NO823824L - Fremgangsmaate for fremstilling av benzylidenderivater - Google Patents
Fremgangsmaate for fremstilling av benzylidenderivaterInfo
- Publication number
- NO823824L NO823824L NO823824A NO823824A NO823824L NO 823824 L NO823824 L NO 823824L NO 823824 A NO823824 A NO 823824A NO 823824 A NO823824 A NO 823824A NO 823824 L NO823824 L NO 823824L
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- phenyl
- compounds
- mol
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 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 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 229910052784 alkaline earth metal Chemical group 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 2
- 230000001773 anti-convulsant effect Effects 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 claims description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 208000012661 Dyskinesia Diseases 0.000 claims 1
- 208000008238 Muscle Spasticity Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 229940125681 anticonvulsant agent Drugs 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 239000002249 anxiolytic agent Substances 0.000 claims 1
- 230000000949 anxiolytic effect Effects 0.000 claims 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 230000002920 convulsive effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 230000001665 lethal effect Effects 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 230000001242 postsynaptic effect Effects 0.000 claims 1
- 208000018198 spasticity Diseases 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 13
- -1 alkyl radical Chemical class 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 241000699670 Mus sp. Species 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LNAURVNIKFHZNB-UHFFFAOYSA-N (5-chloro-2-hydroxy-3-methylphenyl)-(4-chlorophenyl)methanone Chemical compound CC1=CC(Cl)=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1O LNAURVNIKFHZNB-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- MVEPJLNIXKEKMI-UHFFFAOYSA-N 4-aminobutanamide;hydrochloride Chemical compound Cl.NCCCC(N)=O MVEPJLNIXKEKMI-UHFFFAOYSA-N 0.000 description 3
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
- AVTLLLZVYYPGFX-UHFFFAOYSA-N 4-ethylbenzoyl chloride Chemical compound CCC1=CC=C(C(Cl)=O)C=C1 AVTLLLZVYYPGFX-UHFFFAOYSA-N 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- CKMXAIVXVKGGFM-UHFFFAOYSA-N p-cumic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C=C1 CKMXAIVXVKGGFM-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- YZOIBBVTGWATAE-UHFFFAOYSA-N (5-chloro-2-hydroxy-3-methylphenyl)-(4-ethylphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C(=O)C1=CC(Cl)=CC(C)=C1O YZOIBBVTGWATAE-UHFFFAOYSA-N 0.000 description 1
- ZTQHCYJOMKTUNV-UHFFFAOYSA-N (5-chloro-2-hydroxy-3-methylphenyl)-(4-propan-2-ylphenyl)methanone Chemical compound C1=CC(C(C)C)=CC=C1C(=O)C1=CC(Cl)=CC(C)=C1O ZTQHCYJOMKTUNV-UHFFFAOYSA-N 0.000 description 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 1
- SSIMHHUMYMHNID-UHFFFAOYSA-N 4-(chloromethyl)phenol Chemical compound OC1=CC=C(CCl)C=C1 SSIMHHUMYMHNID-UHFFFAOYSA-N 0.000 description 1
- ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-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
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-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
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229960002888 oxitriptan Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR818121559A FR2516509B1 (fr) | 1981-11-18 | 1981-11-18 | Derives benzylideniques, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO823824L true NO823824L (no) | 1983-05-19 |
Family
ID=9264115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO823824A NO823824L (no) | 1981-11-18 | 1982-11-16 | Fremgangsmaate for fremstilling av benzylidenderivater |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4588748A (ja) |
| JP (1) | JPS5892646A (ja) |
| AU (1) | AU9064582A (ja) |
| BE (1) | BE895042A (ja) |
| CA (1) | CA1204773A (ja) |
| CH (1) | CH653011A5 (ja) |
| DE (1) | DE3242442A1 (ja) |
| DK (1) | DK511782A (ja) |
| ES (1) | ES517428A0 (ja) |
| FI (1) | FI823925L (ja) |
| FR (1) | FR2516509B1 (ja) |
| GB (1) | GB2111051B (ja) |
| GR (1) | GR77036B (ja) |
| HU (1) | HU187429B (ja) |
| IT (1) | IT1153062B (ja) |
| LU (1) | LU84473A1 (ja) |
| NL (1) | NL8204462A (ja) |
| NO (1) | NO823824L (ja) |
| NZ (1) | NZ202519A (ja) |
| PT (1) | PT75868B (ja) |
| SE (1) | SE8206548L (ja) |
| ZA (1) | ZA828470B (ja) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2536746A1 (fr) * | 1982-11-29 | 1984-06-01 | Synthelabo | Derives benzylideniques alkyles, leur preparation et leur application en therapeutique |
| FR2544309B1 (fr) * | 1983-04-14 | 1986-01-10 | Synthelabo | Diphenylazomethines hydroxylees, leur preparation et leur application en therapeutique |
| FR2570696B1 (fr) * | 1984-09-27 | 1986-11-21 | Synthelabo | Derives de diphenylazomethines a chaine insaturee, leur preparation et leur application en therapeutique |
| FR2570695A1 (fr) * | 1984-09-27 | 1986-03-28 | Synthelabo | Diphenylazomethines a chaine ramifiee ou cyclique, leur preparation et leur application en therapeutique |
| FR2595695B1 (fr) * | 1986-03-12 | 1988-12-02 | Synthelabo | Derives de n-(((hydroxy-2 phenyl) (phenyl) methylene) amino-2) ethyl) acetamide, leur preparation et leur application en therapeutique |
| US6099869A (en) * | 1995-04-18 | 2000-08-08 | Nutrition 21 | Calcium taurate and antihypertensive drug for hypertension |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3371085A (en) * | 1959-12-10 | 1968-02-27 | Hoffmann La Roche | 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones |
| US3429878A (en) * | 1967-01-31 | 1969-02-25 | Smithkline Corp | 6-amino-5-methyleneaminopyrimidines |
| US4010154A (en) * | 1970-02-03 | 1977-03-01 | Sumitomo Chemical Company, Limited | Benzodiazepinones |
| FR2319338A1 (fr) * | 1975-08-01 | 1977-02-25 | Synthelabo | Nouveaux derives de a- phenyl benzylideniques des acides amines, leur preparation et les medicaments qui en contiennent |
| FR2430936A1 (fr) * | 1978-07-13 | 1980-02-08 | Synthelabo | Derives benzylideniques, leur preparation et leur application en therapeutique |
-
1981
- 1981-11-18 FR FR818121559A patent/FR2516509B1/fr not_active Expired
-
1982
- 1982-11-16 NO NO823824A patent/NO823824L/no unknown
- 1982-11-16 DE DE19823242442 patent/DE3242442A1/de not_active Ceased
- 1982-11-16 FI FI823925A patent/FI823925L/fi not_active Application Discontinuation
- 1982-11-17 DK DK511782A patent/DK511782A/da not_active Application Discontinuation
- 1982-11-17 IT IT24306/82A patent/IT1153062B/it active
- 1982-11-17 CA CA000415782A patent/CA1204773A/en not_active Expired
- 1982-11-17 NZ NZ202519A patent/NZ202519A/en unknown
- 1982-11-17 GR GR69840A patent/GR77036B/el unknown
- 1982-11-17 SE SE8206548A patent/SE8206548L/ not_active Application Discontinuation
- 1982-11-17 JP JP57202836A patent/JPS5892646A/ja active Pending
- 1982-11-17 HU HU823686A patent/HU187429B/hu unknown
- 1982-11-17 ZA ZA828470A patent/ZA828470B/xx unknown
- 1982-11-17 ES ES517428A patent/ES517428A0/es active Granted
- 1982-11-17 AU AU90645/82A patent/AU9064582A/en not_active Abandoned
- 1982-11-17 CH CH6711/82A patent/CH653011A5/fr not_active IP Right Cessation
- 1982-11-17 PT PT75868A patent/PT75868B/pt unknown
- 1982-11-17 LU LU84473A patent/LU84473A1/fr unknown
- 1982-11-17 GB GB08232766A patent/GB2111051B/en not_active Expired
- 1982-11-17 BE BE0/209495A patent/BE895042A/fr not_active IP Right Cessation
- 1982-11-18 NL NL8204462A patent/NL8204462A/nl not_active Application Discontinuation
-
1984
- 1984-09-25 US US06/654,068 patent/US4588748A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NL8204462A (nl) | 1983-06-16 |
| PT75868B (fr) | 1986-01-15 |
| AU9064582A (en) | 1983-05-26 |
| US4588748A (en) | 1986-05-13 |
| DK511782A (da) | 1983-05-19 |
| CA1204773A (en) | 1986-05-20 |
| CH653011A5 (fr) | 1985-12-13 |
| HU187429B (en) | 1986-01-28 |
| SE8206548L (sv) | 1983-05-19 |
| IT8224306A1 (it) | 1984-05-17 |
| LU84473A1 (fr) | 1984-06-13 |
| GB2111051B (en) | 1985-07-10 |
| GB2111051A (en) | 1983-06-29 |
| JPS5892646A (ja) | 1983-06-02 |
| SE8206548D0 (sv) | 1982-11-17 |
| DE3242442A1 (de) | 1983-05-26 |
| PT75868A (fr) | 1982-12-01 |
| NZ202519A (en) | 1985-05-31 |
| FI823925L (fi) | 1983-05-19 |
| BE895042A (fr) | 1983-05-17 |
| ES8308306A1 (es) | 1983-08-16 |
| IT1153062B (it) | 1987-01-14 |
| FR2516509A1 (fr) | 1983-05-20 |
| ZA828470B (en) | 1983-09-28 |
| ES517428A0 (es) | 1983-08-16 |
| FI823925A0 (fi) | 1982-11-16 |
| GR77036B (ja) | 1984-09-04 |
| IT8224306A0 (it) | 1982-11-17 |
| FR2516509B1 (fr) | 1985-07-26 |
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