JPS643874B2 - - Google Patents
Info
- Publication number
- JPS643874B2 JPS643874B2 JP15246679A JP15246679A JPS643874B2 JP S643874 B2 JPS643874 B2 JP S643874B2 JP 15246679 A JP15246679 A JP 15246679A JP 15246679 A JP15246679 A JP 15246679A JP S643874 B2 JPS643874 B2 JP S643874B2
- Authority
- JP
- Japan
- Prior art keywords
- lower alkyl
- acid
- formula
- present
- benzothieno
- 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
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- VSNTWHKMQZSPDY-UHFFFAOYSA-N 1H-[1]benzothiolo[2,3-d]pyrimidin-2-one Chemical compound C12=CC=CC=C2SC2=C1C=NC(=O)N2 VSNTWHKMQZSPDY-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- -1 3-methyl-1,2,3,5,6,7,8,9 -Octahydroimidazo[1,2-a][1]benzothieno[2,3-d]pyrimidin-2-one Chemical compound 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RBBPHGXTPHZELE-UHFFFAOYSA-N 2-chloro-1,4,5,6,7,8-hexahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound C1CCCC2=C1C(CN=C(N1)Cl)=C1S2 RBBPHGXTPHZELE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- CPWQCJFDDILDOU-UHFFFAOYSA-N 2,4-dichloro-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound C1CCCC2=C1C1=C(Cl)N=C(Cl)N=C1S2 CPWQCJFDDILDOU-UHFFFAOYSA-N 0.000 description 1
- DNOZNRBFLLJIBF-UHFFFAOYSA-N 2-chloro-1,4-dihydrothieno[3,2-d]pyrimidine Chemical class N1C(Cl)=NCC2=C1C=CS2 DNOZNRBFLLJIBF-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15246679A JPS5677282A (en) | 1979-11-27 | 1979-11-27 | 3-alkylimidazothienopyrimidin-2-one compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15246679A JPS5677282A (en) | 1979-11-27 | 1979-11-27 | 3-alkylimidazothienopyrimidin-2-one compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5677282A JPS5677282A (en) | 1981-06-25 |
| JPS643874B2 true JPS643874B2 (enrdf_load_stackoverflow) | 1989-01-23 |
Family
ID=15541119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15246679A Granted JPS5677282A (en) | 1979-11-27 | 1979-11-27 | 3-alkylimidazothienopyrimidin-2-one compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5677282A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5862806A (en) * | 1997-10-30 | 1999-01-26 | Mitroflow International, Inc. | Borohydride reduction of biological tissues |
| GB0808950D0 (en) * | 2008-05-16 | 2008-06-25 | Shire Llc | Substituted quinazolines |
-
1979
- 1979-11-27 JP JP15246679A patent/JPS5677282A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5677282A (en) | 1981-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0199127B1 (en) | 5-(6-imidazo[1,2-a]pyridyl) pyridine derivative | |
| EP0314154A2 (de) | Tetrahydro-furo- und -thieno[2,3-c]pyridine, ihre Verwendung als Arzneimittel und Verfahren zu ihrer Herstellung | |
| EP0117403B1 (de) | 6-(Acylaminoaryl)-3(2H)-pyridazinonderivate, ihre Herstellung und Verwendung | |
| JPS627914B2 (enrdf_load_stackoverflow) | ||
| DE69017480T2 (de) | Imidazopyridazine, ihre Herstellung und Verwendung. | |
| JPS623153B2 (enrdf_load_stackoverflow) | ||
| JPH0428269B2 (enrdf_load_stackoverflow) | ||
| JPH0660183B2 (ja) | ピラゾール環がアルキル化されたピラゾロキノリン類の製造中間体 | |
| JPS61183286A (ja) | ２‐アルコキシ‐ｎ‐（１‐アザビシクロ〔２，２，２〕オクタン‐３‐イル）アミノベンズアミドの製法 | |
| JPS643874B2 (enrdf_load_stackoverflow) | ||
| US4609659A (en) | 2,6-disubstituted derivatives of 3-nitropyrazines useful as adjuncts to radiation therapy | |
| EP1444234A2 (de) | Deuterierte pyrazolopyrimidinone sowie diese verbindungen enthaltende arzneimittel | |
| DK169818B1 (da) | Ergolinderivater, fremgangsmåde til fremstilling deraf, samt farmaceutisk præparat indeholdende disse | |
| JPH01132576A (ja) | ２，４−二置換１．３−ジオキソラン | |
| PT87162B (pt) | Processo de preparacao de composto do acido piridilalcanoico contendo um grupo sulfonamido e de composicoes farmaceuticas contendo tais compostos | |
| CH625217A5 (enrdf_load_stackoverflow) | ||
| US4735943A (en) | Eburnamonine oxime derivatives, salts thereof, and pharmaceutical agents containing the same | |
| JPH0339513B2 (enrdf_load_stackoverflow) | ||
| JPS5825678B2 (ja) | オキサゾ−ルユウドウタイ ノ セイゾウホウ | |
| JPS61158980A (ja) | ８α‐アシルアミノエルゴリン類、その製法および医薬組成物 | |
| JP2875605B2 (ja) | ３―エキソメチレンピロロ［２，１―ｂ］チアゾール誘導体 | |
| JPH04225955A (ja) | 置換されたベンズヒドリル２−ヒドロキシプロピルピペラジン誘導体類 | |
| JPH0662608B2 (ja) | カルボスチリル誘導体 | |
| JPH05506654A (ja) | １，５―ベンゾチアゼピノン誘導体、その製法および医薬品用途 | |
| JPS6027676B2 (ja) | ピリミジノアミノメチルエルゴリン誘導体の製法 |