IL95053A - 2-Amino-3-Alkylbenzothiazolines are converted, their preparation and pharmaceutical preparations containing them - Google Patents
2-Amino-3-Alkylbenzothiazolines are converted, their preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL95053A IL95053A IL9505390A IL9505390A IL95053A IL 95053 A IL95053 A IL 95053A IL 9505390 A IL9505390 A IL 9505390A IL 9505390 A IL9505390 A IL 9505390A IL 95053 A IL95053 A IL 95053A
- Authority
- IL
- Israel
- Prior art keywords
- phenyl
- substituted
- alkyl
- alkoxy
- ethyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- -1 1-piperazinyl Chemical group 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 6
- 229930195712 glutamate Natural products 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 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
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical class C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000002483 medication Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000003480 eluent Substances 0.000 description 22
- 238000004587 chromatography analysis Methods 0.000 description 21
- 239000000377 silicon dioxide Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 239000012153 distilled water Substances 0.000 description 16
- 239000012429 reaction media Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- GFLAFHQMFZNYRX-UHFFFAOYSA-N 2-[2-(2,2,2-trifluoroacetyl)imino-6-(trifluoromethoxy)-1,3-benzothiazol-3-yl]ethyl methanesulfonate Chemical compound C1=C(OC(F)(F)F)C=C2SC(=NC(=O)C(F)(F)F)N(CCOS(=O)(=O)C)C2=C1 GFLAFHQMFZNYRX-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- HXZYUJUTRBLKGM-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-(2-hydroxyethyl)-6-(trifluoromethoxy)-1,3-benzothiazol-2-ylidene]acetamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(=NC(=O)C(F)(F)F)N(CCO)C2=C1 HXZYUJUTRBLKGM-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- VDDZSFZWHXDIHW-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)anilino]ethanol Chemical compound OCCNC1=CC=C(OC(F)(F)F)C=C1 VDDZSFZWHXDIHW-UHFFFAOYSA-N 0.000 description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- INBPXLLLINZPQC-UHFFFAOYSA-N 2-[2-imino-6-(trifluoromethoxy)-1,3-benzothiazol-3-yl]ethanol;hydrobromide Chemical compound Br.C1=C(OC(F)(F)F)C=C2SC(=N)N(CCO)C2=C1 INBPXLLLINZPQC-UHFFFAOYSA-N 0.000 description 4
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- FTALBRSUTCGOEG-UHFFFAOYSA-N Riluzole Chemical compound C1=C(OC(F)(F)F)C=C2SC(N)=NC2=C1 FTALBRSUTCGOEG-UHFFFAOYSA-N 0.000 description 4
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 4
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
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- 201000000980 schizophrenia Diseases 0.000 description 4
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- QLFLSUUMFROBCO-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-(3-hydroxypropyl)-6-(trifluoromethoxy)-1,3-benzothiazol-2-ylidene]acetamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(=NC(=O)C(F)(F)F)N(CCCO)C2=C1 QLFLSUUMFROBCO-UHFFFAOYSA-N 0.000 description 3
- ZMOVQZLKMPUSKS-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-[2-(4-phenylpiperazin-1-yl)ethyl]-6-(trifluoromethoxy)-1,3-benzothiazol-2-ylidene]acetamide;hydrochloride Chemical compound Cl.FC(F)(F)C(=O)N=C1SC2=CC(OC(F)(F)F)=CC=C2N1CCN(CC1)CCN1C1=CC=CC=C1 ZMOVQZLKMPUSKS-UHFFFAOYSA-N 0.000 description 3
- VDDVHGVICLNMHU-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-[2-(4-pyridin-2-ylpiperazin-1-yl)ethyl]-6-(trifluoromethoxy)-1,3-benzothiazol-2-ylidene]acetamide Chemical compound FC(F)(F)C(=O)N=C1SC2=CC(OC(F)(F)F)=CC=C2N1CCN(CC1)CCN1C1=CC=CC=N1 VDDVHGVICLNMHU-UHFFFAOYSA-N 0.000 description 3
- MRXWNAKWLZLJJK-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-[3-(4-phenylpiperazin-1-yl)propyl]-6-(trifluoromethoxy)-1,3-benzothiazol-2-ylidene]acetamide;hydrochloride Chemical compound Cl.FC(F)(F)C(=O)N=C1SC2=CC(OC(F)(F)F)=CC=C2N1CCCN(CC1)CCN1C1=CC=CC=C1 MRXWNAKWLZLJJK-UHFFFAOYSA-N 0.000 description 3
- IZKGWIVZPDYOBV-UHFFFAOYSA-N 3-[2-(2,2,2-trifluoroacetyl)imino-6-(trifluoromethoxy)-1,3-benzothiazol-3-yl]propyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCCN1C(=NC(=O)C(F)(F)F)SC2=CC(OC(F)(F)F)=CC=C21 IZKGWIVZPDYOBV-UHFFFAOYSA-N 0.000 description 3
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- OAHAYPNSRUOZBZ-UHFFFAOYSA-N n-[3-[2-(4-benzylpiperazin-1-yl)ethyl]-6-(trifluoromethoxy)-1,3-benzothiazol-2-ylidene]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)N=C1SC2=CC(OC(F)(F)F)=CC=C2N1CCN(CC1)CCN1CC1=CC=CC=C1 OAHAYPNSRUOZBZ-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8909483A FR2649704B1 (fr) | 1989-07-13 | 1989-07-13 | Derives d'imino-2 ethyl-3 benzothiazoline, leurs procedes de preparation et les medicaments les contenant |
| FR9005889A FR2661910B1 (fr) | 1990-05-11 | 1990-05-11 | Derives d'imino-2 heterocyclylalkyl-3 benzothiazoline, leur preparation et les medicaments les contenant. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL95053A0 IL95053A0 (en) | 1991-06-10 |
| IL95053A true IL95053A (en) | 1994-05-30 |
Family
ID=26227474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9505390A IL95053A (en) | 1989-07-13 | 1990-07-12 | 2-Amino-3-Alkylbenzothiazolines are converted, their preparation and pharmaceutical preparations containing them |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0409692B1 (cs) |
| JP (1) | JPH0386871A (cs) |
| AT (1) | ATE102612T1 (cs) |
| AU (1) | AU624972B2 (cs) |
| CA (1) | CA2021031A1 (cs) |
| CZ (1) | CZ281164B6 (cs) |
| DE (1) | DE69007196T2 (cs) |
| DK (1) | DK0409692T3 (cs) |
| ES (1) | ES2062445T3 (cs) |
| FI (1) | FI93109C (cs) |
| HU (1) | HU210827B (cs) |
| IE (1) | IE63318B1 (cs) |
| IL (1) | IL95053A (cs) |
| NO (1) | NO175590C (cs) |
| NZ (1) | NZ234487A (cs) |
| PL (2) | PL164326B1 (cs) |
| PT (1) | PT94701B (cs) |
| RU (1) | RU1836368C (cs) |
| SK (1) | SK278908B6 (cs) |
| YU (1) | YU47723B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2674853B1 (fr) * | 1991-04-03 | 1995-01-20 | Synthelabo | Derives de piperidinylguanidine, leur preparation et leur application en therapeutique. |
| FR2678619B1 (fr) * | 1991-07-04 | 1993-09-17 | Rhone Poulenc Rorer Sa | Derives de 1,2,4-thiadiazolo[3,4-b]benzothiazole, leur preparation et les medicaments les contenant. |
| FR2696457B1 (fr) * | 1992-10-02 | 1994-11-25 | Rhone Poulenc Rorer Sa | Dérivés de 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxyde, leur préparation et les médicaments les contenant. |
| WO1993021170A1 (fr) * | 1992-04-15 | 1993-10-28 | Rhone-Poulenc Rorer S.A. | Derives d'acide 3,4-dihydro-2h-1,2,4-benzothiadiazine 1,1-dioxyde-3-carboxylique, leur preparation et les medicaments les contenant |
| US5889010A (en) * | 1995-05-18 | 1999-03-30 | Pfizer Inc. | Benzimidazole derivatives having dopaminergic activity |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2631163B2 (de) * | 1976-07-10 | 1978-06-29 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 2-Iminobenzothiazolen |
| FR2492258A1 (fr) * | 1980-10-17 | 1982-04-23 | Pharmindustrie | Nouveau medicament a base d'amino-2 trifluoromethoxy-6 benzothiazole |
| 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 |
| EP0375510B1 (fr) * | 1988-12-15 | 1992-11-11 | Rhone-Poulenc Sante | Dérivés d'imino-2 polyfluoroalcoxy-6 benzothiazole, leurs procédés de préparation et les médicaments les contenant |
-
1990
- 1990-07-09 ES ES90401976T patent/ES2062445T3/es not_active Expired - Lifetime
- 1990-07-09 EP EP90401976A patent/EP0409692B1/fr not_active Expired - Lifetime
- 1990-07-09 DK DK90401976.7T patent/DK0409692T3/da active
- 1990-07-09 DE DE69007196T patent/DE69007196T2/de not_active Expired - Fee Related
- 1990-07-09 AT AT90401976T patent/ATE102612T1/de not_active IP Right Cessation
- 1990-07-10 AU AU58847/90A patent/AU624972B2/en not_active Ceased
- 1990-07-11 SK SK3425-90A patent/SK278908B6/sk unknown
- 1990-07-11 YU YU133990A patent/YU47723B/sh unknown
- 1990-07-11 CZ CS903425A patent/CZ281164B6/cs unknown
- 1990-07-12 CA CA002021031A patent/CA2021031A1/fr not_active Abandoned
- 1990-07-12 NO NO903113A patent/NO175590C/no unknown
- 1990-07-12 PL PL90300986A patent/PL164326B1/pl unknown
- 1990-07-12 PL PL90286036A patent/PL164152B1/pl unknown
- 1990-07-12 IE IE255190A patent/IE63318B1/en not_active IP Right Cessation
- 1990-07-12 NZ NZ234487A patent/NZ234487A/en unknown
- 1990-07-12 FI FI903531A patent/FI93109C/fi not_active IP Right Cessation
- 1990-07-12 HU HU904189A patent/HU210827B/hu not_active IP Right Cessation
- 1990-07-12 JP JP2182893A patent/JPH0386871A/ja active Pending
- 1990-07-12 IL IL9505390A patent/IL95053A/en not_active IP Right Cessation
- 1990-07-13 PT PT94701A patent/PT94701B/pt not_active IP Right Cessation
-
1992
- 1992-01-08 RU SU925010496A patent/RU1836368C/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| RH | Patent void |