GB1156825A - Guanidinoalkyl Derivatives of Substituted Anilides - Google Patents

Guanidinoalkyl Derivatives of Substituted Anilides

Info

Publication number
GB1156825A
GB1156825A GB27626/66A GB2762666A GB1156825A GB 1156825 A GB1156825 A GB 1156825A GB 27626/66 A GB27626/66 A GB 27626/66A GB 2762666 A GB2762666 A GB 2762666A GB 1156825 A GB1156825 A GB 1156825A
Authority
GB
United Kingdom
Prior art keywords
phthalimide
cinnamanilide
alkyl
reacting
ethyl
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
Application number
GB27626/66A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ER Squibb and Sons LLC
Original Assignee
ER Squibb and Sons LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC
Publication of GB1156825A publication Critical patent/GB1156825A/en
Expired legal-status Critical Current

Links

Classifications

    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B17/00—Engines characterised by means for effecting stratification of charge in cylinders
    • F02B17/005—Engines characterised by means for effecting stratification of charge in cylinders having direct injection in the combustion chamber
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B23/00—Other engines characterised by special shape or construction of combustion chambers to improve operation
    • F02B23/02—Other engines characterised by special shape or construction of combustion chambers to improve operation with compression ignition
    • F02B23/06—Other engines characterised by special shape or construction of combustion chambers to improve operation with compression ignition the combustion space being arranged in working piston
    • F02B23/0675—Other engines characterised by special shape or construction of combustion chambers to improve operation with compression ignition the combustion space being arranged in working piston the combustion space being substantially spherical, hemispherical, ellipsoid or parabolic
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B23/00—Other engines characterised by special shape or construction of combustion chambers to improve operation
    • F02B23/08—Other engines characterised by special shape or construction of combustion chambers to improve operation with positive ignition
    • F02B23/10—Other engines characterised by special shape or construction of combustion chambers to improve operation with positive ignition with separate admission of air and fuel into cylinder
    • F02B23/104—Other engines characterised by special shape or construction of combustion chambers to improve operation with positive ignition with separate admission of air and fuel into cylinder the injector being placed on a side position of the cylinder
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
    • Y02T10/00—Road transport of goods or passengers
    • Y02T10/10—Internal combustion engine [ICE] based vehicles
    • Y02T10/12—Improving ICE efficiencies

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,156,825. Guanidino derivatives of anilides. E. R. SQUIBB & SONS Inc. 21 June, 1966 [24 June, 1965], No. 27626/66. Heading C2C. Novel compounds of Formula I wherein X is H, halo, trihalomethyl, NO 2 , NH 2 , C 1-7 alkyl, C 1-7 alkoxy, OH, C 1-7 alkylthio, or C 1-7 alkanoyl; Y is C 1-7 alkylene, C 1-7 alkenylene, C 1-7 alkadienylene, or C 1-7 alkynylene; Z is oxa, thia, methylene or carbonyl; R is H, C 1-7 alkyl, cyclo-C 1-7 alkyl, phenyl-C 1-7 alkyl, (X)nphenyl, furyl, thienyl or pyridyl; R<SP>1</SP> is H, C 1-7 alkyl, monocyclic aryl, or monocyclic aryl-C 1-7 alkyl and n is 1-3 or acid addition and quaternary ammonium salts thereof are prepared by reacting a compound of Formula I in which the guanidino group is replaced by -NR<SP>1</SP>H with thiopseudourea, R<SP>1</SP>-substituted thiopseudourea, cyanamide, R<SP>1</SP>-substituted cyanamide or an acid salt thereof. Intermediates isolated are N-[2-(2-aminophenylthio)ethyl] - phthalimide, from 2 - aminobenzenethiol and N - (2 - bromoethyl) phthalimide; 2<SP>1</SP>- (2 - phthalimidoethylthio) cinnamanilide from the former-named intermediate and cinnamoyl chloride; 2<SP>1</SP>-(2-aminoethylthio) cinnamilide hydrochloride; 2-(2-aminoethylthio)- cinnamanilide by reacting the former-named intermediate with sodium hydroxide; 2<SP>1</SP>-(3- phthalimidopropylthio) cinnamanilide by reacting 3,5 - dihydro - 2 - phenyl - 1,5 - benzothiazepin-4-one with sodium methylate and N-(3- bromopropyl) phthalimide; N - (o - nitrophenethyl) phthalimide from o-nitrophenethyl bromide and potassium phthalimide; N-(o-aminophenethyl) phthalimide by reduction of the preceding intermediate; N-[2-(2-nitrophenoxy) - ethyl]-phthalimide from o-nitrophenol and N-(2- bromoethyl) phthalimide; N - [2 - (2 - aminophenoxy) ethyl] phthalimide by reduction of the preceding intermediate; 2<SP>1</SP>-(3-phthalimidopropionyl) cinnamamilide from 2<SP>1 </SP>- (3 - dimethylaminopropionyl) cinnamanilide and phthalimide; and N - methyl - 21 - (2 - phthalimidoethylthio) cinnamanilide by N - methylation of 2<SP>1</SP> - (2 - phthalimido - ethylthio) cinnamanilide. Pharmaceutical compositions comprise a compound I in admixture with a suitable excipient and are administered orally and parenterally. They possess serotonin-inhibitory activity.
GB27626/66A 1965-06-24 1966-06-21 Guanidinoalkyl Derivatives of Substituted Anilides Expired GB1156825A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US46684165A 1965-06-24 1965-06-24

Publications (1)

Publication Number Publication Date
GB1156825A true GB1156825A (en) 1969-07-02

Family

ID=23853304

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27626/66A Expired GB1156825A (en) 1965-06-24 1966-06-21 Guanidinoalkyl Derivatives of Substituted Anilides

Country Status (3)

Country Link
DE (1) DE1593391A1 (en)
FR (1) FR5886M (en)
GB (1) GB1156825A (en)

Also Published As

Publication number Publication date
FR5886M (en) 1968-03-18
DE1593391A1 (en) 1970-07-09

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees