ES301103A1 - New dihydrothieno[3,2-d]pyrimidines - Google Patents
New dihydrothieno[3,2-d]pyrimidinesInfo
- Publication number
- ES301103A1 ES301103A1 ES0301103A ES301103A ES301103A1 ES 301103 A1 ES301103 A1 ES 301103A1 ES 0301103 A ES0301103 A ES 0301103A ES 301103 A ES301103 A ES 301103A ES 301103 A1 ES301103 A1 ES 301103A1
- Authority
- ES
- Spain
- 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
- 150000003230 pyrimidines Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 19
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 8
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 7
- 125000005843 halogen group Chemical group 0.000 abstract 6
- 238000000034 method Methods 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 4
- 231100000252 nontoxic Toxicity 0.000 abstract 4
- 230000003000 nontoxic effect Effects 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 230000002152 alkylating effect Effects 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 239000012435 aralkylating agent Substances 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- -1 with cardiovascular Substances 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 1
- YLXPWYRUCAELPW-UHFFFAOYSA-N 2-hydroxy-2,3-dihydro-1h-thieno[3,2-d]pyrimidin-4-one Chemical compound O=C1NC(O)NC2=C1SC=C2 YLXPWYRUCAELPW-UHFFFAOYSA-N 0.000 abstract 1
- BFQWFNHNECLMAJ-UHFFFAOYSA-N 3-iminothiolane-2-carboxylic acid Chemical compound N=C1C(SCC1)C(=O)O BFQWFNHNECLMAJ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 230000003385 bacteriostatic effect Effects 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical group 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000000824 cytostatic agent Substances 0.000 abstract 1
- 230000001085 cytostatic effect Effects 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 239000006196 drop Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000002526 effect on cardiovascular system Effects 0.000 abstract 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002366 halogen compounds Chemical class 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
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 |
|---|---|
| ES301103A1 true ES301103A1 (en) | 1965-01-16 |
Family
ID=23107339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0301103A Expired ES301103A1 (en) | 1963-06-17 | 1964-06-16 | 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) | GB1072413A (en) |
| NL (4) | NL6406835A (en) |
| SE (2) | SE300213B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3888215T2 (en) * | 1987-01-21 | 1994-09-08 | Merck & Co Inc | Piperazinylpyrimidines as beta-adrenergic receptor blocking agents. |
| EP1847543A1 (en) | 2006-04-19 | 2007-10-24 | Boehringer Ingelheim Pharma GmbH & Co. KG | Dihydrothienopyrimidines for the treatment of inflammatory diseases |
| MX2007012313A (en) | 2006-04-19 | 2007-11-21 | Boehringer Ingelheim Int | Dihydrothienopyrimidines for the treatment of inflammatory diseases. |
| AU2008313660B2 (en) | 2007-10-19 | 2013-11-07 | Boehringer Ingelheim International Gmbh | Substituted piperidino-dihydrothienopyrimidines |
| EP2205609B1 (en) | 2007-10-19 | 2017-03-29 | Boehringer Ingelheim International GmbH | Heterocycle substituted piperazino dihydrothieno pyrimidines |
| WO2009050236A1 (en) | 2007-10-19 | 2009-04-23 | Boehringer Ingelheim International Gmbh | Novel piperazino-dihydrothienopyrimidine derivatives |
| US20130059866A1 (en) | 2011-08-24 | 2013-03-07 | Boehringer Ingelheim International Gmbh | Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma |
| US9802954B2 (en) | 2011-08-24 | 2017-10-31 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
-
0
- NL NL122810A patent/NL122810C/xx active
- NL NL124131A patent/NL124131C/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 SE686764A patent/SE300213B/xx unknown
- 1964-06-05 SE SE686864A patent/SE300214B/xx unknown
- 1964-06-15 FR FR978344A patent/FR3824M/en not_active Expired
- 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 NL NL6406835A patent/NL6406835A/xx unknown
- 1964-06-16 ES ES0301103A patent/ES301103A1/en not_active Expired
- 1964-06-16 BE BE649348A patent/BE649348A/xx unknown
- 1964-06-16 BE BE649347A patent/BE649347A/xx unknown
- 1964-06-16 NL NL6406834A patent/NL6406834A/xx unknown
- 1964-06-17 GB GB2509364A patent/GB1072413A/en not_active Expired
- 1964-06-17 GB GB2509464A patent/GB1072414A/en not_active Expired
- 1964-09-04 FR FR987185A patent/FR3648M/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH442328A (en) | 1967-08-31 |
| BE649347A (en) | 1964-12-16 |
| FR3648M (en) | 1965-10-25 |
| CH446358A (en) | 1967-11-15 |
| FR1555460A (en) | 1969-01-31 |
| FR1555459A (en) | 1969-01-31 |
| NL6406834A (en) | 1964-12-18 |
| GB1072413A (en) | 1967-06-14 |
| SE300214B (en) | 1968-04-22 |
| NL124131C (en) | |
| NL122810C (en) | |
| GB1072414A (en) | 1967-06-14 |
| SE300213B (en) | 1968-04-22 |
| FR3824M (en) | 1966-01-10 |
| NL6406835A (en) | 1964-12-18 |
| BE649348A (en) | 1964-12-16 |
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