Title:
HYDRAZONE AMIDE DERIVATIVES AND USE THEREOF IN PREPARATION OF ANTI-OSTEOPOROSIS DRUGS
Document Type and Number:
WIPO Patent Application WO/2020/258971
Kind Code:
A1
Abstract:
Provided are a new class of hydrazone amide derivatives and the use thereof in the preparation of anti-osteoporosis drugs, wherein the structural formula of the hydrazone amide derivative is as shown in formula (I), and same are a new class of compounds with an anti-osteoporosis effect.
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/CN2020/083067
Publication Date:
December 30, 2020
Filing Date:
April 02, 2020
Export Citation:
Assignee:
SHENZHEN CELL INSPIRE PHARMACEUTICAL DEV CO LTD (CN)
International Classes:
A61K31/196; C07D277/56; A61K31/426; A61K31/428; A61K31/44; A61K31/4402; A61K31/4465; A61K31/472; A61K31/5375; A61P19/08; A61P19/10; C07C251/76; C07D211/58; C07D213/75; C07D213/85; C07D217/06; C07D277/46; C07D277/82; C07D295/185
Foreign References:
| CN110229118A | 2019-09-13 | |||
| CN110330465A | 2019-10-15 | |||
| CN1084512A | 1994-03-30 | |||
| JP2013182058A | 2013-09-12 | |||
| JP2016148729A | 2016-08-18 |
Other References:
SUJIT SURESH KAMBLE ET AL.: "Room temperature diazotization and coupling reaction using a DES-ethanol system: a green approach towards the synthesis of monoazo pigments", CHEM. COMMUN., vol. 55, no. 42, 25 April 2019 (2019-04-25), XP055773348, ISSN: 1359-7345, DOI: 20200611163457X
ZHEN MA 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: 2468-8231, DOI: 20200611170818X
QIAN ZHANG ET AL.: "Formal [4+1] annulation of α-aryl hydrazone ketones and dimethylsulfoxonium methylide: one-pot synthesis of substituted pyrazoles and dihydropyrazoles", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 14, 21 June 2016 (2016-06-21), XP055773353, ISSN: 0022-3263, DOI: 20200611171806X
ZHENG LI ET AL.: "The influence of fluorination on the structure and properties of azo pigments", DYES AND PIGMENTS, vol. 128, 3 February 2016 (2016-02-03), XP029461128, ISSN: 0143-7208, DOI: 20200611172511X
PRATIBHA SHARMA ET AL.: "Studies on synthesis and evaluation of quantitative structure-activity relationship of 5-[(3'-chloro-4', 4'-disubstituted-2-oxoazetidinyl)(N-nitro) amino]-6-hydroxy-3-alkyl/aryl [1, 3] azaphospholo [1, 5-a] pyridin-1-yl-phosphorus dichlorides", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 15, no. 4,, 20 January 2005 (2005-01-20), XP027801875, ISSN: 0960-894X, DOI: 20200611173404X
A. S. SHAWALI ET AL.: "Cyanoacetarylamides-I Preparation and reactions of their arylazo derivatives with diazonium ion and Grignard reagents", TETRAHEDRON, vol. 27, no. 10, 31 December 1971 (1971-12-31), XP055773356, ISSN: 0040-4020, DOI: 20200611175051X
C. W. SCHELLHAMMER ET AL.: "ÜBER ALKYLIERUNGEN VON BENZOTRIAZOL-DERIVATEN", TETRAHEDRON, vol. 26, no. 2, 31 December 1970 (1970-12-31), XP002574283, ISSN: 0040-4020, DOI: 20200611180139X
M. A. ABOUTABL ET AL.: "Polarographic behaviour of α- and γ-substituted acetoacetanilide derivatives in alcoholic aqueous media", MONATSHEFTE FÜR CHEMIE, vol. 123, no. 3, 31 March 1992 (1992-03-31), XP055773343, ISSN: 0026-9247, DOI: 20200611180842X
RAJEEV, JAIN ET AL.: "Synthesis of some new arylazopyrazoles and arylazopyrimidines", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 67, no. 6, 30 June 1990 (1990-06-30), IN , pages 516 - 518, XP009533296, ISSN: 0019-4522
ANTONIN LYCKA ET AL.: "15N, 13C and 1H NMR spectra of the 2:1 cobalt (III) complexes of some azo dyes", MAGNETIC RESONANCE IN CHEMISTRY, vol. 28, no. 5, 31 May 1990 (1990-05-31), XP004418122, ISSN: 0749-1581, DOI: 20200611182516X
ANTONIUS KETTRUP ET AL.: "Spektroskopische untersuchungen an substituierten 2, 3-dioxobutyranilide-2-phenylhydrazonen", MONATSHEFTE FÜR CHEMIE, vol. 107, no. 6, 31 December 1976 (1976-12-31), XP055773366, ISSN: 0026-9247, DOI: 20200612114426X
M. A. ZAYED ET AL.: "The use of thermal and spectrometric analyses for the structure investigation of arylhydrazoneacetoacetylaminopyridines and their copper chelates", THERMOCHIMICA ACTA, vol. 146, 31 December 1989 (1989-12-31), XP055773368, ISSN: 0040-6031, DOI: 20200612125417X
ROBERT M. CHRISTIE ET AL.: "Colour and constitution relationships in organic pigments. Part 1. -Monoazoacetoacetanilides", DYES AND PIGMENTS, vol. 9, no. 1, 31 December 1988 (1988-12-31), XP000488262, ISSN: 0143-7208, DOI: 20200612130453X
GREIG CHISHOLM ET AL.: "Comparison of the structural motifs of acetoacetanilides and related azo pigments", ACTA CRYSTALLOGRAPHICA SECTION B: STRUCTURAL SCIENCE, vol. B56, no. 6, 31 December 2000 (2000-12-31), XP055773374, ISSN: 0108-7681, DOI: 20200612141327X
POUL ERIK HANSEN ET AL.: "Long-range intrinsic and equilibrium deuterium isotope effects on 19F chemical shifts", ACTA CHEMICA SCANDINAVICA, vol. 51, no. 8, 31 August 1997 (1997-08-31), XP055773376, ISSN: 0904-213X, DOI: 20200617102722X
A. A. FADDA ET AL.: "Synthesis of azodisperse dyes with pyridine ring for dyeing polyester fibres", INDIAN JOURNAL OF TEXTILE RESEARCH, vol. 11, no. 1, 31 March 1986 (1986-03-31), XP055773379, ISSN: 0377-8436, DOI: 20200612143549X
MURAT ÇAĞLAR HAMZAÇEBI ET AL.: "Synthesis and structure elucidation of hydrazones derived from N-(2, 4-dimethylphenyl)-3-oxobutanamide", ARKIVOC, vol. 2008, no. 12, 21 May 2008 (2008-05-21), XP055773381, ISSN: 1551-7012, DOI: 20200617103153X
K. M. DYUMAEV ET AL.: "Synthesis and structure of 2-(2-phenylhydrazono) acetoacetanilide and its derivatives", ZHURNAL ORGANICHESKOI KHIMII, vol. 14, no. 3, 31 December 1978 (1978-12-31), pages 562`569, XP009533330, ISSN: 0514-7492
KETTRUP ANTONIUS, GROTE MANFRED: "Die Fragmentierung der Azo- und Hydrazontautomeren von 2.3-Dioxobutyranilid-2-phenylhydrazonen in der Gasphase in Abhängigkeit von Substituenten = The fragmentation of azo and hydrazone tautomers of 2, 3-dioxobutyranilide-2-phenylhydrazones in the gaseous state in dependence of substituents", ZEITSCHRIFT FÜR NATURFORSCHUNG, vol. 32b, no. 8, 31 August 1977 (1977-08-31), DE , pages 863 - 868, XP009533295, ISSN: 0340-5087, DOI: 10.1515/znb-1977-0806
RAJEEV, JAIN ET AL.: "Synthesis of some new isonicotinoylazopyrazoles", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 66, no. 5, 31 May 1989 (1989-05-31), IN , pages 350 - 352, XP009533297, ISSN: 0019-4522
RAJEEV JAIN ET AL.: "Synthesis of some new 1-carbamoyl-3-aminophenyl- and 1-carbamoyl-3-amino-(2-chlorophenyl)-5-methyl-4-arylazopyrazoles as possible potential antidiabetics", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 66, no. 7, 31 July 1989 (1989-07-31), IN , pages 486 - 489, XP009533298, ISSN: 0019-4522
DIETRICH MODERHACK ET AL.: "1, 2, 5, 6-Tetrazocines from Nitrile Imines and tert-Butyl Isocyanide", J. PRAKT. CHEM., vol. 342, no. 7, 17 August 2000 (2000-08-17), XP055773385, ISSN: 1436-9966, DOI: 20200612155722X
R N GOYAL ET AL.: "Electro-chemical investigations of some acetoacetarylides", INDIAN JOURNAL OF CHEMISTRY, vol. (23A), no. 11, 30 November 1984 (1984-11-30), XP055773388, ISSN: 0376-4710, DOI: 20200612160544X
M. I. ALI ET AL.: "Reactions with acetoacetylaminopyridines", EGYPTIAN JOURNAL OF CHEMISTRY, vol. 30, no. 5, 31 December 1989 (1989-12-31), pages 357 - 368, XP009533332, ISSN: 0367-0422
DATABASE REGISTRY 4 June 2019 (2019-06-04), ANONYMOUS: "INDEX NAME NOT YET ASSIGNED", XP055885789, retrieved from STN Database accession no. 2324187-36-0
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Butanamide, 2-[2-(4-methyl-2-nitrophenyl)diazenyl]-N-(4-methylphenyl)-3- oxo- (CA INDEX NAME)", XP055885865, retrieved from STN Database accession no. 57206-92-5
DATABASE REGISTRY 4 October 2013 (2013-10-04), ANONYMOUS: "2-Propenoic acid, 2,3-dimethyl-4-[2-[2-oxo-1- [(phenylamino)carbonyl]propylidene]hydrazinyl]phenyl ester (CA INDEX NAME)", XP055885792, retrieved from STN Database accession no. 1455518-21-4
DATABASE REGISTRY 5 April 2011 (2011-04-05), ANONYMOUS: "Butanamide, 2-[2-(3-chloro-4-methylphenyl)hydrazinylidene]-3-oxo-N-2- pyridinyl- (CA INDEX NAME)", XP055885794, retrieved from STN Database accession no. 1274906-03-4
DATABASE REGISTRY 10 August 2010 (2010-08-10), ANONYMOUS: "Butanamide, 2-[2-(4-methyl-2-nitrophenyl)hydrazinylidene]-N-(2- methylphenyl)-3-oxo- (CA INDEX NAME)", XP055885795, retrieved from STN Database accession no. 1235682-03-7
DATABASE REGISTRY 26 September 2001 (2001-09-26), ANONYMOUS: "Butanamide, 2-[2-(4-hydroxyphenyl)hydrazinylidene]-3-oxo-N-2-pyridinyl- (CA INDEX NAME)", XP055885799, retrieved from STN Database accession no. 358718-99-7
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) OTHER CA INDEX NAMES", XP055885802, retrieved from STN Database accession no. 331968-10-6
DATABASE REGISTRY 16 April 2001 (2001-04-16), ANONYMOUS: "5-Thiazolecarboxylic acid, 4-methyl-2-[[2-[2-(3- nitrophenyl)hydrazinylidene]-1,3-dioxobutyl]amino]-, ethyl ester (CA INDEX NAME)", XP055885805, retrieved from STN Database accession no. 331416-65-0
DATABASE REGISTRY 18 January 2001 (2001-01-18), ANONYMOUS: "5-Thiazolecarboxylic acid, 4-methyl-2-[[2-[2-(2- methylphenyl)hydrazinylidene]-1,3-dioxobutyl]amino]-, ethyl ester (CA INDEX NAME)", XP055885807, retrieved from STN Database accession no. 314763-74-1
DATABASE REGISTRY 8 March 1996 (1996-03-08), ANONYMOUS: "Butanamide, 3-oxo-2-[2-(4-pentylphenyl)hydrazinylidene]-N-phenyl- (CA INDEX NAME)", XP055885810, retrieved from STN Database accession no. 174011-08-6
DATABASE REGISTRY 8 March 1996 (1996-03-08), ANONYMOUS: "Butanamide, 2-[(4-ethylphenyl)hydrazono]-3-oxo-N-phenyl- (9CI) (CA INDEX NAME)", XP055885813, retrieved from STN Database accession no. 174011-05-3
DATABASE REGISTRY 24 February 1985 (1985-02-24), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(6-hydroxy-m-tolyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885816, retrieved from STN Database accession no. 94959-92-9
DATABASE REGISTRY 9 February 1985 (1985-02-09), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(6-hydroxy-5-nitro-m-tolyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885818, retrieved from STN Database accession no. 94674-38-1
DATABASE REGISTRY 12 January 1985 (1985-01-12), ANONYMOUS: "Butanamide, 2-[(5-chloro-2-hydroxyphenyl)hydrazono]-3-oxo-N-phenyl- (9CI) (CA INDEX NAME)", XP055885828, retrieved from STN Database accession no. 94207-41-7
DATABASE REGISTRY 12 January 1985 (1985-01-12), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(5-chloro-2-hydroxy-3-nitrophenyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885833, retrieved from STN Database accession no. 94207-07-5
DATABASE REGISTRY 12 January 1985 (1985-01-12), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(2-hydroxy-3,5-dinitrophenyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885835, retrieved from STN Database accession no. 94206-41-4
DATABASE REGISTRY 18 December 1984 (1984-12-18), ANONYMOUS: "Butanamide, 2-[(2-hydroxy-5-nitrophenyl)hydrazono]-3-oxo-N-phenyl- (9CI) (CA INDEX NAME)", XP055885837, retrieved from STN Database accession no. 93021-19-3
DATABASE REGISTRY 18 December 1984 (1984-12-18), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(2-hydroxy-4-nitrophenyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885841, retrieved from STN Database accession no. 93021-18-2
DATABASE REGISTRY 18 December 1984 (1984-12-18), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(2-hydroxy-3-nitrophenyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885844, retrieved from STN Database accession no. 93021-17-1
DATABASE REGISTRY 17 December 1984 (1984-12-17), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(3-chloro-2-hydroxy-5-nitrophenyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885847, retrieved from STN Database accession no. 92873-78-4
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Butanamide, N-(2-methylphenyl)-2-[2-(2-methylphenyl)hydrazinylidene]-3-oxo- (CA INDEX NAME)", XP055885850, retrieved from STN Database accession no. 90422-20-1
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Benzoic acid, 4-[2-[1-[[(2,4-dimethylphenyl)amino]carbonyl]-2- oxopropylidene]hydrazinyl]-, ethyl ester (CA INDEX NAME)", XP055885853, retrieved from STN Database accession no. 63239-95-2
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Benzoic acid, 4-[2-[1-[[(2,4-dimethylphenyl)amino]carbonyl]-2- oxopropylidene]hydrazinyl]- (CA INDEX NAME)", XP055885855, retrieved from STN Database accession no. 63239-94-1
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
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: "Butanamide, 3-oxo-N-phenyl-2-[2-(3-pyridinyl)hydrazinylidene]- (CA INDEX NAME)", XP055885860, retrieved from STN Database accession no. 50599-23-0
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See also references of EP 3992184A4
ZHEN MA 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: 2468-8231, DOI: 20200611170818X
QIAN ZHANG ET AL.: "Formal [4+1] annulation of α-aryl hydrazone ketones and dimethylsulfoxonium methylide: one-pot synthesis of substituted pyrazoles and dihydropyrazoles", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 14, 21 June 2016 (2016-06-21), XP055773353, ISSN: 0022-3263, DOI: 20200611171806X
ZHENG LI ET AL.: "The influence of fluorination on the structure and properties of azo pigments", DYES AND PIGMENTS, vol. 128, 3 February 2016 (2016-02-03), XP029461128, ISSN: 0143-7208, DOI: 20200611172511X
PRATIBHA SHARMA ET AL.: "Studies on synthesis and evaluation of quantitative structure-activity relationship of 5-[(3'-chloro-4', 4'-disubstituted-2-oxoazetidinyl)(N-nitro) amino]-6-hydroxy-3-alkyl/aryl [1, 3] azaphospholo [1, 5-a] pyridin-1-yl-phosphorus dichlorides", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 15, no. 4,, 20 January 2005 (2005-01-20), XP027801875, ISSN: 0960-894X, DOI: 20200611173404X
A. S. SHAWALI ET AL.: "Cyanoacetarylamides-I Preparation and reactions of their arylazo derivatives with diazonium ion and Grignard reagents", TETRAHEDRON, vol. 27, no. 10, 31 December 1971 (1971-12-31), XP055773356, ISSN: 0040-4020, DOI: 20200611175051X
C. W. SCHELLHAMMER ET AL.: "ÜBER ALKYLIERUNGEN VON BENZOTRIAZOL-DERIVATEN", TETRAHEDRON, vol. 26, no. 2, 31 December 1970 (1970-12-31), XP002574283, ISSN: 0040-4020, DOI: 20200611180139X
M. A. ABOUTABL ET AL.: "Polarographic behaviour of α- and γ-substituted acetoacetanilide derivatives in alcoholic aqueous media", MONATSHEFTE FÜR CHEMIE, vol. 123, no. 3, 31 March 1992 (1992-03-31), XP055773343, ISSN: 0026-9247, DOI: 20200611180842X
RAJEEV, JAIN ET AL.: "Synthesis of some new arylazopyrazoles and arylazopyrimidines", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 67, no. 6, 30 June 1990 (1990-06-30), IN , pages 516 - 518, XP009533296, ISSN: 0019-4522
ANTONIN LYCKA ET AL.: "15N, 13C and 1H NMR spectra of the 2:1 cobalt (III) complexes of some azo dyes", MAGNETIC RESONANCE IN CHEMISTRY, vol. 28, no. 5, 31 May 1990 (1990-05-31), XP004418122, ISSN: 0749-1581, DOI: 20200611182516X
ANTONIUS KETTRUP ET AL.: "Spektroskopische untersuchungen an substituierten 2, 3-dioxobutyranilide-2-phenylhydrazonen", MONATSHEFTE FÜR CHEMIE, vol. 107, no. 6, 31 December 1976 (1976-12-31), XP055773366, ISSN: 0026-9247, DOI: 20200612114426X
M. A. ZAYED ET AL.: "The use of thermal and spectrometric analyses for the structure investigation of arylhydrazoneacetoacetylaminopyridines and their copper chelates", THERMOCHIMICA ACTA, vol. 146, 31 December 1989 (1989-12-31), XP055773368, ISSN: 0040-6031, DOI: 20200612125417X
ROBERT M. CHRISTIE ET AL.: "Colour and constitution relationships in organic pigments. Part 1. -Monoazoacetoacetanilides", DYES AND PIGMENTS, vol. 9, no. 1, 31 December 1988 (1988-12-31), XP000488262, ISSN: 0143-7208, DOI: 20200612130453X
GREIG CHISHOLM ET AL.: "Comparison of the structural motifs of acetoacetanilides and related azo pigments", ACTA CRYSTALLOGRAPHICA SECTION B: STRUCTURAL SCIENCE, vol. B56, no. 6, 31 December 2000 (2000-12-31), XP055773374, ISSN: 0108-7681, DOI: 20200612141327X
POUL ERIK HANSEN ET AL.: "Long-range intrinsic and equilibrium deuterium isotope effects on 19F chemical shifts", ACTA CHEMICA SCANDINAVICA, vol. 51, no. 8, 31 August 1997 (1997-08-31), XP055773376, ISSN: 0904-213X, DOI: 20200617102722X
A. A. FADDA ET AL.: "Synthesis of azodisperse dyes with pyridine ring for dyeing polyester fibres", INDIAN JOURNAL OF TEXTILE RESEARCH, vol. 11, no. 1, 31 March 1986 (1986-03-31), XP055773379, ISSN: 0377-8436, DOI: 20200612143549X
MURAT ÇAĞLAR HAMZAÇEBI ET AL.: "Synthesis and structure elucidation of hydrazones derived from N-(2, 4-dimethylphenyl)-3-oxobutanamide", ARKIVOC, vol. 2008, no. 12, 21 May 2008 (2008-05-21), XP055773381, ISSN: 1551-7012, DOI: 20200617103153X
K. M. DYUMAEV ET AL.: "Synthesis and structure of 2-(2-phenylhydrazono) acetoacetanilide and its derivatives", ZHURNAL ORGANICHESKOI KHIMII, vol. 14, no. 3, 31 December 1978 (1978-12-31), pages 562`569, XP009533330, ISSN: 0514-7492
KETTRUP ANTONIUS, GROTE MANFRED: "Die Fragmentierung der Azo- und Hydrazontautomeren von 2.3-Dioxobutyranilid-2-phenylhydrazonen in der Gasphase in Abhängigkeit von Substituenten = The fragmentation of azo and hydrazone tautomers of 2, 3-dioxobutyranilide-2-phenylhydrazones in the gaseous state in dependence of substituents", ZEITSCHRIFT FÜR NATURFORSCHUNG, vol. 32b, no. 8, 31 August 1977 (1977-08-31), DE , pages 863 - 868, XP009533295, ISSN: 0340-5087, DOI: 10.1515/znb-1977-0806
RAJEEV, JAIN ET AL.: "Synthesis of some new isonicotinoylazopyrazoles", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 66, no. 5, 31 May 1989 (1989-05-31), IN , pages 350 - 352, XP009533297, ISSN: 0019-4522
RAJEEV JAIN ET AL.: "Synthesis of some new 1-carbamoyl-3-aminophenyl- and 1-carbamoyl-3-amino-(2-chlorophenyl)-5-methyl-4-arylazopyrazoles as possible potential antidiabetics", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 66, no. 7, 31 July 1989 (1989-07-31), IN , pages 486 - 489, XP009533298, ISSN: 0019-4522
DIETRICH MODERHACK ET AL.: "1, 2, 5, 6-Tetrazocines from Nitrile Imines and tert-Butyl Isocyanide", J. PRAKT. CHEM., vol. 342, no. 7, 17 August 2000 (2000-08-17), XP055773385, ISSN: 1436-9966, DOI: 20200612155722X
R N GOYAL ET AL.: "Electro-chemical investigations of some acetoacetarylides", INDIAN JOURNAL OF CHEMISTRY, vol. (23A), no. 11, 30 November 1984 (1984-11-30), XP055773388, ISSN: 0376-4710, DOI: 20200612160544X
M. I. ALI ET AL.: "Reactions with acetoacetylaminopyridines", EGYPTIAN JOURNAL OF CHEMISTRY, vol. 30, no. 5, 31 December 1989 (1989-12-31), pages 357 - 368, XP009533332, ISSN: 0367-0422
DATABASE REGISTRY 4 June 2019 (2019-06-04), ANONYMOUS: "INDEX NAME NOT YET ASSIGNED", XP055885789, retrieved from STN Database accession no. 2324187-36-0
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Butanamide, 2-[2-(4-methyl-2-nitrophenyl)diazenyl]-N-(4-methylphenyl)-3- oxo- (CA INDEX NAME)", XP055885865, retrieved from STN Database accession no. 57206-92-5
DATABASE REGISTRY 4 October 2013 (2013-10-04), ANONYMOUS: "2-Propenoic acid, 2,3-dimethyl-4-[2-[2-oxo-1- [(phenylamino)carbonyl]propylidene]hydrazinyl]phenyl ester (CA INDEX NAME)", XP055885792, retrieved from STN Database accession no. 1455518-21-4
DATABASE REGISTRY 5 April 2011 (2011-04-05), ANONYMOUS: "Butanamide, 2-[2-(3-chloro-4-methylphenyl)hydrazinylidene]-3-oxo-N-2- pyridinyl- (CA INDEX NAME)", XP055885794, retrieved from STN Database accession no. 1274906-03-4
DATABASE REGISTRY 10 August 2010 (2010-08-10), ANONYMOUS: "Butanamide, 2-[2-(4-methyl-2-nitrophenyl)hydrazinylidene]-N-(2- methylphenyl)-3-oxo- (CA INDEX NAME)", XP055885795, retrieved from STN Database accession no. 1235682-03-7
DATABASE REGISTRY 26 September 2001 (2001-09-26), ANONYMOUS: "Butanamide, 2-[2-(4-hydroxyphenyl)hydrazinylidene]-3-oxo-N-2-pyridinyl- (CA INDEX NAME)", XP055885799, retrieved from STN Database accession no. 358718-99-7
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) OTHER CA INDEX NAMES", XP055885802, retrieved from STN Database accession no. 331968-10-6
DATABASE REGISTRY 16 April 2001 (2001-04-16), ANONYMOUS: "5-Thiazolecarboxylic acid, 4-methyl-2-[[2-[2-(3- nitrophenyl)hydrazinylidene]-1,3-dioxobutyl]amino]-, ethyl ester (CA INDEX NAME)", XP055885805, retrieved from STN Database accession no. 331416-65-0
DATABASE REGISTRY 18 January 2001 (2001-01-18), ANONYMOUS: "5-Thiazolecarboxylic acid, 4-methyl-2-[[2-[2-(2- methylphenyl)hydrazinylidene]-1,3-dioxobutyl]amino]-, ethyl ester (CA INDEX NAME)", XP055885807, retrieved from STN Database accession no. 314763-74-1
DATABASE REGISTRY 8 March 1996 (1996-03-08), ANONYMOUS: "Butanamide, 3-oxo-2-[2-(4-pentylphenyl)hydrazinylidene]-N-phenyl- (CA INDEX NAME)", XP055885810, retrieved from STN Database accession no. 174011-08-6
DATABASE REGISTRY 8 March 1996 (1996-03-08), ANONYMOUS: "Butanamide, 2-[(4-ethylphenyl)hydrazono]-3-oxo-N-phenyl- (9CI) (CA INDEX NAME)", XP055885813, retrieved from STN Database accession no. 174011-05-3
DATABASE REGISTRY 24 February 1985 (1985-02-24), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(6-hydroxy-m-tolyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885816, retrieved from STN Database accession no. 94959-92-9
DATABASE REGISTRY 9 February 1985 (1985-02-09), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(6-hydroxy-5-nitro-m-tolyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885818, retrieved from STN Database accession no. 94674-38-1
DATABASE REGISTRY 12 January 1985 (1985-01-12), ANONYMOUS: "Butanamide, 2-[(5-chloro-2-hydroxyphenyl)hydrazono]-3-oxo-N-phenyl- (9CI) (CA INDEX NAME)", XP055885828, retrieved from STN Database accession no. 94207-41-7
DATABASE REGISTRY 12 January 1985 (1985-01-12), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(5-chloro-2-hydroxy-3-nitrophenyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885833, retrieved from STN Database accession no. 94207-07-5
DATABASE REGISTRY 12 January 1985 (1985-01-12), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(2-hydroxy-3,5-dinitrophenyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885835, retrieved from STN Database accession no. 94206-41-4
DATABASE REGISTRY 18 December 1984 (1984-12-18), ANONYMOUS: "Butanamide, 2-[(2-hydroxy-5-nitrophenyl)hydrazono]-3-oxo-N-phenyl- (9CI) (CA INDEX NAME)", XP055885837, retrieved from STN Database accession no. 93021-19-3
DATABASE REGISTRY 18 December 1984 (1984-12-18), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(2-hydroxy-4-nitrophenyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885841, retrieved from STN Database accession no. 93021-18-2
DATABASE REGISTRY 18 December 1984 (1984-12-18), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(2-hydroxy-3-nitrophenyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885844, retrieved from STN Database accession no. 93021-17-1
DATABASE REGISTRY 17 December 1984 (1984-12-17), ANONYMOUS: "Butyranilide, 2,3-dioxo-, 2-[(3-chloro-2-hydroxy-5-nitrophenyl)hydrazone] (7CI) (CA INDEX NAME)", XP055885847, retrieved from STN Database accession no. 92873-78-4
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Butanamide, N-(2-methylphenyl)-2-[2-(2-methylphenyl)hydrazinylidene]-3-oxo- (CA INDEX NAME)", XP055885850, retrieved from STN Database accession no. 90422-20-1
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Benzoic acid, 4-[2-[1-[[(2,4-dimethylphenyl)amino]carbonyl]-2- oxopropylidene]hydrazinyl]-, ethyl ester (CA INDEX NAME)", XP055885853, retrieved from STN Database accession no. 63239-95-2
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS: "Benzoic acid, 4-[2-[1-[[(2,4-dimethylphenyl)amino]carbonyl]-2- oxopropylidene]hydrazinyl]- (CA INDEX NAME)", XP055885855, retrieved from STN Database accession no. 63239-94-1
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
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: "Butanamide, 3-oxo-N-phenyl-2-[2-(3-pyridinyl)hydrazinylidene]- (CA INDEX NAME)", XP055885860, retrieved from STN Database accession no. 50599-23-0
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See also references of EP 3992184A4
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