鎮痙剤の研究(第2報)3位置換Quinolizidine類の簡便な新合成法とそれらの立体構造について
スポンサーリンク
概要
- 論文の詳細を見る
A convenient synthesis of 3-substituted quinolizidines was developed. Cyclization of 3-[2-(2-chloroethyl) piperidin-1-yl] propionitrile (10) with a base afforded 3-cyanoquinolizidines (13a and 13b) in good yield, which have been transformed to 5-alkyl-3-diarylmethylenequinolizidinium bromides (5), novel antispasmodics. 3-Cyanoquinolizidines (13a and 13b) were converted to 3-ethoxycarbonyl-(14a and 14b), 3-benzoyl-(17a and 17b) and 3-(2-thenoyl)-quinolizidines (18a and 18b), respectively. 3-Ethoxycarbonyl-(14a and 14b) and 3-benzoyl-quinolizidines (17a and 17b) were also obtained by cyclization of the chloroester (11) and the chlorobenzoyl (12), respectively. The stereochemistry of the 3-substituted quinolizidines synthesized here was determined.
- 社団法人日本薬学会の論文
- 1979-10-25
著者
-
加藤 日出男
北陸製薬株式会社
-
小川 信男
北陸製薬株式会社中央研究所研究開発本部
-
越中 栄一
Research and Development Division, Hokuriku Seiyaku Co., Ltd.,
-
越中 栄一
Research And Development Division Hokuriku Seiyaku Co. Ltd.
-
花岡 美代次
金沢大学薬学部
関連論文
- 気管支喘息治療薬ツロブテロールの経皮吸収型製剤の開発
- 232 新規TXA_2/LTD_4デュアル拮抗薬RS-601の抗喘息作用
- Benzenesulfonamide誘導体の合成とThromboxane A_2及びLeukotriene D_4に対するDual拮抗作用
- Amphoteric Drugs. II. Synthesis and Antiallergic Activity of [4-(5H-Dibenzo[a, d]cycloheptan-5-ylidene)piperidino]alkanoic Acid Derivatives and Related Compounds
- Amphoteric Drugs. I. Synthesis and Antiallergic Activity of [4-(Diphenylmethoxy)piperidino]-, [4-(Diphenylmethyl)piperazinyl]-and [4-(Diphenylmethylene)piperidino]alkanoic Acid Derivatives
- Transport Mechanism of an H_1-Antagonist at the Blood-Brain Barrier : Transport Mechanism of Mepyramine Using the Carotid Injection Technique
- 医薬品の両性イオン化(第3報)1,2,3,4,10,14b-Hexahydrodibenzo-[c, f]pyrazino[1,2-α]azepine及び2,3,4,9-Tetrahydro-1H-dibenzo[3,4 : 6,7]cyclohepta[1,2-c]pyridineのN-Alkylcarboxylic Acid誘導体の合成とその薬理作用
- Study on Zwitter-Ionization of Drugs. II. Synthesis and Pharmacological Activity of Some N-[3-(5H-Dibenzo[a, d]cyclohepten-5-ylidene)propyl]-N-methylamino- and N-[3-(6H-Dibenz[b, e]oxepin-11-ylidene)propyl]-N-methylamino-alkanoic Acid Derivatives and Rela
- INTER-INDIVIDUAL DIFFERENCES OF (+)-4-[4-(4-METHYLPHENYL)PHENYLMETHOXY-1-PIPERIDINYL]BUTYRIC ACID ((+)-MPPB) DISPOSITION IN RATS
- 医薬品の両性イオン化(第1報)4-(2-Chlorodibenz[b, f][1,4]oxazepin-11-yl)piaerazine, 4-(2-Chlorodibenzo[b, f][1,4]thiazepin-11-yl)-piperazine及び4-(11H-Dibenz[b, e]azepin-6-yl)piperazineのN-アルキルカルボン酸誘導体の合成とその薬理作用
- Novel Phenoxyalkylamine Derivatives. VII. Synthesis and Pharmacological Activities of 2-Alkoxy-5-[(Phenoxyalkylamino)alkyl]benzenesulfonamide Derivatives
- Synthesis, Gastrointestinal Prokinetic Activity and Structure-Activity Relationships of Novel N-[[2-(Dialkylamino)ethoxy)benzyl]benzamide Derivatives
- Quinolone系抗菌剤の研究(第3報)5-Amino-7-(2-aminoalkoxy)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid及びその関連化合物の合成と抗菌活性
- Ouinolone系抗菌剤の研究(第2報)7-Aminoalkoxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid及びその関連化合物の合成と抗菌活性
- 新規なPhenoxyalkylamine誘導体(第6報)α-[(Phenoxyethylamino)propyl]-α-phenylacetonitrile誘導体の合成とα-遮断作用
- Studies on Antiallergic Agents. II. : Quantitative Structure-Activity Relationships of Novel 6-Substituted N-(1H-Tetrazol-5-yl)-2-pyrazinecarboxamides
- Quinolone系抗菌剤の研究(第1報)7-(2-Aminoethoxy)-, 7-(2-Aminoethylthio)-及び7-(2-Aminoethylamino)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid及びそれらの誘導体の合成と抗菌活性
- Studies on Antiallergic Agents. I. : Synthesis and Antiallergic Activity of Novel Pyrazine Derivatives
- Novel Phenoxyalkylamine Derivatives. V. : Synthesis, α-Blocking Activity and Quantitative Structure-Activity Analysis of α-[(Phenoxyethylamino)propyl]-α-phenylacetonitrile Derivatives
- Novel Phenoxyalkylamine Derivatives. IV. : Synthesis, Ca^-Antagonistic Activity and Quantitative Structure-Activity Analysis of α-Isopropyl-α-[3[3-(3-methoxyphenoxy)propylamino]propyl]-α-phenylacetonitrile Derivatives
- Synthesis and Histamine H_2-Antagonist Activity of 4-Quinazolinone Derivatives
- Novel Phenoxyalkylamine Derivatives. III. : Quantitative Structure-Activity Relationships of Ca^-Antagonistic α-Alkyla-α-[(phenoxypropylamino)propyl]-3,4,5-trimethoxy-benzeneacetonitrile Derivatives
- Novel Phenoxyalkylamine Derivatives. II. : Synthesis and Ca^-Antagonistic Activities of α-Alkyl-α-[(phenoxypropylamino)propyl]-benzeneacetonitrile Derivatives
- Novel Phenoxyalkylamine Derivatives. I. : Synthesis and Pharmacological Activities of α-Isopropyl-α-[(phenoxyalkylamino)alkyl]-benzeneacetonitrile Derivatives
- (2-Pyrimidinylamino)phenylacetic Acid誘導体の合成と抗炎症作用
- Dexamethasone valerate (DV-17) と他の副腎皮質ステロイド外用剤のラット比較毒性試験
- Dexamethasone valerate (DV-17)と他の副腎皮質ステロイド外用剤のウサギにおける刺激性試験 : 皮膚および眼粘膜一次刺激性試験ならびに皮膚累積刺激性試験
- Study on Zwitter-Ionization of Drugs. II. Synthesis and Pharmacological Activity of Some N-[3-(5H-Dibenzo[a, d]cyclohepten-5-ylidene)propyl]-N-methylamino- and N-[3-(6H-Dibenz[b, e]oxepin-11-ylidene)propyl]-N-methylamino-alkanoic Acid Derivatives and Rela
- Study on Zwitter-Ionization of Drugs. II. Synthesis and Pharmacological Activity of Some N-[3-(5H-Dibenzo[a, d]cyclohepten-5-ylidene)propyl]-N-methylamino- and N-[3-(6H-Dibenz[b, e]oxepin-11-ylidene)propyl]-N-methylamino-alkanoic Acid Derivatives and Rela
- Study on Zwitter-Ionization of Drugs. II. Synthesis and Pharmacological Activity of Some N-[3-(5H-Dibenzo[a, d]cyclohepten-5-ylidene)propyl]-N-methylamino- and N-[3-(6H-Dibenz[b, e]oxepin-11-ylidene)propyl]-N-methylamino-alkanoic Acid Derivatives and Rela
- Study on Zwitter-Ionization of Drugs. II. Synthesis and Pharmacological Activity of Some N-[3-(5H-Dibenzo[a, d]cyclohepten-5-ylidene)propyl]-N-methylamino- and N-[3-(6H-Dibenz[b, e]oxepin-11-ylidene)propyl]-N-methylamino-alkanoic Acid Derivatives and Rela
- Study on Zwitter-Ionization of Drugs. II. Synthesis and Pharmacological Activity of Some N-[3-(5H-Dibenzo[a, d]cyclohepten-5-ylidene)propyl]-N-methylamino- and N-[3-(6H-Dibenz[b, e]oxepin-11-ylidene)propyl]-N-methylamino-alkanoic Acid Derivatives and Rela
- Study on Zwitter-Ionization of Drugs. II. Synthesis and Pharmacological Activity of Some N-[3-(5H-Dibenzo[a, d]cyclohepten-5-ylidene)propyl]-N-methylamino- and N-[3-(6H-Dibenz[b, e]oxepin-11-ylidene)propyl]-N-methylamino-alkanoic Acid Derivatives and Rela
- Study on Zwitter-Ionization of Drugs. II. Synthesis and Pharmacological Activity of Some N-[3-(5H-Dibenzo[a, d]cyclohepten-5-ylidene)propyl]-N-methylamino- and N-[3-(6H-Dibenz[b, e]oxepin-11-ylidene)propyl]-N-methylamino-alkanoic Acid Derivatives and Rela
- Crystal Structures of Polymorphs of α-[(tert-Butylamino) methyl]-2-chloro-4-hydroxybenzyl Alcohol Hydrochloride (HOKU-81)
- 鎮痙剤の研究(第7報)N-Alkyl Diarylmethylenequinolizidinium Bromides, N-Alkyl Diarylmethyleneindolizidinium Bromidesおよび関連化合物の構造活性相関
- 鎮痙薬の薬理学的研究(第1報)Diarylmethylene-5-methyl-transquinolizidinium Bromide類の鎮痙作用への選択性
- Studies on Antispasmodics. VI. Synthesis of N-Alkyl 6- and 7-Diarylmethyleneindolizidinium Bromides
- Studies on Antispasmodics. V. Synthesis and Anticholinergic Activity of N-Alkyl 1- and 2-Diarylmethylene-indolizidinium Bromides
- 鎮痙剤の研究(第4報)Diarylhydroxymethylquinolizidine Methohalidesの合成と抗アセチルコリン作用
- 鎮痙剤の研究(第3報)2位置換Quinolizidine類の簡便な新合成法とそれらの立体構造について
- 鎮痙剤の研究(第2報)3位置換Quinolizidine類の簡便な新合成法とそれらの立体構造について
- Studies on Antispasmodics. I. Synthesis and Anticholinergic Activity of 1-, 2-, and 3-Diarylmethylenequinolizidine Quaternary Ammonium Salts
- o-Chloro-α-(tert-butylaminomethyl)benzylalcohol Hydrochloride(C-78)および関連化合物の合成と気管支拡張作用
- Studies on 1-Azabicyclo Compounds. XXVI. Synthesis of Ten-membered Ring Amines from 9a-Cyanomethyl-, 9a-Ethoxycarbonylmethyl-, and 1-Ethoxycarbonyl-octahydroquinolizine
- Synthesis of (±)-Methyldecamine
- Dacarbazineの光分解によって生成する発痛物質の探索
- Convenient Synthesis of 2,3,9,10-Tetraoxygenated Protoberberine Alkaloids and Their 13-Methyl Alkaloids
- 12-3-B3 ダカルバジン注射剤投与時における血管痛原因物質の探索
- 100(P24) 抗腫瘍性スチリルラクトン化合物の高立体選択的合成(ポスター発表の部)
- (o-トリメチルシリルベンズアルデヒド)クロム錯体を活用する高立体選択的反応の開発
- Erythro-Selective Aldol Reaction of Tricarbonyl(η^6-o-trialkylsilylbenzaldehyde)chromium(0) Complexes with Cyclic Ketene Silyl Acetals
- 18 Protoberberineアルカロイドの新規合成とBenzo[c]phenanthridineアルカロイド(±)-Ambinineの全合成(口頭発表の部)
- Chemical Transformation of Protoberberines. XVII. Biomimetic Introduction of an Oxy Functionality at the C-10 Position in the Benzo[c]phenanthridine Skeleton : Synthesis of 2,3,7,8,10-Pentaoxygenated Benzo[c]phenanthridine Alkaloids, Chelilutine and Sangu
- A FIRST TOTAL SYNTHESIS OF (±)-AMBININE
- Chemical Transformation of Protoberberines. XVI. Regioselective Introduction of an Oxy Functionality at the C_-Position of the Benzo[c]phenanthridine Skeleton : A Convenient Synthesis of Macarpine from Oxychelirubine
- Trimethylsilyl Trifluoromethanesulfonate-Catalyzed Aldol Reaction of Various Aldehydes with Silyl Enol Ethers
- A NOVEL DIASTEREOSELECTIVITY IN THE ALDOL REACTION OF CYCLIC KETENE SILYL ACETALS WITH COBALT-COMPLEXED AND UNCOMPLEXED PROPYNALS
- 学術貢献賞受賞 北 泰行氏の業績
- 故荒田義雄先生を偲んで
- イソキノリンアルカロイドの生合成的合成
- サマリーを重要視(キーワードの使い方)
- 科学研究費の配分について(文部省科学研究費申請と配分の問題点)
- 双環状アミン体から中環状アミン類の合成
- Synthetic Studies on Lythraceae Alkaloids. V. Total Synthesis of (±)-Vertaline
- Synthetic Studies on Lythraceae Alkaloids. IV. Total Synthesis of (±)-Methyldecinine
- Total Synthesis of (±)-Lagerine
- Synthetic Studies on Lythraceae Alkaloids. III. Stereoselective Total Synthesis of (±)-Decaline
- Synthetic Studies on Lythraceae Alkaloids. II. The Mannich Reaction of Isopelletierine with 3-Methoxybenzaldehyde and 3-Hydroxybenzaldehyde
- Studies on 1-Azabicyclo Compounds. XXIV. Synthesis and Stereochemistry of 10-Ethyl-, 10-Vinyl-, and 10-Ethynyl-quinolizidine Methiodides
- Studies on 1-Azabicyclo Compounds. XXII. Stereochemistry of 9a-Substituted Quinolizidine Methiodides
- Chemical Transformation of Protoberberines. XV. : A Novel and Efficient Method for the Introduction of Alkyl Groups on the C-13 Position in the Protoberberine Skeleton
- A NOVEL TOTAL SYNTHESIS OF (±)-CRYPTAUSTOLINE, A DIBENZOPYRROCOLINE ALKALOID
- A NOVEL AND BIOMIMETIC SYNTHESIS OF CHELILUTINE AND SANGUILUTINE
- A TOTAL SYNTHESIS OF (±)-CEPHALOTAXINAMIDE
- 64 ProtoberberineアルカロイドからBenzo [c] phenanthridineアルカロイドの生合成的合成(口頭発表の部)
- 58 ProtoberberineアルカロイドからBenzo[c]phenanthridineアルカロイドの高立体選択的合成
- 33 ProtoberberineからBenzo〔c〕phenanthridine及び3-Arylisoquinolineアルカロイドの合成
- Chemical Transformation of Protoberberines. VIII. A Novel Synthesis of (±)-Fumaricine and a Formal Synthesis of (±)-Alpinigenine
- Chemical Transformation of Protoberberines. VII. Efficient Conversion of Protoberberines into Benzindenoazepines via 8,14-Cycloberbines
- Studies on the Relationship between Physico-chemical Properties and Crystalline Forms of Tulobuterol Hydrochloride. II. Crystal Structure Analyses of the Four Crystalline Forms of Tulobuterol Hydrochloride
- 2-Methyl-3-pyrrolidinopropiophenone誘導体の中枢性筋弛緩作用
- Tulobuterolの生体内運命(第5報)ラット, イヌ, モルモットおよびウサギにおける代謝および排泄に関する種差
- ツロブテロールの生体内運命(第4報)ラット日齢と生体内動態について
- 塩酸ツロブテールの性状と結晶形との相関に関する研究(第3報) : 塩酸ツロブテール多形の吸湿特性
- 塩酸ツロブテロールの性状と結晶形との相関に関する研究(第3報)塩酸ツロブテロール多形の吸湿特性
- Studies on the Relationship between Physico-chemical Properties and Crystalline Forms of Tulobuterol Hydrochloride. I. Polymorphism of Tulobuterol Hydrochloride
- 胃粘膜微小循環に及ぼす3-(Di-2-thienylmethylene)-5-methyl-trans-quinolizidinium Bromide(HSR-902)の影響
- Polymorphism of α-[(tert-Butylamino) methyl]-2-chloro-4-hydroxybenzyl Alcohol Hydrochloride (HOKU-81)
- 1-Azabicyclo化合物の研究(第21報)1,2,3,10,11,11a-Hexahydro-5H-pyrrolo-[2,1-c][1,4]benzodiazepin-11-oneおよび5,6,6a, 7,8,9,10,12-Octahydropyrido[2,1-c][1,4]benzodiazepin-6-oneから中環状AminolactamおよびSpiroaminolactam体の合成
- Studies on 1-Azabicyclo Compounds. XVI. Synthesis of 1'-Methylindan-2-spiro-2'-piperazine and Related Compounds
- Studies on 1-Azabicyclo Compounds. XV. Oxidation of 1,3,4,6,11,11a-Hexahydro-2H-pyrazino [1,2-b] isoquinolin-1-one Derivatives with Mercuric Acetate, and Their Conversion into 1,2,3,4,5,6,7,8-Octahydro-2-methyl-2,5-benzodiazecine and Related Compounds
- 1-Azabicyclo化合物の研究その5 : 4-Oxoquinolizidineの水素化リチウムアルミニウム還元およびQuinolizidineの酢酸第二水銀酸化により得られた二量体の化学構造
- Diazabicycloalkanesの研究(第2報)4-[β-(10-Phenothiazinyl)-ethyl]-1,4-diazabicyclo[4,4,0]-decaneおよび類似化合物の抗ヒスタミン作用ならびに向精神作用
- 臭化チキジウム
- 鎮痙薬の薬理学的研究(第5報) : 3-(Di-2-Thienylmethylene)-5-Methyl-trans-Quinolizidinium Bromide (HSR-902) の骨盤神経終末と膀胱壁筋との神経伝達に及ぼす作用
- 鎮痙薬の薬理学的研究(第3報) 3-(Di-2-Thienylmethylene)-5-Methyl-trans-QuinolizidiniumBromide(HSR-902)の鎮痙作用とその臓器特異性
- 3-(5-Nitro-2-furyl)-benzo-1,2,4-triazine誘導体の合成ならびに抗細菌作用について
- 1-Azabicyclo化合物の研究(第20報)Hexahydroisoquino[3,2-c][1,4]benzodiazepineおよび関連化合物の合成ならびにHexahydroisoquino[3,2-c]-[1,4]benzodiazepin-13-one から6-Methyl-hexahydro-5H-dibenzo[b, g][1,5]diazacycloundecineの生成
- 1-Azabicyclo化合物の研究(第25報)Octahydropyrrolo[1,2-α]pyrazin-1-oneから9員環状Aminolactamおよび関連化合物の合成