NL8006427A - Benzylideenderivaten, de bereiding hiervan en de therapeutische toepassing. - Google Patents

Benzylideenderivaten, de bereiding hiervan en de therapeutische toepassing. Download PDF

Info

Publication number: NL8006427A
Authority: NL; Netherlands
Prior art keywords: formula; hydrogen; atom; benzylidene derivatives; alkyl
Prior art date: 1979-11-27

Application number

NL8006427A

Other languages

English (en)

Dutch (nl)

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.)

1979-11-27

Filing date

1980-11-26

Publication date

1981-07-01

1980-11-26 Application filed by Synthelabo filed Critical Synthelabo

1981-07-01 Publication of NL8006427A publication Critical patent/NL8006427A/nl

Links

238000002360 preparation method Methods 0.000 title description 2
230000001225 therapeutic effect Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
-1 amine compound Chemical class 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
125000003282 alkyl amino group Chemical group 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
239000012965 benzophenone Substances 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
239000013543 active substance Substances 0.000 claims 2
125000005842 heteroatom Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000004455 differential thermal analysis Methods 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 2
GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000036461 convulsion Effects 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
229940031098 ethanolamine Drugs 0.000 description 2
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000000034 method Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
241000234282 Allium Species 0.000 description 1
206010002869 Anxiety symptoms Diseases 0.000 description 1
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 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000037406 food intake Effects 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012261 resinous substance Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- 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
- 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
- A61P25/20—Hypnotics; Sedatives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (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)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Anesthesiology (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)

NL8006427A 1979-11-27 1980-11-26 Benzylideenderivaten, de bereiding hiervan en de therapeutische toepassing. NL8006427A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7929139		1979-11-27
FR7929139A FR2470116A1 (fr)	1979-11-27	1979-11-27	Derives benzylideniques, leur preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
NL8006427A true NL8006427A (nl)	1981-07-01

Family

ID=9232118

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8006427A NL8006427A (nl)	1979-11-27	1980-11-26	Benzylideenderivaten, de bereiding hiervan en de therapeutische toepassing.

Country Status (20)

Country	Link
JP (1)	JPS5692852A (de)
AT (1)	AT372077B (de)
AU (1)	AU535262B2 (de)
BE (1)	BE886361A (de)
CA (1)	CA1145760A (de)
DE (1)	DE3044542A1 (de)
DK (1)	DK503180A (de)
ES (1)	ES497146A0 (de)
FR (1)	FR2470116A1 (de)
GB (1)	GB2063867B (de)
GR (1)	GR72133B (de)
IL (1)	IL61568A (de)
IT (1)	IT1134469B (de)
LU (1)	LU82958A1 (de)
NL (1)	NL8006427A (de)
NO (1)	NO803561L (de)
NZ (1)	NZ195654A (de)
PT (1)	PT72114B (de)
SE (1)	SE8008279L (de)
ZA (1)	ZA807389B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL8220421A (nl) *	1982-07-30	1984-06-01	Inst Organicheskogo Sinteza Ak	Condensatieprodukten van alfa-aminoisopropylfenylketon bij de carbonyl c=o binding met gesubstitueerde amines van functioneel gesubstitueerde hydrazines of met derivaten van in de natuur voorkomende aminozuren, die een antitumoractiviteit hebben.
US5278191A (en) *	1988-08-31	1994-01-11	G. D. Searle & Co.	Diphenylmethylaminoacetamide derivatives as anti-convulsants
AU2019340697B2 (en)	2018-09-14	2025-06-26	Precision Planting Llc	Fluid control assembly and system

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1497456A (fr) *	1964-06-15	1967-10-13	Clin Byla Ets	Ortho-amino aryl cétimines, composés hétérocycliques qui s'y rattachent et prépaation de ces divers corps

1979
- 1979-11-27 FR FR7929139A patent/FR2470116A1/fr active Granted
1980
- 1980-11-26 PT PT72114A patent/PT72114B/pt unknown
- 1980-11-26 SE SE8008279A patent/SE8008279L/ not_active Application Discontinuation
- 1980-11-26 NO NO803561A patent/NO803561L/no unknown
- 1980-11-26 ES ES497146A patent/ES497146A0/es active Granted
- 1980-11-26 IT IT26247/80A patent/IT1134469B/it active
- 1980-11-26 LU LU82958A patent/LU82958A1/fr unknown
- 1980-11-26 ZA ZA00807389A patent/ZA807389B/xx unknown
- 1980-11-26 DE DE19803044542 patent/DE3044542A1/de not_active Withdrawn
- 1980-11-26 CA CA000365550A patent/CA1145760A/en not_active Expired
- 1980-11-26 AT AT0577780A patent/AT372077B/de active
- 1980-11-26 JP JP16736380A patent/JPS5692852A/ja active Pending
- 1980-11-26 DK DK503180A patent/DK503180A/da not_active Application Discontinuation
- 1980-11-26 AU AU64730/80A patent/AU535262B2/en not_active Ceased
- 1980-11-26 NZ NZ195654A patent/NZ195654A/xx unknown
- 1980-11-26 NL NL8006427A patent/NL8006427A/nl not_active Application Discontinuation
- 1980-11-26 BE BE0/202944A patent/BE886361A/fr not_active IP Right Cessation
- 1980-11-26 GR GR63468A patent/GR72133B/el unknown
- 1980-11-26 IL IL61568A patent/IL61568A/xx unknown
- 1980-11-26 GB GB8037869A patent/GB2063867B/en not_active Expired

Also Published As

Publication number	Publication date
GR72133B (de)	1983-09-19
PT72114B (fr)	1981-09-29
ES8107168A1 (es)	1981-10-01
DE3044542A1 (de)	1981-09-03
GB2063867A (en)	1981-06-10
ZA807389B (en)	1981-11-25
JPS5692852A (en)	1981-07-27
DK503180A (da)	1981-05-28
AU6473080A (en)	1981-06-04
IT8026247A0 (it)	1980-11-26
IL61568A0 (en)	1980-12-31
AU535262B2 (en)	1984-03-08
PT72114A (fr)	1980-12-01
FR2470116A1 (fr)	1981-05-29
LU82958A1 (fr)	1982-06-30
NO803561L (no)	1981-05-29
NZ195654A (en)	1982-05-31
SE8008279L (sv)	1981-05-28
CA1145760A (en)	1983-05-03
IL61568A (en)	1984-12-31
FR2470116B1 (de)	1983-07-18
GB2063867B (en)	1983-09-14
ATA577780A (de)	1983-01-15
AT372077B (de)	1983-08-25
BE886361A (fr)	1981-05-26
IT1134469B (it)	1986-08-13
ES497146A0 (es)	1981-10-01

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1985-07-01	BV	The patent application has lapsed

Publication	Publication Date	Title
NL8100081A (nl)	1981-04-29	Werkwijze ter bereiding van een therapeutisch preparaat alsmede werkwijze ter bereiding van de verbinding, die geschikt is om daarbij te worden toegepast.
HUP9800646A2 (hu)	1998-08-28	N-Acil-{2,1-c]pirrolo- és pirazolo[5,1-c][1,4]benzodiazepin}-, valamint -{pirrolo[1,2-a]kinoxalin}-származékok, ezeket tartalmazó gyógyászati készítmények és eljárás előállításukra
WO1995026342A1 (fr)	1995-10-05	DERIVES DE 5H-INDENO[1,2-b]PYRAZINE-2,3-DIONE, LEUR PREPARATION ET LES MEDICAMENTS LES CONTENANT
FR2707643A1 (fr)	1995-01-20	Dérivés d'imidazo[1,2-a]pyrazine-4-one, leur préparation et les médicaments les contenant.
CH641181A5 (fr)	1984-02-15	Indolo-quinolizidines, procede pour leur preparation et compositions therapeutiques les contenant.
EP4135840B1 (de)	2025-01-08	Wasserlösliche modifizierte aminosäurederivate zur behandlung von neurologischen erkrankungen und ausgewählte psychiatrische erkrankungen
CA2037812A1 (fr)	1991-09-10	Derives d'imidazo [1,2-c] quinazoline, leur procede de preparation et les compositions pharmaceutiques les renfermant
WO1997025329A1 (fr)	1997-07-17	DERIVES DE 5H,10H-IMIDAZO[1,2-a]INDOLO[3,2-e]PYRAZINE-4-ONE, LEUR PREPARATION ET LES MEDICAMENTS LES CONTENANT
CZ280084B6 (cs)	1995-10-18	Deriváty 2-(aminoalkyl)-5-(arylalkyl)-1,3-dioxanů způsob jejich přípravy a jejich terapeutické použití
FI85273C (fi)	1992-03-25	Foerfarande foer framstaellning av terapeutiskt anvaendbara pyrimidinderivat.
HUT72064A (en)	1996-03-28	Oxopyridinylquinoxaline derivative and pharmaceutical compositions containing them
MC1113A1 (fr)	1977-05-18	Derives de substitution du sulfure de diphenyle et medicament contenant ces substances
von Sprecher et al.	1998	Synthesis and SAR of a novel, potent and structurally simple LTD4 antagonist of the quinoline class
JPS63132832A (ja)	1988-06-04	アミノ酸誘導体鎮痙薬
EP0079810A1 (de)	1983-05-25	4-Phenyl-quinazolin-Derivate wirksam auf das Zentralnervensystem
Trybulski et al.	1983	2-Benzazepines. 5. Synthesis of pyrimido [5, 4-d][2] benzazepines and their evaluation as anxiolytic agents
Abd-El-Maksoud et al.	2022	Synthesis, characterization, and anticancer evaluation of some heterocycles bearing chloroquinoline moiety
NL8002271A (nl)	1980-11-03	Werkwijze ter bereiding van isopropylaminopyrimidine- hydroxyderivaten.
CA1145760A (en)	1983-05-03	Benzylidene derivatives, their preparation and compositions containing them
JP2798628B2 (ja)	1998-09-17	癲癇治療用の５−アミノカルボニル−５Ｈ−ジベンゾ［ａ，ｄ］シクロヘプテン−５，１０−イミン
SU1473710A3 (ru)	1989-04-15	Способ получени тиокетеновых производных пиперидина или их кислотно-аддитивных солей
JPS6258349B2 (de)	1987-12-05
EP0066762B1 (de)	1985-11-21	1,7-Dihydropyrrolo(3,4-e)(1,4)diazepin-2(1H)on Derivate
US3968230A (en)	1976-07-06	Compositions containing benzodiazepindiones and method of use
Sowell Sr et al.	1976	New synthesis of substituted pyrrolo [1, 2‐α][1, 3] diazepine and its pharmacological activity