NZ334948A - Anthranilic acid derivatives as p-glycoprotein inhibitors useful for the treatment of multi drug-resistant cancers - Google Patents

Anthranilic acid derivatives as p-glycoprotein inhibitors useful for the treatment of multi drug-resistant cancers

Info

Publication number
NZ334948A
NZ334948A NZ334948A NZ33494897A NZ334948A NZ 334948 A NZ334948 A NZ 334948A NZ 334948 A NZ334948 A NZ 334948A NZ 33494897 A NZ33494897 A NZ 33494897A NZ 334948 A NZ334948 A NZ 334948A
Authority
NZ
New Zealand
Prior art keywords
alkyl
ring
halogen
alkoxy
r1or11
Prior art date
Application number
NZ334948A
Inventor
Hamish Ryder
Philip Anthony Ashworth
Michael Bryan Roe
Julie Elizabeth Brumwell
Sukhjit Hunjan
Adrian John Folkes
Jason Terry Sanderson
Susannah Williams
Levi Michael Maximen
Original Assignee
Xenova Ltd
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
Priority claimed from GBGB9717576.4A external-priority patent/GB9717576D0/en
Application filed by Xenova Ltd filed Critical Xenova Ltd
Publication of NZ334948A publication Critical patent/NZ334948A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

An anthranilic acid derivative of formula (I), wherein: each of R, R1 and R2, which are the same or different, is H, C1-C6 alkyl, OH, C1-C6 alkoxy, halogen, nitro, or, N(R1OR11) wherein each of R1O and R11, which are the same or different, is H or C1-C6 alkyl, or R1 and R2, being attached to adjacent positions of ring b, together form a methylenedioxy or ethylenedioxy group; R3 is H or C1-C6 alkyl; R4 is C1-C6 alkyl or R4 represents -CH2- or -CH2CH2- which is attached either (i) to position 2 of ring b to complete a saturated 5- or 6-membered nitrogen-containing ring fused to ring b or (ii) to the position in ring a adjacent to that to which X, being a single bond, is linked, thereby completing a saturated 5- or 6-membered nitrogen-containing ring fused to ring a; R5 is H, OH or C1-C6 alkyl; X is a direct bond, 0, S, -S-(CH2)p- or -0-(CH2)p- wherein p is an integer of 1 to 6; R6 is H, C1-C6 alkyl or C1-C6 alkoxy; q is 0 or 1; Ar is an unsaturated carbocyclic or heterocyclic group selected from furan, thiophene, pyrrole, indole, isoindole, pyrazole, imidazole, isoxazole, oxazole, isothiazole, thiazole, pyridine, quinoline, quinoxaline, isoquinoline, thienopyrazine, pyran, pyrimidine, pyridazine, pyrazine, purine and triazine which is unsubstituted or substituted by one or more substituents selected from OH, halogen, C1-C6 alkyl, which is unsubstituted or substituted by halogen, C1-C6 alkoxy, nitro and N(R1OR11); each of R7 and R8, which are the same or different, is H, C1-C6 alkyl which is unsubstituted or substituted by one or more halogen atoms, C1-C6 alkoxy, hydroxy, halogen, phenyl, NHOH, nitro, N(R1OR11), or SR12 wherein R12 is H or C1-C6 alkyl; or R7 and R8, when situated on adjacent carbon atoms, form together with the carbon atoms to which they are attached a benzene ring or a methylenedioxy substituent; R9 is phenyl or an unsaturated heterocyclic group selected from furan, thiophene, pyrrole, indole, isoindole, pyrazole, imidazole, isoxazole, oxazole, isothiazole, thiazole, pyridine, quinoline, quinoxaline, isoquinoline, thienopyrazine, pyran, pyrimidine, pyridazine, pyrazine, purine and triazine, each of which is unsubstituted or substituted by C1-C6 alkyl, OH, C1-C alkoxy, halogen, C3-C6 cycloalkyl, phenyl, benzyl, trifluoromethyl, nitro, acetyl, benzoyl or N(R1OR11), or two substituents on adjacent ring positions of the phenyl or heterocyclic group together complete a saturated or unsaturated 6-membered ring or form a methylenedioxy group; n is 0 or 1; and m is 0 or an integer of 1 to 6; Also disclosed are pharmaceutical compositions containing the above compound that can be used as an inhibitor of p-glycoprotein. The compound is useful as a modulator for multidrug resistance, for potentiating the cytotoxicity of a chemotherapeutic agent or enhancing the net absorption, distribution, metabolism or elimination characteristics of a therapeutic agent
NZ334948A 1996-10-18 1997-10-17 Anthranilic acid derivatives as p-glycoprotein inhibitors useful for the treatment of multi drug-resistant cancers NZ334948A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9602552 1996-10-18
GBGB9717576.4A GB9717576D0 (en) 1997-08-19 1997-08-19 Pharmaceutical compounds
PCT/GB1997/002885 WO1998017648A1 (en) 1996-10-18 1997-10-17 Anthranilic acid derivatives as multi drug resistance modulators

Publications (1)

Publication Number Publication Date
NZ334948A true NZ334948A (en) 2000-11-24

Family

ID=26308635

Family Applications (1)

Application Number Title Priority Date Filing Date
NZ334948A NZ334948A (en) 1996-10-18 1997-10-17 Anthranilic acid derivatives as p-glycoprotein inhibitors useful for the treatment of multi drug-resistant cancers

Country Status (5)

Country Link
MY (1) MY118642A (en)
NZ (1) NZ334948A (en)
RU (1) RU2195454C2 (en)
SK (1) SK284649B6 (en)
UA (1) UA67730C2 (en)

Also Published As

Publication number Publication date
SK284649B6 (en) 2005-08-04
MY118642A (en) 2004-12-31
UA67730C2 (en) 2004-07-15
SK50999A3 (en) 2000-08-14
RU2195454C2 (en) 2002-12-27

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