Title:
NOVEL PYRAZOLE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2014/133046
Kind Code:
A1
Abstract:
There has been a demand for a pharmaceutical composition which is used for a prophylactic and/or therapeutic agent for various diseases associated with PDE10 (for example, mental disorder, neurodegenerative disorder and the like). The present invention provides: a compound having a PDE10 inhibitory effect, in particular, a compound which is represented by formula (I) and is characterized by having a 4-heteroarylpyrazole-5-carboxylic acid amide structure, a pharmaceutically acceptable salt thereof, and a solvate of the compound or the salt; a pharmaceutical composition which is characterized by containing, as an active ingredient, the compound, a pharmaceutically acceptable salt of the compound, or a solvate of the compound or the salt; and a pharmaceutical use of the compound, a pharmaceutically acceptable salt of the compound, or a solvate of the compound or the salt.
Inventors:
OKANO AKIHIRO (JP)
SAITOH FUMIHIKO (JP)
MAKABE MUNEYOSHI (JP)
OGAWA KOUKI (JP)
SAITOH FUMIHIKO (JP)
MAKABE MUNEYOSHI (JP)
OGAWA KOUKI (JP)
Application Number:
PCT/JP2014/054773
Publication Date:
September 04, 2014
Filing Date:
February 26, 2014
Export Citation:
Assignee:
MOCHIDA PHARM CO LTD (JP)
International Classes:
C07D471/04; A61K31/444; A61K31/497; A61K31/506; A61K31/5377; A61P3/04; A61P25/00; A61P25/08; A61P25/14; A61P25/16; A61P25/18; A61P25/22; A61P25/24; A61P25/28; A61P25/32; A61P25/36; A61P43/00; C07D401/04; C07D417/04
Domestic Patent References:
| WO2012009009A2 | 2012-01-19 | |||
| WO2012076430A1 | 2012-06-14 | |||
| WO2011154327A1 | 2011-12-15 | |||
| WO2011117264A1 | 2011-09-29 | |||
| WO2011036127A1 | 2011-03-31 | |||
| WO2012133607A1 | 2012-10-04 | |||
| WO2005082883A2 | 2005-09-09 | |||
| WO2003000693A1 | 2003-01-03 | |||
| WO2006072828A2 | 2006-07-13 | |||
| WO2011036127A1 | 2011-03-31 | |||
| WO2011154327A1 | 2011-12-15 | |||
| WO2012076430A1 | 2012-06-14 | |||
| WO2006072828A2 | 2006-07-13 | |||
| WO2007121390A1 | 2007-10-25 | |||
| WO2005034867A2 | 2005-04-21 |
Foreign References:
| US20030032579A1 | 2003-02-13 | |||
| EP1250923A2 | 2002-10-23 |
Other References:
DATABASE REGISTRY [online] 15 April 2012 (2012-04-15), "1H-PYRAZOLE-5-CARBOXYLIC ACID, 1-METHYL-4-(2-PYRIDINYL)- (CA INDEX NAME)", XP055284695, retrieved from STN Database accession no. 1368131-71-8
ESSAYAN D M., J ALLERGY CLIN IMMUNOL, vol. 108, 2001, pages 671 - 680
FRANCIS S H., PROG NUCLEIC ACID RES MOL BIO1., vol. 65, 2001, pages 1 - 52
SODERLING S H., PROC NATL ACAD USA, vol. 96, no. 12, 1999, pages 707L - 7076
CHAPPIE T A., JOURNAL OF MEDICINAL CHEMISTRY, vol. 55, 2012, pages 7299 - 7331
MENNITI F S., NAT REV DRUG DISCOV, vol. 5, no. 8, 2006, pages 660 - 670
HOUSLAY M D., CIR RES, vol. 100, no. 7, 2007, pages 950 - 966
OMORI K., J BIOL CHEM, vol. 274, no. 26, 1999, pages 18438 - 18445
LOUGHNEY K., GENE, vol. 234, no. 1, 1999, pages 109 - 117
OMORI K., EUR J BIOCHEM, vol. 266, no. 3, 1999, pages 118 - 1127
MENNITI F S., BRAIN RES, vol. 985, no. 2, 2003, pages L 13 - 126
XIE Z., NEUROSCIENCE, vol. 139, no. 2, 2006, pages 597 - 607
LAPIZ ET AL., NEUROSCI BEHAV PHYSIOL, vol. 33, no. 1, 2003, pages 13 - 29
MUTSCHLER.: "Arzneimittelwirkungen", 2001, WISSENSCHAFTLICHE VERLAGSGESELLSCHAFT MBH
SAWAGUCHI, PARKINSONISM RELAT DISORD., vol. 7, no. 1, 2000, pages 9 - 19
CASTNER SA., SCIENCE, vol. 287, no. 5460, 2000, pages 2020 - 2022
KOSTOWSKI W., PHARMACOL BIOCHEM BEHAV., vol. 5, no. 1, 1976, pages L5 - 17
MENNITI F S., CURR OPIN INVESTIG DRUGS., vol. 8, no. 1, 2007, pages 54 - 59
CAPUANO B., CURR MED CHEM, vol. 9, no. 5, 2002, pages 521 - 548
LINDENMAYER JP, J CLIN PSYCHIATRY, vol. 63, no. 10, 2002, pages 931 - 935
STAHL; WERMUTH: "Handbook of Pharmaceutical Salts: Properties, Selection, and Use", 2002, WILEY-VCH
H. BUNDGAARD: "Design of Prodrugs", 1985, ELSEVIER
RICHARD C. LAROCK ET AL.: "Comprehensive Organic Transformations", October 1999, WILEY-VCH
GREENE ET AL.: "Protective Groups in Organic Synthesis", 2007, JOHN WILEY & SONS
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 60, 1995, pages 7508 - 2665
CHEMISCHE BERICHTE, vol. 42, 1909, pages 3090
CHEMICAL REVIEWS, vol. 108, 2008, pages 288 - 325
JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 307, no. 1, 1986, pages 1 - 6
"Jikken Kagaku Koza,", 2004, MARUZEN, article "Organic Compound Synthesis VI -Organic Synthesis using Metal", pages: 327 - 352
JOURNAL OF MEDICINAL CHEMISTRY, vol. 48, no. 20, 2005, pages 6326 - 6339
"Jikken Kagaku Koza", 1992, MARUZEN, article "Organic Synthesis IV, Acid, Amino Acid, and Peptide", pages: 1 - 43
"Jikken Kagaku Koza", 1992, MARUZEN, article "Organic Synthesis VIII, Asymmetric Synthesis, Reduction, Sugar, and Labeling Compound", pages: 159 - 266
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 109, no. 24, 1987, pages 7488 - 7494
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 52, 2012, pages 137 - 150
"Strategic Applications of Named Reactions in Organic Synthesis", 2005, ELSEVIER ACADEMIC PRESS, pages: 116 - 117
GREENE: "Protective Groups in Organic Synthesis", 2007, JOHN WILEY & SONS
JOURNAL OF MEDICINAL CHEMISTRY, vol. 48, no. 10, 2005, pages 3586 - 3640
JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 39, no. 4, 2002, pages 733 - 735
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 65, no. 5, 2000, pages 1566 - 1568
SYNTHESIS, 2003, pages 1649 - 1652
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 42, no. 14, 1977, pages 2426 - 2431
ORGANIC SYNTHESIS, vol. 78, 2002, pages 23
JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 12, no. 1, 1975, pages 107 - 110
RUSSIAN CHEMICAL BULLETIN, vol. 54, 2005, pages 470
"Jikken Kagaku Koza", 1992, MARUZEN, article "Organic Synthesis IV, Acid, Amino Acid, and Peptide", pages: 191 - 309
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 4, 2004, pages 983 - 988
"Jikken Kagaku Koza", 1992, MARUZEN, article "Organic Synthesis IV, Acid, Amino Acid, and Peptide", pages: 144 - 146
SCHIZOPHRENIA BULLETIN, vol. 36, 2010, pages 1066 - 1072
PSYCHOPHARMACOLOGY, vol. L45, 1999, pages 237 - 250
See also references of EP 2963037A4
ESSAYAN D M., J ALLERGY CLIN IMMUNOL, vol. 108, 2001, pages 671 - 680
FRANCIS S H., PROG NUCLEIC ACID RES MOL BIO1., vol. 65, 2001, pages 1 - 52
SODERLING S H., PROC NATL ACAD USA, vol. 96, no. 12, 1999, pages 707L - 7076
CHAPPIE T A., JOURNAL OF MEDICINAL CHEMISTRY, vol. 55, 2012, pages 7299 - 7331
MENNITI F S., NAT REV DRUG DISCOV, vol. 5, no. 8, 2006, pages 660 - 670
HOUSLAY M D., CIR RES, vol. 100, no. 7, 2007, pages 950 - 966
OMORI K., J BIOL CHEM, vol. 274, no. 26, 1999, pages 18438 - 18445
LOUGHNEY K., GENE, vol. 234, no. 1, 1999, pages 109 - 117
OMORI K., EUR J BIOCHEM, vol. 266, no. 3, 1999, pages 118 - 1127
MENNITI F S., BRAIN RES, vol. 985, no. 2, 2003, pages L 13 - 126
XIE Z., NEUROSCIENCE, vol. 139, no. 2, 2006, pages 597 - 607
LAPIZ ET AL., NEUROSCI BEHAV PHYSIOL, vol. 33, no. 1, 2003, pages 13 - 29
MUTSCHLER.: "Arzneimittelwirkungen", 2001, WISSENSCHAFTLICHE VERLAGSGESELLSCHAFT MBH
SAWAGUCHI, PARKINSONISM RELAT DISORD., vol. 7, no. 1, 2000, pages 9 - 19
CASTNER SA., SCIENCE, vol. 287, no. 5460, 2000, pages 2020 - 2022
KOSTOWSKI W., PHARMACOL BIOCHEM BEHAV., vol. 5, no. 1, 1976, pages L5 - 17
MENNITI F S., CURR OPIN INVESTIG DRUGS., vol. 8, no. 1, 2007, pages 54 - 59
CAPUANO B., CURR MED CHEM, vol. 9, no. 5, 2002, pages 521 - 548
LINDENMAYER JP, J CLIN PSYCHIATRY, vol. 63, no. 10, 2002, pages 931 - 935
STAHL; WERMUTH: "Handbook of Pharmaceutical Salts: Properties, Selection, and Use", 2002, WILEY-VCH
H. BUNDGAARD: "Design of Prodrugs", 1985, ELSEVIER
RICHARD C. LAROCK ET AL.: "Comprehensive Organic Transformations", October 1999, WILEY-VCH
GREENE ET AL.: "Protective Groups in Organic Synthesis", 2007, JOHN WILEY & SONS
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 60, 1995, pages 7508 - 2665
CHEMISCHE BERICHTE, vol. 42, 1909, pages 3090
CHEMICAL REVIEWS, vol. 108, 2008, pages 288 - 325
JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 307, no. 1, 1986, pages 1 - 6
"Jikken Kagaku Koza,", 2004, MARUZEN, article "Organic Compound Synthesis VI -Organic Synthesis using Metal", pages: 327 - 352
JOURNAL OF MEDICINAL CHEMISTRY, vol. 48, no. 20, 2005, pages 6326 - 6339
"Jikken Kagaku Koza", 1992, MARUZEN, article "Organic Synthesis IV, Acid, Amino Acid, and Peptide", pages: 1 - 43
"Jikken Kagaku Koza", 1992, MARUZEN, article "Organic Synthesis VIII, Asymmetric Synthesis, Reduction, Sugar, and Labeling Compound", pages: 159 - 266
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 109, no. 24, 1987, pages 7488 - 7494
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 52, 2012, pages 137 - 150
"Strategic Applications of Named Reactions in Organic Synthesis", 2005, ELSEVIER ACADEMIC PRESS, pages: 116 - 117
GREENE: "Protective Groups in Organic Synthesis", 2007, JOHN WILEY & SONS
JOURNAL OF MEDICINAL CHEMISTRY, vol. 48, no. 10, 2005, pages 3586 - 3640
JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 39, no. 4, 2002, pages 733 - 735
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 65, no. 5, 2000, pages 1566 - 1568
SYNTHESIS, 2003, pages 1649 - 1652
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 42, no. 14, 1977, pages 2426 - 2431
ORGANIC SYNTHESIS, vol. 78, 2002, pages 23
JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 12, no. 1, 1975, pages 107 - 110
RUSSIAN CHEMICAL BULLETIN, vol. 54, 2005, pages 470
"Jikken Kagaku Koza", 1992, MARUZEN, article "Organic Synthesis IV, Acid, Amino Acid, and Peptide", pages: 191 - 309
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 4, 2004, pages 983 - 988
"Jikken Kagaku Koza", 1992, MARUZEN, article "Organic Synthesis IV, Acid, Amino Acid, and Peptide", pages: 144 - 146
SCHIZOPHRENIA BULLETIN, vol. 36, 2010, pages 1066 - 1072
PSYCHOPHARMACOLOGY, vol. L45, 1999, pages 237 - 250
See also references of EP 2963037A4
Attorney, Agent or Firm:
KOBAYASHI, Hiroshi et al. (JP)
Kobayashi 浩 (JP)
Kobayashi 浩 (JP)
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