CH616148A5 - - Google Patents
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- Publication number
- CH616148A5 CH616148A5 CH976976A CH976976A CH616148A5 CH 616148 A5 CH616148 A5 CH 616148A5 CH 976976 A CH976976 A CH 976976A CH 976976 A CH976976 A CH 976976A CH 616148 A5 CH616148 A5 CH 616148A5
- Authority
- CH
- Switzerland
- Prior art keywords
- gaba
- formula
- fluoro
- prepared
- acid
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 22
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- -1 methoxyl radical Chemical class 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 210000004556 brain Anatomy 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
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 2
- 230000003556 anti-epileptic effect Effects 0.000 claims 2
- 230000004888 barrier function Effects 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 239000002858 neurotransmitter agent Substances 0.000 claims 2
- 241000557626 Corvus corax Species 0.000 claims 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 206010039897 Sedation Diseases 0.000 claims 1
- 229940124277 aminobutyric acid Drugs 0.000 claims 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 208000006218 bradycardia Diseases 0.000 claims 1
- 230000036471 bradycardia Effects 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000007123 defense Effects 0.000 claims 1
- 230000007515 enzymatic degradation Effects 0.000 claims 1
- 230000001037 epileptic effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000036543 hypotension Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 210000000653 nervous system Anatomy 0.000 claims 1
- 230000000149 penetrating effect Effects 0.000 claims 1
- 230000036280 sedation Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 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 5
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 5
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 3
- 231100000111 LD50 Toxicity 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- 241001465754 Metazoa Species 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- DSQRQOOSYRTEDM-UHFFFAOYSA-N (3-chloro-5-fluoro-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=C(Cl)C=C(F)C=C1C(=O)C1=CC=CC=C1 DSQRQOOSYRTEDM-UHFFFAOYSA-N 0.000 description 1
- BOCKKQDLHNXQPH-UHFFFAOYSA-N (4,5-difluoro-2-hydroxyphenyl)-phenylmethanone Chemical compound FC=1C(=CC(=C(C(=O)C2=CC=CC=C2)C=1)O)F BOCKKQDLHNXQPH-UHFFFAOYSA-N 0.000 description 1
- BLAFMYLJPCNAIP-UHFFFAOYSA-N (5-fluoro-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=C(F)C=C1C(=O)C1=CC=CC=C1 BLAFMYLJPCNAIP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 101000874159 Mus musculus Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Proteins 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 1
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- VGHOWOWLIXPTOA-UHFFFAOYSA-N cyclohexane;toluene Chemical compound C1CCCCC1.CC1=CC=CC=C1 VGHOWOWLIXPTOA-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000003371 gabaergic effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RBLWMQWAHONKNC-UHFFFAOYSA-N hydroxyazanium Chemical group O[NH3+] RBLWMQWAHONKNC-UHFFFAOYSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960004526 piracetam Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- ZOOPHYLANWVUDY-UHFFFAOYSA-M sodium;undecanoate Chemical compound [Na+].CCCCCCCCCCC([O-])=O ZOOPHYLANWVUDY-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- 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
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/10—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C251/16—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
-
- 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
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7524065A FR2319338A1 (fr) | 1975-08-01 | 1975-08-01 | Nouveaux derives de a- phenyl benzylideniques des acides amines, leur preparation et les medicaments qui en contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616148A5 true CH616148A5 (ja) | 1980-03-14 |
Family
ID=9158650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH976976A CH616148A5 (ja) | 1975-08-01 | 1976-07-30 |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US4094992A (ja) |
| JP (1) | JPS5219644A (ja) |
| AR (1) | AR211548A1 (ja) |
| AT (1) | AT346312B (ja) |
| AU (1) | AU496994B2 (ja) |
| BE (1) | BE844737A (ja) |
| CA (1) | CA1072112A (ja) |
| CH (1) | CH616148A5 (ja) |
| DE (1) | DE2634288A1 (ja) |
| DK (1) | DK346276A (ja) |
| ES (1) | ES450300A1 (ja) |
| FR (1) | FR2319338A1 (ja) |
| GB (1) | GB1506808A (ja) |
| GR (1) | GR60854B (ja) |
| IE (1) | IE43143B1 (ja) |
| IL (1) | IL50019A (ja) |
| LU (1) | LU75514A1 (ja) |
| MX (1) | MX4018E (ja) |
| NL (1) | NL170627C (ja) |
| NO (1) | NO142172C (ja) |
| NZ (1) | NZ181444A (ja) |
| PT (1) | PT65426B (ja) |
| SE (1) | SE429651B (ja) |
| ZA (1) | ZA764096B (ja) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2516509B1 (fr) * | 1981-11-18 | 1985-07-26 | Synthelabo | Derives benzylideniques, leur preparation et leur application en therapeutique |
| FR2484410A2 (fr) * | 1979-02-12 | 1981-12-18 | Synthelabo | Derives benzylideniques et leur application en therapeutique |
| DE3124091C2 (de) | 1981-06-19 | 1983-06-01 | Degussa Ag, 6000 Frankfurt | N-(3-Cyanopropanoyl)-aminocarbonsäureester und deren Verwendung |
| US4478958A (en) * | 1981-07-10 | 1984-10-23 | Kopper Company, Inc. | Method for preparing phenolic foams using anhydrous aryl sulfonic acid catalysts |
| FR2535319B2 (fr) * | 1981-11-18 | 1985-10-31 | Synthelabo | Derives methyles benzylideniques, leur preparation et leur application en therapeutique |
| FR2535318B2 (fr) * | 1981-11-18 | 1985-09-06 | Synthelabo | Derives benzylideniques, leur preparation et leur application en therapeutique |
| FR2536070A1 (fr) * | 1982-11-15 | 1984-05-18 | Synthelabo | Diphenyl-azomethines hydroxylees, leur preparation et leur application en therapeutique |
| FR2536747A1 (fr) * | 1982-11-29 | 1984-06-01 | Synthelabo | Derives benzylideniques soufres, leur preparation et leur application en therapeutique |
| FR2536746A1 (fr) * | 1982-11-29 | 1984-06-01 | Synthelabo | Derives benzylideniques alkyles, leur preparation et leur application en therapeutique |
| FR2544308B1 (fr) * | 1983-04-14 | 1985-06-14 | Synthelabo | Ethines substituees, 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 |
| FR2545822B1 (fr) * | 1983-05-11 | 1985-07-05 | Synthelabo | Diphenylazomethines portant une chaine esterifiee, 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 |
| FR2577923B1 (fr) * | 1985-02-26 | 1988-09-09 | Synthelabo | Diphenylazomethines carboxylees, leur preparation et leur application |
| 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 |
| US5321047A (en) * | 1988-06-03 | 1994-06-14 | John Wyeth & Brother, Limited | Method and amines used therein |
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| FR2647445B1 (fr) * | 1989-05-23 | 1991-08-30 | Oreal | Acides n-carboalkyloxy amino-11 undecanoiques et leurs esters, leurs procedes de preparation et leur utilisation en tant qu'agents epaississants |
| US5247121A (en) * | 1989-05-23 | 1993-09-21 | L'oreal | Alkyl esters of n-carboalkyloxy amino-11-undecanoic acids, their processes of preparation and their use as thickening agents |
| US5210313A (en) * | 1992-01-10 | 1993-05-11 | Maxdem Incorporated | Preparation of 2,5-dichlorobenzophenones |
| SK6092003A3 (en) | 2000-11-30 | 2004-07-07 | Pfizer Prod Inc | Combination of GABA agonists and aldosereductase inhibitors |
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| BRPI0413756A (pt) * | 2003-08-20 | 2006-10-31 | Xenoport Inc | composto, métodos para tratar ou evitar espasticidade ou um sintoma de espasticidade, doença de refluxo gastro-esofágico, vìcio em droga, vìcio em ou abuso de álcool, ou vìcio em ou abuso de nicotina, e tosse ou êmese em um paciente, e, composição farmacêutica |
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| CN101466390B (zh) * | 2006-06-15 | 2014-03-12 | 优时比制药有限公司 | 用于治疗难治性癫痫持续状态的肽类化合物 |
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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 |
| US3966793A (en) * | 1964-06-15 | 1976-06-29 | Clin Midy | Intermediates for preparing 1,4-benzodiazepine-2-ones having a carboxylic acid ester or amide group in the 3-position |
| US3429874A (en) * | 1966-12-22 | 1969-02-25 | Schering Corp | 1-polyhalogenoalkyl-2-oxo-1,3-dihydro-2h-1,4-benzodiazepines |
| IL47712A0 (en) | 1974-08-21 | 1975-10-15 | Sparamedica Ag | Salt of a penicillanic acid derivative,its preparation and pharmaceutical compositions containing it |
| AT348512B (de) * | 1976-08-02 | 1979-02-26 | Hoffmann La Roche | Verfahren zur herstellung von isoindol- derivaten |
-
1975
- 1975-08-01 FR FR7524065A patent/FR2319338A1/fr active Granted
-
1976
- 1976-07-08 NL NLAANVRAGE7607533,A patent/NL170627C/xx not_active IP Right Cessation
- 1976-07-09 ZA ZA764096A patent/ZA764096B/xx unknown
- 1976-07-09 IE IE1521/76A patent/IE43143B1/en unknown
- 1976-07-12 NZ NZ181444A patent/NZ181444A/xx unknown
- 1976-07-12 IL IL50019A patent/IL50019A/xx unknown
- 1976-07-13 CA CA256,882A patent/CA1072112A/en not_active Expired
- 1976-07-16 US US05/705,938 patent/US4094992A/en not_active Expired - Lifetime
- 1976-07-22 MX MX761791U patent/MX4018E/es unknown
- 1976-07-28 AR AR264109A patent/AR211548A1/es active
- 1976-07-28 AT AT556176A patent/AT346312B/de not_active IP Right Cessation
- 1976-07-30 NO NO762658A patent/NO142172C/no unknown
- 1976-07-30 GR GR51384A patent/GR60854B/el unknown
- 1976-07-30 JP JP51092246A patent/JPS5219644A/ja active Granted
- 1976-07-30 DE DE19762634288 patent/DE2634288A1/de active Granted
- 1976-07-30 BE BE169429A patent/BE844737A/xx not_active IP Right Cessation
- 1976-07-30 AU AU16450/76A patent/AU496994B2/en not_active Expired
- 1976-07-30 GB GB31961/76A patent/GB1506808A/en not_active Expired
- 1976-07-30 CH CH976976A patent/CH616148A5/fr not_active IP Right Cessation
- 1976-07-30 LU LU75514A patent/LU75514A1/xx unknown
- 1976-07-30 SE SE7608625A patent/SE429651B/xx not_active IP Right Cessation
- 1976-07-30 ES ES450300A patent/ES450300A1/es not_active Expired
- 1976-07-30 DK DK346276A patent/DK346276A/da not_active Application Discontinuation
- 1976-07-30 PT PT65426A patent/PT65426B/pt unknown
-
1981
- 1981-08-03 US US06/289,148 patent/US4400394A/en not_active Expired - Lifetime
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