CA1105937A - Procede pour la preparation de (cycloalkyl)- alkylbenzamides - Google Patents

Procede pour la preparation de (cycloalkyl)- alkylbenzamides

Info

Publication number: CA1105937A
Authority: CA; Canada
Prior art keywords: methoxy; methyl; process according; cyclopropylmethylpyrrolidin; mol
Prior art date: 1978-02-27
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

CA322,283A

Other languages

English (en)

Inventor

Jean P. Kaplan

Henry Najer

Daniel C.L. Obitz

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.)

Synthelabo SA

Original Assignee

Synthelabo SA

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

1981-07-28

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

1981-07-28 Application granted granted Critical

1981-07-28 Publication of CA1105937A publication Critical patent/CA1105937A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 title description 2
239000002253 acid Substances 0.000 claims abstract description 12
238000000034 method Methods 0.000 claims abstract description 11
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 9
150000007513 acids Chemical class 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims abstract description 4
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 abstract description 3
239000005711 Benzoic acid Substances 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
229940054066 benzamide antipsychotics Drugs 0.000 claims abstract 2
150000003936 benzamides Chemical class 0.000 claims abstract 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
AQZWYQHLYWDFEO-UHFFFAOYSA-N n-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-5-methylbenzenecarbothioamide Chemical compound COC1=CC=C(C)C=C1C(=S)NCC1N(CC2CC2)CCC1 AQZWYQHLYWDFEO-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 3
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 claims description 3
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical group [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 10
210000003169 central nervous system Anatomy 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
239000000203 mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
238000009835 boiling Methods 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
239000000284 extract Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
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
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
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
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
239000000706 filtrate Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
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 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
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-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
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
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
XRLGBRNXGIPAGC-UHFFFAOYSA-N (1-cyclopropyl-2-methylpyrrolidin-2-yl)methanamine Chemical compound NCC1(N(CCC1)C1CC1)C XRLGBRNXGIPAGC-UHFFFAOYSA-N 0.000 description 1
-1 (S)-2-aminomethyl-1-cyclopropyl-methylpyrrolidine Chemical compound 0.000 description 1
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
COVAZHQHYXQLOT-UHFFFAOYSA-N 2-methoxy-3-(trifluoromethyl)benzoic acid Chemical compound COC1=C(C(O)=O)C=CC=C1C(F)(F)F COVAZHQHYXQLOT-UHFFFAOYSA-N 0.000 description 1
MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical class COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-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
208000020401 Depressive disease Diseases 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
QFIYFROFRTUSPW-VIFPVBQESA-N [(2s)-1-(cyclopropylmethyl)pyrrolidin-2-yl]methanamine Chemical compound NC[C@@H]1CCCN1CC1CC1 QFIYFROFRTUSPW-VIFPVBQESA-N 0.000 description 1
QFIYFROFRTUSPW-UHFFFAOYSA-N [1-(cyclopropylmethyl)pyrrolidin-2-yl]methanamine Chemical compound NCC1CCCN1CC1CC1 QFIYFROFRTUSPW-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 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
239000003610 charcoal Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
230000009194 climbing Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 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
239000012071 phase Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate 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
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 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)

CA322,283A 1978-02-27 1979-02-26 Procede pour la preparation de (cycloalkyl)- alkylbenzamides Expired CA1105937A (fr)

Applications Claiming Priority (2)

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
FR7805580		1978-02-27

Publications (1)

Publication Number	Publication Date
CA1105937A true CA1105937A (fr)	1981-07-28

Family

ID=9205110

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA322,283A Expired CA1105937A (fr)	1978-02-27	1979-02-26	Procede pour la preparation de (cycloalkyl)- alkylbenzamides

Country Status (23)

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

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1988009404A1 (fr) *	1987-05-25	1988-12-01	Foreshore Protection Pty Limited	Matelas de revetement de sol

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2245628B1 (fr) *	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/fr 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/fr 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/fr 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 (fr)	1980-11-07
NZ189771A (en)	1980-11-14
JPS54122269A (en)	1979-09-21
IL56747A0 (en)	1979-05-31
GR66973B (fr)	1981-05-15
AT373581B (de)	1984-02-10
NO790648L (no)	1979-08-28
IT1114210B (it)	1986-01-27
ZA799808B (en)	1980-06-25
CH637378A5 (fr)	1983-07-29
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
1998-07-28	MKEX	Expiry

Publication	Publication Date	Title
USRE34878E (en)	1995-03-14	Hypoglycemic agent
CA2575232C (fr)	2012-06-26	5-subsitue-2-phenylamine benzamide agissant en tant qu'inhibiteur mek
US5225585A (en)	1993-07-06	Production of fluoxetine and new intermediates
CA1116611A (fr)	1982-01-19	Derives de l'imidazole utilise comme anticonvulsivant
CH639962A5 (fr)	1983-12-15	N-aryle oxazolidinones et pyrrolidinones.
US4800044A (en)	1989-01-24	Intermediates for the production of 1,2-dithiolan acid (thioctic acid)
US4246267A (en)	1981-01-20	Aminopiperidines, their production and the pharmaceutical compositions incorporating them
EP0094102B1 (fr)	1985-12-27	Nouveaux dérivés de 1-(1-cyclohexénylméthyl) pyrrolidine et leur procédé de préparation
US3551419A (en)	1970-12-29	Amino acid amides and process for their production
CH639078A5 (fr)	1983-10-31	Amides derives d'acides carboxyliques-5 pyrimidiniques, leur preparation et medicaments les contenant.
CA1105937A (fr)	1981-07-28	Procede pour la preparation de (cycloalkyl)- alkylbenzamides
FR2471376A1 (fr)	1981-06-19	Derives de thioethylamide, utiles comme bloqueurs d'histamine h2
US20060135785A1 (en)	2006-06-22	Alpha-phenyl acetanilide derivatives having an acat inhibiting activity and the therapeutic application thereof
KR0181945B1 (ko)	1999-05-01	N,n'-비스(알콕시알킬)-피리딘-2,4-디카복실산 디아미드, 이의 제조방법 및 이를 함유하는 약제학적 조성물
US4183954A (en)	1980-01-15	Benzoic acid derivatives and therapeutic composition containing the same
US4457872A (en)	1984-07-03	2-Hydroxyoxanilic acid derivatives
GB2083022A (en)	1982-03-17	Phenethylamine derivatives and their production
GB2053897A (en)	1981-02-11	Piperazine derivatives
US5100911A (en)	1992-03-31	Thienyloxyalkylamine derivatives, process for their preparation and medicaments containing them
FR2522000A1 (fr)	1983-08-26	Nouvelles thiopyrannopyrimidines, utiles notamment comme agents hypoglycemiants, et leur fabrication
US5091403A (en)	1992-02-25	Sulfinyl imidazole derivatives and antiulcer agents containing the same
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