WO2002012188A3 - Indole compounds useful for the treatment of cancer - Google Patents

Indole compounds useful for the treatment of cancer Download PDF

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Publication number
WO2002012188A3
WO2002012188A3 PCT/US2001/024978 US0124978W WO0212188A3 WO 2002012188 A3 WO2002012188 A3 WO 2002012188A3 US 0124978 W US0124978 W US 0124978W WO 0212188 A3 WO0212188 A3 WO 0212188A3
Authority
WO
WIPO (PCT)
Prior art keywords
lower alkyl
alkoxy
cancer
hydroxy
hydrogen
Prior art date
Application number
PCT/US2001/024978
Other languages
French (fr)
Other versions
WO2002012188A2 (en
WO2002012188B1 (en
Inventor
Dennis A Carson
Lorenzo M Leoni
Howard B Cottam
Original Assignee
Univ California
Dennis A Carson
Lorenzo M Leoni
Howard B Cottam
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 US09/634,207 external-priority patent/US7151100B1/en
Application filed by Univ California, Dennis A Carson, Lorenzo M Leoni, Howard B Cottam filed Critical Univ California
Priority to JP2002518166A priority Critical patent/JP2004518615A/en
Priority to AU8322401A priority patent/AU8322401A/en
Priority to AU2001283224A priority patent/AU2001283224B2/en
Priority to EP01962006A priority patent/EP1307459A2/en
Priority to CA002419060A priority patent/CA2419060A1/en
Publication of WO2002012188A2 publication Critical patent/WO2002012188A2/en
Publication of WO2002012188A3 publication Critical patent/WO2002012188A3/en
Publication of WO2002012188B1 publication Critical patent/WO2002012188B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Abstract

The present invention provides novel indole derivatives of formula (I): (I) wherein R1 is lower alkyl, lower alkenyl, (hydroxy)lower alkyl, lower alkynyl, phenyl, benzyl or 2-thienyl, R?2, R3, R4 and R5¿ are the same or different and are each hydrogen or lower alkyl; each R6 is individually hydrogen, lower alkyl, hydroxy, (hydroxy)lower alkyl, lower alkoxy, benzyloxy, lower alkanoyloxy, nitro or halo, n is 1-3, R7 is hydrogen, lower alkyl or lower alkenyl, X is oxy and thio, Y is carbonyl, (CH¿2?)1-3,(CH2)1-3SO2 or (CH2)1-3C(O), and Z is (φ-(4-pyridyl)(C2-C4 alkoxy), (φ-((R?8)(R9¿) amino)(C¿2?-C4 alkoxy), wherein R?8 and R9¿ are each H, (C¿1?-C3)alkyl or together with N are a 5- or 6-membered heterocyclic ring comprising 1-3 N(R?8¿), S or nonperoxide O; an amino acid ester of (φ-(HO)(C¿2?-C4))alkoxy, N(R?8)CH(R8)CO¿2H, 1'-D-glucuronyloxy; or Y-Z is (CH2)1-3R8; wherein R8 is OH, (C¿2?-C4)acyloxy, SO3H, PO4H2, N(NO)(OH), SO2NH2, PO(OH)(NH2), or a tetrazolyl; or a pharmaceutically acceptable salt thereof, useful to inhibit cancer or sensitize cancer cells to chemotherapeutic agents, radiation or other anti-cancer treatments.
PCT/US2001/024978 2000-08-09 2001-08-09 Indole compounds useful for the treatment of cancer WO2002012188A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2002518166A JP2004518615A (en) 2000-08-09 2001-08-09 Indole compounds useful for treating cancer
AU8322401A AU8322401A (en) 2000-08-09 2001-08-09 Indole compounds useful for the treatment of cancer
AU2001283224A AU2001283224B2 (en) 2000-08-09 2001-08-09 Indole compounds useful for the treatment of cancer
EP01962006A EP1307459A2 (en) 2000-08-09 2001-08-09 Indole compounds useful for the treatment of cancer
CA002419060A CA2419060A1 (en) 2000-08-09 2001-08-09 Indole compounds useful for the treatment of cancer

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/634,207 US7151100B1 (en) 1999-07-23 2000-08-09 Indole compounds useful for the treatment of cancer
US09/634,207 2000-08-09

Publications (3)

Publication Number Publication Date
WO2002012188A2 WO2002012188A2 (en) 2002-02-14
WO2002012188A3 true WO2002012188A3 (en) 2002-10-03
WO2002012188B1 WO2002012188B1 (en) 2003-03-20

Family

ID=24542833

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/024978 WO2002012188A2 (en) 2000-08-09 2001-08-09 Indole compounds useful for the treatment of cancer

Country Status (5)

Country Link
EP (1) EP1307459A2 (en)
JP (1) JP2004518615A (en)
AU (2) AU8322401A (en)
CA (1) CA2419060A1 (en)
WO (1) WO2002012188A2 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2255287T3 (en) 1998-07-09 2006-06-16 Cephalon, Inc. COMPOSITIONS FOR THE TREATMENT OF CHRONIC LYMPHOCYTIC LEUKEMIA.
US7105560B1 (en) 1999-07-23 2006-09-12 The Regents Of The University Of California Use of etodolac in the treatment of multiple myeloma
US7151100B1 (en) 1999-07-23 2006-12-19 The Regents Of The University Of California Indole compounds useful for the treatment of cancer
US7129262B2 (en) 1999-07-23 2006-10-31 The Regents Of The University Of California Indole compounds useful for the treatment of cancer
US7361680B2 (en) 1999-07-23 2008-04-22 The Regents Of The University Of California Indole compounds useful for the treatment of cancer
US6545034B1 (en) 1999-07-23 2003-04-08 The Regents Of The University Of California Use of etodolac for the treatment of chronic lymphocytic leukemia
US20040152672A1 (en) * 2000-08-09 2004-08-05 Carson Dennis A. Indole compounds useful for the treatment of cancer
AU2003295336A1 (en) 2002-09-19 2004-04-08 Dennis A. Carson Use of etodoclac to treat hyperplasia
JP2007507524A (en) 2003-10-02 2007-03-29 セフアロン・インコーポレーテツド Indole derivatives
FR2869231B1 (en) * 2004-04-27 2008-03-14 Sod Conseils Rech Applic THERAPEUTIC COMPOSITION CONTAINING AT LEAST ONE PYRROLOBENZODIAZEPINE DERIVATIVE AND FLUDARABINE
CN107898791A (en) 2010-06-03 2018-04-13 药品循环有限责任公司 The application of bruton's tyrosine kinase (BTK) inhibitor
CN110801454A (en) * 2011-10-19 2020-02-18 药品循环有限责任公司 Use of Bruton's Tyrosine Kinase (BTK) inhibitors
KR20150032340A (en) 2012-07-24 2015-03-25 파마시클릭스, 인코포레이티드 Mutations associated with resistance to inhibitors of bruton's tyrosine kinase (btk)
US9885086B2 (en) 2014-03-20 2018-02-06 Pharmacyclics Llc Phospholipase C gamma 2 and resistance associated mutations

Citations (4)

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DE2226340A1 (en) * 1971-06-01 1973-03-15 American Home Prod INDOLDER DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND INTERMEDIATE PRODUCTS USED IN THESE PROCESSES
US4337760A (en) * 1978-10-13 1982-07-06 Adolf Schwimmer Method for the treatment of tumors with β-glucuronidase activity dependent pharmaceuticals
EP0289262A2 (en) * 1987-04-27 1988-11-02 Syntex Pharmaceuticals International Limited Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal antiinflammatory drugs
WO1998009603A2 (en) * 1996-09-06 1998-03-12 Loma Linda University Medical Center Compositions including r-nsaids and therapeutic and prophylactic methods employing said compositions

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US4337760A (en) * 1978-10-13 1982-07-06 Adolf Schwimmer Method for the treatment of tumors with β-glucuronidase activity dependent pharmaceuticals
EP0289262A2 (en) * 1987-04-27 1988-11-02 Syntex Pharmaceuticals International Limited Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal antiinflammatory drugs
WO1998009603A2 (en) * 1996-09-06 1998-03-12 Loma Linda University Medical Center Compositions including r-nsaids and therapeutic and prophylactic methods employing said compositions

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CHEMICAL ABSTRACTS, vol. 112, no. 13, 26 March 1990, Columbus, Ohio, US; abstract no. 111681y, VENUTI, MICHAEL C. ET AL.: "Synthesis and biological evaluation of omega-(N,N,N-trialkylammonium)alkyl esters and thioesters of carboxylic acid nonsteroidal antiinflammatory agents." XP002201414 *
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Also Published As

Publication number Publication date
AU2001283224B2 (en) 2007-06-28
WO2002012188A2 (en) 2002-02-14
AU8322401A (en) 2002-02-18
EP1307459A2 (en) 2003-05-07
JP2004518615A (en) 2004-06-24
WO2002012188B1 (en) 2003-03-20
CA2419060A1 (en) 2002-02-14

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