LU80975A1 - Methoxy-2 benzamides - Google Patents

Methoxy-2 benzamides Download PDF

Info

Publication number: LU80975A1
Authority: LU; Luxembourg
Prior art keywords: mole; hydrochloride; water; ether; acetone
Prior art date: 1978-02-27

Application number

LU80975A

Other languages

English (en)

French (fr)

Inventor

J Kaplan

D Obitz

H Najer

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

1978-02-27 Priority claimed from FR7805579A external-priority patent/FR2418225A1/fr

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

1980-09-24 Publication of LU80975A1 publication Critical patent/LU80975A1/fr

Links

229940054066 benzamide antipsychotics Drugs 0.000 title 1
150000003936 benzamides Chemical class 0.000 title 1
229940079593 drug Drugs 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
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 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000007787 solid Substances 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
150000001875 compounds Chemical class 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000003921 oil Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
150000003839 salts Chemical class 0.000 description 5
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
238000001914 filtration Methods 0.000 description 4
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000000155 melt Substances 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical class [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
-1 2-methyl 2-ethyl Chemical group 0.000 description 1
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 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
240000007049 Juglans regia Species 0.000 description 1
235000009496 Juglans regia Nutrition 0.000 description 1
241000283986 Lepus Species 0.000 description 1
101100518501 Mus musculus Spp1 gene Proteins 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
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
101150052863 THY1 gene Proteins 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001721 carbon Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000009194 climbing Effects 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
235000020234 walnut Nutrition 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- 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
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Landscapes

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

LU80975A 1978-02-27 1979-02-27 Methoxy-2 benzamides LU80975A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR7805579A FR2418225A1 (fr)	1978-02-27	1978-02-27	Methoxy-2 benzamides et leur application en therapeutique
FR7805579		1978-02-27
FR7900259A FR2445829A2 (fr)	1978-02-27	1979-01-05	Methoxy-2 benzamides et leur application en therapeutique
FR7900259		1979-01-05

Publications (1)

Publication Number	Publication Date
LU80975A1 true LU80975A1 (fr)	1980-09-24

Family

ID=26220462

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU80975A LU80975A1 (fr)	1978-02-27	1979-02-27	Methoxy-2 benzamides

Country Status (18)

Country	Link
JP (1)	JPS54135765A (da)
AU (1)	AU521027B2 (da)
BE (1)	BE874489A (da)
DE (1)	DE2907378A1 (da)
DK (1)	DK82179A (da)
ES (1)	ES478072A1 (da)
FI (1)	FI790657A7 (da)
FR (1)	FR2445829A2 (da)
GB (1)	GB2016467A (da)
GR (1)	GR66972B (da)
IL (1)	IL56738A0 (da)
IT (1)	IT1113417B (da)
LU (1)	LU80975A1 (da)
NL (1)	NL7901473A (da)
NO (1)	NO790647L (da)
NZ (1)	NZ189770A (da)
PT (1)	PT69289A (da)
SE (1)	SE7901707L (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0320630A1 (en) *	1987-11-19	1989-06-21	The Vanderbilt University	Enantiometric iodobenzamides

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH584688A5 (da) *	1972-06-23	1977-02-15	Delmar Chem
FR2294698A1 (fr) *	1974-12-18	1976-07-16	Synthelabo	Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment
FR2393794A2 (fr) *	1977-06-06	1979-01-05	Synthelabo	Preparation de methoxy-2 benzamides
JPS52106863A (en) *	1976-03-03	1977-09-07	Teikoku Hormone Mfg Co Ltd	Synthesis of substituted benzamides
FR2360572A1 (fr) *	1976-08-05	1978-03-03	Synthelabo	Pyrrolidines substituees et leur preparation
JPS5365875A (en) *	1976-11-24	1978-06-12	Teijin Ltd	Preparation of benzenesulfone amide derivs.

1979
- 1979-01-05 FR FR7900259A patent/FR2445829A2/fr active Granted
- 1979-02-26 DK DK82179A patent/DK82179A/da not_active Application Discontinuation
- 1979-02-26 NO NO790647A patent/NO790647L/no unknown
- 1979-02-26 NZ NZ189770A patent/NZ189770A/xx unknown
- 1979-02-26 NL NL7901473A patent/NL7901473A/xx not_active Application Discontinuation
- 1979-02-26 JP JP2247779A patent/JPS54135765A/ja active Pending
- 1979-02-26 SE SE7901707A patent/SE7901707L/xx not_active Application Discontinuation
- 1979-02-26 ES ES478072A patent/ES478072A1/es not_active Expired
- 1979-02-26 IL IL56738A patent/IL56738A0/xx unknown
- 1979-02-26 IT IT20541/79A patent/IT1113417B/it active
- 1979-02-26 PT PT69289A patent/PT69289A/pt unknown
- 1979-02-26 AU AU44603/79A patent/AU521027B2/en not_active Expired - Fee Related
- 1979-02-26 DE DE19792907378 patent/DE2907378A1/de not_active Withdrawn
- 1979-02-27 BE BE0/193729A patent/BE874489A/xx unknown
- 1979-02-27 FI FI790657A patent/FI790657A7/fi not_active Application Discontinuation
- 1979-02-27 GB GB7906952A patent/GB2016467A/en not_active Withdrawn
- 1979-02-27 GR GR58491A patent/GR66972B/el unknown
- 1979-02-27 LU LU80975A patent/LU80975A1/fr unknown

Also Published As

Publication number	Publication date
NZ189770A (en)	1980-11-14
FR2445829B2 (da)	1982-09-10
NO790647L (no)	1979-08-28
GR66972B (da)	1981-05-15
IT1113417B (it)	1986-01-20
SE7901707L (sv)	1979-08-28
PT69289A (fr)	1979-03-01
IL56738A0 (en)	1979-05-31
FR2445829A2 (fr)	1980-08-01
FI790657A7 (fi)	1979-08-28
BE874489A (fr)	1979-08-27
IT7920541A0 (it)	1979-02-26
AU4460379A (en)	1979-09-06
AU521027B2 (en)	1982-03-11
NL7901473A (nl)	1979-08-29
JPS54135765A (en)	1979-10-22
ES478072A1 (es)	1979-07-01
DK82179A (da)	1979-08-28
DE2907378A1 (de)	1979-09-06
GB2016467A (en)	1979-09-26

Publication	Publication Date	Title
CH645091A5 (fr)	1984-09-14	Derives de la glycinamide, leur preparation et compositions pharmaceutiques les contenant.
BE1000164A5 (fr)	1988-07-05	Nouveaux derives de dihydrobenzofuranne- et de chromane - carboxamides, leurs procedes de preparation et leur utilisation comme neuroleptiques.
FR2548666A1 (fr)	1985-01-11	Nouveaux derives du nor-tropane et du granatane, leur procede de preparation et leur application en therapeutique
FR2468601A1 (fr)	1981-05-08	Nouveaux derives de flavanne utiles notamment comme anticonvulsivants
EP0486386A2 (fr)	1992-05-20	Nouveaux dérivés de la N-benzoyl proline, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
EP0351255B1 (fr)	1993-10-13	Dérivés de [(pipéridinyl-4)méthyl]-2 tétrahydro-1,2,3,4 isoquinoléine, leur préparation et leur application en thérapeutique
CA2565293C (fr)	2012-10-30	Derives de tetrahydroisoquinolilsulfonamides, leur preparation et leur utilisation en therapeutique
EP0461986A1 (fr)	1991-12-18	Dérivés d'hexahydroazépines, un procédé pour leur préparation et compositions pharmaceutiques les contenant
JPS6326099B2 (da)	1988-05-27
EP0002978B1 (fr)	1982-10-06	Dérivés de thiazolidinedione-2,4, leur préparation et leur application en thérapeutique
EP0064445B1 (fr)	1984-10-24	Dialcoxy (2,4) benzènesulfonamides N-substitués
BG62349B2 (bg)	1999-08-31	N-заместени производни на 3-азабицикло/3.2.0/хептан като невролептици
EP0077427A1 (fr)	1983-04-27	Dérivés de pipéridine, leur procédé de préparation et leur application en thérapeutique
LU80975A1 (fr)	1980-09-24	Methoxy-2 benzamides
FR2634207A1 (fr)	1990-01-19	Derives de ((piperidinyl-4)methyl) benzazepines, leur preparation et leur application en therapeutique
CH653011A5 (fr)	1985-12-13	Derives benzylideniques, leur preparation et les medicaments et compositions pharmaceutiques les renfermant.
WO1994020466A1 (fr)	1994-09-15	Nouveaux derives de la phenoxy-2 ethylamine, leur preparation et leur application en therapeutique
CA1276644C (fr)	1990-11-20	Benzamides, leur procede de preparation et leur application dans le domaine therapeutique
CH407087A (fr)	1966-02-15	Procédé de préparation de nouveaux dérivés de la diphénylacétamide
EP0067094A1 (fr)	1982-12-15	Dérivés hétérocycliques d'amidoximes, leur préparation et leur application en thérapeutique
EP0351283A1 (fr)	1990-01-17	Dérivés de [(pipéridinyl-4) méthyl]-2 dihydro-2,3 1H-isoindole et tétrahydro-2,3,4,5 1H-benzazépines, leur préparation et leur application en thérapeutique
EP0106860B1 (fr)	1988-01-20	Nouvelles carboxamidoguanidines, leur procede d'obtention et les compositions pharmaceutiques en renfermant
MC706A1 (fr)	1968-12-17	Procédé de synthèse de nouveaux 2-arylakyloxy benzamides substitués
CA1265799A (fr)	1990-02-13	Procede de preparation de nouveaux derives de l'acide thiophene acetique
CH637378A5 (fr)	1983-07-29	Benzamides cycloalkylalkyliques.