LU80976A1 - Benzamides cycloalkylalkyliques - Google Patents

Benzamides cycloalkylalkyliques Download PDF

Info

Publication number: LU80976A1
Authority: LU; Luxembourg
Prior art keywords: benzamides; mole; acid; acetone; methoxy
Prior art date: 1978-02-27

Application number

LU80976A

Other languages

English (en)

French (fr)

Inventor

J Kaplan

H Najer

D Obtiz

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

1979-02-27

Publication date

1980-09-24

1979-02-27 Application filed by Synthelabo filed Critical Synthelabo

1980-09-24 Publication of LU80976A1 publication Critical patent/LU80976A1/fr

Links

229940054066 benzamide antipsychotics Drugs 0.000 title claims 4
150000003936 benzamides Chemical class 0.000 title claims 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
239000005711 Benzoic acid Substances 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
235000010233 benzoic acid Nutrition 0.000 claims description 3
238000000034 method Methods 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
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 1
229910052799 carbon Inorganic materials 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000284 extract Substances 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
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
-1 1-cyclopropylmethyl-2-pyrrolidinyl Chemical group 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
AJGHIKKOAMKRMC-UHFFFAOYSA-N 2-methoxy-5-methylbenzenecarbothioamide Chemical compound COC1=CC=C(C)C=C1C(N)=S AJGHIKKOAMKRMC-UHFFFAOYSA-N 0.000 description 1
KZZUPJSYJCNYMW-UHFFFAOYSA-N 2-methoxy-5-methylbenzenecarbothioyl chloride Chemical compound COC1=CC=C(C)C=C1C(Cl)=S KZZUPJSYJCNYMW-UHFFFAOYSA-N 0.000 description 1
NUFFXGAGGYWFAV-UHFFFAOYSA-N 3-methylbenzenecarbothioamide Chemical compound CC1=CC=CC(C(N)=S)=C1 NUFFXGAGGYWFAV-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 description 1
241000751100 Pityopus Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
241000212342 Sium Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
230000009194 climbing Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
150000002680 magnesium Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000003109 potassium Chemical class 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
239000003507 refrigerant Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000003643 water by type Substances 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)

LU80976A 1978-02-27 1979-02-27 Benzamides cycloalkylalkyliques LU80976A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7805580		1978-02-27
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
LU80976A1 true LU80976A1 (fr)	1980-09-24

Family

ID=9205110

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU80976A LU80976A1 (fr)	1978-02-27	1979-02-27	Benzamides cycloalkylalkyliques

Country Status (23)

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

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 (it) *	1973-09-28	1977-03-11	Ile De France

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

Also Published As

Publication number	Publication date
IT1114210B (it)	1986-01-27
BE874490A (fr)	1979-08-27
FR2418226A1 (fr)	1979-09-21
DE2907377A1 (de)	1979-09-06
PT69290A (fr)	1979-03-01
ZA799808B (en)	1980-06-25
NL7901472A (nl)	1979-08-29
JPS54122269A (en)	1979-09-21
SE7901708L (sv)	1979-08-28
ES478073A1 (es)	1979-05-16
AT373581B (de)	1984-02-10
GB2014995A (en)	1979-09-05
IT7920542A0 (it)	1979-02-26
ATA149479A (de)	1983-06-15
AU4460479A (en)	1979-09-06
GB2014995B (en)	1982-07-28
FR2418226B1 (it)	1980-11-07
NO790648L (no)	1979-08-28
CH637378A5 (fr)	1983-07-29
SE430501B (sv)	1983-11-21
AU521854B2 (en)	1982-05-06
IL56747A0 (en)	1979-05-31
GR66973B (it)	1981-05-15
IE47897B1 (en)	1984-07-11
FI790658A7 (fi)	1979-08-28
IE790558L (en)	1979-08-27
NZ189771A (en)	1980-11-14
DK82379A (da)	1979-08-28
CA1105937A (en)	1981-07-28

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