CH460032A - Procédé de préparation de 2-isopropyl-ou 2-sec.butyl-3-oxo-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxyde - Google Patents
Procédé de préparation de 2-isopropyl-ou 2-sec.butyl-3-oxo-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxydeInfo
- Publication number
- CH460032A CH460032A CH1130466A CH1130466A CH460032A CH 460032 A CH460032 A CH 460032A CH 1130466 A CH1130466 A CH 1130466A CH 1130466 A CH1130466 A CH 1130466A CH 460032 A CH460032 A CH 460032A
- Authority
- CH
- Switzerland
- Prior art keywords
- isopropyl
- sec
- formula
- butyl
- phosgene
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 4
- PFMDLZQSUMZMHZ-UHFFFAOYSA-N 2-amino-n-propan-2-ylbenzenesulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CC=CC=C1N PFMDLZQSUMZMHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- HLCWZOAUZCVKIK-UHFFFAOYSA-N 2-amino-3-butylbenzenesulfonamide Chemical compound C(CCC)C=1C(=C(C=CC=1)S(N)(=O)=O)N HLCWZOAUZCVKIK-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000000147 hypnotic effect Effects 0.000 description 5
- 231100000111 LD50 Toxicity 0.000 description 3
- 230000002936 tranquilizing effect Effects 0.000 description 3
- 229940086542 triethylamine Drugs 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000003326 hypnotic agent Substances 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PYJUGUHFUHILLG-UHFFFAOYSA-N 1,1-dioxo-2-propan-2-yl-4H-1lambda6,2,4-benzothiadiazin-3-one Chemical compound C1=CC=C2S(=O)(=O)N(C(C)C)C(=O)NC2=C1 PYJUGUHFUHILLG-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 244000061121 Rauvolfia serpentina Species 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR77000630A FR5571M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-12-23 | 1965-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH460032A true CH460032A (fr) | 1968-07-31 |
Family
ID=9696129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1130466A CH460032A (fr) | 1965-12-23 | 1966-08-05 | Procédé de préparation de 2-isopropyl-ou 2-sec.butyl-3-oxo-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxyde |
Country Status (3)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0268990A3 (en) * | 1986-11-21 | 1988-08-10 | Fujisawa Pharmaceutical Co., Ltd. | New benzothiadiazine compounds, processes for the preparation thereof and pharmaceutical composition comprising the same |
-
1965
- 1965-12-23 FR FR77000630A patent/FR5571M/fr not_active Expired
-
1966
- 1966-08-05 CH CH1130466A patent/CH460032A/fr unknown
- 1966-08-05 ES ES0329927A patent/ES329927A2/es not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0268990A3 (en) * | 1986-11-21 | 1988-08-10 | Fujisawa Pharmaceutical Co., Ltd. | New benzothiadiazine compounds, processes for the preparation thereof and pharmaceutical composition comprising the same |
| US4889851A (en) * | 1986-11-21 | 1989-12-26 | Fujisawa Pharmaceutical Co, Ltd. | Benzothiadiazine compounds, and pharmaceutical composition comprising the same |
| AU603842B2 (en) * | 1986-11-21 | 1990-11-29 | Fujisawa Pharmaceutical Co., Ltd. | New benzothiadiazine compounds, processes for the preparation thereof and pharmaceutical composition comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| ES329927A2 (es) | 1967-11-16 |
| FR5571M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-11-27 |
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