CA1166159A - Medicament a base d'amino-2 trifluoromethoxy-6 benzothiazole - Google Patents
Medicament a base d'amino-2 trifluoromethoxy-6 benzothiazoleInfo
- Publication number
- CA1166159A CA1166159A CA000387977A CA387977A CA1166159A CA 1166159 A CA1166159 A CA 1166159A CA 000387977 A CA000387977 A CA 000387977A CA 387977 A CA387977 A CA 387977A CA 1166159 A CA1166159 A CA 1166159A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- benzothiazole
- character
- composition according
- composition
- 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
- FTALBRSUTCGOEG-UHFFFAOYSA-N Riluzole Chemical compound C1=C(OC(F)(F)F)C=C2SC(N)=NC2=C1 FTALBRSUTCGOEG-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 7
- 239000001961 anticonvulsive agent Substances 0.000 claims abstract description 7
- 239000013543 active substance Substances 0.000 claims abstract description 6
- 230000001773 anti-convulsant effect Effects 0.000 claims abstract description 6
- 229960003965 antiepileptics Drugs 0.000 claims abstract description 6
- 230000000949 anxiolytic effect Effects 0.000 claims abstract description 5
- 230000000147 hypnotic effect Effects 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000002249 anxiolytic agent Substances 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 18
- 239000002775 capsule Substances 0.000 claims description 14
- 239000003826 tablet Substances 0.000 claims description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 7
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 5
- 229930195725 Mannitol Natural products 0.000 claims description 5
- 239000000594 mannitol Substances 0.000 claims description 5
- 235000010355 mannitol Nutrition 0.000 claims description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000000829 suppository Substances 0.000 claims description 4
- 239000000454 talc Substances 0.000 claims description 4
- 229910052623 talc Inorganic materials 0.000 claims description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 239000008119 colloidal silica Substances 0.000 claims description 3
- 125000005456 glyceride group Chemical group 0.000 claims description 3
- 235000019359 magnesium stearate Nutrition 0.000 claims description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 3
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- -1 2-amino trifluoro-6-methoxy benzothiazole Chemical compound 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical class NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 2
- 108010085654 methylated casein Proteins 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 claims 2
- DHITZHCZUWQDBD-UHFFFAOYSA-N 6-(trifluoromethoxy)-1,3-benzothiazole Chemical compound FC(F)(F)OC1=CC=C2N=CSC2=C1 DHITZHCZUWQDBD-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 6
- 241001279009 Strychnos toxifera Species 0.000 description 6
- 229960005453 strychnine Drugs 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 5
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 229960003350 isoniazid Drugs 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960002695 phenobarbital Drugs 0.000 description 2
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 229940116357 potassium thiocyanate Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000723 toxicological property Toxicity 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- AHOIGFLSEXUWNV-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazole Chemical compound COC1=CC=C2N=CSC2=C1 AHOIGFLSEXUWNV-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- LORDTWZDPFCZQH-UHFFFAOYSA-N FC=1C(=CC2=C(N=C(S2)F)C1F)OC Chemical compound FC=1C(=CC2=C(N=C(S2)F)C1F)OC LORDTWZDPFCZQH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 101000874172 Rattus norvegicus Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Proteins 0.000 description 1
- 108050007496 Shikimate kinase 2 Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- YGCODSQDUUUKIV-UHFFFAOYSA-N Zoxazolamine Chemical compound ClC1=CC=C2OC(N)=NC2=C1 YGCODSQDUUUKIV-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003371 gabaergic effect Effects 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229950006967 zoxazolamine Drugs 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8022218 | 1980-10-17 | ||
| FR8022218A FR2492258A1 (fr) | 1980-10-17 | 1980-10-17 | Nouveau medicament a base d'amino-2 trifluoromethoxy-6 benzothiazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1166159A true CA1166159A (fr) | 1984-04-24 |
Family
ID=9247013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000387977A Expired CA1166159A (fr) | 1980-10-17 | 1981-10-15 | Medicament a base d'amino-2 trifluoromethoxy-6 benzothiazole |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4370338A (enExample) |
| EP (1) | EP0050551B1 (enExample) |
| JP (1) | JPS5795910A (enExample) |
| AR (1) | AR227069A1 (enExample) |
| AU (1) | AU545437B2 (enExample) |
| CA (1) | CA1166159A (enExample) |
| DE (1) | DE3163230D1 (enExample) |
| DK (1) | DK444281A (enExample) |
| FR (1) | FR2492258A1 (enExample) |
| GR (1) | GR75804B (enExample) |
| HU (1) | HU184893B (enExample) |
| IL (1) | IL63880A0 (enExample) |
| MA (1) | MA19364A1 (enExample) |
| NO (1) | NO813492L (enExample) |
| PT (1) | PT73828B (enExample) |
| ZA (1) | ZA817187B (enExample) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4826860A (en) * | 1987-03-16 | 1989-05-02 | Warner-Lambert Company | Substituted 2-aminobenzothiazoles and derivatives useful as cerebrovascular agents |
| FR2619713B1 (fr) * | 1987-08-25 | 1990-08-31 | Rhone Poulenc Sante | Application de l'amino-2 trifluoromethoxy-6 benzothiazole pour obtenir un medicament destine au traitement des troubles du sommeil et de la depression |
| FR2619712B1 (fr) * | 1987-08-25 | 1990-08-31 | Rhone Poulenc Sante | Application de l'amino-2 trifluoromethoxy-6 benzothiazole pour obtenir un medicament destine au traitement de la schizophrenie |
| FR2649705B2 (fr) * | 1989-07-13 | 1994-09-23 | Rhone Poulenc Sante | Medicaments a base de derives de la benzothiazolamine-2, nouveaux derives et leur preparation |
| FR2640622B1 (fr) * | 1988-12-15 | 1991-03-22 | Rhone Poulenc Sante | Derives de l'imino-2 benzothiazoline, leurs procedes de preparation et les medicaments les contenant |
| US5236940A (en) * | 1988-12-15 | 1993-08-17 | Rhone-Poulenc Sante | Pharmaceutical compositions, 2-benzothiazolamine derivatives, and their preparation |
| FR2640624B1 (fr) * | 1988-12-15 | 1994-08-12 | Rhone Poulenc Sante | Medicaments a base de derives de la benzothiazolamine-2, nouveaux derives et leur preparation |
| FR2649701B2 (fr) * | 1988-12-15 | 1991-11-22 | Rhone Poulenc Sante | Derives d'imino-2 benzothiazoline, leurs procedes de preparation et les medicaments les contenant |
| FR2649703B1 (fr) * | 1989-07-13 | 1991-11-22 | Rhone Poulenc Sante | Derives d'imino-2 polyfluoroalcoxy-6 benzothiazole, leurs procedes de preparation et les medicaments les contenant |
| ES2052954T3 (es) * | 1988-12-15 | 1994-07-16 | Rhone Poulenc Sante | Derivados de imino-2-polifluoroalcoxi-6-benzotiazol, sus procedimientos de preparacion y los medicamentos que les contienen. |
| FR2640623B1 (fr) * | 1988-12-15 | 1991-03-22 | Rhone Poulenc Sante | Derives de la benzothiazoline, leurs procedes de preparation et les medicaments les contenant |
| EP0374041B1 (fr) * | 1988-12-15 | 1992-06-17 | Rhone-Poulenc Sante | Médicaments à base de dérivés de la benzothiazolamine-2, dérivés et leur préparation |
| DK0409692T3 (da) * | 1989-07-13 | 1994-04-05 | Rhone Poulenc Sante | Derivater af 2-imino-3-heterocycloalkylbenzothiazolin, deres fremstilling og lægemidler med indhold deraf |
| US5260297A (en) * | 1989-07-13 | 1993-11-09 | Rhone Poulenc Rorer, S.A. | 2-imino-3-alkylbenzothiazoline derivatives bearing a heterocyclic substituent on the alkyl group, their preparation and medicinal products containing them. |
| FR2661910B1 (fr) * | 1990-05-11 | 1992-08-21 | Rhone Poulenc Sante | Derives d'imino-2 heterocyclylalkyl-3 benzothiazoline, leur preparation et les medicaments les contenant. |
| FR2649702B1 (fr) * | 1989-07-13 | 1991-11-22 | Rhone Poulenc Sante | Derives d'alkylimino-2 benzothiazoline, leurs procedes de preparation et les medicaments les contenant |
| FR2649704B1 (fr) * | 1989-07-13 | 1991-11-22 | Rhone Poulenc Sante | Derives d'imino-2 ethyl-3 benzothiazoline, leurs procedes de preparation et les medicaments les contenant |
| FR2662160B1 (fr) * | 1990-05-18 | 1992-07-24 | Rhone Poulenc Sante | Derives d'alkylthio-3 propyl-3 benzothiazoline leur preparation et les medicaments les contenant. |
| FR2662694A1 (fr) * | 1990-06-05 | 1991-12-06 | Rhone Poulenc Sante | Derives du benzoselenazole, leur preparation et les medicaments les contenant. |
| FR2663030A1 (fr) * | 1990-06-05 | 1991-12-13 | Rhone Poulenc Sante | Derives selenies de benzothiazoline leur preparation et les medicaments les contenant. |
| FR2662695A1 (fr) * | 1990-06-05 | 1991-12-06 | Rhone Poulenc Sante | Amino-2 polyfluoroalcoxy-6 benzoselenazoles, leur preparation et les medicaments les contenant. |
| FR2663029B1 (fr) * | 1990-06-07 | 1992-07-31 | Rhone Poulenc Sante | Derives de benzothiazole, leur preparation et les medicaments les contenant. |
| FR2688138B1 (fr) * | 1992-03-06 | 1995-05-05 | Rhone Poulenc Rorer Sa | Application de l'amino-2 trifluoromethoxy-6 benzothiazole pour obtenir un medicament destine au traitement de la sclerose laterale amyotrophique. |
| FR2699077B1 (fr) * | 1992-12-16 | 1995-01-13 | Rhone Poulenc Rorer Sa | Application d'anticonvulsivants dans le traitement de lésions neurologiques liées à des traumatismes. |
| FR2700116B1 (fr) * | 1993-01-07 | 1995-02-03 | Rhone Poulenc Rorer Sa | Application d'anticonvulsivants comme radioprotecteurs. |
| FR2700117B1 (fr) * | 1993-01-07 | 1995-02-03 | Rhone Poulenc Rorer Sa | Application d'anticonvulsivants dans le traitement de la maladie de Parkinson et des syndromes parkinsoniens. |
| FR2702148B1 (fr) * | 1993-03-05 | 1995-04-07 | Rhone Poulenc Rorer Sa | Application d'anticonvulsivants dans le traitement du neuro-sida. |
| FR2726271B1 (fr) * | 1994-10-26 | 1996-12-06 | Rhone Poulenc Rorer Sa | Derives de 6-polyfluoroalcoxy-2-aminobenzothiazole |
| FR2786101B1 (fr) | 1998-11-24 | 2002-07-05 | Aventis Laboratoire | Utilisation de la nicergoline dans le traitement de la spasticite |
| FR2787028B1 (fr) | 1998-12-15 | 2002-10-18 | Aventis Pharma Sa | Utilisation du riluzole dans le traitement des traumatismes acoustiques |
| CA2361924A1 (en) * | 1999-01-12 | 2000-07-20 | Izumi Kamo | Compositions for treating frequent urination and urinary incontinence |
| CZ20031387A3 (cs) | 2000-11-30 | 2004-04-14 | Pfizer Products Inc. | Farmaceutický prostředek, kterým je směs agonistů gama-aminomáselné kyseliny a inhibitorů aldózreduktázy |
| EP1337271B1 (en) * | 2000-11-30 | 2004-11-03 | Pfizer Products Inc. | Combination of gaba agonists and sorbitol dehydrogenase inhibitors |
| EP1490090A4 (en) | 2002-02-22 | 2006-09-20 | New River Pharmaceuticals Inc | SYSTEMS FOR DELIVERING ACTIVE AGENTS AND METHODS FOR PROTECTING AND DELIVERING ACTIVE AGENTS |
| KR20060011873A (ko) * | 2003-05-16 | 2006-02-03 | 화이자 프로덕츠 인코포레이티드 | 비정형 항정신약과 ｇａｂａ 조절제, 항경련성 약물 또는 벤조다이아제핀의 치료 혼합물 |
| PL1691811T3 (pl) | 2003-12-11 | 2014-12-31 | Sunovion Pharmaceuticals Inc | Skojarzenie leku uspokajającego i modulatora neuroprzekaźnikowego oraz sposoby poprawy jakości snu i leczenia depresji |
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Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879531A (en) * | 1972-07-17 | 1975-04-22 | Uniroyal Inc | 2-aminothiazoles compositions and methods for using them as psychotherapeutic agents |
| US3876653A (en) * | 1973-03-26 | 1975-04-08 | Kyowa Hakko Kogyo Kk | Benzothiazole derivatives |
-
1980
- 1980-10-17 FR FR8022218A patent/FR2492258A1/fr active Granted
-
1981
- 1981-09-18 IL IL63880A patent/IL63880A0/xx not_active IP Right Cessation
- 1981-10-01 GR GR66186A patent/GR75804B/el unknown
- 1981-10-05 US US06/308,695 patent/US4370338A/en not_active Expired - Lifetime
- 1981-10-07 DK DK444281A patent/DK444281A/da not_active Application Discontinuation
- 1981-10-09 EP EP81401564A patent/EP0050551B1/fr not_active Expired
- 1981-10-09 DE DE8181401564T patent/DE3163230D1/de not_active Expired
- 1981-10-15 CA CA000387977A patent/CA1166159A/fr not_active Expired
- 1981-10-15 PT PT73828A patent/PT73828B/pt unknown
- 1981-10-16 AU AU76545/81A patent/AU545437B2/en not_active Ceased
- 1981-10-16 ZA ZA817187A patent/ZA817187B/xx unknown
- 1981-10-16 JP JP56165586A patent/JPS5795910A/ja active Granted
- 1981-10-16 NO NO813492A patent/NO813492L/no unknown
- 1981-10-16 HU HU812994A patent/HU184893B/hu not_active IP Right Cessation
- 1981-10-16 MA MA19508A patent/MA19364A1/fr unknown
- 1981-10-19 AR AR287142A patent/AR227069A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0050551A1 (fr) | 1982-04-28 |
| JPH0148884B2 (enExample) | 1989-10-20 |
| IL63880A0 (en) | 1981-12-31 |
| PT73828A (fr) | 1981-11-01 |
| HU184893B (en) | 1984-10-29 |
| FR2492258A1 (fr) | 1982-04-23 |
| MA19364A1 (fr) | 1982-07-01 |
| EP0050551B1 (fr) | 1984-04-18 |
| PT73828B (fr) | 1983-01-17 |
| ZA817187B (en) | 1982-09-29 |
| AU545437B2 (en) | 1985-07-11 |
| FR2492258B1 (enExample) | 1982-11-26 |
| AR227069A1 (es) | 1982-09-15 |
| DE3163230D1 (en) | 1984-05-24 |
| GR75804B (enExample) | 1984-08-02 |
| AU7654581A (en) | 1982-04-22 |
| DK444281A (da) | 1982-04-18 |
| JPS5795910A (en) | 1982-06-15 |
| NO813492L (no) | 1982-04-19 |
| US4370338A (en) | 1983-01-25 |
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