GB1329447A - 4-adamantylaminoalkylamino-2-styryl-quinolines salts and derivatives thereof - Google Patents

4-adamantylaminoalkylamino-2-styryl-quinolines salts and derivatives thereof

Info

Publication number
GB1329447A
GB1329447A GB4818670A GB4818670A GB1329447A GB 1329447 A GB1329447 A GB 1329447A GB 4818670 A GB4818670 A GB 4818670A GB 4818670 A GB4818670 A GB 4818670A GB 1329447 A GB1329447 A GB 1329447A
Authority
GB
United Kingdom
Prior art keywords
general formula
adamantylaminoalkylamino
reaction
resulting
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
GB4818670A
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 GB1329447A publication Critical patent/GB1329447A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1329447 4-(Adamantylaminoalkylamino)-2- styrylquinolines E R SQUIBB & SONS Inc 9 Oct 1970 [27 Oct 1969] 48186/70 Heading C2C Novel 4-(adamantylaminoalkylamino)-2-styryl-quinolines of the general formula wherein each of R and R<SP>1</SP> is a hydrogen or halogen atom or a nitro, hydroxyl or alkoxy group, R<SP>2</SP> is a hydrogen atom or a C 1-8 alkyl group, each of R<SP>3</SP> and R<SP>4</SP> is a hydrogen or halogen atom or an alkyl, hydroxyl, alkoxy or phenyl group, R<SP>5</SP> is a hydrogen atom or a C 1-8 alkyl, C 2-8 alkenyl or phenyl-C 1-8 alkyl group and n is 2,3 or 4, and pharmaecutically acceptable acid addition salts thereof are prepared by reaction of a 4-halo-2-methylquinoline of the general formula wherein X is a chlorine, bromine or iodine atom, with an adamantylaminoalkylamine of the general formula and reaction of the resulting 4-(adamantylaminoalkylamino)-2-methylquinoline of the general formula with a benzaldehyde of the general formula followed optionally by salification of the product. N-(1-Adamantyl)-1,3-propanediamine is prepared by reaction of 1-adamantylamine with acrylonitrile and reduction of the resulting 3-(1- adamantylamino)propionitrile with lithium aluminium hydride. N-(1-Adamantyl)-N-ethyl-ethylenediamine is prepared by reduction of 1-acetamidoadamantane with lithium aluminium hydride, reaction of the resulting N-ethyl-1- adamantylamine with ethyleneimine and tosyl chloride and reaction of the resulting-N-}2-[N<SP>1</SP>- (1-adamanytl)-N<SP>1</SP>-ethylamino]ethyl}-p-toluenesulphonamide with ammonia. Pharmaceutical compositions having antiviral, antibacterial, antifungal and antiprotozoal activity comprise, as active ingredient, a 4- (adamantylaminoalkylamino) -2 -styrylquinoline of the first general formula above or a physiologically acceptable acid addition salt thereof, together with a suitable carrier, and may be administered orally or parenterally.
GB4818670A 1969-10-27 1970-10-09 4-adamantylaminoalkylamino-2-styryl-quinolines salts and derivatives thereof Expired GB1329447A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US86985269A 1969-10-27 1969-10-27

Publications (1)

Publication Number Publication Date
GB1329447A true GB1329447A (en) 1973-09-05

Family

ID=25354374

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4818670A Expired GB1329447A (en) 1969-10-27 1970-10-09 4-adamantylaminoalkylamino-2-styryl-quinolines salts and derivatives thereof

Country Status (4)

Country Link
CH (2) CH530400A (en)
DE (1) DE2050074A1 (en)
FR (1) FR2070165B1 (en)
GB (1) GB1329447A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000073283A1 (en) * 1999-06-02 2000-12-07 Nps Pharmaceuticals, Inc. Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases
AU2004202776B2 (en) * 1997-11-21 2008-06-19 Astrazeneca Ab Metabotropic glutamate receptor antagonists for treating central nervous system diseases

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6429207B1 (en) 1997-11-21 2002-08-06 Nps Pharmaceuticals, Inc. Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2004202776B2 (en) * 1997-11-21 2008-06-19 Astrazeneca Ab Metabotropic glutamate receptor antagonists for treating central nervous system diseases
WO2000073283A1 (en) * 1999-06-02 2000-12-07 Nps Pharmaceuticals, Inc. Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases
EP1595871A3 (en) * 1999-06-02 2005-11-30 Nps Pharmaceuticals, Inc. Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases

Also Published As

Publication number Publication date
FR2070165B1 (en) 1975-10-10
CH530400A (en) 1972-11-15
FR2070165A1 (en) 1971-09-10
DE2050074A1 (en) 1971-05-06
CH525888A (en) 1972-07-31

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Legal Events

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