Title:
NITROGEN-CONTAINING SIX-MEMBERED RING COMPOUND
Document Type and Number:
WIPO Patent Application WO/2019/131582
Kind Code:
A1
Abstract:
Provided are a novel compound which is represented by general formula (1) and which has excellent agonistic activity on EP4 receptors, or a salt thereof, and a medicine that contains the compound or a salt thereof as an active ingredient, and that can be used for promotion of osteogenesis or treatment and/or promotion of healing of bone fracture, or the like.
Inventors:
SHIKANAI DAISUKE (JP)
ISHIGURO NORIKO (JP)
OMORI OSAMU (JP)
ISHIGURO NORIKO (JP)
OMORI OSAMU (JP)
Application Number:
PCT/JP2018/047450
Publication Date:
July 04, 2019
Filing Date:
December 25, 2018
Export Citation:
Assignee:
ASAHI KASEI PHARMA CORP (JP)
International Classes:
C07D417/14; A61K31/5395; A61K31/549; A61P19/08; A61P43/00; C07D417/06
Domestic Patent References:
| WO2006080323A1 | 2006-08-03 | |||
| WO2002024647A1 | 2002-03-28 | |||
| WO2002042268A2 | 2002-05-30 | |||
| WO2003007941A1 | 2003-01-30 | |||
| WO2003035064A1 | 2003-05-01 | |||
| WO2004063158A1 | 2004-07-29 | |||
| WO2004085430A1 | 2004-10-07 | |||
| WO2006080323A1 | 2006-08-03 |
Foreign References:
| JP2016516050A | 2016-06-02 | |||
| US6747037B1 | 2004-06-08 |
Other References:
ZHAO, Z. ET AL.: "Synthesis and evaluation of novel pyrazolidinone analogs of PGE2 as EP 2 and EP 4 receptors agonists", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 17, 2007, pages 6572 - 6575, XP022325938, doi:10.1016/j.bmcl.2007.09.074
C. COOPER ET AL., AM. J. EPIDEMIOL., vol. 137, 1993, pages 1001 - 1005
P. SARRAZIN, G ET AL., PROSTAGLANDINS LEUKOT. ESSENT. FATTY ACIDS, vol. 64, 2001, pages 203 - 210
I. FORTIER ET AL., PROSTAGLANDINS LEUKOT. ESSENT. FATTY ACIDS, vol. 70, 2004, pages 431 - 439
"Protective Groups in Organic Synthesis", 2007, JOHN WILEY AND SONS
ISHIYAMA, M. ET AL., IN VITRO TOXICOLOGY, vol. 8, 1995, pages 187
CLIVE, D. ET AL., MUTAT. RES., vol. 31, 1975, pages 17 - 29
COLE, J. ET AL., MUTAT. RES., vol. Ill, 1983, pages 371 - 386
HAYASHI M. ET AL., MUTAT. RES., vol. 312, 1994, pages 293 - 304
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. ET AL., 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
"Drug Nonclinical Test Guideline Commentary 2002", 2002, YAKUJI NIPPO, article "Reproductive and Developmental Toxicity Test", 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, I.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
MATSUO, S., MEDICINA, vol. 40, 2003, pages 188
MURAKI, K. ET AL., AM. J. PHYSIOL., vol. 269, 1995, pages H524 - 532
DUCIC, I. 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
DORN, 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 (BERL., 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
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
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
See also references of EP 3733665A4
C. COOPER ET AL., AM. J. EPIDEMIOL., vol. 137, 1993, pages 1001 - 1005
P. SARRAZIN, G ET AL., PROSTAGLANDINS LEUKOT. ESSENT. FATTY ACIDS, vol. 64, 2001, pages 203 - 210
I. FORTIER ET AL., PROSTAGLANDINS LEUKOT. ESSENT. FATTY ACIDS, vol. 70, 2004, pages 431 - 439
"Protective Groups in Organic Synthesis", 2007, JOHN WILEY AND SONS
ISHIYAMA, M. ET AL., IN VITRO TOXICOLOGY, vol. 8, 1995, pages 187
CLIVE, D. ET AL., MUTAT. RES., vol. 31, 1975, pages 17 - 29
COLE, J. ET AL., MUTAT. RES., vol. Ill, 1983, pages 371 - 386
HAYASHI M. ET AL., MUTAT. RES., vol. 312, 1994, pages 293 - 304
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. ET AL., 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
"Drug Nonclinical Test Guideline Commentary 2002", 2002, YAKUJI NIPPO, article "Reproductive and Developmental Toxicity Test", 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, I.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
MATSUO, S., MEDICINA, vol. 40, 2003, pages 188
MURAKI, K. ET AL., AM. J. PHYSIOL., vol. 269, 1995, pages H524 - 532
DUCIC, I. 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
DORN, 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 (BERL., 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
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
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
See also references of EP 3733665A4
Attorney, Agent or Firm:
SIKS & CO. (JP)
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