CH637378A5 - Benzamides cycloalkylalkyliques. - Google Patents

Benzamides cycloalkylalkyliques. Download PDF

Info

Publication number: CH637378A5
Authority: CH; Switzerland
Prior art keywords: formula; compounds; benzamides; methoxy; acid
Prior art date: 1978-02-27

Application number

CH188379A

Other languages

English (en)

French (fr)

Inventor

Jean Pierre Kaplan

Henry Najer

Daniel Charles Leon Obitz

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.)

1978-02-27

Filing date

1979-02-26

Publication date

1983-07-29

1979-02-26 Application filed by Synthelabo filed Critical Synthelabo

1983-07-29 Publication of CH637378A5 publication Critical patent/CH637378A5/fr

Links

229940054066 benzamide antipsychotics Drugs 0.000 title claims description 7
150000003936 benzamides Chemical class 0.000 title claims 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 5
238000000034 method Methods 0.000 claims description 4
235000010233 benzoic acid Nutrition 0.000 claims description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
208000020401 Depressive disease Diseases 0.000 claims description 2
208000028017 Psychotic disease Diseases 0.000 claims description 2
210000003169 central nervous system Anatomy 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 6
150000007513 acids Chemical class 0.000 claims 4
239000005711 Benzoic acid Substances 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
150000002148 esters Chemical class 0.000 claims 2
150000004820 halides Chemical class 0.000 claims 2
238000002360 preparation method Methods 0.000 claims 2
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical group [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000001816 cooling Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
-1 1-cyclopropylmethyl-2-pyrrolidinyl Chemical group 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
AJGHIKKOAMKRMC-UHFFFAOYSA-N 2-methoxy-5-methylbenzenecarbothioamide Chemical compound COC1=CC=C(C)C=C1C(N)=S AJGHIKKOAMKRMC-UHFFFAOYSA-N 0.000 description 2
KZZUPJSYJCNYMW-UHFFFAOYSA-N 2-methoxy-5-methylbenzenecarbothioyl chloride Chemical compound COC1=CC=C(C)C=C1C(Cl)=S KZZUPJSYJCNYMW-UHFFFAOYSA-N 0.000 description 2
OUBZCDOQEMLMAB-UHFFFAOYSA-N 5-chlorosulfonyl-2-methoxybenzoic acid Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1C(O)=O OUBZCDOQEMLMAB-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
BZKGHSWMKGRQMK-UHFFFAOYSA-N N-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-5-(trifluoromethyl)benzamide Chemical compound C1(CC1)CN1C(CCC1)CNC(C1=C(C=CC(=C1)C(F)(F)F)OC)=O BZKGHSWMKGRQMK-UHFFFAOYSA-N 0.000 description 2
ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000001559 benzoic acids Chemical class 0.000 description 2
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
IUTPSVNWIWQIDX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)pyrazol-4-yl]ethanone Chemical compound C1=C(C(=O)C)C=NN1C1=CC=C(Cl)C=C1 IUTPSVNWIWQIDX-UHFFFAOYSA-N 0.000 description 1
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 1
NAKZCKOHULJEID-UHFFFAOYSA-N 2-methoxy-5-(trifluoromethyl)benzoic acid Chemical compound COC1=CC=C(C(F)(F)F)C=C1C(O)=O NAKZCKOHULJEID-UHFFFAOYSA-N 0.000 description 1
YRNOLZJRZSOMLM-UHFFFAOYSA-N 2-methoxy-5-(trifluoromethyl)benzoyl chloride Chemical compound COC1=CC=C(C(F)(F)F)C=C1C(Cl)=O YRNOLZJRZSOMLM-UHFFFAOYSA-N 0.000 description 1
LWNHLPYZJKAQFR-UHFFFAOYSA-N 5-ethyl-2-methoxybenzenecarbothioamide Chemical compound CCC1=CC=C(OC)C(C(N)=S)=C1 LWNHLPYZJKAQFR-UHFFFAOYSA-N 0.000 description 1
WBRILLISQMMNMD-UHFFFAOYSA-N 5-ethyl-2-methoxybenzenecarbothioyl chloride Chemical compound COC1=C(C(=S)Cl)C=C(C=C1)CC WBRILLISQMMNMD-UHFFFAOYSA-N 0.000 description 1
BOLLTSUCKRNILK-UHFFFAOYSA-N COC1=C(C(=S)O)C=C(C=C1)CC Chemical compound COC1=C(C(=S)O)C=C(C=C1)CC BOLLTSUCKRNILK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
SSBVKRBRXURZDE-UHFFFAOYSA-N N-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-5-ethyl-2-methoxybenzenecarbothioamide Chemical compound C1(CC1)CN1C(CCC1)CNC(C1=C(C=CC(=C1)CC)OC)=S SSBVKRBRXURZDE-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
229960004046 apomorphine Drugs 0.000 description 1
SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
230000009194 climbing Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000003507 refrigerant Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyrrole Compounds (AREA)

CH188379A 1978-02-27 1979-02-26 Benzamides cycloalkylalkyliques. CH637378A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7805580A FR2418226A1 (fr)	1978-02-27	1978-02-27	Methoxy-2 alkylthio-5 benzamides et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
CH637378A5 true CH637378A5 (fr)	1983-07-29

Family

ID=9205110

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH188379A CH637378A5 (fr)	1978-02-27	1979-02-26	Benzamides cycloalkylalkyliques.

Country Status (23)

Country	Link
JP (1)	JPS54122269A (de)
AT (1)	AT373581B (de)
AU (1)	AU521854B2 (de)
BE (1)	BE874490A (de)
CA (1)	CA1105937A (de)
CH (1)	CH637378A5 (de)
DE (1)	DE2907377A1 (de)
DK (1)	DK82379A (de)
ES (1)	ES478073A1 (de)
FI (1)	FI790658A7 (de)
FR (1)	FR2418226A1 (de)
GB (1)	GB2014995B (de)
GR (1)	GR66973B (de)
IE (1)	IE47897B1 (de)
IL (1)	IL56747A0 (de)
IT (1)	IT1114210B (de)
LU (1)	LU80976A1 (de)
NL (1)	NL7901472A (de)
NO (1)	NO790648L (de)
NZ (1)	NZ189771A (de)
PT (1)	PT69290A (de)
SE (1)	SE430501B (de)
ZA (1)	ZA799808B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1988009404A1 (en) *	1987-05-25	1988-12-01	Foreshore Protection Pty Limited	Revetment mattress

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2245628B1 (de) *	1973-09-28	1977-03-11	Ile De France

1978
- 1978-02-27 FR FR7805580A patent/FR2418226A1/fr active Granted
1979
- 1979-02-26 ZA ZA00799808A patent/ZA799808B/xx unknown
- 1979-02-26 IT IT20542/79A patent/IT1114210B/it active
- 1979-02-26 JP JP2247679A patent/JPS54122269A/ja active Pending
- 1979-02-26 AU AU44604/79A patent/AU521854B2/en not_active Ceased
- 1979-02-26 NL NL7901472A patent/NL7901472A/xx not_active Application Discontinuation
- 1979-02-26 NZ NZ189771A patent/NZ189771A/xx unknown
- 1979-02-26 SE SE7901708A patent/SE430501B/sv unknown
- 1979-02-26 CA CA322,283A patent/CA1105937A/en not_active Expired
- 1979-02-26 DK DK82379A patent/DK82379A/da not_active Application Discontinuation
- 1979-02-26 CH CH188379A patent/CH637378A5/fr not_active IP Right Cessation
- 1979-02-26 DE DE19792907377 patent/DE2907377A1/de not_active Withdrawn
- 1979-02-26 PT PT69290A patent/PT69290A/pt unknown
- 1979-02-26 ES ES478073A patent/ES478073A1/es not_active Expired
- 1979-02-26 NO NO790648A patent/NO790648L/no unknown
- 1979-02-27 FI FI790658A patent/FI790658A7/fi not_active Application Discontinuation
- 1979-02-27 IL IL56747A patent/IL56747A0/xx unknown
- 1979-02-27 GB GB7906954A patent/GB2014995B/en not_active Expired
- 1979-02-27 AT AT0149479A patent/AT373581B/de not_active IP Right Cessation
- 1979-02-27 BE BE0/193730A patent/BE874490A/xx not_active IP Right Cessation
- 1979-02-27 LU LU80976A patent/LU80976A1/fr unknown
- 1979-02-27 GR GR58492A patent/GR66973B/el unknown
- 1979-08-08 IE IE558/79A patent/IE47897B1/en unknown

Also Published As

Publication number	Publication date
IT7920542A0 (it)	1979-02-26
IE47897B1 (en)	1984-07-11
LU80976A1 (fr)	1980-09-24
DE2907377A1 (de)	1979-09-06
ATA149479A (de)	1983-06-15
AU521854B2 (en)	1982-05-06
FR2418226A1 (fr)	1979-09-21
GB2014995B (en)	1982-07-28
PT69290A (fr)	1979-03-01
FR2418226B1 (de)	1980-11-07
NZ189771A (en)	1980-11-14
JPS54122269A (en)	1979-09-21
IL56747A0 (en)	1979-05-31
GR66973B (de)	1981-05-15
AT373581B (de)	1984-02-10
NO790648L (no)	1979-08-28
IT1114210B (it)	1986-01-27
ZA799808B (en)	1980-06-25
CA1105937A (en)	1981-07-28
AU4460479A (en)	1979-09-06
BE874490A (fr)	1979-08-27
GB2014995A (en)	1979-09-05
IE790558L (en)	1979-08-27
ES478073A1 (es)	1979-05-16
FI790658A7 (fi)	1979-08-28
DK82379A (da)	1979-08-28
SE430501B (sv)	1983-11-21
SE7901708L (sv)	1979-08-28
NL7901472A (nl)	1979-08-29

Legal Events

Date	Code	Title	Description
1984-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
FR2619109A1 (fr)	1989-02-10	Acides sulfonamidothienylcarboxyliques a action therapeutique
EP0015038A1 (de)	1980-09-03	Ein Diphenylhydantoin-Derivat enthaltende pharmazeutische Zusammensetzung, verwendete Derivate und ihre Herstellung
FR2733750A1 (fr)	1996-11-08	Derives de l'acide gamma-oxo-alpha-(phenylmethyl)-5,6- dihydro-4h-thieno(3,4-c)pyrrole-5-butanoique, leur preparation et leur application en therapeutique
FR2468601A1 (fr)	1981-05-08	Nouveaux derives de flavanne utiles notamment comme anticonvulsivants
EP0461958B1 (de)	1994-09-14	2-(Aminoalkyl)-5-(arylalkyl)1,3-dioxanderivate, ihre Herstellung und ihre Anwendung in der Therapeutik
EP0021940B1 (de)	1983-01-19	Aminoderivate von Benzothiazol, Verfahren zu ihrer Herstellung und ihre Anwendung in der Heilkunde
FR2584713A1 (fr)	1987-01-16	Nouveaux derives de l'indole carboxamide, leurs sels, procede et intermediaires de preparation, application a titre de medicaments et compositions les renfermant
CH617923A5 (de)	1980-06-30
EP0239436B1 (de)	1990-06-20	Tricyclisches Derivat, nämlich 5-(3-Chloro-6-methyl-5,5-dioxo-6,11-dihydro-dibenzo[c,f] [1,2]-thiazepin-11-yl amino)-pentansäure, Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel
EP0002978B1 (de)	1982-10-06	Thiazolidindion-2,4 Derivate, deren Herstellung und Verwendung als Arzneimittel
CH619935A5 (de)	1980-10-31
CH675245A5 (de)	1990-09-14
CH615414A5 (de)	1980-01-31
CH637378A5 (fr)	1983-07-29	Benzamides cycloalkylalkyliques.
CH637112A5 (fr)	1983-07-15	Derives benzylideniques.
EP0869952B1 (de)	2001-09-19	Derivate von 5-naphthalin-1-yl-1,3-dioxanen, ihre herstellung und therapeutische anwendung
CA1076117A (fr)	1980-04-22	Procede d'obtention de nouveaux ethers aryliques et les produits en resultant
CH407087A (fr)	1966-02-15	Procédé de préparation de nouveaux dérivés de la diphénylacétamide
EP0002401B1 (de)	1980-12-10	Naphtalen-Derivate, Verfahren zu deren Herstellung und deren Verwendung in der Therapeutik
EP0275762B1 (de)	1993-11-18	Indol-Carboxamid-Derivate und ihre Salze, Verfahren und Zwischenprodukte zur Herstellung, Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten
EP0100257B1 (de)	1988-02-24	Aminoalkylnaphthalen-Derivate, ihre Salze und Verfahren zu ihrer Herstellung und die Verwendung dieser Derivate und Salze in der Therapeutik
EP0067094A1 (de)	1982-12-15	Heterocyclische Derivate von Amidoxinen, ihre Herstellung und therapeutische Verwendung
CH392483A (fr)	1965-05-31	Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques
CH667873A5 (fr)	1988-11-15	Derive de n-imidazolidinylmethyl benzamide.
EP0125975B1 (de)	1986-03-26	Diphenylazometine mit veresterter Kette, Herstellungsverfahren und therapeutische Verwendung