FR2459239A1 - Nouveaux derives amines du benzothiazole, leur procede de preparation et leur application en therapeutique - Google Patents
Nouveaux derives amines du benzothiazole, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2459239A1 FR2459239A1 FR7915774A FR7915774A FR2459239A1 FR 2459239 A1 FR2459239 A1 FR 2459239A1 FR 7915774 A FR7915774 A FR 7915774A FR 7915774 A FR7915774 A FR 7915774A FR 2459239 A1 FR2459239 A1 FR 2459239A1
- Authority
- FR
- France
- Prior art keywords
- formula
- tetrahydro
- yield
- benzo
- prepared
- 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.)
- Granted
Links
- 150000001412 amines Chemical class 0.000 title claims description 18
- 230000001225 therapeutic effect Effects 0.000 title claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 8
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- -1 N-methylaminomethyl Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 15
- 125000005605 benzo group Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical group [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 14
- 238000006467 substitution reaction Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000007547 defect Effects 0.000 description 5
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- IGOWSOGBQMBHIY-UHFFFAOYSA-N ethyl 3-bromo-4-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCC(=O)C(Br)C1 IGOWSOGBQMBHIY-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ORLSLKMDNKEXQM-UHFFFAOYSA-N (2-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-4-yl)methyl 4-methylbenzenesulfonate Chemical compound C1CCC=2SC(C)=NC=2C1COS(=O)(=O)C1=CC=C(C)C=C1 ORLSLKMDNKEXQM-UHFFFAOYSA-N 0.000 description 2
- HALOWOFMAIDLKM-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazol-4-ylmethanamine Chemical compound NCC1CCCC2=C1N=CS2 HALOWOFMAIDLKM-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- VKCMWLOBUILIOQ-UHFFFAOYSA-N ethyl 3-bromo-2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCC(Br)C1=O VKCMWLOBUILIOQ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000003556 thioamides Chemical class 0.000 description 2
- 125000005490 tosylate group Chemical group 0.000 description 2
- GDSLLGUBDBYYID-UHFFFAOYSA-N (2-ethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)methanol Chemical compound C1CC(CO)CC2=C1N=C(CC)S2 GDSLLGUBDBYYID-UHFFFAOYSA-N 0.000 description 1
- VQVKKIYLIHOYPJ-UHFFFAOYSA-N (2-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-5-yl)methanol Chemical compound C1C(CO)CCC2=C1N=C(C)S2 VQVKKIYLIHOYPJ-UHFFFAOYSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- NPCLRBQYESMUPD-UHFFFAOYSA-N 2-methylpropanethioamide Chemical compound CC(C)C(N)=S NPCLRBQYESMUPD-UHFFFAOYSA-N 0.000 description 1
- CAJANQXVJVNVKK-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazol-4-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1C(N=CS2)=C2CCC1 CAJANQXVJVNVKK-UHFFFAOYSA-N 0.000 description 1
- VTXJLZDBWYUHPI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazol-5-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1CC(N=CS2)=C2CC1 VTXJLZDBWYUHPI-UHFFFAOYSA-N 0.000 description 1
- KZMOYPDEKDQCQQ-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazol-6-ylmethanamine Chemical compound C1C(CN)CCC2=C1SC=N2 KZMOYPDEKDQCQQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010065929 Cardiovascular insufficiency Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- SGOAPFUNJHCMTL-UHFFFAOYSA-N ethyl 2-bromo-3-oxocyclohexane-1-carboxylate Chemical compound BrC1C(CCCC1=O)C(=O)OCC SGOAPFUNJHCMTL-UHFFFAOYSA-N 0.000 description 1
- NOJBYOKLFOGIKG-UHFFFAOYSA-N ethyl 2-propan-2-yl-4,5,6,7-tetrahydro-1,3-benzothiazole-5-carboxylate Chemical compound C1C(C(=O)OCC)CCC2=C1N=C(C(C)C)S2 NOJBYOKLFOGIKG-UHFFFAOYSA-N 0.000 description 1
- UDLLBXAEMDYVSW-UHFFFAOYSA-N ethyl 4-bromo-3-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCC(Br)C(=O)C1 UDLLBXAEMDYVSW-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- NTBCNTTYBCAVOY-UHFFFAOYSA-N methyl 4-bromo-3-oxocyclohexane-1-carboxylate Chemical compound COC(=O)C1CCC(Br)C(=O)C1 NTBCNTTYBCAVOY-UHFFFAOYSA-N 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- WPZSAUFQHYFIPG-UHFFFAOYSA-N propanethioamide Chemical compound CCC(N)=S WPZSAUFQHYFIPG-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RLUJQBLWUQZMDG-UHFFFAOYSA-N toluene;hydrochloride Chemical compound Cl.CC1=CC=CC=C1 RLUJQBLWUQZMDG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7915774A FR2459239A1 (fr) | 1979-06-20 | 1979-06-20 | Nouveaux derives amines du benzothiazole, leur procede de preparation et leur application en therapeutique |
| EP80400831A EP0021940B1 (fr) | 1979-06-20 | 1980-06-10 | Nouveaux dérivés aminés du benzothiazole, leur procédé de préparation et leur application en thérapeutique |
| DE8080400831T DE3061672D1 (en) | 1979-06-20 | 1980-06-10 | Amino derivatives of benzothiazole, process for their preparation and their use in therapy |
| CA000353873A CA1140136A (en) | 1979-06-20 | 1980-06-12 | Process for the preparation of new amino derivatives of benzothiazole and therapeutical application thereof |
| US06/160,458 US4337343A (en) | 1979-06-20 | 1980-06-18 | 4,5 or 6-Alkylaminoalkyl-2-alkyl-4,5,6,7-tetrahydro benzo[d]thiazoles |
| ES492578A ES8103071A1 (es) | 1979-06-20 | 1980-06-19 | Procedimiento de preparacion de nuevos derivados aminicos del benzotiazol |
| JP8384480A JPS567772A (en) | 1979-06-20 | 1980-06-20 | Novel amino derivative of benzothiazole and its manufacture |
| US06/356,617 US4423056A (en) | 1979-06-20 | 1982-03-10 | 5(Aminomethyl)-4,5,6,7-tetrahydro[d]thiazole containing compositions for and medical use in treating circulatory insufficiencies |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7915774A FR2459239A1 (fr) | 1979-06-20 | 1979-06-20 | Nouveaux derives amines du benzothiazole, leur procede de preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2459239A1 true FR2459239A1 (fr) | 1981-01-09 |
| FR2459239B1 FR2459239B1 (cg-RX-API-DMAC10.html) | 1982-09-10 |
Family
ID=9226843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7915774A Granted FR2459239A1 (fr) | 1979-06-20 | 1979-06-20 | Nouveaux derives amines du benzothiazole, leur procede de preparation et leur application en therapeutique |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US4337343A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0021940B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPS567772A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1140136A (cg-RX-API-DMAC10.html) |
| DE (1) | DE3061672D1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES8103071A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2459239A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE45735T1 (de) * | 1984-12-22 | 1989-09-15 | Thomae Gmbh Dr K | Tetrahydro-benzthiazole, deren herstellung und deren verwendung als zwischenprodukte oder als arnzneimittel. |
| JPS62292229A (ja) * | 1986-06-13 | 1987-12-18 | Toyo Seikan Kaisha Ltd | 易開口性蓋の製造方法 |
| DE3620813A1 (de) | 1986-06-21 | 1987-12-23 | Boehringer Ingelheim Kg | Neue tetrahydro-benzothiazole, ihre herstellung und verwendung |
| WO2008001200A2 (en) * | 2006-06-29 | 2008-01-03 | Antares Pharma Ipl Ag | Transdermal composition having enhanced color stability |
| KR102505085B1 (ko) | 2009-12-04 | 2023-02-28 | 선오비온 파마슈티컬스 인코포레이티드 | 다환형 화합물 및 이의 사용 방법 |
| JP2019523279A (ja) | 2016-07-29 | 2019-08-22 | サノビオン ファーマシューティカルズ インクＳｕｎｏｖｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | 化合物および組成物ならびにそれらの使用 |
| SG11201900689RA (en) | 2016-07-29 | 2019-02-27 | Sunovion Pharmaceuticals Inc | Compounds and compositions and uses thereof |
| CA3053903A1 (en) | 2017-02-16 | 2018-08-23 | Sunovion Pharmaceuticals Inc. | Methods of treating schizophrenia |
| AU2018312559B2 (en) | 2017-08-02 | 2022-06-02 | Pgi Drug Discovery Llc | Isochroman compounds and uses thereof |
| MY208150A (en) | 2018-02-16 | 2025-04-18 | Sunovion Pharmaceuticals Inc | Salts, crystal forms, and production methods thereof |
| JP7703449B2 (ja) | 2019-03-14 | 2025-07-07 | スミトモ・ファーマ・アメリカ・インコーポレイテッド | イソクロマニル化合物の塩およびその結晶体、ならびにそれらの製造方法、治療用途および医薬組成物 |
| US11738002B2 (en) | 2020-04-14 | 2023-08-29 | Sunovion Pharmaceuticals Inc. | Methods of treating neurological and psychiatric disorders |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2406635A1 (fr) * | 1977-10-24 | 1979-05-18 | Logeais Labor Jacques | Nouveaux derives du benzo(d)thiazole, leur procede de preparation et leurs applications en therapeutique |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792402A (fr) * | 1971-12-07 | 1973-06-07 | Ciba Geigy | Composes heterocycliques azotes et medicaments anthelminthiqueset antimicrobiens qui en contiennent |
| JPS4930360A (cg-RX-API-DMAC10.html) * | 1972-03-04 | 1974-03-18 | ||
| JPS50108261A (cg-RX-API-DMAC10.html) * | 1974-02-12 | 1975-08-26 |
-
1979
- 1979-06-20 FR FR7915774A patent/FR2459239A1/fr active Granted
-
1980
- 1980-06-10 DE DE8080400831T patent/DE3061672D1/de not_active Expired
- 1980-06-10 EP EP80400831A patent/EP0021940B1/fr not_active Expired
- 1980-06-12 CA CA000353873A patent/CA1140136A/en not_active Expired
- 1980-06-18 US US06/160,458 patent/US4337343A/en not_active Expired - Lifetime
- 1980-06-19 ES ES492578A patent/ES8103071A1/es not_active Expired
- 1980-06-20 JP JP8384480A patent/JPS567772A/ja active Granted
-
1982
- 1982-03-10 US US06/356,617 patent/US4423056A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2406635A1 (fr) * | 1977-10-24 | 1979-05-18 | Logeais Labor Jacques | Nouveaux derives du benzo(d)thiazole, leur procede de preparation et leurs applications en therapeutique |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6342622B2 (cg-RX-API-DMAC10.html) | 1988-08-24 |
| JPS567772A (en) | 1981-01-27 |
| US4423056A (en) | 1983-12-27 |
| EP0021940A1 (fr) | 1981-01-07 |
| FR2459239B1 (cg-RX-API-DMAC10.html) | 1982-09-10 |
| EP0021940B1 (fr) | 1983-01-19 |
| US4337343A (en) | 1982-06-29 |
| ES492578A0 (es) | 1981-02-16 |
| ES8103071A1 (es) | 1981-02-16 |
| CA1140136A (en) | 1983-01-25 |
| DE3061672D1 (en) | 1983-02-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |