GB1390658A - Thiazolopyrimidine derivatives - Google Patents
Thiazolopyrimidine derivativesInfo
- Publication number
- GB1390658A GB1390658A GB5205072A GB5205072A GB1390658A GB 1390658 A GB1390658 A GB 1390658A GB 5205072 A GB5205072 A GB 5205072A GB 5205072 A GB5205072 A GB 5205072A GB 1390658 A GB1390658 A GB 1390658A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- general formula
- thiomorpholino
- reacting
- hexahydro
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2155963A DE2155963A1 (en) | 1971-11-11 | 1971-11-11 | 5,7-diamino-thiazolo(5,4-d)pyrimidines - with hypotensive and antithrombotic activity |
DE19722248791 DE2248791A1 (en) | 1972-10-05 | 1972-10-05 | Thiazolo (5,4-d) pyrimidines - by reaction of halothiazolo pyrimidines with amines,for treating thrombosis,hypotension |
DE19722248792 DE2248792A1 (en) | 1972-10-05 | 1972-10-05 | Thiazolo (5,4-d) pyrimidines - by reaction of halothiazolo pyrimidines with amines,for treating thrombosis,hypotension |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1390658A true GB1390658A (en) | 1975-04-16 |
Family
ID=27183827
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5205072A Expired GB1390658A (en) | 1971-11-11 | 1972-11-10 | Thiazolopyrimidine derivatives |
Country Status (11)
Country | Link |
---|---|
JP (1) | JPS4885596A (en) |
AU (1) | AU4875672A (en) |
BE (1) | BE791242A (en) |
DD (1) | DD105450A5 (en) |
FR (1) | FR2159421B1 (en) |
GB (1) | GB1390658A (en) |
HU (1) | HU165855B (en) |
IL (1) | IL40800A0 (en) |
NL (1) | NL7215222A (en) |
PL (1) | PL79689B1 (en) |
SU (1) | SU493974A3 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009042607A1 (en) | 2007-09-24 | 2009-04-02 | Genentech, Inc. | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
WO2010138589A1 (en) | 2009-05-27 | 2010-12-02 | Genentech, Inc. | Bicyclic pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
CN103896857A (en) * | 2012-12-26 | 2014-07-02 | 上海医药工业研究院 | Preparation method of 4,6-dichloro-2-(propythio)pyrimidine-5-amine |
US20140315885A1 (en) * | 2011-11-10 | 2014-10-23 | Ucb Pharma S.A. | Therapeutically Active Thiazolo-Pyrimidine Derivatives |
US9777018B2 (en) | 2011-06-09 | 2017-10-03 | Rhizen Pharmaceuticals Sa | Compounds as modulators of GPR-119 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2665277T3 (en) * | 2009-03-13 | 2018-04-25 | Katholieke Universiteit Leuven K.U. Leuven R&D | Purine analogues and their use as immunosuppressive agents |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB786007A (en) * | 1956-01-30 | 1957-11-06 | Wellcome Found | Thiazolo-pyrimidines |
-
0
- BE BE791242D patent/BE791242A/en unknown
-
1972
- 1972-11-09 FR FR7239745A patent/FR2159421B1/fr not_active Expired
- 1972-11-09 JP JP47112502A patent/JPS4885596A/ja active Pending
- 1972-11-09 DD DD166766A patent/DD105450A5/xx unknown
- 1972-11-09 HU HUTO892A patent/HU165855B/hu unknown
- 1972-11-10 IL IL40800A patent/IL40800A0/en unknown
- 1972-11-10 GB GB5205072A patent/GB1390658A/en not_active Expired
- 1972-11-10 AU AU48756/72A patent/AU4875672A/en not_active Expired
- 1972-11-10 NL NL7215222A patent/NL7215222A/xx unknown
- 1972-11-10 PL PL1972158800A patent/PL79689B1/en unknown
-
1974
- 1974-01-28 SU SU1991262A patent/SU493974A3/en active
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009042607A1 (en) | 2007-09-24 | 2009-04-02 | Genentech, Inc. | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
WO2010138589A1 (en) | 2009-05-27 | 2010-12-02 | Genentech, Inc. | Bicyclic pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
US9777018B2 (en) | 2011-06-09 | 2017-10-03 | Rhizen Pharmaceuticals Sa | Compounds as modulators of GPR-119 |
US20140315885A1 (en) * | 2011-11-10 | 2014-10-23 | Ucb Pharma S.A. | Therapeutically Active Thiazolo-Pyrimidine Derivatives |
US9096614B2 (en) * | 2011-11-10 | 2015-08-04 | Ucb Pharma S.A. | Therapeutically active thiazolo-pyrimidine derivatives |
CN103896857A (en) * | 2012-12-26 | 2014-07-02 | 上海医药工业研究院 | Preparation method of 4,6-dichloro-2-(propythio)pyrimidine-5-amine |
CN103896857B (en) * | 2012-12-26 | 2015-12-23 | 上海医药工业研究院 | A kind of preparation method of 4,6-bis-chloro-2-(rosickyite base) pyrimidine-5-amine |
Also Published As
Publication number | Publication date |
---|---|
SU493974A3 (en) | 1975-11-28 |
IL40800A0 (en) | 1973-01-30 |
HU165855B (en) | 1974-11-28 |
NL7215222A (en) | 1973-05-15 |
BE791242A (en) | 1973-05-10 |
JPS4885596A (en) | 1973-11-13 |
DD105450A5 (en) | 1974-04-20 |
AU4875672A (en) | 1974-05-16 |
FR2159421A1 (en) | 1973-06-22 |
PL79689B1 (en) | 1975-06-30 |
FR2159421B1 (en) | 1976-03-05 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |