CA1119613A - Methode de preparation de derives de la benzylidene - Google Patents

Methode de preparation de derives de la benzylidene

Info

Publication number: CA1119613A
Authority: CA; Canada
Prior art keywords: compounds; alkyl; process according; compound; formula
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

CA000322406A

Other languages

English (en)

Inventor

Jean P. Kaplan

Bernard M. Raizon

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

1979-02-27

Publication date

1982-03-09

1978-02-27 Priority claimed from FR7805578A external-priority patent/FR2418222A2/fr

1978-07-13 Priority claimed from FR7820940A external-priority patent/FR2430936A1/fr

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

1982-03-09 Application granted granted Critical

1982-03-09 Publication of CA1119613A publication Critical patent/CA1119613A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 6
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 46
150000002576 ketones Chemical class 0.000 claims abstract description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
150000001340 alkali metals Chemical group 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
125000005843 halogen group Chemical group 0.000 claims abstract description 5
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims abstract description 5
150000002825 nitriles Chemical class 0.000 claims abstract description 5
238000003797 solvolysis reaction Methods 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
239000002585 base Substances 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims abstract 12
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract 2
230000002152 alkylating effect Effects 0.000 claims abstract 2
230000005494 condensation Effects 0.000 claims abstract 2
238000009833 condensation Methods 0.000 claims abstract 2
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 claims description 3
229940124277 aminobutyric acid Drugs 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
229940067621 aminobutyrate Drugs 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 1
235000019253 formic acid Nutrition 0.000 claims 1
239000007789 gas Substances 0.000 claims 1
210000003169 central nervous system Anatomy 0.000 abstract description 3
239000001961 anticonvulsive agent Substances 0.000 abstract description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
230000001773 anti-convulsant effect Effects 0.000 abstract 1
229940125681 anticonvulsant agent Drugs 0.000 abstract 1
206010015037 epilepsy Diseases 0.000 abstract 1
125000001309 chloro group Chemical group Cl* 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 21
239000000243 solution Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
239000013078 crystal Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
239000003610 charcoal Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000011282 treatment Methods 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229960001701 chloroform Drugs 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
235000013311 vegetables Nutrition 0.000 description 5
-1 BENZYLIDENE Chemical class 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
239000000155 melt Substances 0.000 description 3
150000003254 radicals Chemical group 0.000 description 3
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 2
239000008298 dragée Substances 0.000 description 2
229960003692 gamma aminobutyric acid Drugs 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
KJQMWRYFJFWFES-UHFFFAOYSA-N (4-chlorophenyl) 2,4-dichlorobenzoate Chemical compound C1=CC(Cl)=CC=C1OC(=O)C1=CC=C(Cl)C=C1Cl KJQMWRYFJFWFES-UHFFFAOYSA-N 0.000 description 1
CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
208000012902 Nervous system disease Diseases 0.000 description 1
208000025966 Neurological disease Diseases 0.000 description 1
208000028017 Psychotic disease Diseases 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
238000004458 analytical method Methods 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000002981 blocking agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000002920 convulsive effect Effects 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
201000010099 disease Diseases 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
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
230000003371 gabaergic effect Effects 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000007911 parenteral administration 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
230000001242 postsynaptic effect Effects 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic

Landscapes

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

CA000322406A 1978-02-27 1979-02-27 Methode de preparation de derives de la benzylidene Expired CA1119613A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR7805578A FR2418222A2 (fr)	1975-08-01	1978-02-27	Procede de preparation de derives benzylideniques
FR7805578		1978-02-27
FR7820940		1978-07-13
FR7820940A FR2430936A1 (fr)	1978-07-13	1978-07-13	Derives benzylideniques, leur preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
CA1119613A true CA1119613A (fr)	1982-03-09

Family

ID=26220461

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000322406A Expired CA1119613A (fr)	1978-02-27	1979-02-27	Methode de preparation de derives de la benzylidene

Country Status (20)

Country	Link
JP (1)	JPS54125644A (fr)
AT (1)	AT365564B (fr)
AU (1)	AU520618B2 (fr)
BE (1)	BE874488A (fr)
CA (1)	CA1119613A (fr)
CH (1)	CH637112A5 (fr)
DE (1)	DE2907379A1 (fr)
DK (1)	DK82079A (fr)
ES (1)	ES478070A1 (fr)
FI (1)	FI790656A7 (fr)
GB (1)	GB2021559B (fr)
GR (1)	GR66971B (fr)
IE (1)	IE47930B1 (fr)
IT (1)	IT1113010B (fr)
LU (1)	LU80974A1 (fr)
NL (1)	NL7901474A (fr)
NO (1)	NO790646L (fr)
NZ (1)	NZ189769A (fr)
PT (1)	PT69288A (fr)
SE (1)	SE7901706L (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0047516B1 (fr) *	1980-09-04	1984-01-04	Toray Industries, Inc.	Dérivés de la propylamine et leur procédé de préparation
JPS5746951A (en) *	1980-09-04	1982-03-17	Toray Ind Inc	Production of 2-amino-4-cyanobutyric derivative
FR2536746A1 (fr) *	1982-11-29	1984-06-01	Synthelabo	Derives benzylideniques alkyles, leur preparation et leur application en therapeutique
FR2544308B1 (fr) *	1983-04-14	1985-06-14	Synthelabo	Ethines substituees, leur preparation et leur application en therapeutique
ES2058580T3 (es) *	1988-11-03	1994-11-01	Fournier Ind & Sante	Nuevos beta-d-feniltioxilosidos, su metodo de preparacion y su uso como medicamentos.
WO1991007380A1 (fr) *	1989-11-08	1991-05-30	Dunlena Pty. Ltd.	Arthropodicides
JP2005232103A (ja) *	2004-02-20	2005-09-02	Nagase & Co Ltd	光学活性なビシナルジアミンおよびその製造方法

1979
- 1979-02-26 ES ES478070A patent/ES478070A1/es not_active Expired
- 1979-02-26 DK DK82079A patent/DK82079A/da not_active Application Discontinuation
- 1979-02-26 SE SE7901706A patent/SE7901706L/xx not_active Application Discontinuation
- 1979-02-26 NL NL7901474A patent/NL7901474A/xx active Search and Examination
- 1979-02-26 NO NO790646A patent/NO790646L/no unknown
- 1979-02-26 DE DE19792907379 patent/DE2907379A1/de not_active Withdrawn
- 1979-02-26 AU AU44602/79A patent/AU520618B2/en not_active Ceased
- 1979-02-26 IT IT20543/79A patent/IT1113010B/it active
- 1979-02-26 NZ NZ189769A patent/NZ189769A/xx unknown
- 1979-02-26 JP JP2247179A patent/JPS54125644A/ja active Pending
- 1979-02-26 CH CH188579A patent/CH637112A5/fr not_active IP Right Cessation
- 1979-02-26 PT PT69288A patent/PT69288A/fr unknown
- 1979-02-27 GB GB7906963A patent/GB2021559B/en not_active Expired
- 1979-02-27 GR GR58490A patent/GR66971B/el unknown
- 1979-02-27 BE BE0/193728A patent/BE874488A/fr not_active IP Right Cessation
- 1979-02-27 CA CA000322406A patent/CA1119613A/fr not_active Expired
- 1979-02-27 AT AT0149179A patent/AT365564B/de not_active IP Right Cessation
- 1979-02-27 FI FI790656A patent/FI790656A7/fi not_active Application Discontinuation
- 1979-02-27 LU LU80974A patent/LU80974A1/fr unknown
- 1979-08-08 IE IE556/79A patent/IE47930B1/en unknown

Also Published As

Publication number	Publication date
NL7901474A (nl)	1979-08-29
GB2021559A (en)	1979-12-05
LU80974A1 (fr)	1980-09-24
ES478070A1 (es)	1979-07-01
NZ189769A (en)	1981-07-13
IE790556L (en)	1979-08-27
FI790656A7 (fi)	1979-08-28
BE874488A (fr)	1979-08-27
AU520618B2 (en)	1982-02-11
IT1113010B (it)	1986-01-20
AU4460279A (en)	1979-09-06
DE2907379A1 (de)	1979-09-06
ATA149179A (de)	1981-06-15
IT7920543A0 (it)	1979-02-26
DK82079A (da)	1979-08-28
JPS54125644A (en)	1979-09-29
PT69288A (fr)	1979-03-01
NO790646L (no)	1979-08-28
SE7901706L (sv)	1979-08-28
CH637112A5 (fr)	1983-07-15
IE47930B1 (en)	1984-07-25
AT365564B (de)	1982-01-25
GB2021559B (en)	1982-07-07
GR66971B (fr)	1981-05-15

Legal Events

Date	Code	Title	Description
1999-03-09	MKEX	Expiry

Publication	Publication Date	Title
FI69451C (fi)	1986-02-10	Foerfarande foer framstaellning av antiinflammatoriska 4,5-diaryl-2-nitroimidazoler
KR860001864B1 (ko)	1986-10-24	치환이미다졸 유도체의 제조방법
FI77448B (fi)	1988-11-30	Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-fenyl-2-piperidinopropanolderivat.
SU820659A3 (ru)	1981-04-07	Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/
US4350705A (en)	1982-09-21	Cyclohexane derivatives, process for preparation thereof and medicines containing these cyclohexane derivatives
US4110337A (en)	1978-08-29	Triazolobenzodiazepines
JPS582936B2 (ja)	1983-01-19	５↓−アロイルピロ−ル酢酸およびその塩類の製法
US5236940A (en)	1993-08-17	Pharmaceutical compositions, 2-benzothiazolamine derivatives, and their preparation
HU198030B (en)	1989-07-28	Process for production of derivatives of benzotiasole and benzotiophen and medical preparatives containing these compounds as active substance
CA1302417C (fr)	1992-06-02	1-naphtols substitues en 2 utilises comme inhibiteurs de la 5-lipogenase
CA1187505A (fr)	1985-05-21	Derives de 3,5-di-tert-butylstyrene, leurs sels et les produits pharmaceutiques qui les emploient comme principe actif
FR2649612A1 (fr)	1991-01-18	Medicaments a base de derives de 1h-benzoxadiazine-4,1,2 nouveaux derives et leurs procedes de preparation
US4927835A (en)	1990-05-22	Acylphenol derivatives, useful as anti-inflammatory agents and pain suppressants
US4238498A (en)	1980-12-09	Antimycotic substituted diphenyl-imidazolyl-methanes
IE47930B1 (en)	1984-07-25	Benzylidene derivatives
US4639521A (en)	1987-01-27	Isoquinoline derivatives
Wells et al.	1969	Synthesis of 2-azetidinones
JPS6135991B2 (fr)	1986-08-15
US4208425A (en)	1980-06-17	Novel diketones
US4432991A (en)	1984-02-21	Therapeutically active 3-amino-1-phenyl(and substituted phenyl)-2-pyrazolines
US5489592A (en)	1996-02-06	3,4-dihydro-4-oxo-3-(2-propenyl)-1-phthalazineacetic acids and derivatives, their preparations and medicines containing them
US4400536A (en)	1983-08-23	Benzylidene derivatives
US4478851A (en)	1984-10-23	Benzylidene derivatives and compositions containing them
US4447442A (en)	1984-05-08	3-Trifluoroacetylamino-1-aryl-2-pyrazolines
US4511566A (en)	1985-04-16	2-N-Cycloalkylmethyl 3-oxo 5,6-diaryl-as-triazines