GB1324849A - Thieno 3,4-d pyrimidines - Google Patents
Thieno 3,4-d pyrimidinesInfo
- Publication number
- GB1324849A GB1324849A GB3414470A GB1324849DA GB1324849A GB 1324849 A GB1324849 A GB 1324849A GB 3414470 A GB3414470 A GB 3414470A GB 1324849D A GB1324849D A GB 1324849DA GB 1324849 A GB1324849 A GB 1324849A
- Authority
- GB
- United Kingdom
- Prior art keywords
- halogen atom
- alkyl
- reaction
- thieno
- hydrogen
- 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 1
- 125000005843 halogen group Chemical group 0.000 abstract 13
- 150000001875 compounds Chemical class 0.000 abstract 12
- 125000003545 alkoxy group Chemical group 0.000 abstract 10
- 238000006243 chemical reaction Methods 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 3
- 150000001342 alkaline earth metals Chemical group 0.000 abstract 3
- KQWHKLZRDFJOCN-UHFFFAOYSA-N thieno[3,4-d]pyrimidine Chemical class N1=CN=CC2=CSC=C21 KQWHKLZRDFJOCN-UHFFFAOYSA-N 0.000 abstract 3
- JGIRDDQLZLXRKQ-UHFFFAOYSA-N (4-methoxycarbonylthiophen-3-yl)azanium;chloride Chemical compound Cl.COC(=O)C1=CSC=C1N JGIRDDQLZLXRKQ-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000005660 chlorination reaction Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
- RZBNSEBSVPLRMA-UHFFFAOYSA-N 1h-thieno[3,4-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)NC2=CSC=C21 RZBNSEBSVPLRMA-UHFFFAOYSA-N 0.000 abstract 1
- CGYZVYDIFMJANQ-UHFFFAOYSA-N 2,4-dichloro-5-methylthieno[3,4-d]pyrimidine Chemical compound N1=C(Cl)N=C(Cl)C2=C(C)SC=C21 CGYZVYDIFMJANQ-UHFFFAOYSA-N 0.000 abstract 1
- FUFRGBBMQQJFMJ-UHFFFAOYSA-N 2,4-dichlorothieno[3,4-d]pyrimidine Chemical compound N1=C(Cl)N=C(Cl)C2=CSC=C21 FUFRGBBMQQJFMJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 abstract 1
- QIHFLAURTFZSEX-UHFFFAOYSA-N 2-propyl-1h-thieno[3,4-d]pyrimidin-4-one Chemical compound N1=C(CCC)N=C(O)C2=CSC=C21 QIHFLAURTFZSEX-UHFFFAOYSA-N 0.000 abstract 1
- YIPSVEOBIUFLDC-UHFFFAOYSA-N 4-(butanoylamino)thiophene-3-carboxylic acid Chemical compound CCCC(=O)NC1=CSC=C1C(O)=O YIPSVEOBIUFLDC-UHFFFAOYSA-N 0.000 abstract 1
- OSMPALRXWMHPRD-UHFFFAOYSA-N 4-chloro-2-propylthieno[3,4-d]pyrimidine Chemical compound N1=C(CCC)N=C(Cl)C2=CSC=C21 OSMPALRXWMHPRD-UHFFFAOYSA-N 0.000 abstract 1
- -1 N-methylpiperazino group Chemical group 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000003555 analeptic effect Effects 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000003385 bacteriostatic effect Effects 0.000 abstract 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 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
- 230000000881 depressing effect Effects 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000002526 effect on cardiovascular system Effects 0.000 abstract 1
- OLYAZPRGVAYQKH-UHFFFAOYSA-N ethyl 4-amino-2-methylthiophene-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C=1C(N)=CSC=1C OLYAZPRGVAYQKH-UHFFFAOYSA-N 0.000 abstract 1
- 230000001408 fungistatic effect Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- LROFLRPIPNWJJG-UHFFFAOYSA-N methyl 4-(butanoylamino)thiophene-3-carboxylate Chemical compound CCCC(=O)NC1=CSC=C1C(=O)OC LROFLRPIPNWJJG-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000000241 respiratory effect Effects 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 230000004936 stimulating effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3414470 | 1970-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1324849A true GB1324849A (en) | 1973-07-25 |
Family
ID=10361935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3414470A Expired GB1324849A (en) | 1970-07-14 | 1970-07-14 | Thieno 3,4-d pyrimidines |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3850919A (enExample) |
| JP (2) | JPS5344476B1 (enExample) |
| BE (1) | BE769843A (enExample) |
| DE (1) | DE2134880C3 (enExample) |
| FR (1) | FR2100899B1 (enExample) |
| GB (1) | GB1324849A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931204A (en) * | 1971-07-13 | 1976-01-06 | U.C.B. Societe Anonyme | Thieno[3,4-d]pyrimidines |
| GB1570494A (en) * | 1975-11-28 | 1980-07-02 | Ici Ltd | Thienopyrimidine derivatives and their use as pesticides |
| JPS58152593U (ja) * | 1982-04-07 | 1983-10-12 | 三洋電機株式会社 | 遠隔操作式電気機器 |
| JPS5980171U (ja) * | 1982-11-24 | 1984-05-30 | ティー・シー・エム株式会社 | 荷役車両のボンネツト |
-
1970
- 1970-07-14 GB GB3414470A patent/GB1324849A/en not_active Expired
-
1971
- 1971-07-09 FR FR7125563A patent/FR2100899B1/fr not_active Expired
- 1971-07-12 BE BE769843A patent/BE769843A/xx not_active IP Right Cessation
- 1971-07-13 US US00162255A patent/US3850919A/en not_active Expired - Lifetime
- 1971-07-13 DE DE2134880A patent/DE2134880C3/de not_active Expired
- 1971-07-13 JP JP5206171A patent/JPS5344476B1/ja active Pending
-
1978
- 1978-03-24 JP JP3399178A patent/JPS53124291A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2134880C3 (de) | 1978-08-31 |
| JPS5748118B2 (enExample) | 1982-10-14 |
| BE769843A (fr) | 1972-01-12 |
| DE2134880B2 (de) | 1977-12-15 |
| US3850919A (en) | 1974-11-26 |
| JPS53124291A (en) | 1978-10-30 |
| FR2100899A1 (enExample) | 1972-03-24 |
| DE2134880A1 (de) | 1972-05-25 |
| FR2100899B1 (enExample) | 1974-11-15 |
| JPS5344476B1 (enExample) | 1978-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |