SU561512A3 - Способ получени производных бензотиазола - Google Patents
Способ получени производных бензотиазолаInfo
- Publication number
- SU561512A3 SU561512A3 SU2055109A SU2055109A SU561512A3 SU 561512 A3 SU561512 A3 SU 561512A3 SU 2055109 A SU2055109 A SU 2055109A SU 2055109 A SU2055109 A SU 2055109A SU 561512 A3 SU561512 A3 SU 561512A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzothiazole derivatives
- oil
- sodium hydride
- preparing
- preparing benzothiazole
- Prior art date
Links
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 6
- 239000012312 sodium hydride Substances 0.000 claims description 6
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- QVKPPRYUGJFISN-UHFFFAOYSA-N n-methyl-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(NC)=NC2=C1 QVKPPRYUGJFISN-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- COSWCAGTKRUTQV-UHFFFAOYSA-N 1,1,3-trimethylurea Chemical compound CNC(=O)N(C)C COSWCAGTKRUTQV-UHFFFAOYSA-N 0.000 description 1
- FWZDAGFEKMXNOA-UHFFFAOYSA-N 1-(5-chloro-1,3-benzothiazol-2-yl)-1,3,3-trimethylurea Chemical compound ClC1=CC=C2SC(N(C)C(=O)N(C)C)=NC2=C1 FWZDAGFEKMXNOA-UHFFFAOYSA-N 0.000 description 1
- FOLKKLNIMJCBRR-UHFFFAOYSA-N 1-(5-tert-butyl-1,3-benzothiazol-2-yl)-1,3,3-trimethylurea Chemical compound CC(C)(C)C1=CC=C2SC(N(C)C(=O)N(C)C)=NC2=C1 FOLKKLNIMJCBRR-UHFFFAOYSA-N 0.000 description 1
- -1 5- Butylbenzothiazole - 2-yl Chemical group 0.000 description 1
- CKUBLIGEZAFCFL-UHFFFAOYSA-N 5-butyl-n-methyl-1,3-benzothiazol-2-amine Chemical compound CCCCC1=CC=C2SC(NC)=NC2=C1 CKUBLIGEZAFCFL-UHFFFAOYSA-N 0.000 description 1
- RURGIRFUEZESGQ-UHFFFAOYSA-N 5-ethyl-n-methyl-1,3-benzothiazol-2-amine Chemical compound CCC1=CC=C2SC(NC)=NC2=C1 RURGIRFUEZESGQ-UHFFFAOYSA-N 0.000 description 1
- PNJKZDLZKILFNF-UHFFFAOYSA-N 5-methoxy-1,3-benzothiazole Chemical compound COC1=CC=C2SC=NC2=C1 PNJKZDLZKILFNF-UHFFFAOYSA-N 0.000 description 1
- LWXZUFYKLCKILN-UHFFFAOYSA-N 5-methoxy-n-methyl-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2SC(NC)=NC2=C1 LWXZUFYKLCKILN-UHFFFAOYSA-N 0.000 description 1
- VGEJRMTVGUNZNN-UHFFFAOYSA-N 5-tert-butyl-n-methyl-1,3-benzothiazol-2-amine Chemical compound CC(C)(C)C1=CC=C2SC(NC)=NC2=C1 VGEJRMTVGUNZNN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (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 |
|---|---|---|---|
| JP7461073A JPS5614643B2 (enExample) | 1973-07-02 | 1973-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU561512A3 true SU561512A3 (ru) | 1977-06-05 |
Family
ID=13552100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2055109A SU561512A3 (ru) | 1973-07-02 | 1974-07-02 | Способ получени производных бензотиазола |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3967950A (enExample) |
| JP (1) | JPS5614643B2 (enExample) |
| AU (1) | AU467889B2 (enExample) |
| BR (1) | BR7405219A (enExample) |
| EG (1) | EG11174A (enExample) |
| ES (1) | ES427893A1 (enExample) |
| FR (1) | FR2235937B1 (enExample) |
| GB (1) | GB1445210A (enExample) |
| HU (1) | HU169897B (enExample) |
| NL (1) | NL7408862A (enExample) |
| PL (1) | PL90880B1 (enExample) |
| RO (1) | RO64482A (enExample) |
| SU (1) | SU561512A3 (enExample) |
| ZA (1) | ZA744140B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4029491A (en) * | 1976-04-29 | 1977-06-14 | Velsicol Chemical Corporation | 1-Benzothiazolyl-5-hydroxyimidazolidinones |
| DE2644425A1 (de) * | 1976-09-30 | 1978-04-06 | Schering Ag | 2-(dimethylcarbamoylimino)-benzthiazolin-3-carbonsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| EP1458382A1 (en) * | 2001-12-21 | 2004-09-22 | Novo Nordisk A/S | Amide derivatives as gk activators |
| CA2488642C (en) * | 2002-06-27 | 2011-09-06 | Dharma Rao Polisetti | Aryl carbonyl derivatives as glucokinase activators |
| PL1723128T3 (pl) | 2004-01-06 | 2013-04-30 | Novo Nordisk As | Pochodne heteroarylowe mocznika oraz ich zastosowanie jako aktywatory glukokinazy |
| WO2007006760A1 (en) * | 2005-07-08 | 2007-01-18 | Novo Nordisk A/S | Dicycloalkyl urea glucokinase activators |
| JP2009500378A (ja) * | 2005-07-08 | 2009-01-08 | ノボ・ノルデイスク・エー／エス | グルコキナーゼ活性化剤としてのジシクロアルキルカルバモイル尿素 |
| MX2008000255A (es) | 2005-07-14 | 2008-04-02 | Novo Nordisk As | Activadores de urea glucocinasa. |
| EP2118083A1 (en) * | 2007-01-09 | 2009-11-18 | Novo Nordisk A/S | Urea glucokinase activators |
| JP5226008B2 (ja) * | 2007-01-11 | 2013-07-03 | ノボ・ノルデイスク・エー／エス | ウレアグルコキナーゼアクチベーター |
| JP2021526130A (ja) | 2018-06-12 | 2021-09-30 | ブイティーブイ・セラピューティクス・エルエルシー | インスリンまたはインスリン類似体と組み合わせたグルコキナーゼ活性化薬の治療的使用 |
| WO2021167840A1 (en) | 2020-02-18 | 2021-08-26 | Vtv Therapeutics Llc | Sulfoxide and sulfone glucokinase activators and methods of use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2756135A (en) * | 1955-07-13 | 1956-07-24 | Du Pont | 1-methyl-3-(2-benzothiazolyl)-ureas and their use as herbicides |
| US3714177A (en) * | 1970-04-09 | 1973-01-30 | Exxon Research Engineering Co | Urea derivatives of2-aminobenzothiazoles |
| BE787660A (fr) * | 1971-08-19 | 1973-02-19 | Bayer Ag | Nouvelles 1-(2-benzothiazolyl)1,3-dialkylurees, leur preparation et leur application comme herbicides |
| FR2155831A1 (en) * | 1971-10-08 | 1973-05-25 | Nippon Soda Co | N,n'-dimethyl-n-benzothiazolyl -ureas - as herbicides |
| US3818024A (en) * | 1972-02-16 | 1974-06-18 | Velsicol Chemical Corp | Benzothiazol substituted thiadiazolidines |
-
1973
- 1973-07-02 JP JP7461073A patent/JPS5614643B2/ja not_active Expired
-
1974
- 1974-06-10 US US05/477,930 patent/US3967950A/en not_active Expired - Lifetime
- 1974-06-12 GB GB2602574A patent/GB1445210A/en not_active Expired
- 1974-06-19 AU AU70249/74A patent/AU467889B2/en not_active Expired
- 1974-06-21 FR FR7421742A patent/FR2235937B1/fr not_active Expired
- 1974-06-25 BR BR5219/74A patent/BR7405219A/pt unknown
- 1974-06-27 ZA ZA00744140A patent/ZA744140B/xx unknown
- 1974-07-01 NL NL7408862A patent/NL7408862A/xx unknown
- 1974-07-01 HU HUNI177A patent/HU169897B/hu unknown
- 1974-07-01 PL PL1974172371A patent/PL90880B1/pl unknown
- 1974-07-02 SU SU2055109A patent/SU561512A3/ru active
- 1974-07-02 EG EG258/74A patent/EG11174A/xx active
- 1974-07-02 ES ES427893A patent/ES427893A1/es not_active Expired
- 1974-07-10 RO RO7479366A patent/RO64482A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU467889B2 (en) | 1975-12-18 |
| GB1445210A (en) | 1976-08-04 |
| JPS5614643B2 (enExample) | 1981-04-06 |
| RO64482A (fr) | 1979-05-15 |
| ZA744140B (en) | 1975-06-25 |
| HU169897B (enExample) | 1977-02-28 |
| PL90880B1 (enExample) | 1977-02-28 |
| EG11174A (en) | 1977-01-31 |
| NL7408862A (nl) | 1975-01-06 |
| BR7405219A (pt) | 1976-02-24 |
| JPS5024274A (enExample) | 1975-03-15 |
| AU7024974A (en) | 1975-12-18 |
| DE2431801A1 (de) | 1975-01-23 |
| FR2235937B1 (enExample) | 1978-01-20 |
| ES427893A1 (es) | 1976-11-16 |
| US3967950A (en) | 1976-07-06 |
| DE2431801B2 (de) | 1976-01-15 |
| FR2235937A1 (enExample) | 1975-01-31 |
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