WO2001092232A1 - 4-aminoquinolines utilisees comme agents anti-infectieux - Google Patents

4-aminoquinolines utilisees comme agents anti-infectieux Download PDF

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Publication number
WO2001092232A1
WO2001092232A1 PCT/GB2001/002369 GB0102369W WO0192232A1 WO 2001092232 A1 WO2001092232 A1 WO 2001092232A1 GB 0102369 W GB0102369 W GB 0102369W WO 0192232 A1 WO0192232 A1 WO 0192232A1
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WIPO (PCT)
Prior art keywords
group
formula
alkyl
compound according
dealkylation
Prior art date
Application number
PCT/GB2001/002369
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English (en)
Inventor
Feodor Scheinmann
Original Assignee
Ufc 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
Application filed by Ufc Ltd. filed Critical Ufc Ltd.
Priority to AU58649/01A priority Critical patent/AU5864901A/en
Publication of WO2001092232A1 publication Critical patent/WO2001092232A1/fr

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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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • C07D215/18—Halogen atoms or nitro radicals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
    • C07D215/60—N-oxides
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to 4-aminoquinolines and derivatives thereof for pharmaceutical application. More particularly, the present invention relates to 4-aminoquinolines and derivatives thereof for use as anti- infective agents for Gram positive and Gram negative bacteria.
  • Amodiaquine differs chemically from chloroquine in that it contains a 4-hydroxy anilino function on its side chain. Both amodiaquine and chloroquine do however have four carbon atoms between the secondary and tertiary nitrogen atoms.
  • the presence of a basic side chain (dialkylamino) has previously been considered an essential element in giving both chloroquine and amodiaquine their antimalarial activity (WHO Practical Chemotherapy of Malaria 1 990, Technical Report Series No. 805, WHO, Geneva; P.M. O'Neill, A.C. Harrison, R.C. Storr, S.R. Hawley, S.A. Ward and B.K.
  • W is halogen or a halogen-containing group
  • R is selected from: i) R 2 -NH-R r Z- where:
  • Z is NH, S, O, or CH 2 ;
  • R ⁇ is a C, to C 4 alkyl group;
  • R 2 -NH- is a group resistant to dealkylation in vivo; provided that, compounds in which:
  • X is N
  • R 2 is alkyl, are specifically excluded; or ii) R 3 N-R r Z- where:
  • R 3 N- is a group resistant to dealkylation in vivo; provided that, compounds in which:
  • X is N; Z is NH;
  • R T is C 2 to C 4 ;
  • R 3 N- is pyrrolidine, piperidine, or pyrrolidine or piperidine substituted by (C, to C 4 )-alkyl, octahydroindole or 3-azabicyclo[3,2,2]nonane, are specifically excluded; or iii) R 4 -Ar-Z- where:
  • Ar is a substituted or unsubstituted aromatic ring structure; and R 4 is a planar or non planar, alkyl or cycloalkyl substituent on the 5' position of the aromatic ring Ar, and pharmaceutically acceptable salts thereof.
  • W is CI, F or CF 3 .
  • R T may be, for example, methyl, ethyl, propyl, or butyl, but is preferably methyl or ethyl.
  • R 2 -NH- comprises a group resistant to dealkylation in vivo (by, for example, P450 oxidation), wherein R 2 may be alkyl, cycloalkyl, alkenyl, aryl or aralkyl, for example tert-butyl.
  • the heterocycle R 3 N- comprises a group resistant to dealkylation in vivo, such as, for example, a cyclic amine, such as, for example those given below:
  • a group resistant to dealkylation in vivo such as, for example, a cyclic amine, such as, for example those given below:
  • Ar comprises a substituted or unsubstituted aromatic ring structure, such as, for example, a benzyl ring.
  • R 4 comprises a planar or non planar, alkyl or cylcloalkyl substituent on the 5' position of the aromatic ring Ar, such as, for example, a C, to C 4 alkyl group, a secondary alkyl group, a tertiary alkyl group or a cycloalkyl group, such as, for example, a methyl, ethyl, propyl, iso-propyl, s-butyl, t-butyl or cyclohexyl group.
  • a planar or non planar, alkyl or cylcloalkyl substituent on the 5' position of the aromatic ring Ar such as, for example, a C, to C 4 alkyl group, a secondary alkyl group, a tertiary alkyl group or a cycloalkyl group, such as, for example, a methyl, ethyl, propyl, iso-propyl, s-buty
  • the aromatic ring is a six membered ring and includes substituents, most preferably a hydroxyl group, preferably in the 4' position, and a group which is less susceptible to metabolism than a diethyl amino group, preferably in the 3' position, such as, for example, a 3' tert nitrogen group, such as, for example, a N-tert butyl amino methyl group.
  • substituents most preferably a hydroxyl group, preferably in the 4' position, and a group which is less susceptible to metabolism than a diethyl amino group, preferably in the 3' position, such as, for example, a 3' tert nitrogen group, such as, for example, a N-tert butyl amino methyl group.
  • R groups of the formula (iii) R 4 -Ar-Z- are exemplified by the general formula shown below:
  • Z is NH or a group less susceptible to undergo oxidation to a quinone-imine derivative, such as, for example, S, O, or CH 2 ; oxidation may also be prevented by replacing the 4'-hydroxyl with fluorine;
  • R 4 comprises a lipid solubilizing group, for example, a planar alkyl group, such as, for example, methyl, ethyl or propyl, or a non planar group, for example t-butyl, isopropyl, s-butyl or cyclohexyl;
  • Y is a group less susceptible to metabolism than a 3' diethyl amino group, such as, for example, a N-tert-alkyl amino alkyl group, such as, for example, that given below:
  • Preferred compounds of the invention include compounds of the formulae identified below:
  • the chlorine substituent in Formula XIII may be replaced by other halogens, preferably fluorine, or by CF 3 ;
  • W, X, Y, Z and R 4 are as previously defined and preferably where
  • Z is NH
  • R 4 and Y are both CH 2 NEt 2 (Formula XVa) .
  • chlorine substituent may be replaced by other halogens, preferably fluorine, or by CF 3 .
  • a pharmaceutical preparation comprising, as an active ingredient, a compound of the invention, or a pharmaceutically acceptable salt thereof.
  • a compound of the invention or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament.
  • W is halogen or a halogen-containing group
  • R is selected from: i) R 2 -NH-R r Z- where:
  • Z is NH, S, O, or CH 2 ;
  • R T is a C, to C 4 alkyl group
  • R 2 -NH- is a group resistant to dealkylation in vivo; or ii) R 3 N-R Z- where:
  • R 3 N - is a group resistant to dealkylation in vivo; or iii) R 4 -Ar-Z- where:
  • Ar is a substituted or unsubstituted aromatic ring structure
  • R 4 is a planar or non planar, alkyl or cycloalkyl substituent on the 5' position of the aromatic ring Ar, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment of Gram positive and Gram negative bacterial infections.
  • Preferred compounds for said use include those compounds of the invention as hereinbefore described, and additionally include compounds exemplified by the following formulae: Formula X
  • the chlorine substituent may be replaced by other halogens, preferably fluorine, or by CF 3 .
  • a method for the treatment of Gram positive and Gram negative bacterial infections comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of
  • W is halogen or a halogen-containing group
  • R is selected from:
  • Z is NH, S, O, or CH 2 ;
  • R. is a C, to C 4 alkyl group
  • R 2 -NH- is a group resistant to dealkylation in vivo
  • R 3 N- is a group resistant to dealkylation in vivo
  • Ar is a substituted or unsubstituted aromatic ring structure; and R 4 is a planar or non planar, alkyl or cycloalkyl substituent on the 5' position of the aromatic ring Ar, or a pharmaceutically acceptable salt thereof.
  • Preferred compounds for said use include those compounds of the invention as hereinbefore described, and additionally include compounds of Formulae X, Xa, XI and XII.
  • the invention will now be described, by way of example only, with reference to the following examples and test data.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne l'utilisation comme substances pharmaceutiques des composés représentés par la formule générale (IV), dans laquelle W représente un groupe halogène ou renfermant un halogène ; X représente N ou N=O ; et R représente un élément sélectionné parmi : i) R2-NH-R1-Z-, Z représentant NH, S, O, ou CH2; R1 représentant un groupe alkyle C1 à C4 ; et R2-NH- représentant un groupe résistant à la désalkylation in vivo; ou ii) la formule (a), Z et R1 représentant les éléments décrits en (i), et la formule (b) représentant un groupe résistant à la désalkylation in vivo; ou iii) R4-Ar-Z-, Z représentant un élément décrit en (i); Ar représentant une structure cyclique aromatique substituée ou non substituée; et R4 représentant un substituant cycloalkyle ou alkyle planaire ou non planaire en position 5' du cycle aromatique Ar, ainsi que des sels pharmaceutiquement acceptables de ces composés.
PCT/GB2001/002369 2000-05-27 2001-05-29 4-aminoquinolines utilisees comme agents anti-infectieux WO2001092232A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU58649/01A AU5864901A (en) 2000-05-27 2001-05-29 4-aminoquinolines as antiinfective agents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0012874.4A GB0012874D0 (en) 2000-05-27 2000-05-27 4-Aminoquinolines
GB0012874.4 2000-05-27

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WO2001092232A1 true WO2001092232A1 (fr) 2001-12-06

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1513825A2 (fr) * 2002-05-17 2005-03-16 Department of Health and Human Services Medicament anti-tuberculeux: compositions et methodes
US8198303B2 (en) 2002-05-17 2012-06-12 Sequella, Inc. Methods of use and compositions for the diagnosis and treatment of infectious diseases
WO2016061280A1 (fr) * 2014-10-14 2016-04-21 La Jolla Institute Of Allergy & Immunology Inhibiteurs de la protéine tyrosine phosphatase de faible poids moléculaire et utilisations
US11066420B2 (en) 2017-05-01 2021-07-20 Sanford Burnham Prebys Medical Discovery Institute Inhibitors of low molecular weight protein tyrosine phosphatase (LMPTP) and uses thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3136769A (en) * 1961-03-28 1964-06-09 Parke Davis & Co Quinoline nu-oxides
GB974348A (en) * 1961-01-25 1964-11-04 Parke Davis & Co Basic 7-chloroquinoline-1-oxide derivatives and methods for their production
US4288595A (en) * 1980-04-24 1981-09-08 American Home Products Corporation 7-(Substituted)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamines
WO1986006718A1 (fr) * 1985-05-17 1986-11-20 The Australian National University Composes antipaludiques
EP0656353A1 (fr) * 1993-10-28 1995-06-07 F. Hoffmann-La Roche Ag Dérivés d'aminoquinoleines utiles pour le traitement de la malaria
WO2000050404A1 (fr) * 1999-02-25 2000-08-31 The University Of Liverpool 4-aminoquinolines utilisees comme antipaludeens

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB974348A (en) * 1961-01-25 1964-11-04 Parke Davis & Co Basic 7-chloroquinoline-1-oxide derivatives and methods for their production
US3136769A (en) * 1961-03-28 1964-06-09 Parke Davis & Co Quinoline nu-oxides
US4288595A (en) * 1980-04-24 1981-09-08 American Home Products Corporation 7-(Substituted)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamines
WO1986006718A1 (fr) * 1985-05-17 1986-11-20 The Australian National University Composes antipaludiques
EP0656353A1 (fr) * 1993-10-28 1995-06-07 F. Hoffmann-La Roche Ag Dérivés d'aminoquinoleines utiles pour le traitement de la malaria
WO2000050404A1 (fr) * 1999-02-25 2000-08-31 The University Of Liverpool 4-aminoquinolines utilisees comme antipaludeens

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KAYLENE J RAYNES ET AL: "New 4-aminoquinoline Mannich base antimalarials.1. Effect of an alkyl substituent in the 5'-position of the 4'-hydroyanilino side chain", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 42, no. 15, pages 2747 - 2751, XP002139018, ISSN: 0022-2623 *
WERBEL LESLIE M ET AL: "Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N-oxides", JOURNAL OF MEDICINAL CHEMISTRY, vol. 29, no. 6, 1986, WASHINGTON, US, pages 924 - 39, XP002177677 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1513825A2 (fr) * 2002-05-17 2005-03-16 Department of Health and Human Services Medicament anti-tuberculeux: compositions et methodes
EP1513825A4 (fr) * 2002-05-17 2011-01-05 Dept of Health and Human Services Medicament anti-tuberculeux: compositions et methodes
US8198303B2 (en) 2002-05-17 2012-06-12 Sequella, Inc. Methods of use and compositions for the diagnosis and treatment of infectious diseases
US8268894B2 (en) 2002-05-17 2012-09-18 The United States Of America As Represented By The Secretary, Department Of Health And Human Services Compositions and methods for the treatment of infectious diseases
WO2016061280A1 (fr) * 2014-10-14 2016-04-21 La Jolla Institute Of Allergy & Immunology Inhibiteurs de la protéine tyrosine phosphatase de faible poids moléculaire et utilisations
US10626094B2 (en) 2014-10-14 2020-04-21 Sanford Burnham Prebys Medical Discovery Institute Inhibitors of low molecular weight protein tyrosine phosphatase and uses thereof
US11220486B2 (en) 2014-10-14 2022-01-11 La Jolla Institute Of Allergy & Immunology Inhibitors of low molecular weight protein tyrosine phosphatase and uses thereof
US11066420B2 (en) 2017-05-01 2021-07-20 Sanford Burnham Prebys Medical Discovery Institute Inhibitors of low molecular weight protein tyrosine phosphatase (LMPTP) and uses thereof
US11731986B2 (en) 2017-05-01 2023-08-22 Sanford Burnham Prebys Medical Discovery Institute Inhibitors of low molecular weight protein tyrosine phosphatase (LMPTP) and uses thereof

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AU5864901A (en) 2001-12-11
GB0012874D0 (en) 2000-07-19

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