Title:
USE OF DERIVATIVES OF INDOLES FOR THE TREATMENT OF CANCER
Document Type and Number:
WIPO Patent Application WO/2010/150211
Kind Code:
A3
Abstract:
The present invention relates to the use of derivatives of indoles having a general formula (I) as follow: for the manufacture of a pharmaceutical composition intended for the treatment of cancer.
Inventors:
GUILLOU CATHERINE (FR)
KOZIELSKI FRANK (GB)
LABRIERE CHRISTOPHE (FR)
GUERITTE FRANCOISE (FR)
TCHERNIUK SERGEY (FR)
SKOUFIAS DIMITRIOS (FR)
THAL CLAUDE (FR)
HUSSON HENRI-PHILIPPE (FR)
KOZIELSKI FRANK (GB)
LABRIERE CHRISTOPHE (FR)
GUERITTE FRANCOISE (FR)
TCHERNIUK SERGEY (FR)
SKOUFIAS DIMITRIOS (FR)
THAL CLAUDE (FR)
HUSSON HENRI-PHILIPPE (FR)
Application Number:
PCT/IB2010/052866
Publication Date:
August 25, 2011
Filing Date:
June 23, 2010
Export Citation:
Assignee:
CENTRE NAT RECH SCIENT (FR)
GUILLOU CATHERINE (FR)
KOZIELSKI FRANK (GB)
LABRIERE CHRISTOPHE (FR)
GUERITTE FRANCOISE (FR)
TCHERNIUK SERGEY (FR)
SKOUFIAS DIMITRIOS (FR)
THAL CLAUDE (FR)
HUSSON HENRI-PHILIPPE (FR)
GUILLOU CATHERINE (FR)
KOZIELSKI FRANK (GB)
LABRIERE CHRISTOPHE (FR)
GUERITTE FRANCOISE (FR)
TCHERNIUK SERGEY (FR)
SKOUFIAS DIMITRIOS (FR)
THAL CLAUDE (FR)
HUSSON HENRI-PHILIPPE (FR)
International Classes:
A61K31/404; A61K31/4439; A61K31/506; A61P35/00
Domestic Patent References:
| WO2001098299A1 | 2001-12-27 | |||
| WO2005062795A2 | 2005-07-14 | |||
| WO2008121670A1 | 2008-10-09 | |||
| WO1994026260A1 | 1994-11-24 | |||
| WO2010008427A1 | 2010-01-21 |
Foreign References:
| US20060030583A1 | 2006-02-09 | |||
| US20070049615A1 | 2007-03-01 | |||
| US20060074075A1 | 2006-04-06 |
Other References:
FORTUNA COSIMO G ET AL: "Synthesis and applications of new trans 1-indolyl-2-(1-methylpyridin ium and quinolinium-2-yl)ethylenes", ARKIVOC : FREE ONLINE JOURNAL OF ORGANIC CHEMISTRY, ARKAT USA, INC, US, vol. 8, 1 January 2009 (2009-01-01), pages 222 - 229, XP008135850, ISSN: 1551-7012, Retrieved from the Internet
LIU JIE ET AL: "Synthesis and antitumor activity of 3-[(substituted phenyl)vinyl]indole derivatives", CAPLUS, 1 December 1999 (1999-12-01), XP002319004
LOW, KAM HUNG ET AL: "Phosphine-mediated coupling of gramines with aldehydes: A remarkably simple synthesis of 3-vinylindoles", ORGANIC LETTERS , 7(10), 2003-2005 CODEN: ORLEF7; ISSN: 1523-7060, 2005, XP002634703
SINGH, ANIL K. ET AL: "A fluorescence study of differently substituted 3-styrylindoles and their interaction with bovine serum albumin", LUMINESCENCE , 24(2), 123-130 CODEN: LUMIFC; ISSN: 1522-7235, 27 February 2009 (2009-02-27), XP002634704
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; SONAR, VIJAYAKUMAR N. ET AL: "(Z)-3-(1H-Indol-3-yl)-2-(3-thienyl)acrylonitrile and (Z)-3-[1-(4-tert-butylbenzyl)-1H-indol-3-yl]-2-(3-thienyl)acrylonitrile", XP002634705, retrieved from STN Database accession no. 2005:97123
NARUTO, SHUNSUKE ET AL: "Synthesis and spasmolytic activity of 2-substituted-3-(.omega.-dialkylaminoalkoxyphenyl)acrylonitriles and related compounds", CHEMICAL & PHARMACEUTICAL BULLETIN , 31(6), 2023-32 CODEN: CPBTAL; ISSN: 0009-2363, 1983, pages 2023 - 2032, XP008113347
EFREMOVA, T. M. ET AL: "Carbolines. VII. 1-Methyl-4-hetarylmethyl-.beta.-carbolines", KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII , (10), 1382-7 CODEN: KGSSAQ; ISSN: 0132-6244, 1974, XP008113349
DE SILVA, S. OSMUND ET AL: "Wittig synthesis and photocyclodehydrogenation of 3-(2-aryl)vinylindole derivatives", CANADIAN JOURNAL OF CHEMISTRY , 52(8, PT. 1), 1294-306 CODEN: CJCHAG; ISSN: 0008-4042, 1974, XP008113342
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; JIN, QING-XIAN ET AL: "Synthesis of trans-5-methyloxy-3-styrenylindole", XP002634706, retrieved from STN Database accession no. 2006:662977
MINOT, C. ET AL: "Photocyclization of stilbenes and of related indolic compounds: contribution of the use of reactivity indexes", TETRAHEDRON , 36(9), 1209-14 CODEN: TETRAB; ISSN: 0040-4020, 1980, XP003006763
MORIYA, TAMON ET AL: "Preparation and reactions of 3-(aminomethylene)-3H-indoles", CHEMICAL & PHARMACEUTICAL BULLETIN , 28(6), 1711-21 CODEN: CPBTAL; ISSN: 0009-2363, 1980, XP008113344
DIENG C ET AL: "Carbolines. VII. 1-Metyl-4-hetarylmethyl-beta-carbolines", JOURNAL OF HETEROCYCLIC CHEMISTRY, HETEROCORPORATION. PROVO, US, vol. 12, no. 3, 1 June 1975 (1975-06-01), pages 455 - 460, XP003006766, ISSN: 0022-152X
LEVITZKI ALEXANDER: "Tyrosine kinases as targets for cancer therapy.", EUROPEAN JOURNAL OF CANCER, vol. 38, no. Supplement 5, September 2002 (2002-09-01), pages S11 - S18, XP002550687, ISSN: 0959-8049
ANAFI, MORDECHAI ET AL: "Tyrphostin-induced inhibition of p210bcr-abl tyrosine kinase activity induces K562 to differentiate", BLOOD , 82(12), 3524-9 CODEN: BLOOAW; ISSN: 0006-4971, 1993, XP002550688
TCHERNIUK SERGEY ET AL: "Relocation of Aurora B and Survivin from Centromeres to the Central Spindle Impaired by a Kinesin-Specific MKLP-2 Inhibitor", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY VCH VERLAG, WEINHEIM, vol. 49, no. 44, 1 January 2010 (2010-01-01), pages 8228 - 8231, XP008135676, ISSN: 1433-7851, DOI: DOI:10.1002/ANIE.201003254
LIU JIE ET AL: "Synthesis and antitumor activity of 3-[(substituted phenyl)vinyl]indole derivatives", CAPLUS, 1 December 1999 (1999-12-01), XP002319004
LOW, KAM HUNG ET AL: "Phosphine-mediated coupling of gramines with aldehydes: A remarkably simple synthesis of 3-vinylindoles", ORGANIC LETTERS , 7(10), 2003-2005 CODEN: ORLEF7; ISSN: 1523-7060, 2005, XP002634703
SINGH, ANIL K. ET AL: "A fluorescence study of differently substituted 3-styrylindoles and their interaction with bovine serum albumin", LUMINESCENCE , 24(2), 123-130 CODEN: LUMIFC; ISSN: 1522-7235, 27 February 2009 (2009-02-27), XP002634704
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; SONAR, VIJAYAKUMAR N. ET AL: "(Z)-3-(1H-Indol-3-yl)-2-(3-thienyl)acrylonitrile and (Z)-3-[1-(4-tert-butylbenzyl)-1H-indol-3-yl]-2-(3-thienyl)acrylonitrile", XP002634705, retrieved from STN Database accession no. 2005:97123
NARUTO, SHUNSUKE ET AL: "Synthesis and spasmolytic activity of 2-substituted-3-(.omega.-dialkylaminoalkoxyphenyl)acrylonitriles and related compounds", CHEMICAL & PHARMACEUTICAL BULLETIN , 31(6), 2023-32 CODEN: CPBTAL; ISSN: 0009-2363, 1983, pages 2023 - 2032, XP008113347
EFREMOVA, T. M. ET AL: "Carbolines. VII. 1-Methyl-4-hetarylmethyl-.beta.-carbolines", KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII , (10), 1382-7 CODEN: KGSSAQ; ISSN: 0132-6244, 1974, XP008113349
DE SILVA, S. OSMUND ET AL: "Wittig synthesis and photocyclodehydrogenation of 3-(2-aryl)vinylindole derivatives", CANADIAN JOURNAL OF CHEMISTRY , 52(8, PT. 1), 1294-306 CODEN: CJCHAG; ISSN: 0008-4042, 1974, XP008113342
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; JIN, QING-XIAN ET AL: "Synthesis of trans-5-methyloxy-3-styrenylindole", XP002634706, retrieved from STN Database accession no. 2006:662977
MINOT, C. ET AL: "Photocyclization of stilbenes and of related indolic compounds: contribution of the use of reactivity indexes", TETRAHEDRON , 36(9), 1209-14 CODEN: TETRAB; ISSN: 0040-4020, 1980, XP003006763
MORIYA, TAMON ET AL: "Preparation and reactions of 3-(aminomethylene)-3H-indoles", CHEMICAL & PHARMACEUTICAL BULLETIN , 28(6), 1711-21 CODEN: CPBTAL; ISSN: 0009-2363, 1980, XP008113344
DIENG C ET AL: "Carbolines. VII. 1-Metyl-4-hetarylmethyl-beta-carbolines", JOURNAL OF HETEROCYCLIC CHEMISTRY, HETEROCORPORATION. PROVO, US, vol. 12, no. 3, 1 June 1975 (1975-06-01), pages 455 - 460, XP003006766, ISSN: 0022-152X
LEVITZKI ALEXANDER: "Tyrosine kinases as targets for cancer therapy.", EUROPEAN JOURNAL OF CANCER, vol. 38, no. Supplement 5, September 2002 (2002-09-01), pages S11 - S18, XP002550687, ISSN: 0959-8049
ANAFI, MORDECHAI ET AL: "Tyrphostin-induced inhibition of p210bcr-abl tyrosine kinase activity induces K562 to differentiate", BLOOD , 82(12), 3524-9 CODEN: BLOOAW; ISSN: 0006-4971, 1993, XP002550688
TCHERNIUK SERGEY ET AL: "Relocation of Aurora B and Survivin from Centromeres to the Central Spindle Impaired by a Kinesin-Specific MKLP-2 Inhibitor", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY VCH VERLAG, WEINHEIM, vol. 49, no. 44, 1 January 2010 (2010-01-01), pages 8228 - 8231, XP008135676, ISSN: 1433-7851, DOI: DOI:10.1002/ANIE.201003254
Attorney, Agent or Firm:
LE COUPANEC, Pascale (3 rue de Penthièvre, PARIS, FR)
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