30
FR2393802A1 (fr)	1979-01-05
NZ187474A (en)	1981-03-16
IT7849764A0 (it)	1978-06-08
DE2825407A1 (de)	1978-12-14
PT68159A (fr)	1978-07-01
YU135378A (en)	1982-08-31
ATA420878A (de)	1980-06-15
JPS545987A (en)	1979-01-17
DE2825407B2 (de)	1980-07-10
GR63662B (en)	1979-11-28
NL7806321A (nl)	1978-12-12
AT360545B (de)	1981-01-12
IT1104750B (it)	1985-10-28
FR2393802B1 (de)	1981-04-17
AU3692878A (en)	1979-12-13
ES470679A1 (es)	1979-03-16

Legal Events

Date	Code	Title	Description
1998-03-31	MKEX	Expiry

Publication	Publication Date	Title
EP0015038B1 (de)	1984-12-19	Ein Diphenylhydantoin-Derivat enthaltende pharmazeutische Zusammensetzung, verwendete Derivate und ihre Herstellung
EP0217700A1 (de)	1987-04-08	Benzimidazolderivate, Verfahren zu deren Herstellung und deren therapeutische Anwendung
FR2488890A1 (fr)	1982-02-26	Derives tricycliques de l'imidazole, leur preparation et leurs utilisations therapeutiques
EP0061386A1 (de)	1982-09-29	(2-Oxo-3-tetrahydrothienylcarbamoyl)-alkylthio-essigsäure, ihre Salze und Ester, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
CH635080A5 (fr)	1983-03-15	Pyrazoles substitues en position 4, leur preparation et leur utilisation therapeutique.
EP0151072B1 (de)	1988-03-09	Methylendiphosphonsäure-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende antirheumatische Arzneimittel
CA1213892A (fr)	1986-11-12	Procede de preparation de nouveaux derives de la sulfonyluree
EP0024960B1 (de)	1984-12-12	Substituierte heterocyclische Phenoxyamine, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel für lokale Anästhesie
FR2595695A1 (fr)	1987-09-18	Derives de n-(((hydroxy-2 phenyl) (phenyl) methylene) amino-2) ethyl) acetamide, leur preparation et leur application en therapeutique
EP0006789A1 (de)	1980-01-09	Bis(aryloxyalkancarbonsäure)verbindungen, ihre Herstellung und ihre therapeutische Verwendung
EP0533827A1 (de)	1993-03-31	Oxazolederivate, ihre herstellung und diese enthaltende pharmazeutischen zubereitungen.
CA1139763A (fr)	1983-01-18	Procede d'obtention de nouveaux aryltrifluoroethanols
FR2521140A1 (fr)	1983-08-12	Derives d'imidazolidine, leur preparation et leur application en therapeutique
EP0110795B1 (de)	1986-03-12	Pyrrolidin-Derivate, Herstellung und Verwendung als Heilmittel
CA1100968A (fr)	1981-05-12	Procedes de preparation de nouvelles piperazines disubstituees
CA1082716A (fr)	1980-07-29	Procede de preparation de nouveaux derives de 5- thiazole methane amine
EP0196943B1 (de)	1990-01-24	8-Thiotetrahydrochinoleinderivate und deren Salze
EP0005091B1 (de)	1981-11-25	Monosubstituierte Piperazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
CH633010A5 (fr)	1982-11-15	Derives de l'isoquinoleine, leur preparation et medicament qui les contient.
FR2576900A1 (fr)	1986-08-08	Derives de cyclohepto-imidazole 2-substitue, agents anti-ulcereux et procede pour leur preparation
BE1004489A3 (fr)	1992-12-01	Derives de dihydropyrimidothiazine, leur procede de preparation et compositions pharmaceutiques les contenant.
CH630909A5 (en)	1982-07-15	New 3,5-disubstituted-1H-1,2,4-triazoles
EP0070753A1 (de)	1983-01-26	10-(Aza-1-bicyclo(2,2,2)octyl-3)-10H-Phenothiazin-sulfonamid-2, und seine Derivate
FR2692894A1 (fr)	1993-12-31	Aryl-1-(o-alcoxy-phényl-4-pipérazinyl-1)-2, 3- ou 4-alcanols, leur procédé de préparation et leur utilisation pour la préparation de médicaments.
CH667873A5 (fr)	1988-11-15	Derive de n-imidazolidinylmethyl benzamide.