GB1345552A - Process for the preparation of 2-aminobenzothiazoles and products prepared thereby - Google Patents
Process for the preparation of 2-aminobenzothiazoles and products prepared therebyInfo
- Publication number
- GB1345552A GB1345552A GB3166471A GB3166471A GB1345552A GB 1345552 A GB1345552 A GB 1345552A GB 3166471 A GB3166471 A GB 3166471A GB 3166471 A GB3166471 A GB 3166471A GB 1345552 A GB1345552 A GB 1345552A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aminobenzothiazoles
- general formula
- group
- july
- starting materials
- 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
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 title abstract 4
- -1 alkoxybenzoyl Chemical group 0.000 abstract 7
- 239000007858 starting material Substances 0.000 abstract 2
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000006331 halo benzoyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1345552 2-Aminobenzothiazoles SOC NATIONALE DES PETROLES D'AQUITAINE 6 July 1971 [6 July 1970 10 June 1971] 31664/71 Heading C2C 2-Aminobenzothiazoles of the general formula wherein R is an optionally substituted aryl, aralkyl, aroyl or alkaryl group and R<SP>1</SP> represents the optional presence of one or more substituents of the benzene nucleus A, are prepared by reaction of an isothiocyanate of the general formula RNCS or SCNR<SP>11</SP>NCS, wherein R<SP>11</SP> is a divalent group corresponding to R, but with one fewer hydrogen atom, with a 2-aminothiophenol of the general formula or an acid addition salt thereof, in a non-acidic solvent which is inert to the starting materials and product obtained and to H 2 S, which is capable of dissolving the starting materials and which has a boiling point higher than the temperature at which the reaction occurs. 2-Aminobenzothiazoles of the first general formula above, wherein R is a halophenyl, alkoxyphenyl, alkoxybenzoyl, halobenzoyl, acetoxybenzoyl, alkylthiobenzoyl, nitrobenzoyl, methylthiophenyl, naphthyl or benzothiazolylaminophenyl group and wherein R is a phenyl, benzoyl or chlorobenzoyl group and R<SP>1</SP> is a halogen atom are novel.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7024954A FR2097405A5 (en) | 1970-07-06 | 1970-07-06 | Benzthiazoles prepn - products useful as eg bactericides and local anaesthetics |
| FR7121070A FR2140862A6 (en) | 1971-06-10 | 1971-06-10 | Benzthiazoles prepn - products useful as eg bactericides and local anaesthetics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1345552A true GB1345552A (en) | 1974-01-30 |
Family
ID=26215835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3166471A Expired GB1345552A (en) | 1970-07-06 | 1971-07-06 | Process for the preparation of 2-aminobenzothiazoles and products prepared thereby |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE769490A (en) |
| DE (1) | DE2133649A1 (en) |
| GB (1) | GB1345552A (en) |
| IT (1) | IT1005045B (en) |
| LU (1) | LU63457A1 (en) |
| NL (1) | NL7109150A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63313729A (en) * | 1987-03-16 | 1988-12-21 | ワーナー−ランバート・コンパニー | Substituted 2 aminobenzothiazole and derivative useful as cerebral blood vessel agent |
| WO2001097786A3 (en) * | 2000-06-21 | 2002-12-12 | Hoffmann La Roche | Benzothiazole derivatives |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| US7238808B2 (en) | 2005-03-23 | 2007-07-03 | Hoffmann-La Roche Inc. | Acetylenyl-pyrazolo-pyrimidine derivatives |
| US7338956B2 (en) * | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| US7368446B2 (en) | 2004-05-24 | 2008-05-06 | Hoffmann-La Roche Inc. | 4-hydroxy-4-methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide |
| US7459563B2 (en) | 2004-11-05 | 2008-12-02 | Hoffmann-La Roche Inc. | Process for the preparation of isonicotinic acid derivatives |
| US7504404B2 (en) | 2005-09-27 | 2009-03-17 | Hoffmann-La Roche Inc. | Compounds as metabotropic glutamate receptor antagonists |
| JP2010518136A (en) * | 2007-02-14 | 2010-05-27 | ビーエーエスエフ ソシエタス・ヨーロピア | Electroluminescent metal complex |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9711805A (en) | 1996-06-20 | 2002-01-15 | Regents The Univesity Of Texas | Compounds and methods for providing pharmacologically active preparations and use |
| US7470712B2 (en) | 2004-01-21 | 2008-12-30 | Bristol-Myers Squibb Company | Amino-benzazoles as P2Y1 receptor inhibitors |
-
1971
- 1971-07-02 LU LU63457D patent/LU63457A1/xx unknown
- 1971-07-02 NL NL7109150A patent/NL7109150A/xx unknown
- 1971-07-05 BE BE769490A patent/BE769490A/en unknown
- 1971-07-06 GB GB3166471A patent/GB1345552A/en not_active Expired
- 1971-07-06 DE DE19712133649 patent/DE2133649A1/en active Pending
- 1971-07-06 IT IT4294471A patent/IT1005045B/en active
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63313729A (en) * | 1987-03-16 | 1988-12-21 | ワーナー−ランバート・コンパニー | Substituted 2 aminobenzothiazole and derivative useful as cerebral blood vessel agent |
| WO2001097786A3 (en) * | 2000-06-21 | 2002-12-12 | Hoffmann La Roche | Benzothiazole derivatives |
| US6835732B2 (en) | 2000-06-21 | 2004-12-28 | Hoffman-La Roche Inc. | Benzothiazole derivatives with activity as adenosine receptor ligands |
| RU2251419C2 (en) * | 2000-06-21 | 2005-05-10 | Ф. Хоффманн-Ля Рош Аг | Benzothiazole derivatives |
| US6963000B2 (en) | 2000-06-21 | 2005-11-08 | Hoffman-La Roche Inc. | Benzothiazole derivatives with activity as adenosine receptor ligands |
| AU2001281817B2 (en) * | 2000-06-21 | 2005-11-24 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives |
| US7317007B2 (en) | 2000-06-21 | 2008-01-08 | Hoffmann-La Roche Inc. | Benzothiazole derivatives with activity as adenosine receptor ligands |
| US7338956B2 (en) * | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| US7368446B2 (en) | 2004-05-24 | 2008-05-06 | Hoffmann-La Roche Inc. | 4-hydroxy-4-methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide |
| US7459563B2 (en) | 2004-11-05 | 2008-12-02 | Hoffmann-La Roche Inc. | Process for the preparation of isonicotinic acid derivatives |
| US7238808B2 (en) | 2005-03-23 | 2007-07-03 | Hoffmann-La Roche Inc. | Acetylenyl-pyrazolo-pyrimidine derivatives |
| US7446113B2 (en) | 2005-03-23 | 2008-11-04 | Hoffman-La Roche Inc. | Acetylenyl-pyrazolo-pyrimidine derivatives |
| US7718661B2 (en) | 2005-03-23 | 2010-05-18 | Hoffmann-La Roche Inc. | Acetylenyl-pyrazolo-pyrimidine derivatives |
| US8063048B2 (en) | 2005-03-23 | 2011-11-22 | Hoffmann-La Roche Inc. | Acetylenyl-pyrazolo-pyrimidine derivatives |
| US7504404B2 (en) | 2005-09-27 | 2009-03-17 | Hoffmann-La Roche Inc. | Compounds as metabotropic glutamate receptor antagonists |
| US8093263B2 (en) | 2005-09-27 | 2012-01-10 | Hoffmann-La Roche Inc. | Substituted pyrazolo [1,5-a] pyrimidines as metabotropic glutamate antagonists |
| US8349844B2 (en) | 2005-09-27 | 2013-01-08 | Hoffmann-La Roche Inc. | Substituted pyrazolo [1,5-A] pyrimidines as metabotropic glutamate antagonists |
| JP2010518136A (en) * | 2007-02-14 | 2010-05-27 | ビーエーエスエフ ソシエタス・ヨーロピア | Electroluminescent metal complex |
| US9284278B2 (en) | 2007-02-14 | 2016-03-15 | Basf Se | Electroluminescent metal complex |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1005045B (en) | 1976-08-20 |
| NL7109150A (en) | 1972-01-10 |
| BE769490A (en) | 1971-11-16 |
| LU63457A1 (en) | 1971-11-12 |
| DE2133649A1 (en) | 1972-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |