Title:
N-MONOACYLATED DERIVATIVES OF O-PHENYLENEDIAMINES, THEIR SIX MEMBERED HETEROCYCLIC ANALOGUES AND THEIR USE AS PHARMACEUTICAL AGENTS
Document Type and Number:
WIPO Patent Application WO/2003/013484
Kind Code:
A2
Abstract:
Compounds of formula (I), in which X independently from each other denotes a CH group or a nitrogen atom and R represents an optionally substituted five or six membered nonaromatic carbocyclic ring or an nonaromatic or aromatic heterocyclic ring, whereby the ring system may also be condensed with a 6-membered, optionally substituted carbocyclic aromatic ring; and its pharmaceutically acceptable salts; as pharmaceuticals for the treatment of cancer.
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Inventors:
HAAG RAINER
LESER-REIFF ULRIKE
LIMBERG ANJA
WEIDNER MICHAEL
ZIMMERMANN GERD
LESER-REIFF ULRIKE
LIMBERG ANJA
WEIDNER MICHAEL
ZIMMERMANN GERD
Application Number:
PCT/EP2002/008708
Publication Date:
February 20, 2003
Filing Date:
August 05, 2002
Export Citation:
Assignee:
HOFFMANN LA ROCHE (CH)
International Classes:
C07D249/06; A61K31/167; A61K31/341; A61K31/343; A61K31/381; A61K31/40; A61K31/4015; A61K31/403; A61K31/404; A61K31/4045; A61K31/415; A61K31/4164; A61K31/4192; A61K31/42; A61K31/421; A61K31/426; A61K31/44; A61K31/445; A61K31/4525; A61K31/4535; A61K31/454; A61K31/50; A61K31/505; A61K31/506; A61P35/00; A61P43/00; C07C231/02; C07C233/62; C07D207/16; C07D207/416; C07D209/42; C07D209/60; C07D211/62; C07D213/75; C07D231/06; C07D231/14; C07D233/90; C07D237/04; C07D261/18; C07D263/34; C07D277/20; C07D277/56; C07D307/68; C07D307/85; C07D333/38; C07D333/70; C07D401/12; C07D405/12; C07D409/12; C07D413/12; C07D417/12; (IPC1-7): A61K31/00; A61K31/167; A61K31/341; A61K31/343; A61K31/381; A61K31/40; A61K31/4015; A61K31/404; A61K31/41; A61K31/415; A61K31/4152; A61K31/4164; A61K31/42; A61K31/421; A61K31/426; A61K31/44; A61K31/443; A61K31/4436; A61K31/4439; A61K31/445; A61K31/50; A61K31/505; A61K31/506; A61P35/00; C07D307/85; C07D333/70
Domestic Patent References:
| WO2001038322A1 | 2001-05-31 | |||
| WO2001068604A2 | 2001-09-20 | |||
| WO2001072705A1 | 2001-10-04 |
Foreign References:
| EP0847992A1 | 1998-06-17 | |||
| FR2150961A1 | 1973-04-13 | |||
| GB2165537A | 1986-04-16 | |||
| FR2167954A1 | 1973-08-24 | |||
| US4001416A | 1977-01-04 | |||
| FR2193548A1 | 1974-02-22 | |||
| EP0242851A1 | 1987-10-28 |
Other References:
RASTOGI, RASHMI ET AL: "Synthesis of 2-substituted benzofurans as potential anthelmintics" INDIAN J. CHEM., SECT. B (1982), 21B(5), 485-7, XP008000123 cited in the application
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; PREWYSZ-KWINTO, A.: "Synthesis of 2-carbethoxybenzofurans" retrieved from STN Database accession no. 108:112109 XP002188608 & KHIM. GETEROTSIKL. SOEDIN. (1987), (6), 756-9,
MOLL, RAINER ET AL: "Reaction behavior of 3-chlorobenzothiophene-2-carboxylic acid chloride" Z. CHEM. (1977), 17(4), 133-4, XP008000124
HASSAN, H. M. ET AL: "Condensed pyrroles: N1-benzyl-2,5,6-trimethylpyrrolo[2,3-d]-1, 3-oxazin-4- ones and N1-benzyl-2,5,6-trimethyl-3-substituted-py rrolo[2,3-d]pyrimidin- ones" INDIAN J. CHEM., SECT. B: ORG. CHEM. INCL. MED. CHEM. (2000), 39B(10), 764-768, XP008000122
BANIHASHEMI, A. ET AL: "Polycondensation of pyridine-2,6-dicarboxylic acid with some di- and tetra-amino compounds" J. APPL. POLYM. SCI.: APPL. POLYM. SYMP. (1979), 35(LONG-TERM PROP. POLYM. POLYM. MATER.), 51-7, XP001042054
VYAS, RAJEEV R. ET AL: "Synthesis of some new Schiff bases from 8-methoxycoumarin-3-carboxy(o- amino)anilide as possible antibacterial agents" J. INDIAN CHEM. SOC. (1991), 68(5), 294-5, XP008000120
KABANOS T A (REPRINT) ET AL: "SYNTHESIS, STRUCTURAL AND PHYSICAL STUDIES OF TIN(IV) COMPLEXES WITH 2-(2-PYRIDYL)BENZIMIDAZOLE" JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, (21 SEP 1992) NO. 18 PP. 2729-2733. ISSN: 0300-9246., XP001053094 UNIV IOANNINA, DEPT CHEM, INORGAN & GEN CHEM LAB, GR-45110 IOANNINA, GREECE (Reprint);NRPCS DEMOKRITOS, INST MAT SCI, GR-15310 ATHENS, GREECE UNIV PADUA, DIPARTIMENTO CHIM INORGAN MET ORGAN & ANALIT, I-35131 PADUA, ITALY
ADEMBRI, GIORGIO ET AL: "Polyazaheterocyclic compounds. Condensation reactions of pyridazine-4,5-dicarboxylic acid derivatives with o-phenylenediamine" J. CHEM. SOC., PERKIN TRANS. 1 (1974), (9), 1022-6, XP001053092
CHIMICHI, STEFANO ET AL: "Ring-chain isomerism of some 4,5-disubstituted pyridazines involving heterospiro compounds" J. CHEM. SOC., PERKIN TRANS. 2 (1980), (9), 1339-43, XP001053093
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; Database accession no. 804345 (BRN) XP002228873 & ADEMBRI ET AL.: J. CHEM. SOC. PERKIN TRANS. 1, 1974, pages 1022-1024,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 674208 (BRN) XP002228920 & HATCHARD W.R.: J. ORG. CHEM., vol. 29, 1964, pages 665-668,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 400802 (BRN) XP002228921 & ZARIN', P.P. ET AL.: CHEM. HETEROCYCL. COMPD. (ENGL. TRANSL.), vol. 10, 1974, pages 96-98,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 184580 (BRN) XP002228922 & GORTINSKAJA ET AL.: ZH. OBSHCH. KHIM., vol. 25, 1955, pages 2313-2315,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 14194 (BRN) XP002228923 & BALABAN; KING: J. CHEM. SOC., vol. 127, 1925, page 2710
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 1113394 (BRN) XP002228924 & HU 155 098 A (CHINOIN GYOGYSZER ES VEGYESZETI TERMEKEK GYORA RT) 1966
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 1624358 (BRN) XP002228925 & HOLAN G. ET AL.: J. CHEM. SOC. C, 1967, pages 20-25,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 1643278 (BNR) XP002228926 & DE SELMS R.C.: J. ORG. CHEM., vol. 27, 1962, pages 2163-2165,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 4529791 (BRN) XP002228927 & PREWYSZ-KWINTO A.: CHEM. HETEROCYCL. COMPD. (ENGL. TRANSL.), vol. 23, no. 6, 1987, pages 624-627,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 6222330 (BRN) XP002228928 & BEDAIR A.H.: J. PRAKT. CHEM., vol. 329, no. 2, 1987, pages 359-364,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Database accession no. 7299290 (BRN) XP002228929 & HUDKINS R.L.: HETEROCYCLES, vol. 41, no. 5, 1995, pages 1045-1050,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 7711721 (BRN) XP002228930 & ZALESOV V.V. ET AL.: RUSS. J. ORG. CHEM., vol. 31, no. 8, 1995, pages 1104-1108,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 8223573 (BRN) XP002228931 & BURGART YA. V. ET AL.: RUSS. J. ORG. CHEM., vol. 34, no. 3, 1998, pages 375-380,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 8332695 (BRN) XP002228932 & SALAKHOV M.S. ET AL.: RUSS. J. ORG. CHEM., vol. 35, no. 3, 1999, pages 397-401,
DATABASE BIOSIS [Online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 16 November 2000 (2000-11-16) MURPHY TIMOTHY J ET AL: "Depsipeptide induces histone acetylation and promotes apoptosis in human acute myelogenous leukemia cells with the t(8;21)(q22;q22) translocation." Database accession no. PREV200100300012 XP002228933 & BLOOD, vol. 96, no. 11 Part 2, 16 November 2000 (2000-11-16), page 214b 42nd Annual Meeting of the American Society of Hematology;San Francisco, California, USA; December 01-05, 2000 ISSN: 0006-4971
NICOLAUS B J R: "Symbiotic Approach to Drug Design" DECISION MAKING IN DRUG RESEARCH, XX, XX, 1983, pages 173-186, XP002197412
See also references of EP 1416928A2
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; PREWYSZ-KWINTO, A.: "Synthesis of 2-carbethoxybenzofurans" retrieved from STN Database accession no. 108:112109 XP002188608 & KHIM. GETEROTSIKL. SOEDIN. (1987), (6), 756-9,
MOLL, RAINER ET AL: "Reaction behavior of 3-chlorobenzothiophene-2-carboxylic acid chloride" Z. CHEM. (1977), 17(4), 133-4, XP008000124
HASSAN, H. M. ET AL: "Condensed pyrroles: N1-benzyl-2,5,6-trimethylpyrrolo[2,3-d]-1, 3-oxazin-4- ones and N1-benzyl-2,5,6-trimethyl-3-substituted-py rrolo[2,3-d]pyrimidin- ones" INDIAN J. CHEM., SECT. B: ORG. CHEM. INCL. MED. CHEM. (2000), 39B(10), 764-768, XP008000122
BANIHASHEMI, A. ET AL: "Polycondensation of pyridine-2,6-dicarboxylic acid with some di- and tetra-amino compounds" J. APPL. POLYM. SCI.: APPL. POLYM. SYMP. (1979), 35(LONG-TERM PROP. POLYM. POLYM. MATER.), 51-7, XP001042054
VYAS, RAJEEV R. ET AL: "Synthesis of some new Schiff bases from 8-methoxycoumarin-3-carboxy(o- amino)anilide as possible antibacterial agents" J. INDIAN CHEM. SOC. (1991), 68(5), 294-5, XP008000120
KABANOS T A (REPRINT) ET AL: "SYNTHESIS, STRUCTURAL AND PHYSICAL STUDIES OF TIN(IV) COMPLEXES WITH 2-(2-PYRIDYL)BENZIMIDAZOLE" JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, (21 SEP 1992) NO. 18 PP. 2729-2733. ISSN: 0300-9246., XP001053094 UNIV IOANNINA, DEPT CHEM, INORGAN & GEN CHEM LAB, GR-45110 IOANNINA, GREECE (Reprint);NRPCS DEMOKRITOS, INST MAT SCI, GR-15310 ATHENS, GREECE UNIV PADUA, DIPARTIMENTO CHIM INORGAN MET ORGAN & ANALIT, I-35131 PADUA, ITALY
ADEMBRI, GIORGIO ET AL: "Polyazaheterocyclic compounds. Condensation reactions of pyridazine-4,5-dicarboxylic acid derivatives with o-phenylenediamine" J. CHEM. SOC., PERKIN TRANS. 1 (1974), (9), 1022-6, XP001053092
CHIMICHI, STEFANO ET AL: "Ring-chain isomerism of some 4,5-disubstituted pyridazines involving heterospiro compounds" J. CHEM. SOC., PERKIN TRANS. 2 (1980), (9), 1339-43, XP001053093
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; Database accession no. 804345 (BRN) XP002228873 & ADEMBRI ET AL.: J. CHEM. SOC. PERKIN TRANS. 1, 1974, pages 1022-1024,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 674208 (BRN) XP002228920 & HATCHARD W.R.: J. ORG. CHEM., vol. 29, 1964, pages 665-668,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 400802 (BRN) XP002228921 & ZARIN', P.P. ET AL.: CHEM. HETEROCYCL. COMPD. (ENGL. TRANSL.), vol. 10, 1974, pages 96-98,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 184580 (BRN) XP002228922 & GORTINSKAJA ET AL.: ZH. OBSHCH. KHIM., vol. 25, 1955, pages 2313-2315,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 14194 (BRN) XP002228923 & BALABAN; KING: J. CHEM. SOC., vol. 127, 1925, page 2710
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 1113394 (BRN) XP002228924 & HU 155 098 A (CHINOIN GYOGYSZER ES VEGYESZETI TERMEKEK GYORA RT) 1966
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 1624358 (BRN) XP002228925 & HOLAN G. ET AL.: J. CHEM. SOC. C, 1967, pages 20-25,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 1643278 (BNR) XP002228926 & DE SELMS R.C.: J. ORG. CHEM., vol. 27, 1962, pages 2163-2165,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 4529791 (BRN) XP002228927 & PREWYSZ-KWINTO A.: CHEM. HETEROCYCL. COMPD. (ENGL. TRANSL.), vol. 23, no. 6, 1987, pages 624-627,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 6222330 (BRN) XP002228928 & BEDAIR A.H.: J. PRAKT. CHEM., vol. 329, no. 2, 1987, pages 359-364,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Database accession no. 7299290 (BRN) XP002228929 & HUDKINS R.L.: HETEROCYCLES, vol. 41, no. 5, 1995, pages 1045-1050,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 7711721 (BRN) XP002228930 & ZALESOV V.V. ET AL.: RUSS. J. ORG. CHEM., vol. 31, no. 8, 1995, pages 1104-1108,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main, DE; Database accession no. 8223573 (BRN) XP002228931 & BURGART YA. V. ET AL.: RUSS. J. ORG. CHEM., vol. 34, no. 3, 1998, pages 375-380,
DATABASE CROSSFIRE BEILSTEIN [Online] Beilstein Institut zur Förderung der Chemischen Wissenschaften; Frankfurt am Main; DE; Database accession no. 8332695 (BRN) XP002228932 & SALAKHOV M.S. ET AL.: RUSS. J. ORG. CHEM., vol. 35, no. 3, 1999, pages 397-401,
DATABASE BIOSIS [Online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 16 November 2000 (2000-11-16) MURPHY TIMOTHY J ET AL: "Depsipeptide induces histone acetylation and promotes apoptosis in human acute myelogenous leukemia cells with the t(8;21)(q22;q22) translocation." Database accession no. PREV200100300012 XP002228933 & BLOOD, vol. 96, no. 11 Part 2, 16 November 2000 (2000-11-16), page 214b 42nd Annual Meeting of the American Society of Hematology;San Francisco, California, USA; December 01-05, 2000 ISSN: 0006-4971
NICOLAUS B J R: "Symbiotic Approach to Drug Design" DECISION MAKING IN DRUG RESEARCH, XX, XX, 1983, pages 173-186, XP002197412
See also references of EP 1416928A2
Attorney, Agent or Firm:
Schreiner, Siegfried (Roche Diagnostics GmbH Patent Department P.O.
Box 11 52 Penzberg, DE)
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