Title:
HYDRAZONE AMIDE DERIVATIVE AND APPLICATION THEREOF IN PREPARATION OF MEDICAMENTS FOR PREVENTING AND TREATING ALOPECIA
Document Type and Number:
WIPO Patent Application WO/2020/258972
Kind Code:
A1
Abstract:
The present invention provides a brand-new hydrazone amide derivative and an application thereof in preparation of medicaments for preventing and treating alopecia. The structural formula of the hydrazone amide derivative is as shown formula (I), and the hydrazone amide derivative is a brand-new compound for stimulating hair follicle growth and preventing and treating alopecia.
Inventors:
HUANG DANE (CN)
ZHAO CHAO (CN)
GU QIONG (CN)
XU JUN (CN)
ZHAO CHAO (CN)
GU QIONG (CN)
XU JUN (CN)
Application Number:
PCT/CN2020/083076
Publication Date:
December 30, 2020
Filing Date:
April 02, 2020
Export Citation:
Assignee:
SHENZHEN CELL INSPIRE PHARMACEUTICAL DEV CO LTD (CN)
International Classes:
C07D277/587; A61K31/426; A61K31/428; A61K31/44; A61K31/4402; A61K31/4465; A61K31/472; A61K31/5375; A61P17/00; A61P17/14; C07D211/58; C07D213/75; C07D213/85; C07D217/06; C07D277/82; C07D295/185
Foreign References:
| CN110330465A | 2019-10-15 | |||
| CN110229118A | 2019-09-13 | |||
| CN1084512A | 1994-03-30 | |||
| CN1132510A | 1996-10-02 | |||
| US4139619A | 1979-02-13 | |||
| CN1671695A | 2005-09-21 |
Other References:
DATABASE REGISTRY 20 April 2001 (2001-04-20), ANONYMOUS: "5-Thiazolecarboxylic acid, 2-[[2-[2-(2-carboxyphenyl)hydrazinylidene]-1,3- dioxobutyl]amino]-4-methyl-, 5-ethyl ester (CA INDEX NAME)", XP055885802, retrieved from STN Database accession no. 331968-10-6
ZHENG, X. H. ET AL.: "Screening, Synthesis, Crystal Structure, and Molecular Basis of 6-Amino-4-Phenyl-1, 4-Dihydropyrano[2, 3-c]Pyrazole-5-Carbonitriles as Novel AKR1C3 Inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 26, no. 22, 3 November 2018 (2018-11-03), XP055773251, ISSN: 0968-0896, DOI: 20200524152442X
LYČKA, A. ET AL.: "27Al, 15N, 13C and 1H NMR Spectra and Negative-Ion Electrospray Mass Spectra of the 2:1 Aluminium(III) Complexes of Azo Dyes Derived from Anthranilic Acid", DYES AND PIGMENTS, vol. 50, no. 3, 30 September 2001 (2001-09-30), XP004307496, ISSN: 0143-7208, DOI: 20200524152802X
GURBANOV, A. V. ET AL.: "The Henry Reaction Catalyzed by NiII and CuII Complexes Bearing Arylhydrazones of Acetoacetanilide", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 869, 31 May 2018 (2018-05-31), XP055773255, ISSN: 0022-328X, DOI: 20200524152905X
MA, ZHEN ET AL.: "Effective Cyanosilylation of Aldehydes with Copper(II)-Based Polymeric Catalysts", JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 428, 28 November 2016 (2016-11-28), XP055773260, ISSN: 1381-1169, DOI: 20200524154519X
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Benzoic acid, 4-[2-[2-oxo-1-[(phenylamino)carbonyl]propylidene]hydrazinyl]- (CA INDEX NAME)", XP055885858, retrieved from STN Database accession no. 63239-81-6
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Benzoic acid, 4-[2-[2-oxo-1-[(phenylamino)carbonyl]propylidene]hydrazinyl]- , ethyl ester (CA INDEX NAME)", XP055885857, retrieved from STN Database accession no. 63239-82-7
A. S. FOUDA , S.A. GOMHA , M.N. MOUSSA: "Inhibition of the Acid Corrosion of Iron with 2-(Acetoacetamido)Pyridine Aryl Hydrazone Derivatives", BULLETIN OF ELECTROCHEMISTRY, vol. 17, no. 7, 31 July 2001 (2001-07-31), pages 303 - 310, XP009533323, ISSN: 0256-1654
ABOUTABL, M. A. ET AL.: "Polarographic Behaviour of α- and γ-Substituted Acetoacetanilide Derivatives in Alcoholic Aqueous Media", MONATSHEFTE FÜR CHEMIE, vol. 123, 31 March 1992 (1992-03-31), XP055773343, ISSN: 0026-9247, DOI: 20200524155036X
KHEDER, N. A. ET AL.: "Facile and Convenient Synthesis of Pyrazole, Pyridine, Pyridazine, Pyrazolo[3, 4-b]Pyridine, and Pyrazolo[5, 1-c][1, 2, 4]Triazine Derivatives", SYNTHETIC COMMUNICATIONS, vol. 38,, no. 18, 9 September 2008 (2008-09-09), XP055773346, ISSN: 1532-2432, DOI: 20200524155317X
CHEN SHUXIN,LI JIEHUAMO YUFANG,: "Clinical observation on the clinical efficacy of minoxidil lotion combined with finasteride in treatment of androgenetic alopecia", INTERNATIONAL MEDICINE & HEALTH GUIDANCE NEWS, vol. 12, no. 6, 2006, pages 64 - 65
"McGraw-Hill Dictionary of Chemical Terms", 1984, MCGRAW-HILL BOOK COMPANY
ELIEL, E.WILEN, S.: "Stereochemistry of Organic Compounds", 1994, JOHN WILEY & SONS, INC.
JACQUES ET AL.: "Enantiomers, Racemates and Resolutions", 1981, WILEY INTERSCIENCE
"Principles of Asymmetric Synthesis", 2012, ELSEVIER
ELIEL, E.L.: "Stereochemistry of Carbon Compounds", 1962, MCGRAW-HILL
"Tables of Resolving Agents and Optical Resolutions", vol. 11, 1972, UNIV. OF NOTRE DAME PRESS, article "IUPAC-IUB Commission on Biochemical Nomenclature", pages: 942 - 944
"Chiral Separation Techniques: A Practical Approach", 2007, WILEY-VCH VERLAG GMBH & CO
L. W. DEADY, SYN. COMM., vol. 7, 1977, pages 509 - 514
T. HIGUCHIV. STELLA: "Bioreversible Carriers in Drug Design", vol. 14, 1987, AMERICAN PHARMACEUTICAL ASSOCIATION AND PERGAMON PRESS, article "Pro-drugs as Novel Delivery Systems"
J. RAUTIO ET AL.: "Prodrugs: Design and Clinical Applications", NATURE REVIEW DRUG DISCOVERY, vol. 7, 2008, pages 255 - 270, XP055227338, DOI: 10.1038/nrd2468
S. J. HECKER ET AL.: "Prodrugs of Phosphates and Phosphonates", JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, 2008, pages 2328 - 2345, XP008148502, DOI: 10.1021/jm701260b
S. M. BERGE ET AL., J. PHARMACEUTICAL SCIENCES, vol. 66, 1977, pages 1 - 19
See also references of EP 3992185A4
ZHENG, X. H. ET AL.: "Screening, Synthesis, Crystal Structure, and Molecular Basis of 6-Amino-4-Phenyl-1, 4-Dihydropyrano[2, 3-c]Pyrazole-5-Carbonitriles as Novel AKR1C3 Inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 26, no. 22, 3 November 2018 (2018-11-03), XP055773251, ISSN: 0968-0896, DOI: 20200524152442X
LYČKA, A. ET AL.: "27Al, 15N, 13C and 1H NMR Spectra and Negative-Ion Electrospray Mass Spectra of the 2:1 Aluminium(III) Complexes of Azo Dyes Derived from Anthranilic Acid", DYES AND PIGMENTS, vol. 50, no. 3, 30 September 2001 (2001-09-30), XP004307496, ISSN: 0143-7208, DOI: 20200524152802X
GURBANOV, A. V. ET AL.: "The Henry Reaction Catalyzed by NiII and CuII Complexes Bearing Arylhydrazones of Acetoacetanilide", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 869, 31 May 2018 (2018-05-31), XP055773255, ISSN: 0022-328X, DOI: 20200524152905X
MA, ZHEN ET AL.: "Effective Cyanosilylation of Aldehydes with Copper(II)-Based Polymeric Catalysts", JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 428, 28 November 2016 (2016-11-28), XP055773260, ISSN: 1381-1169, DOI: 20200524154519X
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Benzoic acid, 4-[2-[2-oxo-1-[(phenylamino)carbonyl]propylidene]hydrazinyl]- (CA INDEX NAME)", XP055885858, retrieved from STN Database accession no. 63239-81-6
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Benzoic acid, 4-[2-[2-oxo-1-[(phenylamino)carbonyl]propylidene]hydrazinyl]- , ethyl ester (CA INDEX NAME)", XP055885857, retrieved from STN Database accession no. 63239-82-7
A. S. FOUDA , S.A. GOMHA , M.N. MOUSSA: "Inhibition of the Acid Corrosion of Iron with 2-(Acetoacetamido)Pyridine Aryl Hydrazone Derivatives", BULLETIN OF ELECTROCHEMISTRY, vol. 17, no. 7, 31 July 2001 (2001-07-31), pages 303 - 310, XP009533323, ISSN: 0256-1654
ABOUTABL, M. A. ET AL.: "Polarographic Behaviour of α- and γ-Substituted Acetoacetanilide Derivatives in Alcoholic Aqueous Media", MONATSHEFTE FÜR CHEMIE, vol. 123, 31 March 1992 (1992-03-31), XP055773343, ISSN: 0026-9247, DOI: 20200524155036X
KHEDER, N. A. ET AL.: "Facile and Convenient Synthesis of Pyrazole, Pyridine, Pyridazine, Pyrazolo[3, 4-b]Pyridine, and Pyrazolo[5, 1-c][1, 2, 4]Triazine Derivatives", SYNTHETIC COMMUNICATIONS, vol. 38,, no. 18, 9 September 2008 (2008-09-09), XP055773346, ISSN: 1532-2432, DOI: 20200524155317X
CHEN SHUXIN,LI JIEHUAMO YUFANG,: "Clinical observation on the clinical efficacy of minoxidil lotion combined with finasteride in treatment of androgenetic alopecia", INTERNATIONAL MEDICINE & HEALTH GUIDANCE NEWS, vol. 12, no. 6, 2006, pages 64 - 65
"McGraw-Hill Dictionary of Chemical Terms", 1984, MCGRAW-HILL BOOK COMPANY
ELIEL, E.WILEN, S.: "Stereochemistry of Organic Compounds", 1994, JOHN WILEY & SONS, INC.
JACQUES ET AL.: "Enantiomers, Racemates and Resolutions", 1981, WILEY INTERSCIENCE
"Principles of Asymmetric Synthesis", 2012, ELSEVIER
ELIEL, E.L.: "Stereochemistry of Carbon Compounds", 1962, MCGRAW-HILL
"Tables of Resolving Agents and Optical Resolutions", vol. 11, 1972, UNIV. OF NOTRE DAME PRESS, article "IUPAC-IUB Commission on Biochemical Nomenclature", pages: 942 - 944
"Chiral Separation Techniques: A Practical Approach", 2007, WILEY-VCH VERLAG GMBH & CO
L. W. DEADY, SYN. COMM., vol. 7, 1977, pages 509 - 514
T. HIGUCHIV. STELLA: "Bioreversible Carriers in Drug Design", vol. 14, 1987, AMERICAN PHARMACEUTICAL ASSOCIATION AND PERGAMON PRESS, article "Pro-drugs as Novel Delivery Systems"
J. RAUTIO ET AL.: "Prodrugs: Design and Clinical Applications", NATURE REVIEW DRUG DISCOVERY, vol. 7, 2008, pages 255 - 270, XP055227338, DOI: 10.1038/nrd2468
S. J. HECKER ET AL.: "Prodrugs of Phosphates and Phosphonates", JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, 2008, pages 2328 - 2345, XP008148502, DOI: 10.1021/jm701260b
S. M. BERGE ET AL., J. PHARMACEUTICAL SCIENCES, vol. 66, 1977, pages 1 - 19
See also references of EP 3992185A4
Attorney, Agent or Firm:
TSINGYIHUA INTELLECTUAL PROPERTY LLC (CN)
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