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)
Description
本発明は式（）
（式中R1とR2は同一かもしくは異なつてもよ
く水素、低級アルキル、クロル等のハロゲン原子
を示すか、またはR1とR2は一緒になつて低級ア
ルキルが置換することもある環状アルキレン鎖を
形成してもよい。R3は低級アルキルを示す）で
示される３―置換イミダゾチエノピリミジン―２
―オン類またはその酸付加塩に関するものであ
る。
本発明の化合物（）は数個の互変異性体の形
（Ia）及び（Ib）としても表わすことができる。
さらに本発明の化合物（）は１ケの不整炭素
を持つているので、ラセミ形とともに光学活性形
としても存在しうる。これらの互変異性体、ラセ
ミ体、光学活性体がいずれも本発明の技術的範囲
に含まれることは明らかである。
本発明の中で低級アルキルなる用語は炭素数１
〜４個の直鎖状もしくは分枝状のアルキル基を示
す。
本発明で特に好適の化合物としては次のものを
あげることができる。
３―メチル―１，２，３，５，６，７，８，９
―オクタヒドロイミダゾ〔１，２―ａ〕〔１〕ベ
ンゾチエノ〔２，３―ｄ〕ピリミジン―２―オン
及び３，６，７―トリメチル―１，２，３，５―
テトラヒドロイミダゾ〔１，２―ａ〕チエノ
〔２，３―ｄ〕ピリミジン―２―オン
本発明の化合物は適当な酸との塩としても使用
できる。医薬として使用可能な毒性のない酸は、
塩酸、臭化水素酸、硫酸、アルキルまたはアリル
スルホン酸、リン酸、フマール酸、マレイン酸、
コハク酸、酒石酸、クエン酸等当該技術上普通に
用いられる酸である。
本発明の化合物は強力な血小板凝集抑制作用を
もつことから血管内血栓症の予防、短期局所貧血
の予防、補綴装置（人工心臓、人工腎臓等）の使
用時の血小板血栓の予防に有用である。
本発明の血小板凝集抑制作用を次に表示する。
The present invention is based on the formula () (In the formula, R 1 and R 2 may be the same or different and represent a halogen atom such as hydrogen, lower alkyl, chloro, etc., or R 1 and R 2 together represent a cyclic group which may be substituted with lower alkyl. 3-substituted imidazothienopyrimidine-2, which may form an alkylene chain (R 3 represents lower alkyl)
- Concerning ons or their acid addition salts. The compounds of the invention () can also be represented in several tautomeric forms (Ia) and (Ib). Furthermore, since the compound () of the present invention has one asymmetric carbon, it can exist in an optically active form as well as a racemic form. It is clear that all of these tautomers, racemates, and optically active forms are included within the technical scope of the present invention. In the present invention, the term lower alkyl refers to
~4 linear or branched alkyl groups. Particularly suitable compounds in the present invention include the following. 3-methyl-1,2,3,5,6,7,8,9
-Octahydroimidazo[1,2-a][1]benzothieno[2,3-d]pyrimidin-2-one and 3,6,7-trimethyl-1,2,3,5-
Tetrahydroimidazo[1,2-a]thieno[2,3-d]pyrimidin-2-one The compounds of the invention can also be used as salts with suitable acids. Non-toxic acids that can be used as medicines are
Hydrochloric acid, hydrobromic acid, sulfuric acid, alkyl or allyl sulfonic acid, phosphoric acid, fumaric acid, maleic acid,
Acids commonly used in the art, such as succinic acid, tartaric acid, and citric acid. The compound of the present invention has a strong platelet aggregation inhibitory effect and is therefore useful for preventing intravascular thrombosis, short-term local anemia, and platelet thrombosis when using prosthetic devices (artificial heart, artificial kidney, etc.). . The platelet aggregation inhibiting effect of the present invention is shown below.
【表】
本発明の化合物は次の図に例示される工程で製
造することができる。
（式中R1，R2，R3は前記と同じものを示し、
R4は低級アルキルを、Ｘはヨード、ブロム、ク
ロル等のハロゲン原子を示す）
工程に従つてその製法を説明すると既知の方法
で合成された式（）の既知もしくは新規の２，
４―ジクロルチエノピリミジン類をメタノール、
エタノールもしくはクロロホルムあるいはその他
の不活性溶媒、さらにはこれらの混合溶媒中、水
素化ホウ素アルカリ金属類、例えば水素化ホウ素
ナトリウム、水素化ホウ素リチウム等と室温ない
し40〜50℃の数時間ないし一夜撹拌すると好収率
で式（）で示される２―クロル―３，４―ジヒ
ドロチエノピリミジン類がえられる。
次にこをアセトン、メチルエチルケトン等の溶
媒中、脱酸剤好ましくは粉末状の炭酸カリウム、
炭酸ナトリウム等とともに式（）で示されるα
―ハロ脂肪酸エステル類、例えばα―ブロムプロ
ピン酸エチルエステル、α―ブロム酪酸エチルエ
ステル等と不活性ガス気流下にはげしく撹拌しな
がら加熱還流すると式（）で示される２―クロ
ル―３―（α―低級アルコキシカルボニルアルキ
ル）―３，４―ジヒドロチエノピリミジン類がえ
られる。続いてこれをメタノール、エタレールま
たはその他のアルコール性溶媒中アンモニアと封
管中120〜150℃の浴中、数時間ないし20時間加熱
すると本発明の式（）の化合物がえられる。
本発明の化合物を血小板凝集抑制作用を目的に
医薬として用いるには適当な賦形剤、崩壊剤、結
合剤を適宜用いて経口投与用の錠剤、カプセル
剤、散剤にすることができる。ヒトに対する投与
量は10〜200mg／日で充分である。
以下製造例に従つて本発明を説明する。
例 １
２―クロル―３，４，５，６，７，８―ヘキサ
ヒドロ〔１〕ベンゾチエノ〔２，３―ｄ〕ピリミ
ジン9.07ｇとα―ブロムプロピオン酸エチルエス
テル9.05ｇ、粉末炭酸カリウム16.6ｇをメチルエ
チルケトン300mlに加えて窒素気流下にはげしく
撹拌しながら６時間加熱還流する。冷後無機塩を
濾別し、濾液を減圧乾固すると粗製の２―クロル
―３―（α―エトキシカルボニルエチル）―３，
４，５，６，７，８―ヘキサヒドロ〔１〕ベンゾ
チエノ〔２，３―ｄ〕ピリミジンがえられる。こ
れは油状で不安定な化合物なので粗製のまま10％
アンモニア―エタノール30mlとともに窒素気流下
に封管中120〜130℃に６時間加熱する。冷後析出
して来る結晶を濾取、よく水洗したのち常法に従
つて塩酸塩とすると３―メチル―１，２，３，
５，６，７，８，９―オクタヒドロイミダゾ
〔１，２―ａ〕〔１〕ベンゾチエノ〔２，３―ｄ〕
ピリミジン―２―オンが4.10ｇえられた。融点
232〜235℃（dec.）
元素分析 C13H16ClN3OS・1/2H2Oとして
計算値 Ｃ 50.89，Ｈ 5.59，Ｎ 13.70
分析値 Ｃ 50.88，Ｈ 5.84，Ｎ 13.67
ここで用いた出発物質は次のようにして製造し
た。
２，４―ジクロル―５，６，７，８―テトラヒ
ドロ〔１〕ベンゾチエノ〔２，３―ｄ〕ピリミジ
ン9.07ｇをクロロホルム100ml、エタノール100ml
の混合溶媒に溶解し、水素化ホウ素ナトリウム
8.0ｇを加えて45〜55℃で14時間撹拌する。溶媒
を減圧留去し、残渣は水を加えてよく振りまぜて
不溶分を濾取、よく水洗する。少量のメタノー
ル、エーテルで洗つて粗製の２―クロル―３，
４，５，６，７，８―ヘキサヒドロ〔１〕ベンゾ
チエノ〔２，３―ｄ〕ピリミジンを殆んど定量的
収率でうる。
例 ２―６
例１と同様にして次の化合物を合成した。一括
表示する。[Table] The compound of the present invention can be produced by the process illustrated in the following figure. (In the formula, R 1 , R 2 , R 3 are the same as above,
(R 4 represents lower alkyl, X represents a halogen atom such as iodo, bromine, chloro, etc.)
4-dichlorothienopyrimidines with methanol,
When stirred with alkali metal borohydrides, such as sodium borohydride, lithium borohydride, etc., at room temperature to 40-50°C for several hours or overnight in ethanol or chloroform or other inert solvents, or even mixed solvents thereof, 2-chloro-3,4-dihydrothienopyrimidines represented by the formula () are obtained in good yield. This is then mixed with a deoxidizer, preferably powdered potassium carbonate, in a solvent such as acetone or methyl ethyl ketone.
α shown in the formula () along with sodium carbonate, etc.
- When heated under reflux with halo fatty acid esters, such as α-bromoproponic acid ethyl ester, α-bromobutyric acid ethyl ester, etc., with vigorous stirring under a stream of inert gas, 2-chloro-3-(α- Lower alkoxycarbonylalkyl)-3,4-dihydrothienopyrimidines are obtained. This is then heated with ammonia in methanol, ethanol or other alcoholic solvent in a sealed tube in a bath at 120-150° C. for several hours to 20 hours to obtain the compound of formula () of the present invention. In order to use the compound of the present invention as a medicine for the purpose of inhibiting platelet aggregation, it can be made into tablets, capsules, and powders for oral administration using appropriate excipients, disintegrants, and binders. A dose of 10 to 200 mg/day is sufficient for humans. The present invention will be explained below with reference to production examples. Example 1 9.07 g of 2-chloro-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine, 9.05 g of α-bromopropionic acid ethyl ester, and 16.6 g of powdered potassium carbonate. Add to 300 ml of methyl ethyl ketone and heat under reflux for 6 hours with vigorous stirring under a nitrogen stream. After cooling, the inorganic salts were filtered off, and the filtrate was dried under reduced pressure to obtain crude 2-chloro-3-(α-ethoxycarbonylethyl)-3,
4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine is obtained. This is an oily and unstable compound, so 10% of it remains crude.
Heat in a sealed tube with 30 ml of ammonia-ethanol to 120-130°C for 6 hours under nitrogen flow. After cooling, the precipitated crystals are collected by filtration, thoroughly washed with water, and converted into hydrochloride using a conventional method to obtain 3-methyl-1,2,3,
5,6,7,8,9-octahydroimidazo[1,2-a][1]benzothieno[2,3-d]
4.10g of pyrimidine-2-one was obtained. melting point
232-235℃ (dec.) Elemental analysis C 13 H 16 ClN 3 OS・1/2H 2 O Calculated value C 50.89, H 5.59, N 13.70 Analytical value C 50.88, H 5.84, N 13.67 Starting material used here was manufactured as follows. Add 9.07 g of 2,4-dichloro-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine to 100 ml of chloroform and 100 ml of ethanol.
Sodium borohydride dissolved in a mixed solvent of
Add 8.0g and stir at 45-55°C for 14 hours. The solvent is distilled off under reduced pressure, water is added to the residue, the mixture is shaken well, the insoluble matter is filtered off, and the residue is thoroughly washed with water. Wash with a small amount of methanol and ether to obtain crude 2-chloro-3,
4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine is obtained in almost quantitative yield. Example 2-6 The following compound was synthesized in the same manner as in Example 1. Display all at once.
【表】【table】
Claims (1)
素、低級アルキルもしくはハロゲン原子を示す
か、またはR1とR2は一緒になつて低級アルキル
が置換することもある環状アルキレン鎖を形成し
てもよい。R3は低級アルキルを示す）で示され
る３―アルキルイミダゾチエノピリミジン―２―
オン類化合物またはその酸付加塩。 ２ ３―メチル―１，２，３，５，６，７，８，
９―オクタヒドロイミダゾ［１，２―ａ］［１］
ベンゾチエノ［２，３―ｄ］ピリミジン―２―オ
ンまたはその酸付加塩である特許請求の範囲第１
項記載の化合物。[Claims] 1 formula In the formula, R 1 and R 2 may be the same or different and represent hydrogen, lower alkyl or halogen atoms, or R 1 and R 2 together form a cyclic alkylene chain which may be substituted with lower alkyl. It's okay. R 3 represents lower alkyl) 3-alkylimidazothienopyrimidine-2-
On-class compounds or their acid addition salts. 2 3-methyl-1,2,3,5,6,7,8,
9-octahydroimidazo[1,2-a][1]
Claim 1, which is benzothieno[2,3-d]pyrimidin-2-one or an acid addition salt thereof
Compounds described in Section.
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 (en) | 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 (en) |
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/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5677282A (en) | 1981-06-25 |
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