JPS5813554B2 - Sinquinapiride -1,4- Diazepine - Google Patents
Sinquinapiride -1,4- DiazepineInfo
- Publication number
- JPS5813554B2 JPS5813554B2 JP10639274A JP10639274A JPS5813554B2 JP S5813554 B2 JPS5813554 B2 JP S5813554B2 JP 10639274 A JP10639274 A JP 10639274A JP 10639274 A JP10639274 A JP 10639274A JP S5813554 B2 JPS5813554 B2 JP S5813554B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrido
- diazepine
- melting point
- group
- solvent
- 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 10
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- -1 sulfonyloxy group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- PVLMWYLLNNCFEO-UHFFFAOYSA-N 1h-pyrido[3,2-e][1,4]diazepine Chemical class N1C=CN=CC2=NC=CC=C12 PVLMWYLLNNCFEO-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 235000007575 Calluna vulgaris Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- ZGLDQGIONSGJCN-UHFFFAOYSA-N diazepin-5-one Chemical compound O=C1C=CN=NC=C1 ZGLDQGIONSGJCN-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は一般式
（式中、Ｒはフエニル基又はハロゲン原子、ニト四基、
トリフルオロメチル基で置換されたフエニル基を意味す
る）で表わされる新規なピリドー１，４−ジアセピン誘
導体の製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (wherein R is a phenyl group or a halogen atom,
The present invention relates to a method for producing a novel pyrido-1,4-diacepine derivative represented by a phenyl group substituted with a trifluoromethyl group.
更にくわしくは一般式（ＩＩ）
（式中、Ｘはハロゲン原子及び有機スルホニルオキシ基
を、Ｒは前記と同じ意味を有する）で表わされる化合物
をアルカリ中加熱することによって前記一般式（１）で
表わされる化合物を製造する方法に関するものである。More specifically, the compound represented by the general formula (II) (wherein, X represents a halogen atom and an organic sulfonyloxy group, and R has the same meaning as above) is heated in an alkali to produce the compound represented by the general formula (1). The present invention relates to methods for producing the represented compounds.
前記一般式（１）及び（Ｉｆ）におけるＲはフエニル基
、又は塩素、臭素、弗素、沃素等のハロゲン原子、ニト
ロ基又はトリフルオロメチル基が任意の位置に１〜２個
置換したフエニル基を表わす。R in the general formulas (1) and (If) is a phenyl group, or a phenyl group substituted with 1 to 2 halogen atoms such as chlorine, bromine, fluorine, iodine, nitro group or trifluoromethyl group at any position. represent.
又、Ｘのハロゲン原子は塩素、臭素、沃素を、有機スル
ホニルオキシ基はベンゼンスルホニルオキシ、トシルオ
キシ、ｐ−ニトロベンゼンスルホニルオキシ等のアリー
ルスルホニルオキシ基、メチルスルホニルオキシ、エチ
ルスルホニルオキシ等のアルキルスルホニルオキシ基及
びベンジルスルホニルオキシ等のアルアルキルスルホニ
ルオキシ基を表わす。In addition, the halogen atom of and an aralkylsulfonyloxy group such as benzylsulfonyloxy.
本発明の出発原料である一般式（ｉｌ）の化合物は１一
置換ピリド〔２，３−ａ〕ピリミジン−２，４（ ＩＨ
，３Ｈ）一ジオンに１，２−ジハロエタン等を反応させ
ることによって好収量で得られる。The compound of general formula (il) which is the starting material of the present invention is 1-monosubstituted pyrido[2,3-a]pyrimidine-2,4(IH
, 3H) in good yield by reacting monodione with 1,2-dihaloethane or the like.
本発明を反応式で示すと次の通りである。The reaction formula of the present invention is as follows.
前記反応はメタノール、エタノール、プロパノール等の
アルコール類及びアセトン、テトラヒド口フラン、ジグ
リム、ジメチルホルムアミド等の有機溶媒中、ナトリウ
ムアルコラート、水酸化ナトリウム、水酸化カリウム、
水酸化カルシウム等のアルカリ触媒の存在下、加熱反応
させることに．よって進行する。The reaction is carried out in alcohols such as methanol, ethanol, and propanol, and organic solvents such as acetone, tetrahydrofuran, diglyme, and dimethylformamide, using sodium alcoholate, sodium hydroxide, potassium hydroxide,
In the presence of an alkaline catalyst such as calcium hydroxide, the reaction is carried out by heating. Therefore, proceed.
生成した反応混合物はこれから有機溶媒を留去し、残渣
をエーテル、メタノール、酢酸エステル等の有機溶媒で
再結晶するか又はカラムクロマト法によって分離精製す
ることによって純品を得る．ことが出来る。The organic solvent is distilled off from the resulting reaction mixture, and the residue is recrystallized with an organic solvent such as ether, methanol, or acetate, or purified by column chromatography to obtain a pure product. I can do it.
杢発明によって得られた化合物は文献未載の新規化合物
で有り、抗炎症作用、中枢神経抑制作用、例えば鎮静作
用、筋弛緩作用、抗痙彎作用、催眠作用等を有し医薬品
として産業上有用な化合物である。The compound obtained by the heather invention is a new compound that has not been described in any literature, and has anti-inflammatory effects, central nervous system depressant effects, such as sedative effects, muscle relaxant effects, anti-spasmodic effects, hypnotic effects, etc., and is industrially useful as a pharmaceutical. It is a compound.
又、医薬品の中間原料としても有用な化合物である。It is also a useful compound as an intermediate raw material for pharmaceuticals.
以下に実施例を示し本発明を更に具体的に説明する。EXAMPLES The present invention will be explained in more detail with reference to Examples below.
実施例 １
１−（ｍ−クロロフエニル）−３−（２−クロロエチル
）ピリド［２，３−ａ’ｌピリミジン−２，４ （ Ｉ
Ｈ，３Ｈ）一ジオン９．８ｇをエタノール３００ｒＩＬ
ｌに溶解後、水酸化カリウム８．２ｇを加え還流下３．
５時間反応させた。Example 1 1-(m-chlorophenyl)-3-(2-chloroethyl)pyrido[2,3-a'lpyrimidine-2,4 (I
H,3H) monodione 9.8g in ethanol 300rIL
After dissolving in 3.1 g of potassium hydroxide, 8.2 g of potassium hydroxide was added and the mixture was refluxed.
The reaction was allowed to proceed for 5 hours.
冷後、酢酸で中和し減圧下に溶媒を留去し、残渣を酢酸
エステルに溶かしアルミナを充填したカラムに吸着させ
、酢酸エステルで展開し第一溶出部の溶媒を留去し残渣
をエーテルより再結晶して、無色プリズム晶の１？（ｍ
−クロロフエニル）−１．２，３．４−テトラヒド口−
５Ｈ−ピリド［２，３−ｅ’）１．４ージアゼピン−５
−オン５．４ｇを得た。After cooling, the solvent was neutralized with acetic acid and the solvent was distilled off under reduced pressure. The residue was dissolved in acetic acid ester and adsorbed on a column packed with alumina, developed with acetic acid ester, the solvent of the first eluate was distilled off, and the residue was dissolved in ether. More recrystallized, colorless prismatic crystal 1? (m
-chlorophenyl)-1.2,3.4-tetrahydride-
5H-pyrido[2,3-e')1,4-diazepine-5
5.4 g of -one was obtained.
この物質．の融点及び元素分析値は次の通りであった。This substance. The melting point and elemental analysis values were as follows.
融 点 １１８〜１１９℃
元素分析値 Ｃ１４Ｈ，ＣＩＮ３０
理論値Ｃ ： ６１．４３Ｈ： ４．４２Ｎ ： １５
．３５実測値Ｃ ： ６１．３２Ｈ： ４．４９Ｎ ：
１５．２１実施例 ２
１−（ｍ−フルオロフエニル）−３−（２−クロロエチ
ル→ピリド（ ２ ． ３−ａ ）ピリミジン−２．４
ＣＩＨ，３Ｈ）一ジオン３．２ｇとナトリウムエチラー
ト５．４ｇをアルコー／Ｌ’ｌ ０ ０ＩｒＬｌ中還流
下４時間反応させた。Melting point 118-119℃ Elemental analysis value C14H, CIN30 Theoretical value C: 61.43H: 4.42N: 15
．． 35 Actual measurement value C: 61.32H: 4.49N:
15.21 Example 2 1-(m-fluorophenyl)-3-(2-chloroethyl→pyrido(2.3-a)pyrimidine-2.4
3.2 g of CIH, 3H) dione and 5.4 g of sodium ethylate were reacted under reflux in alcohol/L'l00IrLl for 4 hours.
玲後、酢酸で中和し減圧下に溶媒を留去し、残渣に水を
加えクロロホルムで抽出後シリカゲルを充填したカラム
に吸着させクロロホルムで展開し、第一溶出部の溶媒を
留去し残渣をエーテルより再結晶して、無色プリズム晶
の１−（ｍ−フルオロフエニル） Ｉｓ２ｔ３ｓ４−
テトラヒド口−５Ｈ−ピリド（２，３−ｅ）−１，４−
ジアゼピン−５−オン１．９ｇを得た。After cooling, neutralize with acetic acid and evaporate the solvent under reduced pressure, add water to the residue, extract with chloroform, adsorb on a column packed with silica gel, develop with chloroform, evaporate the solvent of the first eluate, and leave a residue. was recrystallized from ether to obtain colorless prismatic crystals of 1-(m-fluorophenyl)Is2t3s4-
Tetrahydro-5H-pyrido(2,3-e)-1,4-
1.9 g of diazepin-5-one was obtained.
この物質の融点及び元素分析値は次の通りであった。The melting point and elemental analysis values of this substance were as follows.
融 点 ８８〜９０°Ｃ
元素分析値 Ｃ１′４Ｈ１ＦＮ３０
理論値Ｃ ： ６５．３６Ｈ ： ４．７０ Ｎ ：１
６．３４実測値Ｃ ： ６５．２８ Ｈ ： ４．６７
Ｎ ： １６．３２実施例 ３
１−（ｍ一トリフルオ口メチルフエニル）一３−（２−
１−シルオキシエチル）ピリド［，２．３−ａ〕ピリミ
ジン−２．４（ ＩＨ，３Ｈ）一ジオン２．５ｇをエタ
ノール２０ｒｎｌとアセトン２ｏｒｒＬｌ混合溶媒に溶
解後、水酸化カリウム１．４ｇを加え還流下４時間反応
させた。Melting point 88-90°C Elemental analysis value C1'4H1FN30 Theoretical value C: 65.36H: 4.70 N: 1
6.34 Actual value C: 65.28 H: 4.67
N: 16.32 Example 3 1-(m-trifluoromethylphenyl)-3-(2-
After dissolving 2.5 g of 1-syloxyethyl)pyrido[,2.3-a]pyrimidine-2.4(IH,3H) monodione in a mixed solvent of 20rnl of ethanol and 2orrLl of acetone, 1.4g of potassium hydroxide was added. The reaction was carried out under reflux for 4 hours.
反応終了後、減圧下に溶媒を留去し残渣に氷を加えエー
テルで抽出、脱水後、アルミナを充填したカラムに吸着
させ第一溶出液の溶媒を濃縮し放置すると、無色プリズ
ム晶の１−（ｍ− トリフルオ口メチルフエニル）−１
．２，３，４−テトラヒドロ−５Ｈ−ピリド（２，３−
ｅ）−１．４−ジアゼピン−５−オン０．８８ｇを得た
。After the reaction is complete, the solvent is distilled off under reduced pressure, ice is added to the residue, extracted with ether, dehydrated, adsorbed on a column packed with alumina, concentrated the solvent of the first eluate, and left to stand, resulting in colorless prism crystals of 1- (m-trifluoromethylphenyl)-1
．． 2,3,4-tetrahydro-5H-pyrido (2,3-
e) 0.88 g of -1,4-diazepin-5-one was obtained.
この物質の融点及び元素分析値は次の通りであった。The melting point and elemental analysis values of this substance were as follows.
融 点 １０９〜１１０℃
元素分析値 Ｃ１５ Ｈ１２ Ｆ３ Ｎ３ ０理論値Ｃ
： ５８．６３Ｈ： ３．９４Ｎ： １３．６８実測
値Ｃ：５８．５２Ｈ： ３．８９Ｎ： １３．７２以下
実施例１〜３の方法に準じて次に示す化合物を合成した
。Melting point 109-110℃ Elemental analysis value C15 H12 F3 N3 0 Theoretical value C
: 58.63H: 3.94N: 13.68 Actual value C: 58.52H: 3.89N: 13.72 The following compounds were synthesized according to the methods of Examples 1 to 3.
１−フエニル−１．２，３．４−テトラヒド口−５Ｈ−
ピリド［− ２ ． ３−ｅ ：］−１ ， ４−ジア
ゼピン＝５オン 融点６４〜６６°Ｃ
■−（０−クロロフエニル）−１，２，３．４一テトラ
ヒド口−５Ｈ−ピリドＣ２，３−ｅ，］−１，４−ジア
ゼピン−５オン 融点１１１〜１１２°Ｃ
１−（０−フルオロフエニル）−１．２，３，４−テト
ラヒド口−５Ｈ−ピリド〔２，３−ｅ）−１，４−ジア
ゼピン−５オン 融点８７〜８６℃
■−（ｍ−ニトロフエニル）−１，２，３．４−テトラ
ヒド口−５Ｈ−ピリド（２．３−ｅ）−１，４−ジアゼ
ピン−５オン 融点１７７〜１７８℃
１−（３．４−ジクロ口フエニル）−１．２，３，４−
テトラヒド口−５Ｈ−ピリド［、２，３一ｅ）−１．４
−ジアゼピン−５オン 融点１２９〜１３０’Ｃ1-phenyl-1.2,3.4-tetrahydro-5H-
Pyrido [-2. 3-e:]-1,4-diazepine=5one Melting point 64-66°C ■-(0-chlorophenyl)-1,2,3.4-tetrahydride-5H-pyridoC2,3-e,]- 1,4-Diazepine-5one Melting point 111-112°C 1-(0-fluorophenyl)-1.2,3,4-tetrahydride-5H-pyrido[2,3-e)-1,4- Diazepine-5one Melting point 87~86℃ ■-(m-nitrophenyl)-1,2,3.4-tetrahydride-5H-pyrido(2.3-e)-1,4-diazepine-5one Melting point 177~ 178℃ 1-(3.4-dichlorophenyl)-1.2,3,4-
Tetrahydro-5H-pyrido[,2,31e)-1.4
-Diazepine-5one Melting point 129-130'C
Claims (1)
を、Ｒはフエニル基又はハロゲン原子、ニトロ基、トリ
フルオロメチル基で置換されたフエニル基を意味する）
で表わされる化合物にアルカリを反応させることを特徴
とする一般式（式中、Ｒは前記と同じ意味を有する）で
表わされる新規なピリドー１，４−ジアゼピン誘導体の
製造法。[Claims] 1 General formula (wherein, X represents a halogen atom or an organic sulfonyloxy group, and R represents a phenyl group or a phenyl group substituted with a halogen atom, a nitro group, or a trifluoromethyl group)
A method for producing a novel pyrido-1,4-diazepine derivative represented by the general formula (wherein R has the same meaning as above), which comprises reacting a compound represented by the above with an alkali.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10639274A JPS5813554B2 (en) | 1974-09-12 | 1974-09-12 | Sinquinapiride -1,4- Diazepine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10639274A JPS5813554B2 (en) | 1974-09-12 | 1974-09-12 | Sinquinapiride -1,4- Diazepine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5136485A JPS5136485A (en) | 1976-03-27 |
| JPS5813554B2 true JPS5813554B2 (en) | 1983-03-14 |
Family
ID=14432408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10639274A Expired JPS5813554B2 (en) | 1974-09-12 | 1974-09-12 | Sinquinapiride -1,4- Diazepine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5813554B2 (en) |
-
1974
- 1974-09-12 JP JP10639274A patent/JPS5813554B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5136485A (en) | 1976-03-27 |
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