JPS6155486B2 - - Google Patents
Info
- Publication number
- JPS6155486B2 JPS6155486B2 JP53133754A JP13375478A JPS6155486B2 JP S6155486 B2 JPS6155486 B2 JP S6155486B2 JP 53133754 A JP53133754 A JP 53133754A JP 13375478 A JP13375478 A JP 13375478A JP S6155486 B2 JPS6155486 B2 JP S6155486B2
- Authority
- JP
- Japan
- Prior art keywords
- thiazolo
- pyrimidine
- inflammatory
- effects
- tetrahydro
- 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
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 10
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 5
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- CDUYCVWBLGEWSY-UHFFFAOYSA-N 5h-[1,3]thiazolo[3,2-a]pyrimidine Chemical class C1C=CN=C2SC=CN12 CDUYCVWBLGEWSY-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 description 7
- 206010030113 Oedema Diseases 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 235000010418 carrageenan Nutrition 0.000 description 5
- 239000000679 carrageenan Substances 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- 229940113118 carrageenan Drugs 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 150000003230 pyrimidines Chemical class 0.000 description 5
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 5
- 244000215068 Acacia senegal Species 0.000 description 4
- 229920000084 Gum arabic Polymers 0.000 description 4
- 235000010489 acacia gum Nutrition 0.000 description 4
- 239000000205 acacia gum Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 230000003444 anaesthetic effect Effects 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000147 hypnotic effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007721 medicinal effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002587 enol group Chemical group 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNZPLHRZXUJATK-UHFFFAOYSA-N 2-sulfanylidene-5-[[5-[2-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,3-diazinane-4,6-dione Chemical compound FC(F)(F)C1=CC=CC=C1C(O1)=CC=C1CC1C(=O)NC(=S)NC1=O DNZPLHRZXUJATK-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 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
- 239000002674 ointment Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明はチアゾロ〔３・２−ａ〕ピリミジン誘
導体を含有する消炎剤に関する。更に詳細には本
発明はバルビツール酸誘導体として知られるチア
ゾロ〔３・２−ａ〕ピリミジン誘導体を含有する
抗炎症作用、解熱作用、鎮痛作用の消炎作用を有
する消炎剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to antiinflammatory agents containing thiazolo[3.2-a]pyrimidine derivatives. More specifically, the present invention relates to an anti-inflammatory agent containing a thiazolo[3,2-a]pyrimidine derivative known as a barbituric acid derivative and having anti-inflammatory, antipyretic and analgesic effects.
文献、「ジヤーナル・オブ・アメリカン・ケミ
カル・ソサイエテイー、64巻、2709〜2712ページ
（1942）」に特定のチアゾロ〔３・２−ａ〕ピリミ
ジン誘導体が催眠作用、麻酔作用を有し得る化合
物として有用であることが記載されている。しか
し上記の薬効以外の作用に関しては何ら記載され
ていない。 The literature, "Journal of the American Chemical Society, Vol. 64, pp. 2709-2712 (1942)" states that certain thiazolo[3.2-a]pyrimidine derivatives are useful as compounds that can have hypnotic and anesthetic effects. It is stated that However, there is no description of any effects other than the above-mentioned medicinal effects.
本発明者らは前記チアゾロ〔３・２−ａ〕ピリ
ミジン誘導体の動物における各種の病態モデルに
対する薬効を詳しく検討した結果、驚くべきこと
にこれらの化合物が公知の催眠作用又は麻酔作用
とは全く異なる薬理作用に基づく優れた消炎作用
を有し、抗炎症作用、解熱作用、鎮痛作用等の薬
効を有する化合物として極めて有用であることを
新たに見出し本発明に到達したものである。 The present inventors have investigated in detail the medicinal effects of the above-mentioned thiazolo[3,2-a]pyrimidine derivatives on various disease models in animals, and have surprisingly found that these compounds have completely different hypnotic or anesthetic effects from known hypnotic or anesthetic effects. The present invention was achieved by newly discovering that it has an excellent anti-inflammatory effect based on pharmacological action, and is extremely useful as a compound having medicinal effects such as anti-inflammatory action, antipyretic action, and analgesic action.
すなわち、本発明は下記式〔〕
〔式中、Ｒはフエニル基又はベンジル基を表わ
す。〕
で表わされるチアゾロ〔３・２−ａ〕ピリミジン
誘導体を消炎活性成分として含有する消炎剤であ
る。 That is, the present invention is based on the following formula [] [In the formula, R represents a phenyl group or a benzyl group. ] This is an anti-inflammatory agent containing a thiazolo[3,2-a]pyrimidine derivative represented by the following as an anti-inflammatory active ingredient.
上記式〔〕においてＲはフエニル基又はベン
ジル基を表わす。特にＲはフエニル基が好まし
い。 In the above formula [], R represents a phenyl group or a benzyl group. In particular, R is preferably a phenyl group.
かかるチアゾロ〔３・２−ａ〕ピリミジン誘導
体は１部エノール型となつていることが確かめら
れており、そして本発明における消炎活性成分が
エノール型であつても消炎活性を有することが確
かめられている。 It has been confirmed that such thiazolo[3.2-a]pyrimidine derivatives are partially in the enol form, and it has been confirmed that the anti-inflammatory active ingredient in the present invention has anti-inflammatory activity even if it is in the enol form. There is.
消炎症作用の測定は、カラゲニン浮腫法を用い
て行つた。 The anti-inflammatory effect was measured using the carrageenan edema method.
すなわちSD系雄性ラツトを用い、被検薬の５
％アラビアゴム懸濁液を該SD系雄性ラツトに経
口投与し、１時間後にラツトの右足蹠皮内に１％
カラゲニン0.1mlを注入し、炎症を惹起せしめ、
カラゲニン投与３時間後の足容積変化より、浮腫
率を求め、対照群、被検薬を含まない５％アラビ
アゴム懸濁液の場合と比較して浮腫抑制率を算出
し、被検薬の消炎作用を測定した。 That is, using SD male rats,
% gum arabic suspension was orally administered to the SD male rats, and 1 hour later, 1% gum arabic suspension was administered intradermally to the rat's right foot pad.
Inject 0.1ml of carrageenan to induce inflammation.
The edema rate was determined from the change in foot volume 3 hours after carrageenan administration, and the edema suppression rate was calculated by comparing it with the control group and 5% gum arabic suspension that did not contain the test drug. The effect was measured.
前記チアゾロ〔３・２−ａ〕ピリミジン誘導体
及び／又はその薬学的に許容される非毒性塩の有
効量は、投与方法によつても異なるが、好ましく
は0.1〜50mg/Kg、より好ましくは１〜20mg/Kgの
範囲にある。投与回数は病状により１日数回に及
ぶことも可能である。 The effective amount of the thiazolo[3.2-a]pyrimidine derivative and/or its pharmaceutically acceptable non-toxic salt varies depending on the administration method, but is preferably 0.1 to 50 mg/Kg, more preferably 1 In the range of ~20mg/Kg. The number of administrations can be several times a day depending on the disease state.
投与形態は、病態の症状、発現部位によつて、
例えば錠剤、カプセル剤、散剤、顆剤等の経口投
与用剤型、あるいは坐剤、液剤、軟膏剤、あるい
は静脈注射、筋肉注射等の注射剤などから適宜選
択される。なかでも特に、使用の簡便性、安全性
の面から、経口投与用剤型が好ましい。これらの
剤型への製剤にあたつては、例えば注射剤の場合
には注射用蒸留水、緩衝液等を加え減菌操作を施
せばよく、また錠剤の場合には結合剤、練合、製
粒、打錠操作を行うなど一般的製剤化の手法に従
つて各々の剤型にすることができる。 The dosage form depends on the symptoms of the pathology and the site of onset.
For example, it is appropriately selected from oral administration dosage forms such as tablets, capsules, powders, and granules, suppositories, liquids, ointments, and injections such as intravenous injection and intramuscular injection. Among these, from the viewpoint of ease of use and safety, dosage forms for oral administration are particularly preferred. When formulating into these dosage forms, for example, in the case of injections, it is sufficient to add distilled water for injection, a buffer solution, etc. and sterilize it, and in the case of tablets, binders, kneading agents, etc. Each dosage form can be prepared according to general formulation methods such as granulation and tabletting operations.
かくして調整されたチアゾロ〔３・２−ａ〕ピ
リミジン誘導体を有効量含有する薬剤は抗炎症作
用、解熱作用、鎮痛作用等の消炎作用を有する消
炎剤として極めて有効である。 A drug containing an effective amount of the thiazolo[3.2-a]pyrimidine derivative thus prepared is extremely effective as an anti-inflammatory agent having anti-inflammatory effects such as anti-inflammatory, antipyretic and analgesic effects.
以下に実施例をあげて本発明を更に詳細に説明
する。 The present invention will be explained in more detail with reference to Examples below.
実施例 １
１群４匹のSD系雄性ラツト（５週令）を用
い、前記式〔〕においてＲがフエニルである化
合物、すなわち5H−２・３・６・７−テトラヒ
ドロ−５・７−ジオキソ−６−フエニルチアゾロ
〔３・２−ａ〕ピリミジン25mgを５％アラビアゴ
ム水溶液５mlに懸濁せしめた懸濁液を該SD系雄
性ラツトに25mg/Kg、経口投与し、１時間後にラ
ツトの右足蹠皮内に１％カラゲニン0.1mlを注入
し、炎症を惹起せしめ、カラゲニン投与３時間後
の足容積変化より、浮腫率を求め、対照群すなわ
ち、上記被検薬を含まない５％のアラビアゴム水
溶液と比較して浮腫抑制率を算出したところ11.7
％であつた。Example 1 Using a group of 4 male SD rats (5 weeks old), a compound in which R is phenyl in the above formula [], that is, 5H-2,3,6,7-tetrahydro-5,7-dioxo A suspension of 25 mg of -6-phenylthiazolo[3,2-a]pyrimidine in 5 ml of 5% gum arabic aqueous solution was orally administered at 25 mg/Kg to the SD male rats, and 1 hour later, the right footpad of the rats was administered. Inflammation was induced by intradermally injecting 0.1 ml of 1% carrageenan, and the edema rate was determined from the change in foot volume 3 hours after carrageenan administration. The edema suppression rate was calculated as 11.7 compared to
It was %.
5H−２・３・６・７−テトラヒドロ−５・７
−ジオキソ−６−ベンジルチアゾロ〔３・２−
ａ〕ピリミジンを用いて、SD系雄性ラツトに25
mg/Kg経口投与し、同様にして浮腫抑制率を算出
したところ13.9％であつた。 5H-2,3,6,7-tetrahydro-5,7
-dioxo-6-benzylthiazolo[3,2-
a] Using pyrimidine, 25
When mg/Kg was administered orally, the edema suppression rate was calculated in the same manner and was 13.9%.
実施例 ２
〔錠剤の製造〕
経腸投与に適した次の成分を含有する錠剤を通
常の方法で製造した。Example 2 [Preparation of tablets] Tablets suitable for enteral administration containing the following ingredients were prepared in a conventional manner.
成 分 重 量
5H−２・３・６・７−テトラヒドロ
−５・７−ジオキソ−６−フエニル
チアゾロ〔３・２−ａ〕ピリミジン 30mg
ラクトース 69.05mg
トウモロコシ澱分 14mg
ポリビニルピロリドン ５mg
ステアリン酸マグネシウム 0.7mg
タルク 1.2mg
着色剤 0.05/120mg
実施例 ３
〔カプセル剤の製造〕
経腸投与に適した次の成分を含有するハードゼ
ラチンカプセルを通常の方法で製造した。 Ingredients Weight 5H-2.3.6.7-tetrahydro-5.7-dioxo-6-phenyl Thiazolo[3.2-a]pyrimidine 30mg Lactose 69.05mg Corn starch 14mg Polyvinylpyrrolidone 5mg Magnesium stearate 0.7mg Talc 1.2 mg Colorant 0.05/120 mg Example 3 [Manufacture of capsules] Hard gelatin capsules suitable for enteral administration containing the following ingredients were manufactured in a conventional manner.
成 分 重 量
5H−２・３・６・７−テトラヒドロ−５・７−
ジオキソ−６−フエニルチアゾロ〔３・２−ａ〕
ピリミジン 30mg
ラクトース 78mg
トウモロコシ澱分 20mg
タルク 4.5mg
ステアリン酸マグネシウム 1.5mg
必要に応じ着色剤 十分な量／135mg
実施例 ４
〔坐剤の製造〕
次の成分を含有する坐剤を通常の方法で製造し
た。 Component Weight 5H-2・3・6・7-Tetrahydro-5・7-
Dioxo-6-phenylthiazolo[3.2-a]
Pyrimidine 30mg Lactose 78mg Corn starch 20mg Talc 4.5mg Magnesium stearate 1.5mg Coloring agent if necessary Sufficient amount/135mg Example 4 [Manufacture of suppositories] A suppository containing the following ingredients was manufactured in a conventional manner. .
成 分 重 量
5H−２・３・６・７−テトラヒドロ
−５・７−ジオキソ−６−フエニル
チアゾロ〔３・２−ａ〕ピリミジン 30mg
カカオ脂 十分な量／1.5ｇ
実施例 ５
〔関節内注入剤の製造〕
次の成分を含有する関節内注入剤を通常の方法
で製造した。 Ingredients Weight 5H-2,3,6,7-tetrahydro-5,7-dioxo-6-phenyl Thiazolo[3,2-a]pyrimidine 30mg Cocoa butter Adequate amount/1.5g Example 5 [Intra-articular injection Manufacture of agent] An intra-articular injection agent containing the following ingredients was manufactured by a conventional method.
成 分 重 量
5H−２・３・６・７−テトラヒドロ
−５・７−ジオキソ−６−フエニル
チアゾロ〔３・２−ａ〕ピリミジン 10mg
所望の安定度にPHを調整する緩和剤 十分な量
水 注射用1.5mlに十分な量
実施例 ６
６−フエニル−5H−２・３・６・７−テトラ
ハイドロ−５・７−ジオキソチアゾロ〔３・２−
ａ〕ピリミジンを雄性ICRマウス（６週令）に１
ｇ/Klの投与量で経口投与しマウスの状態を観察
した。 Ingredients Weight 5H-2,3,6,7-tetrahydro-5,7-dioxo-6-phenyl Thiazolo[3,2-a]pyrimidine 10mg Relaxant to adjust pH to desired stability Sufficient amount of water Sufficient amount for 1.5 ml for injection Example 6 6-phenyl-5H-2,3,6,7-tetrahydro-5,7-dioxothiazolo[3,2-
a] Pyrimidine was administered to male ICR mice (6 weeks old).
The condition of the mice was observed after oral administration at a dose of g/Kl.
経口投与後においてもマウスになんらの変化も
認められず、本発明化合物の毒性は低いものと考
えられる。 No changes were observed in mice even after oral administration, and the toxicity of the compound of the present invention is considered to be low.
Claims (1)
す。〕 で表わされるチアゾロ〔３・２−ａ〕ピリミジン
誘導体を消炎活性成分として含有する消炎剤。[Claims] 1. The following formula [] [In the formula, R represents a phenyl group or a benzyl group. ] An anti-inflammatory agent containing a thiazolo[3,2-a]pyrimidine derivative represented by the following as an anti-inflammatory active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13375478A JPS5562092A (en) | 1978-11-01 | 1978-11-01 | Antiphlogistic agent containing thiazolo 3,2-a pyrimidine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13375478A JPS5562092A (en) | 1978-11-01 | 1978-11-01 | Antiphlogistic agent containing thiazolo 3,2-a pyrimidine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5562092A JPS5562092A (en) | 1980-05-10 |
| JPS6155486B2 true JPS6155486B2 (en) | 1986-11-28 |
Family
ID=15112150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13375478A Granted JPS5562092A (en) | 1978-11-01 | 1978-11-01 | Antiphlogistic agent containing thiazolo 3,2-a pyrimidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5562092A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0049902A3 (en) * | 1980-10-15 | 1982-09-01 | Teijin Limited | Novel thiazolo(3,2-a)pyrimidines, derivatives thereof, processes for production thereof, and pharmaceutical use thereof |
-
1978
- 1978-11-01 JP JP13375478A patent/JPS5562092A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5562092A (en) | 1980-05-10 |
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