Title:
NITROGEN-CONTAINING BICYCLIC COMPOUND WHICH CONTAINS PYRIMIDINE
Document Type and Number:
WIPO Patent Application WO/2022/070289
Kind Code:
A1
Abstract:
This compound, or salt thereof, is represented by general formula (1), exhibits excellent IRAK-4 inhibitory activity and is useful as an active ingredient of a medicine for preventing and/or treating a disease which pertains to IRAK-4 inhibition.
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Inventors:
ARAI KOICHIRO (JP)
TAKABA KENICHIRO (JP)
ATOBE MASAKAZU (JP)
TAKASHIMA MISATO (JP)
AONO NAOMI (JP)
POTTER ANDREW JOHN (GB)
MADDOX DANIEL PAUL (GB)
TAKABA KENICHIRO (JP)
ATOBE MASAKAZU (JP)
TAKASHIMA MISATO (JP)
AONO NAOMI (JP)
POTTER ANDREW JOHN (GB)
MADDOX DANIEL PAUL (GB)
Application Number:
PCT/JP2020/037048
Publication Date:
April 07, 2022
Filing Date:
September 30, 2020
Export Citation:
Assignee:
ASAHI KASEI PHARMA CORP (JP)
VERNALIS R&D LTD (GB)
VERNALIS R&D LTD (GB)
International Classes:
C07D417/04; C07D417/14; C07D471/04; C07D491/08; C07D491/10; C07D498/08
Domestic Patent References:
| WO2019070093A1 | 2019-04-11 | |||
| WO2012068546A1 | 2012-05-24 | |||
| WO2013106614A1 | 2013-07-18 | |||
| WO2016144846A1 | 2016-09-15 | |||
| WO2016053771A1 | 2016-04-07 | |||
| WO2015048281A1 | 2015-04-02 | |||
| WO2013042137A1 | 2013-03-28 | |||
| WO2012068546A1 | 2012-05-24 | |||
| WO2015150995A1 | 2015-10-08 |
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MATTSON, J.L ET AL.: "Functional Observational Battery", J. AMERICAN COLLEGE OF TECHNOLOGY, vol. 15, no. 3, 1996, pages 239 - 254
IRWIN, S., COMPREHENSIVE OBSERVATIONAL ASSESSMENT, vol. 13, 1968, pages 222 - 257
DRORBAUGH, J.E ET AL., PEDIATRICS, vol. 16, 1955, pages 81 - 87
EPSTEIN, M.A ET AL., RESPIR. PHYSIOL., vol. 32, 1978, pages 105 - 120
IYAKUSHIN, APPENDIX, ''GUIDELINE FOR DRUG TOXICITY TEST, no. 1834, 2000
GOMEZ-LECHON, M.J ET AL., CURR. DRUG METAB., vol. 5, no. 5, 2004, pages 443 - 462
MILLER, V.P ET AL., ANN. N.Y. ACAD. SCI., vol. 919, 2000, pages 26 - 32
HENGSTLER, J.G ET AL., DRUG METAB. REV., vol. 32, 2000, pages 81 - 118
KATO, M ET AL., DRUG METAB. PHARMACOKINET., vol. 20, no. 4, 2005, pages 236 - 243
JUNPING GAN ET AL., CHEM. RES. TOXICOL., vol. 18, 2005, pages 896 - 903
BAILLIE T.A.: "Cytochrome P450 and Other Enzymes in Drug Discovery and Development", DRUG METABOLIZING ENZYMES, 2003, pages 147 - 154
DELIE, F ET AL., CRIT. REV. THER. DRUG CARRIER SYST., vol. 14, 1997, pages 221 - 286
YAMASHITA, S ET AL., EUR. J. PHAM. SCI., vol. 10, 2000, pages 195 - 204
INGELS, F.M ET AL., J. PHAM. SCI., vol. 92, 2003, pages 1545 - 1558
IRVINE, J.D ET AL., J. PHAM. SCI., vol. 88, 1999, pages 28 - 33
GERMANN, U.A., METHODS ENZYMOL., vol. 292, 1998, pages 427 - 41
TAMAI I ET AL., PHARM. RES., vol. 18, no. 9, September 2001 (2001-09-01), pages 1262 - 1269
"Newest Mass Spectrometry for Life Science", 2002, KODANSHA SCIENTIFIC
SHOU, W.Z ET AL., J. MASS SPECTROM., vol. 40, no. 10, 2005, pages 1347 - 1356
LI, C ET AL., DRUG METAB. DISPOS., vol. 34, no. 6, 2006, pages 901 - 905
LIPINSKI, C.A ET AL., ADV. DRUG DELIV. REV., vol. 23, 1997, pages 3 - 26
BEVAN, C.D ET AL., ANAL. CHEM., vol. 72, 2000, pages 1781 - 1787
"Physiology", 1986, BUNKODO
NAIR, S. ET AL.: "Optimization of Nicotinamides as Potent and Selective IRAK 4 Inhibitors with Efficacy in a Murine Model of Psoriasis", ACS MEDICINAL CHEMISTRY LETTERS, vol. 11, no. 7, 10 June 2020 (2020-06-10), pages 1402 - 1409, XP055923635, DOI: 10.1021/acsmedchemlett.0c00082 entire text
FLANNERY SBOWIE A.G., BIOCHEMICAL PHARMACOLOGY, vol. 80, 2010, pages 1981 - 1991
JAIN A ET AL., FRONITERS IN IMMUNOLOGY, vol. 5, 2014
PICAD C ET AL., SCIENCE, vol. 299, 2003, pages 2076 - 2079
SUZUKI N ET AL., NATURE, vol. 416, 2002, pages 750 - 754
WAN Y ET AL., J. BIOL. CHEM., vol. 284, 2009, pages 10367 - 10375
KOZICZAK-HOLBRO M ET AL., ARTHRITIS & RHEUMATISM, vol. 60, 2009, pages 1661 - 1671
PETER G.M.WUTS: "Greene's Protective Groups in Organic Synthesis", vol. 1-12, 2014, JOHN WILEY AND SONS
HAYASHI M ET AL., MUTAT. RES., vol. 312, 1994, pages 293 - 304
ISHIYAMA, M. ET AL., IN VITRO TOXICOLOGY, vol. 8, 1995, pages 187
IYAKUSHIN, GUIDELINE FOR GENOTOXICITY TEST, no. 1604, 1999, pages II-4 - 3
CLIVE, D ET AL., MUTAT. RES., vol. 31, 1975, pages 17 - 29
COLE, J. ET AL., MUTAT. RES., vol. 111, 1983, pages 371 - 386
HAYASHI, M ET AL., ENVIRON. MOL. MUTAGEN., vol. 35, 2000, pages 234 - 252
FENECH M. ET AL., MUTAT. RES., vol. 147, 1985, pages 29 - 36
MILLER, B. ET AL., MUTAT. RES., vol. 392, 1997, pages 45 - 59
BUEHLER, E.V., ARCH. DERMATOL., vol. 91, 1965, pages 171 - 177
MAGNUSSON B. ET AL., J. INVEST. DERMATOL., vol. 52, 1969, pages 268 - 276
SATO, Y ET AL., CONTACT DERMATITIS, vol. 7, 1981, pages 225 - 237
TAKEYOSHI, M, TOXICOL. LETT., vol. 119, no. 3, 2001, pages 203 - 8
TAKEYOSHI, M ET AL., J. APPL. TOXICOL., vol. 25, no. 2, 2005, pages 129 - 34
YAKUJI NIPPO, DRUG NONCLINICAL TEST GUIDELINE COMMENTARY 2002, 2002, pages 1 - 6
ICHIKAWA, H ET AL., J. INVEST. DERMATOL., vol. 76, 1981, pages 498 - 501
HARBER, L.C., ARCH. DERMATOL., vol. 96, 1967, pages 646 - 653
HORIO, T., J. INVEST. DERMATOL., vol. 67, 1976, pages 591 - 593
JORDAN, W.P., CONTACT DERMATITIS, vol. 8, 1982, pages 109 - 116
KOCHEVER, L.E ET AL., J. INVEST. DERMATOL., vol. 73, 1979, pages 144 - 146
MAURER, T ET AL., BR. J. DERMATOL., vol. 63, 1980, pages 593 - 605
MORIKAWA, F ET AL.: "Sunlight and Man", 1974, TOKYO UNIV. PRESS, pages: 529 - 557
VINSON, L.J., J. SOC. COSM. CHEM., vol. 17, 1966, pages 123 - 130
FUKUI, N ET AL., GENDAI NO RINSHO, vol. 4, no. 7, 1970, pages 277 - 289
SUGANO S.TSUBONE H.NAKADA Y, MARUZEN, 2003
MURAKI, K ET AL., AM. J. PHYSIOL., vol. 269, 1995, pages 524 - 532
DUCIC ET AL., J. CARDIOVASC. PHARMACOL., vol. 30, no. 1, 1997, pages 42 - 54
CHACHIN, M ET AL., NIPPON YAKURIGAKU ZASSHI, vol. 119, 2002, pages 345 - 351
GILBERT, J.D ET AL., J. PHARM. TOX. METHODS, vol. 50, 2004, pages 187 - 199
CHENG, C.S ET AL., DRUG DEVELOP. INDUST. PHARM., vol. 28, 2002, pages 177 - 191
DOM, A ET AL., J. BIOMOL. SCREEN., vol. 10, 2005, pages 339 - 347
MATTSON, J.L ET AL.: "Functional Observational Battery", J. AMERICAN COLLEGE OF TECHNOLOGY, vol. 15, no. 3, 1996, pages 239 - 254
IRWIN, S., COMPREHENSIVE OBSERVATIONAL ASSESSMENT, vol. 13, 1968, pages 222 - 257
DRORBAUGH, J.E ET AL., PEDIATRICS, vol. 16, 1955, pages 81 - 87
EPSTEIN, M.A ET AL., RESPIR. PHYSIOL., vol. 32, 1978, pages 105 - 120
IYAKUSHIN, APPENDIX, ''GUIDELINE FOR DRUG TOXICITY TEST, no. 1834, 2000
GOMEZ-LECHON, M.J ET AL., CURR. DRUG METAB., vol. 5, no. 5, 2004, pages 443 - 462
MILLER, V.P ET AL., ANN. N.Y. ACAD. SCI., vol. 919, 2000, pages 26 - 32
HENGSTLER, J.G ET AL., DRUG METAB. REV., vol. 32, 2000, pages 81 - 118
KATO, M ET AL., DRUG METAB. PHARMACOKINET., vol. 20, no. 4, 2005, pages 236 - 243
JUNPING GAN ET AL., CHEM. RES. TOXICOL., vol. 18, 2005, pages 896 - 903
BAILLIE T.A.: "Cytochrome P450 and Other Enzymes in Drug Discovery and Development", DRUG METABOLIZING ENZYMES, 2003, pages 147 - 154
DELIE, F ET AL., CRIT. REV. THER. DRUG CARRIER SYST., vol. 14, 1997, pages 221 - 286
YAMASHITA, S ET AL., EUR. J. PHAM. SCI., vol. 10, 2000, pages 195 - 204
INGELS, F.M ET AL., J. PHAM. SCI., vol. 92, 2003, pages 1545 - 1558
IRVINE, J.D ET AL., J. PHAM. SCI., vol. 88, 1999, pages 28 - 33
GERMANN, U.A., METHODS ENZYMOL., vol. 292, 1998, pages 427 - 41
TAMAI I ET AL., PHARM. RES., vol. 18, no. 9, September 2001 (2001-09-01), pages 1262 - 1269
"Newest Mass Spectrometry for Life Science", 2002, KODANSHA SCIENTIFIC
SHOU, W.Z ET AL., J. MASS SPECTROM., vol. 40, no. 10, 2005, pages 1347 - 1356
LI, C ET AL., DRUG METAB. DISPOS., vol. 34, no. 6, 2006, pages 901 - 905
LIPINSKI, C.A ET AL., ADV. DRUG DELIV. REV., vol. 23, 1997, pages 3 - 26
BEVAN, C.D ET AL., ANAL. CHEM., vol. 72, 2000, pages 1781 - 1787
"Physiology", 1986, BUNKODO
Attorney, Agent or Firm:
SIKS & CO. (JP)
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