JPS6258357B2 - - Google Patents
Info
- Publication number
- JPS6258357B2 JPS6258357B2 JP4650480A JP4650480A JPS6258357B2 JP S6258357 B2 JPS6258357 B2 JP S6258357B2 JP 4650480 A JP4650480 A JP 4650480A JP 4650480 A JP4650480 A JP 4650480A JP S6258357 B2 JPS6258357 B2 JP S6258357B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- dibenz
- piperidinyl
- dihydro
- propyl
- 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
- -1 piperidine compound Chemical class 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 239000002253 acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 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
- YLKKRCYFGKGCKZ-UHFFFAOYSA-N 1-methyl-3-phenylimidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1C1=CC=CC=C1 YLKKRCYFGKGCKZ-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
- 239000005711 Benzoic acid Substances 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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 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
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (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 で表わされるピペリジン化合物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the general formula This invention relates to a piperidine compound represented by:
上記式中、X1，X2はそれぞれ水素、ハロゲン
（フツ素、塩素、臭素など）を、
R2は水素、低級アルキル（メチル、エチル、
プロピル、ブチルなど）、フエニルを、Ａは直鎖
または分枝状の低級アルキレン（メチレン、エチ
レン、トリメチレン、プロピレン、２−メチルト
リメチレンなど）、を、Ｂはアルキレン（メチレ
ン、エチレン、トリメチレン、プロピレン、な
ど）、アルキリデン（エチリデン、プロピリデン
など）を示す。 In the above formula, X 1 and X 2 are hydrogen and halogen (fluorine, chlorine, bromine, etc.), respectively, and R 2 is hydrogen, lower alkyl (methyl, ethyl,
A is a linear or branched lower alkylene (methylene, ethylene, trimethylene, propylene, 2-methyltrimethylene, etc.), B is an alkylene (methylene, ethylene, trimethylene, propylene, etc.) , etc.), alkylidene (ethylidene, propylidene, etc.).
本発明の一般式（）の化合物は、一般式
（式中、Ｑは塩素、臭素、メタンスルホニルオ
キシ、ｐ−トルエンスルホニルオキシなどの活性
エステル残基を示し、他の記号は前記と同義であ
る。）
で表わされる化合物と一般式
（式中、各記号は前記と同義である。）
で表わされる化合物とを、不活性溶媒（メタノー
ル、エタノール、イソプロパノール、メチルエチ
ルケトン、メチルイソブチルケトン、テトラヒド
ロフラン、ジオキサン、１，２−ジメトキシエタ
ン、エチルエーテル、イソプロピルエーテル、ベ
ンゼン、トルエン、キシレン、酢酸エチル、ジメ
チルホルムアミド、ジメチルスルホキシド、ピリ
ジン、水またはこれらの混合溶媒）中、必要に応
じて脱酸剤（炭酸ナトリウム、炭酸カリウム、水
酸化ナトリウムなど）の存在下、０℃から用いた
溶媒の沸点までの温度で数時間から数十時間で反
応させ反応生成物を再結晶、酸アルカリ処理、カ
ラムクロマトグラフイーなどの常法により精製し
て得られる。 The compound of the general formula () of the present invention has the general formula (In the formula, Q represents an active ester residue such as chlorine, bromine, methanesulfonyloxy, p-toluenesulfonyloxy, and other symbols have the same meanings as above.) Compounds represented by the general formula (In the formula, each symbol has the same meaning as above.) A compound represented by , isopropyl ether, benzene, toluene, xylene, ethyl acetate, dimethylformamide, dimethyl sulfoxide, pyridine, water or a mixed solvent thereof), and if necessary, a deoxidizing agent (sodium carbonate, potassium carbonate, sodium hydroxide, etc.). The reaction product is reacted for several hours to several tens of hours in the presence of the solvent at a temperature from 0° C. to the boiling point of the solvent used, and the reaction product is purified by conventional methods such as recrystallization, acid-alkali treatment, and column chromatography.
このようにして得られた一般式（）の化合物
は、無機酸（塩酸、臭化水素酸、硫酸、リン酸な
ど）、有機酸（マレイン酸、フマール酸、シユウ
酸、酒石酸、安息香酸、サリチル酸、メタンスル
ホン酸、ベンゼンスルホン酸など）と常法に従つ
て処理することにより対応する酸付加塩とするこ
とができる。 The compounds of the general formula () obtained in this way are inorganic acids (hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, etc.), organic acids (maleic acid, fumaric acid, oxalic acid, tartaric acid, benzoic acid, salicylic acid, etc.). , methanesulfonic acid, benzenesulfonic acid, etc.) in a conventional manner to form the corresponding acid addition salt.
一般式（）の化合物およびその酸付加塩は、
精神分裂病、そう病、うつ病などの治療のための
精神神経安定剤として有用である。 Compounds of general formula () and acid addition salts thereof are:
It is useful as a neuroleptic for the treatment of schizophrenia, mania, depression, etc.
本発明の化合物を医薬として用いる場合には、
それ自体または薬理上許容されうる担体、賦形
剤、希釈剤などと混合して錠剤、散剤、カプセル
剤、注射用剤の形で、経口的または非経口的に精
紳病患者に投与されうる。投与量は年齢、症状な
どにより異なるが、成人１日あたり、経口投与の
場合、１回５〜100mgが好ましい。 When using the compound of the present invention as a medicine,
It can be administered orally or parenterally to patients with senile syndrome in the form of tablets, powders, capsules, or injections by itself or mixed with pharmaceutically acceptable carriers, excipients, diluents, etc. . Although the dosage varies depending on age, symptoms, etc., it is preferably 5 to 100 mg per adult per day for oral administration.
以下、実施例により本発明を具体的に説明す
る。 Hereinafter, the present invention will be specifically explained with reference to Examples.
実施例
５−（３−クロロプロピル）−10，11−ジヒドロ
−5H−ジベンズ（ｂ，ｆ〕アゼピン10ｇおよび
１−（４−ピペリジニル）ヒドロウラシル10ｇを
メタノール40ml中で60時間還流煮沸する。冷却し
不溶物を除去した後、室温で一夜放置する。析出
した結晶を取し、クロロホルム100mlに溶か
し、エタノール性塩酸を加える。放置後、析出し
た結晶を取し、メタノールから再結晶すると、
融点268℃の１−〔１−（３−（10，11−ジヒドロ−
5H−ジベンズ〔ｂ，ｆ〕アゼピン−５−イル）
プロピル）−４−ピペリジニル〕ヒドロウラシ
ル・塩酸塩が白色結晶として得られる。収率65％
同様にして以下の化合物が得られる。Example 5 10 g of -(3-chloropropyl)-10,11-dihydro-5H-dibenz(b,f)azepine and 10 g of 1-(4-piperidinyl)hydrouracil are boiled under reflux in 40 ml of methanol for 60 hours. Cooled. After removing insoluble matter, leave it at room temperature overnight.Take the precipitated crystals, dissolve them in 100 ml of chloroform, and add ethanolic hydrochloric acid.After leaving to stand, take the precipitated crystals and recrystallize from methanol.
1-[1-(3-(10,11-dihydro-
5H-dibenz[b,f]azepin-5-yl)
Propyl)-4-piperidinyl]hydrouracil hydrochloride is obtained as white crystals. The following compounds are obtained in the same manner with a yield of 65%.
◎ １−〔１−（３−（10，11−ジヒドロ−5H−ジ
ベンズ〔ｂ，ｆ〕アゼピン−５−イル）プロピ
ル）−４−ピペリジニル〕−３−メチルヒドロウ
ラシル、塩酸塩の融点223℃
◎ １−〔１−（３−（３−クロロ−10，11−ジヒ
ドロ−5H−ジベンズ〔ｂ，ｆ〕アゼピン−５
−イル）プロピル）−４−ピペリジニル〕−３，
５−ジメチルヒドロウラシル、マレイン酸塩の
融点187℃
◎ １−〔１−（３−（３−クロロ−10，11−ジヒ
ドロ−5H−ジベンズ〔ｂ，ｆ〕アゼピン−５
−イル）プロピル）−４−ピペリジニル〕ヒド
ロウラシル、塩酸塩の融点279℃
◎ １−〔１−（３−（10，11−ジヒドロ−5H−ジ
ベンズ〔ｂ，ｆ〕アゼピン−５−イル）プロピ
ル）−４−ピペリジニル〕−３，５−ジメチルヒ
ダントイン、塩酸塩の融点251℃
◎ １−〔１−（３−（３−クロロ−10，11−ジヒ
ドロ−5H−ジベンズ〔ｂ，ｆ〕アゼピン−５
−イル）プロピル）−４−ピペリジニル〕−３，
５−ジメチルヒダントイン、マレイン酸塩の融
点200℃
◎ １−〔１−（３−（３−クロロ−10，11−ジヒ
ドロ−5H−ジベンズ〔ｂ，ｆ〕アゼピン−５
−イル）プロピル）−４−ピペリジニル〕−５−
メチル−３−フエニルヒダントイン、マレイン
酸塩の融点223℃
◎ １−〔１−（３−（10，11−ジヒドロ−5H−ジ
ベンズ〔ｂ，ｆ〕アゼピン−５−イル）プロピ
ル）−４−ピペリジニル〕−５−メチルヒダント
イン。◎ Melting point of 1-[1-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl)-4-piperidinyl]-3-methylhydrouracil, hydrochloride 223℃ ◎ 1-[1-(3-(3-chloro-10,11-dihydro-5H-dibenz[b,f]azepine-5
-yl)propyl)-4-piperidinyl]-3,
Melting point of 5-dimethylhydrouracil, maleate salt 187℃ ◎ 1-[1-(3-(3-chloro-10,11-dihydro-5H-dibenz[b,f]azepine-5)
-yl)propyl)-4-piperidinyl]hydrouracil, melting point of hydrochloride 279℃ ◎ 1-[1-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl )-4-piperidinyl]-3,5-dimethylhydantoin, hydrochloride melting point 251℃ ◎ 1-[1-(3-(3-chloro-10,11-dihydro-5H-dibenz[b,f]azepine- 5
-yl)propyl)-4-piperidinyl]-3,
Melting point of 5-dimethylhydantoin, maleate salt 200℃ ◎ 1-[1-(3-(3-chloro-10,11-dihydro-5H-dibenz[b,f]azepine-5)
-yl)propyl)-4-piperidinyl]-5-
Melting point of methyl-3-phenylhydantoin, maleate salt 223℃ ◎ 1-[1-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl)-4- piperidinyl]-5-methylhydantoin.
Claims (1)
を、R2は水素、低級アルキル、フエニルを、Ａ
は直鎖または分枝状の低級アルキレンを、Ｂはア
ルキレン、アルキリデンを示す。[Claims] 1. General formula A piperidine compound represented by In the above formula, X 1 and X 2 are hydrogen and halogen, respectively, R 2 is hydrogen, lower alkyl, and phenyl, and A
represents linear or branched lower alkylene, and B represents alkylene or alkylidene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4650480A JPS56142280A (en) | 1980-04-08 | 1980-04-08 | Piperidine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4650480A JPS56142280A (en) | 1980-04-08 | 1980-04-08 | Piperidine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56142280A JPS56142280A (en) | 1981-11-06 |
| JPS6258357B2 true JPS6258357B2 (en) | 1987-12-05 |
Family
ID=12749070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4650480A Granted JPS56142280A (en) | 1980-04-08 | 1980-04-08 | Piperidine compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56142280A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2807577B2 (en) * | 1990-06-15 | 1998-10-08 | エーザイ株式会社 | Cyclic amide derivative |
| DE19952146A1 (en) * | 1999-10-29 | 2001-06-07 | Boehringer Ingelheim Pharma | Arylalkanes, arylalkenes and aryl-azaalkanes, medicaments containing these compounds and process for their preparation |
-
1980
- 1980-04-08 JP JP4650480A patent/JPS56142280A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56142280A (en) | 1981-11-06 |
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