NL8006427A - Benzylideenderivaten, de bereiding hiervan en de therapeutische toepassing. - Google Patents
Benzylideenderivaten, de bereiding hiervan en de therapeutische toepassing. Download PDFInfo
- Publication number
- NL8006427A NL8006427A NL8006427A NL8006427A NL8006427A NL 8006427 A NL8006427 A NL 8006427A NL 8006427 A NL8006427 A NL 8006427A NL 8006427 A NL8006427 A NL 8006427A NL 8006427 A NL8006427 A NL 8006427A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- hydrogen
- atom
- benzylidene derivatives
- alkyl
- Prior art date
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)
- 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 |
|---|---|
| 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 (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 |
| 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 |
| CA1145760A (en) | 1983-05-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |