NO791221L - Fremgangsmaate for fremstilling av benzylidenderivater - Google Patents

Fremgangsmaate for fremstilling av benzylidenderivater

Info

Publication number: NO791221L
Authority: NO; Norway
Prior art keywords: formula; above meaning; alkyl; carbon atoms; evaporated
Prior art date: 1978-04-14

Application number

NO791221A

Other languages

English (en)

Norwegian (no)

Inventor

Jean Pierre Kaplan

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.)

1978-04-14

Filing date

1979-04-10

Publication date

1979-10-16

1979-04-10 Application filed by Synthelabo filed Critical Synthelabo

1979-10-16 Publication of NO791221L publication Critical patent/NO791221L/no

Links

238000000034 method Methods 0.000 title claims abstract description 10
238000002360 preparation method Methods 0.000 title claims description 3
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
239000012965 benzophenone Substances 0.000 claims description 3
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
YEYZALQTJCVXIJ-HXUWFJFHSA-N (2R)-2-amino-2-(methoxymethyl)-4-(4-octylphenyl)butan-1-ol Chemical compound CCCCCCCCC1=CC=C(CC[C@@](N)(CO)COC)C=C1 YEYZALQTJCVXIJ-HXUWFJFHSA-N 0.000 claims description 2
SDGHXWKVBZYHRR-UHFFFAOYSA-N 2-(1h-imidazol-2-ylsulfonyl)-1h-imidazole Chemical compound N=1C=CNC=1S(=O)(=O)C1=NC=CN1 SDGHXWKVBZYHRR-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000000047 product Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 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 description 2
231100000111 LD50 Toxicity 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
-1 alkyl radical Chemical class 0.000 description 2
150000008366 benzophenones Chemical class 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
230000036461 convulsion Effects 0.000 description 2
229960003692 gamma aminobutyric acid Drugs 0.000 description 2
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
DDHMCCRLAXGXQJ-UHFFFAOYSA-N (4-chloro-5-fluoro-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(Cl)=C(F)C=C1C(=O)C1=CC=CC=C1 DDHMCCRLAXGXQJ-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
150000007513 acids Chemical class 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000000654 additive Substances 0.000 description 1
229940124277 aminobutyric acid Drugs 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
YTMCEWHSHANFEP-UHFFFAOYSA-N butyl 4-aminobutanoate Chemical compound CCCCOC(=O)CCCN YTMCEWHSHANFEP-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
230000003371 gabaergic effect Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000001228 spectrum Methods 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
INPWKHSGGJNIIM-UHFFFAOYSA-N tetradecyl 2-chloroacetate Chemical compound CCCCCCCCCCCCCCOC(=O)CCl INPWKHSGGJNIIM-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Emergency Medicine (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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO791221A 1978-04-14 1979-04-10 Fremgangsmaate for fremstilling av benzylidenderivater NO791221L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7811025A FR2422628A1 (fr)	1978-04-14	1978-04-14	Esters benzylideniques et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
NO791221L true NO791221L (no)	1979-10-16

Family

ID=9207131

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO791221A NO791221L (no)	1978-04-14	1979-04-10	Fremgangsmaate for fremstilling av benzylidenderivater

Country Status (16)

Country	Link
JP (1)	JPS54138548A (fr)
AU (1)	AU4590979A (fr)
BE (1)	BE875588A (fr)
DE (1)	DE2914801A1 (fr)
DK (1)	DK149179A (fr)
ES (1)	ES479537A1 (fr)
FI (1)	FI791186A7 (fr)
FR (1)	FR2422628A1 (fr)
GB (1)	GB2018755A (fr)
IL (1)	IL57060A0 (fr)
IT (1)	IT1111922B (fr)
LU (1)	LU81146A1 (fr)
NL (1)	NL7902952A (fr)
NO (1)	NO791221L (fr)
PT (1)	PT69486A (fr)
SE (1)	SE7903233L (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5746951A (en) *	1980-09-04	1982-03-17	Toray Ind Inc	Production of 2-amino-4-cyanobutyric derivative
EP0047516B1 (fr) *	1980-09-04	1984-01-04	Toray Industries, Inc.	Dérivés de la propylamine et leur procédé de préparation
FR2536746A1 (fr) *	1982-11-29	1984-06-01	Synthelabo	Derives benzylideniques alkyles, leur preparation et leur application en therapeutique

1978
- 1978-04-14 FR FR7811025A patent/FR2422628A1/fr active Granted
1979
- 1979-04-10 DK DK149179A patent/DK149179A/da not_active IP Right Cessation
- 1979-04-10 NO NO791221A patent/NO791221L/no unknown
- 1979-04-10 AU AU45909/79A patent/AU4590979A/en not_active Abandoned
- 1979-04-11 FI FI791186A patent/FI791186A7/fi not_active Application Discontinuation
- 1979-04-11 DE DE19792914801 patent/DE2914801A1/de not_active Withdrawn
- 1979-04-11 IL IL57060A patent/IL57060A0/xx unknown
- 1979-04-11 IT IT21794/79A patent/IT1111922B/it active
- 1979-04-11 SE SE7903233A patent/SE7903233L/xx unknown
- 1979-04-11 ES ES479537A patent/ES479537A1/es not_active Expired
- 1979-04-12 LU LU81146A patent/LU81146A1/fr unknown
- 1979-04-12 NL NL7902952A patent/NL7902952A/xx not_active Application Discontinuation
- 1979-04-12 PT PT69486A patent/PT69486A/fr unknown
- 1979-04-12 GB GB7912933A patent/GB2018755A/en not_active Withdrawn
- 1979-04-13 JP JP4595679A patent/JPS54138548A/ja active Pending
- 1979-04-13 BE BE0/194613A patent/BE875588A/fr unknown

Also Published As

Publication number	Publication date
DK149179A (da)	1979-10-15
NL7902952A (nl)	1979-10-16
AU4590979A (en)	1979-10-18
FR2422628B1 (fr)	1980-10-03
JPS54138548A (en)	1979-10-27
BE875588A (fr)	1979-10-15
IT7921794A0 (it)	1979-04-11
PT69486A (fr)	1979-05-01
FR2422628A1 (fr)	1979-11-09
DE2914801A1 (de)	1979-10-18
IL57060A0 (en)	1979-07-25
ES479537A1 (es)	1979-11-01
LU81146A1 (fr)	1980-12-16
GB2018755A (en)	1979-10-24
FI791186A7 (fi)	1979-10-15
IT1111922B (it)	1986-01-13
SE7903233L (sv)	1979-10-15

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NO142172B (no)	1980-03-31	Analogifremgangsmaate for fremstilling av som antikonvulsiva virksomme alfa-fenyl-benzyliden-aminosyrederivater
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NO147104B (no)	1982-10-25	Analogifremgangsmaate ved fremstilling av terapeutisk aktive acetylenderivater av aminosyrer
SU1356960A3 (ru)	1987-11-30	Способ получени производных пиридазина
DE3035086C2 (fr)	1991-01-03
DE69115744T2 (de)	1996-05-30	Konjugate von Difluoroglutaminsäure mit Fölaten und Antifölaten für die Behandlung von neoplastischen Krankheiten
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PL84190B1 (en)	1976-03-31	3-aroyl-alkenyleneimines[us3835149a]
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NO791221L (no)	1979-10-16	Fremgangsmaate for fremstilling av benzylidenderivater
US4521619A (en)	1985-06-04	Therapeutically useful sulphur-containing benzylidene derivatives
IE921319A1 (en)	1992-11-04	2-aminopyrimidine-4-carboxamide derivatives, their¹preparation and their application in therapy
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