GB1195491A - 4-Substituted 7- and 8-Chloroquinolines, the Preparation thereof, and Compositions Containing the same - Google Patents

4-Substituted 7- and 8-Chloroquinolines, the Preparation thereof, and Compositions Containing the same

Info

Publication number
GB1195491A
GB1195491A GB17091/68A GB1709168A GB1195491A GB 1195491 A GB1195491 A GB 1195491A GB 17091/68 A GB17091/68 A GB 17091/68A GB 1709168 A GB1709168 A GB 1709168A GB 1195491 A GB1195491 A GB 1195491A
Authority
GB
United Kingdom
Prior art keywords
chloroquinoline
group
alkyl
general formula
alkali metal
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
GB17091/68A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1195491A publication Critical patent/GB1195491A/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
    • C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms

Landscapes

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

Abstract

1,195,491. 4 - Anilino - 7 - or 8 - chloroquinoline derivatives. ROUSSEL UCLAF. 9 April, 1968 [12 April, 1967], No. 17091/68. Heading C2C. Novel 4 - anilino - 7 - or 8 - chloroquinoline derivatives of the general formula wherein R is a C 1-5 alkyl, C 2-5 alkenyl or C 2-6 carboxyalkyl group and R 1 is a hydrogen atom or a C 1-8 alkyl group, the chlorine atom being in the 7- or 8-position of the quinoline ring, and non-toxic acid addition salts thereof are prepared (a) when R is a C 1-5 alkyl or C 2-5 alkenyl group, by reaction of an alkali metal salt of a 4 - [N - (2<SP>1</SP> - alkoxycarbonylphenyl)- amino] - 7 - or 8-chloroquinoline of the general formula wherein R 2 is a C 1-8 alkyl group and M is an alkali metal, with a C 1-5 alkyl or C 2-5 alkenyl halide, followed by optional hydrolysis of the esterified carboxylic group in the product; or (b) when R is a C 2-6 carboxyalkyl group, by reaction of a 4-[N-(2<SP>1</SP>-alkoxycarbonylphenyl)- amino]-7- or 8-chloroquinoline of the second general formula above with an alkali metal halogenoalkanoate and conversion of the resulting alkali metal salt to the corresponding free carboxy derivative, followed by optional hydrolysis of the esterified carboxylic group in the product; followed in either method by optional conversion of the product to a non- toxic acid addition salt thereof. Pharmaceutical compositions comprising, as active ingredient, a 4-anilino-7- or 8-chloroquinoline derivative of the first general formula above or a non-toxic acid addition salt thereof, in association with a pharmaceutical carrier or excipient, have anti-inflammatory activity and may be administered orally, subcutaneously, rectally or topically.
GB17091/68A 1967-04-12 1968-04-09 4-Substituted 7- and 8-Chloroquinolines, the Preparation thereof, and Compositions Containing the same Expired GB1195491A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR102441A FR6198M (en) 1967-04-12 1967-04-12

Publications (1)

Publication Number Publication Date
GB1195491A true GB1195491A (en) 1970-06-17

Family

ID=8628702

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17091/68A Expired GB1195491A (en) 1967-04-12 1968-04-09 4-Substituted 7- and 8-Chloroquinolines, the Preparation thereof, and Compositions Containing the same

Country Status (11)

Country Link
BE (1) BE713064A (en)
CH (1) CH489499A (en)
DE (1) DE1770187C3 (en)
DK (1) DK120338B (en)
ES (1) ES352632A1 (en)
FR (1) FR6198M (en)
GB (1) GB1195491A (en)
IL (1) IL29660A (en)
NL (1) NL6805173A (en)
OA (1) OA03359A (en)
SE (1) SE326961B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7989462B2 (en) 2003-07-03 2011-08-02 Myrexis, Inc. 4-arylamin-or-4-heteroarylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
US8258145B2 (en) 2005-01-03 2012-09-04 Myrexis, Inc. Method of treating brain cancer
US8309562B2 (en) 2003-07-03 2012-11-13 Myrexis, Inc. Compounds and therapeutical use thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7989462B2 (en) 2003-07-03 2011-08-02 Myrexis, Inc. 4-arylamin-or-4-heteroarylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
US8309562B2 (en) 2003-07-03 2012-11-13 Myrexis, Inc. Compounds and therapeutical use thereof
US8258145B2 (en) 2005-01-03 2012-09-04 Myrexis, Inc. Method of treating brain cancer

Also Published As

Publication number Publication date
CH489499A (en) 1970-04-30
DE1770187C3 (en) 1978-10-05
FR6198M (en) 1968-07-22
DE1770187B2 (en) 1978-02-23
DK120338B (en) 1971-05-17
OA03359A (en) 1970-12-15
SE326961B (en) 1970-08-10
NL6805173A (en) 1968-10-14
ES352632A1 (en) 1969-07-16
BE713064A (en) 1968-10-01
DE1770187A1 (en) 1971-09-30
IL29660A (en) 1971-02-25

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee