http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1390658-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_2e5edd48190cba3fa70dd3975efd9831 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D239-42 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D239-50 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D513-04 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D239-50 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D513-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D239-42 |
| filingDate | 1972-11-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1975-04-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1390658-A |
| titleOfInvention | Thiazolopyrimidine derivatives |
| abstract | 1390658 Thiazolo[5,4-d]pyrimidines DR KARL THOMAE GmbH 10 Nov 1972 [11 Nov 1971 5 Oct 1972 (2)] 52050/72 Heading C2C Novel thiazolo[5,4-d]pyrimidines of the general formula wherein R 1 is a hydrogen atom or phenyl or C 1-3 alkyl group and each of R 2 and R 3 is a piperazino or 1,4-diazacycloheptan-1-y1 group optionally substituted at the 4-position by an acyl, carbamoyl, benzyl, C 1-3 alkyl or C 2-3 hydroxyalkyl group, or a morpholino, hexahydro-1,4-oxoazepin-4-yl, thiomorpholino, 1- oxido - thiomorpholino, 1,1 - dioxido - thiomorpholino, hexahydro - 1,4 - thiazepin - 4 - yl, 1 - oxido - hexahydro - 1,4 - thiazepino - 4 - yl, 1,1 - dioxido - hexahydro - 1,4 - thiazepin - 4- yl, N - hydroxyalkylamino, N,N - di(hydroxyalkyl)amino, N - methoxyalkyl - N - hydroxyalkylamino, N - alkyl - N - hydroxyalkylamino, N - alkyl - N - (dihydroxyalkyl)amino, N -cycloalkyl - N - (dihydroxyalkyl)amino, N - hydroxyalkyl - N - (dihydroxyalkyl) - amino or aminoalkylamino group, the C skeleton of each of the above heterocyclic groups being either unsubstituted or substituted by one or two C 1-3 alkyl groups, and acid addition salts thereof are prepared (a) by reacting a thiazolo[5,4-d]pyrimidine of the general formula wherein one of Z 2 and Z 3 is a radical replaceable by an R 2 or R 3 radical upon reaction with an appropriate amine and the other is the same or as R 2 or R 3 , with an amine of the general formula R 2 H or R 3 H; (b) when one of R 2 and R 3 is a 1-oxido-thiomorpholino, 1,1-dioxidothiomorpholino, 1 -oxido-hexahydro- 1 ,4-thiazepin-4-yl or 1,1-dioxido-1,4-thiazepin-4-yl group which is optionally substituted by one or two C 1-3 alkyl groups and the other is not an optionally substituted thiomorpholino or hexahydro-1,4-thiazepin-4-yl group, by oxidizing the corresponding compound of the first general formula above wherein at least one of R 2 and R 3 is a thiomorpholino or hexahydro-1,4-thiazepin-4-yl group, optionally substituted by one or two C 1-3 alkyl groups; (c) when one of R 2 and R 3 is a thiomorpholino or hexahydro-1,4-thiazepin-4-yl group, optionally substituted by one or two C 1-3 alkyl groups and the other is not a group containing an S-oxide radical or a piperazino or 1,4-diazacycloheptan-1-yl group substituted in the 4-position by an acyl or carbamoyl group, by reacting the corresponding compound of the first general formula above wherein at least one of R 2 and R 3 is an S-oxide-containing group with a hydrohalic acid, and (d) by reacting a 5-amino-6-mercaptopyrimidine of the general formula with a carboxylic acid of the general formula R 1 -COOH or an amide thereof; followed optionally by salification of the product with an acid. Thiazolo[5,4 - d]pyrimidines of the second general formula above are prepared (a) when one of Z 2 and Z 3 is a hydrogen atom and the other is as R 2 or R 3 , by reacting the corresponding compound in which each of Z 2 and Z 3 is a halogen atom with an amine of the third or fourth general formula above at a relatively low temperature, (b) when one of Z 2 and Z 3 is an alkoxy, phenoxy or alkylthio group and the other is a halogen atom or as R 2 or R 3 , by reacting the corresponding compound in which at least one of Z 2 and Z 3 is a halogen atom with an alkali metal alkoxide, phenolate or an alkylmercaptide, (c) when one of Z 2 and Z 3 is an alkylsulphinyl or alkylsulphonyl group and the other is a 1-oxido- or 1,1 .dioxido-thiomorpholin-4-yl group, by oxidizing the corresponding compound in which one of Z 2 and Z 3 is an alkylthio group and the other is a thiomorpholino group, (d) when one of Z 2 and Z 3 is an alkoxy group and the other is as R 2 or R 3 , by reacting the corresponding compound in which one of Z 2 and Z 3 is a halogen atom and the other is as R 2 or R 3 with an amine of the third or fourth general formula above and (e) when one of Z 2 and Z 3 is a halogen atom and the other is as R 2 or R 3 , by saponifying the corresponding compound in which one of Z 2 and Z 3 is an alkoxy group and the other is as R 2 or R 3 with an acid and reacting the resulting hydroxy - amino - thiazolo[5,4 - d]pyrimidine with a phosphoryl halide at an elevated temperature. 2 - N - Formylpiperazino - 4 - (1 - oxidothiomorpholino) - 5 - nitro - 6 mercaptopyrimidine is prepared by reacting 2,4,6-trichloropyrimidine with thiomorpholine, reacting the resulting 2,6 - dichloro - 4 - thiomorpholinopyrimidine with N-formylpiperazine, reaching the resulting 2-N- formylpiperazino - 4 - thiomorpholino - 6 -chloropyrimidine with conc. H 2 SO 4 /HNO 3 and reacting the resulting 2 - N - formylpiperazino - 4 - (1- oxidothiomorpholino) - 5 - nitro - 6 - chloropyrimidine with hydrogen sulphide in the presence of sodium. It may be reduced with sodium dithionite to give the corresponding 5-amino derivative or heated in the presence of hydrogen sulphide to give the corresponding 4-thiomorpholino-5-amino derivative. Pharmaceutical compositions having blood pressure-lowering and antithrombotic activity comprise, as active ingredient, a thiazolo[5,4-d]- pyrimidine of the first general formula above or a physiologically compatible acid addition salt thereof, in association with a pharmaceutical carrier or excipient, and may be administered orally, rectally or parenterally. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2010138589-A1 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-9096614-B2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-2014315885-A1 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-103896857-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2009042607-A1 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-103896857-B http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-9777018-B2 |
| priorityDate | 1971-11-11-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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