CA1145760A - Benzylidene derivatives, their preparation and compositions containing them - Google Patents
Benzylidene derivatives, their preparation and compositions containing themInfo
- Publication number
- CA1145760A CA1145760A CA000365550A CA365550A CA1145760A CA 1145760 A CA1145760 A CA 1145760A CA 000365550 A CA000365550 A CA 000365550A CA 365550 A CA365550 A CA 365550A CA 1145760 A CA1145760 A CA 1145760A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- formula
- phenyl
- alpha
- hydrogen
- Prior art date
- 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
Links
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title claims abstract description 6
- 239000000203 mixture Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 amino compound Chemical class 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 8
- 239000012965 benzophenone Substances 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 23
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 206010010904 Convulsion Diseases 0.000 abstract description 3
- 230000036461 convulsion Effects 0.000 abstract description 3
- 208000019901 Anxiety disease Diseases 0.000 abstract description 2
- 230000036506 anxiety Effects 0.000 abstract description 2
- 206010015037 epilepsy Diseases 0.000 abstract description 2
- 125000005122 aminoalkylamino group Chemical group 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 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
- 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
- 239000007787 solid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 238000004455 differential thermal analysis Methods 0.000 description 3
- 229940031098 ethanolamine Drugs 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 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 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
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 239000000155 melt Substances 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
- 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
- HQMLIDZJXVVKCW-UHFFFAOYSA-N 2-aminopropanamide Chemical compound CC(N)C(N)=O HQMLIDZJXVVKCW-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa 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
- 238000004458 analytical method Methods 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
- 150000008366 benzophenones Chemical class 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 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
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent 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)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7929139A FR2470116A1 (fr) | 1979-11-27 | 1979-11-27 | Derives benzylideniques, leur preparation et leur application en therapeutique |
| FR7929139 | 1979-11-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1145760A true CA1145760A (en) | 1983-05-03 |
Family
ID=9232118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000365550A Expired CA1145760A (en) | 1979-11-27 | 1980-11-26 | Benzylidene derivatives, their preparation and compositions containing them |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5692852A (OSRAM) |
| AT (1) | AT372077B (OSRAM) |
| AU (1) | AU535262B2 (OSRAM) |
| BE (1) | BE886361A (OSRAM) |
| CA (1) | CA1145760A (OSRAM) |
| DE (1) | DE3044542A1 (OSRAM) |
| DK (1) | DK503180A (OSRAM) |
| ES (1) | ES8107168A1 (OSRAM) |
| FR (1) | FR2470116A1 (OSRAM) |
| GB (1) | GB2063867B (OSRAM) |
| GR (1) | GR72133B (OSRAM) |
| IL (1) | IL61568A (OSRAM) |
| IT (1) | IT1134469B (OSRAM) |
| LU (1) | LU82958A1 (OSRAM) |
| NL (1) | NL8006427A (OSRAM) |
| NO (1) | NO803561L (OSRAM) |
| NZ (1) | NZ195654A (OSRAM) |
| PT (1) | PT72114B (OSRAM) |
| SE (1) | SE8008279L (OSRAM) |
| ZA (1) | ZA807389B (OSRAM) |
Families Citing this family (3)
| 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 |
| EP4627902A3 (en) | 2018-09-14 | 2026-01-14 | Precision Planting LLC | Fluid control assembly and system |
Family Cites Families (1)
| 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 NZ NZ195654A patent/NZ195654A/xx unknown
- 1980-11-26 AT AT0577780A patent/AT372077B/de active
- 1980-11-26 NO NO803561A patent/NO803561L/no unknown
- 1980-11-26 CA CA000365550A patent/CA1145760A/en not_active Expired
- 1980-11-26 IL IL61568A patent/IL61568A/xx unknown
- 1980-11-26 NL NL8006427A patent/NL8006427A/nl not_active Application Discontinuation
- 1980-11-26 IT IT26247/80A patent/IT1134469B/it active
- 1980-11-26 GR GR63468A patent/GR72133B/el unknown
- 1980-11-26 ES ES497146A patent/ES8107168A1/es not_active Expired
- 1980-11-26 PT PT72114A patent/PT72114B/pt unknown
- 1980-11-26 JP JP16736380A patent/JPS5692852A/ja active Pending
- 1980-11-26 GB GB8037869A patent/GB2063867B/en not_active Expired
- 1980-11-26 DE DE19803044542 patent/DE3044542A1/de not_active Withdrawn
- 1980-11-26 AU AU64730/80A patent/AU535262B2/en not_active Ceased
- 1980-11-26 DK DK503180A patent/DK503180A/da not_active Application Discontinuation
- 1980-11-26 LU LU82958A patent/LU82958A1/fr unknown
- 1980-11-26 ZA ZA00807389A patent/ZA807389B/xx unknown
- 1980-11-26 BE BE0/202944A patent/BE886361A/fr not_active IP Right Cessation
- 1980-11-26 SE SE8008279A patent/SE8008279L/ not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ES497146A0 (es) | 1981-10-01 |
| IT8026247A0 (it) | 1980-11-26 |
| AT372077B (de) | 1983-08-25 |
| FR2470116A1 (fr) | 1981-05-29 |
| IL61568A0 (en) | 1980-12-31 |
| DK503180A (da) | 1981-05-28 |
| IT1134469B (it) | 1986-08-13 |
| NL8006427A (nl) | 1981-07-01 |
| AU535262B2 (en) | 1984-03-08 |
| GB2063867A (en) | 1981-06-10 |
| BE886361A (fr) | 1981-05-26 |
| LU82958A1 (fr) | 1982-06-30 |
| ZA807389B (en) | 1981-11-25 |
| GB2063867B (en) | 1983-09-14 |
| FR2470116B1 (OSRAM) | 1983-07-18 |
| PT72114A (fr) | 1980-12-01 |
| AU6473080A (en) | 1981-06-04 |
| JPS5692852A (en) | 1981-07-27 |
| DE3044542A1 (de) | 1981-09-03 |
| PT72114B (fr) | 1981-09-29 |
| NO803561L (no) | 1981-05-29 |
| GR72133B (OSRAM) | 1983-09-19 |
| SE8008279L (sv) | 1981-05-28 |
| IL61568A (en) | 1984-12-31 |
| ES8107168A1 (es) | 1981-10-01 |
| ATA577780A (de) | 1983-01-15 |
| NZ195654A (en) | 1982-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |