GB1072413A - New dihydrothieno[3,2-d]pyrimidines - Google Patents
New dihydrothieno[3,2-d]pyrimidinesInfo
- Publication number
- GB1072413A GB1072413A GB2509364A GB2509364A GB1072413A GB 1072413 A GB1072413 A GB 1072413A GB 2509364 A GB2509364 A GB 2509364A GB 2509364 A GB2509364 A GB 2509364A GB 1072413 A GB1072413 A GB 1072413A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- formula
- alkyl
- compound
- free
- 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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the Formula I wherein R represents a halogen atom or an aryl a free hydroxy or a C1- 5 alkylmercapto group or a group of the formula -NR3R4 (in which R3 represents a C1- 6 alkyl or an aralkyl group and R4 represents a hydrogen atom or a C1- 6 alkyl group or R3 and R4, together with the adjacent nitrogen atom, represent a heterocyclic ring which may contain a further hetero-atom and which may be substituted with a C1- 3 alkyl group or an aryl group); R1 represents a hydrogen or halogen atom, or a mercapto group, a hydroxy group (which may be free or substituted by a C1- 6 alkyl, C2- 6 alkenyl or (C1- 6 alkoxy)-C1- 6 alkyl group) or a group of the formula -NR5R6 (in which R5 represents a hydrogen atom or an amine, C1- 6 alkyl, C2- 6 alkenyl, C1- 6 hydroxyalkyl, (C1- 6 alkoxy) C1- 6 alkyl, [di-(C1- 6 alkyl) amino] C1- 6 alkyl, aryl, aralkyl or cycloalkyl group and R6 represents a hydrogen atom or a C1- 6 alkyl, C2- 6 alkenyl or C1- 6 hydroxyalkyl group or R5 and R6, together with the adjacent nitrogen atom, represent a heterocyclic ring which may contain a further hetero-atom and which may be substituted by a C1- 3 alkyl group); R2 represents (where present) a C1- 10 alkyl or phenyl group and n represents 0 or 1, and (where at least one of R, R1 and R2 represents a basic group) non-toxic acid addition salts thereof, and (where R and/or R1 represents a free hydroxy group or R1 represents a free mercapto group) non-toxic salts with bases; a process for the preparation of compounds of the Formula I (in which R1 represents a free hydroxy group) where a compound of the Formula II (in which X represents a carboxylic ester group and Y represents an oxo group) is reacted with a compound of the formula R-C(NH2)=Z or a tautomer thereof of the formula R-C(=NH)-ZH (in which Z represents an imino group); a process for the preparation of compounds of the Formula I wherein a compound of the Formula V (in which at least one of A and A1 represents a halogen atom or a free or C1- 5 alkyl substituted mercapto group and the other, if not representing a halogen atom or a free or C1- 5 alkyl substituted mercapto group, represents any of the other groups which may be represented by R and R1) is reacted with a compound of the formula R7H, whereby A1 is replaced by R7, and A either remains unreplaced or is replaced by R7 in the same reaction stage or a further reagent R8H is added to replace A by a group R8 (where R7 and R8, the same or different), represent any of the atoms or groups which may be represented by R and R1 other than a hydrogen or halogen atom or an alkyl, aryl or aralkyl group; the process for preparing compounds of the Formula I (in which R is as defined above, with the exception of a hydroxy group, and R1 represents a hydroxy group substituted by a C1- 6 alkyl, C2- 6 alkenyl or (C1- 6 alkoxy)-C1- 6 alkyl group) in which a compound of the Formula I in which R and/or R1 represents a free hydroxy group is reacted with an appropriate alkylating, alkenylating or aralkylating agent; the process for the preparation of compounds of the Formula I (in which R1 represents an amino group of the formula -NR3R4, wherein R3 and R4 are as defined above except that R3 does not represent an aryl or pyridyl group and R3 and R4 do not together represent a heterocylic group) in which the corresponding compound of the Formula I, in which R1 represents a free amino group, is reacted with an appropriate alkylating, alkenylating or aralkylating agent; and the process for the preparation of compounds of the Formula I (in which R and/or R1 represents a hydrogen atom) in which a corresponding compound of the Formula I, in which R and/or R1 represent a mercapto group, is reduced. <FORM:1072413/C2/1> Dihydrothieno[3,2-d]pyrimidines of the Formula V may be prepared by the method described above, in which a compound of the Formula II is reacted with a compound of the formula R-C(NH2)=Z or its tautomer of the formula R-C(:NH)-ZH, or, where A and/or A1 represent free or C1- 5 alkyl substituted mercapto groups, by cyclization, e.g. by reaction of a 3 - imino - tetrahydrothiophene - 2 - carboxylic acid thioamide with a thiourea, by reacting the dihydroxy compound with P2S5, followed if desired by alkylation; or from the corresponding halogen compound by reaction with thiourea, an alkali metal hydrosulphide or an alkali metal mercaptide, or, where A and/or A1 represent halogen atoms, cyclizing a compound of the Formula II (in which X represents a carbalkoxy group) with urea and converting the resulting 2,4-dihydroxy-dihydrothieno[3,2-d]pyrimidine into the dihalo compound by known methods. Therapeutic compositions, with cardiovascular, sedative, analgesic diuretic, cytostatic, bacteriostatic, antiphlogistic and/or antipyretic activity, which may take the forms of capsules, dragees, powders, drop solutions, suspensions, solutions, ampoules or suppositories, for oral, parenteral or rectal administration, comprise compounds of the Formula I or (where at least one of R, R1 and R2 represents a basic group) non-toxic acid addition salts thereof or (where R and/or R1 represents a free hydroxy group or R1 represents a free mercapto group) non-toxic salts thereof with bases, together with a pharmaceutical carrier.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US288491A US3272811A (en) | 1962-07-04 | 1963-06-17 | Dihydrothieno-[3, 4-d]-pyrimidines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1072413A true GB1072413A (en) | 1967-06-14 |
Family
ID=23107339
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2509464A Expired GB1072414A (en) | 1963-06-17 | 1964-06-17 | New dihydrothieno(3,2-d)pyrimidines |
GB2509364A Expired GB1072413A (en) | 1963-06-17 | 1964-06-17 | New dihydrothieno[3,2-d]pyrimidines |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2509464A Expired GB1072414A (en) | 1963-06-17 | 1964-06-17 | New dihydrothieno(3,2-d)pyrimidines |
Country Status (7)
Country | Link |
---|---|
BE (2) | BE649348A (en) |
CH (2) | CH446358A (en) |
ES (1) | ES301103A1 (en) |
FR (4) | FR3824M (en) |
GB (2) | GB1072414A (en) |
NL (4) | NL6406834A (en) |
SE (2) | SE300214B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0276057A2 (en) * | 1987-01-21 | 1988-07-27 | Merck & Co. Inc. | Piperazinylpyrimidines as beta-adrenergic receptor blocking agents |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005019201A1 (en) | 2006-04-19 | 2006-11-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New compounds for the treatment of inflammatory diseases |
EP1847543A1 (en) | 2006-04-19 | 2007-10-24 | Boehringer Ingelheim Pharma GmbH & Co. KG | Dihydrothienopyrimidines for the treatment of inflammatory diseases |
CA2705414C (en) | 2007-10-19 | 2016-05-24 | Boehringer Ingelheim International Gmbh | Substituted piperidino-dihydrothienopyrimidines |
WO2009050236A1 (en) | 2007-10-19 | 2009-04-23 | Boehringer Ingelheim International Gmbh | Novel piperazino-dihydrothienopyrimidine derivatives |
CN101827853A (en) | 2007-10-19 | 2010-09-08 | 贝林格尔.英格海姆国际有限公司 | Heterocycle-substituted piperazino-dihydrothienopyrimidines |
US9802954B2 (en) | 2011-08-24 | 2017-10-31 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
US20130059866A1 (en) | 2011-08-24 | 2013-03-07 | Boehringer Ingelheim International Gmbh | Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma |
-
0
- NL NL124131A patent/NL124131C/xx active
- NL NL122810A patent/NL122810C/xx active
-
1964
- 1964-05-28 CH CH695264A patent/CH446358A/en unknown
- 1964-05-28 CH CH695364A patent/CH442328A/en unknown
- 1964-06-05 SE SE686864A patent/SE300214B/xx unknown
- 1964-06-05 SE SE686764A patent/SE300213B/xx unknown
- 1964-06-15 FR FR978344A patent/FR3824M/en active Active
- 1964-06-15 FR FR978342A patent/FR1555459A/fr not_active Expired
- 1964-06-15 FR FR978343A patent/FR1555460A/fr not_active Expired
- 1964-06-16 BE BE649348A patent/BE649348A/xx unknown
- 1964-06-16 NL NL6406834A patent/NL6406834A/xx unknown
- 1964-06-16 ES ES0301103A patent/ES301103A1/en not_active Expired
- 1964-06-16 BE BE649347A patent/BE649347A/xx unknown
- 1964-06-16 NL NL6406835A patent/NL6406835A/xx unknown
- 1964-06-17 GB GB2509464A patent/GB1072414A/en not_active Expired
- 1964-06-17 GB GB2509364A patent/GB1072413A/en not_active Expired
- 1964-09-04 FR FR987185A patent/FR3648M/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0276057A2 (en) * | 1987-01-21 | 1988-07-27 | Merck & Co. Inc. | Piperazinylpyrimidines as beta-adrenergic receptor blocking agents |
EP0276057A3 (en) * | 1987-01-21 | 1989-09-06 | Merck & Co. Inc. | Piperazinylpyrimidines as b-adrenergic receptor blocking agents |
Also Published As
Publication number | Publication date |
---|---|
FR1555459A (en) | 1969-01-31 |
SE300214B (en) | 1968-04-22 |
NL122810C (en) | |
ES301103A1 (en) | 1965-01-16 |
FR3648M (en) | 1965-10-25 |
CH442328A (en) | 1967-08-31 |
CH446358A (en) | 1967-11-15 |
NL6406834A (en) | 1964-12-18 |
NL6406835A (en) | 1964-12-18 |
FR3824M (en) | 1966-01-10 |
SE300213B (en) | 1968-04-22 |
BE649347A (en) | 1964-12-16 |
BE649348A (en) | 1964-12-16 |
GB1072414A (en) | 1967-06-14 |
NL124131C (en) | |
FR1555460A (en) | 1969-01-31 |
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