Title:
SMALL MOLECULE INHIBITORS OF ACETYL COENZYME A SYNTHETASE SHORT CHAIN 2 (ACSS2)
Document Type and Number:
WIPO Patent Application WO/2021/014415
Kind Code:
A3
Abstract:
The present invention relates to compounds of formula (I). The compounds may be used to modulate the acetyl coenzyme A synthetase short chain2(ACSS2) protein and may thereby treat, ameliorate or prevent a disease selected from cancer, bacterial infection, viral infection, parasitic infection, fungal infection, neurodegenerative disease, neurological disorder, cerebrovascular disease, cardiovascular disease, non-alcoholic fatty liver disease and obesity. Alternatively, or additionally, the compounds may be used to promote healthy ageing. (I)
Inventors:
BASU SOURAV (IN)
YADAV B (IN)
GHOSH RAJIB (IN)
SHRIVASTAVA RITESH (IN)
MIDDYA SANDIP (IN)
PRYDE DAVID (GB)
BANERJEE MONALI (IN)
SURYA ARJUN (IN)
YADAV B (IN)
GHOSH RAJIB (IN)
SHRIVASTAVA RITESH (IN)
MIDDYA SANDIP (IN)
PRYDE DAVID (GB)
BANERJEE MONALI (IN)
SURYA ARJUN (IN)
Application Number:
PCT/IB2020/057007
Publication Date:
March 04, 2021
Filing Date:
July 24, 2020
Export Citation:
Assignee:
CURADEV PHARMA PVT LTD (IN)
International Classes:
C07D215/233; A61K31/4375; A61K31/47; A61K31/4706; A61K31/4725; A61K31/5025; A61P1/16; A61P3/04; A61P9/00; A61P25/00; A61P31/04; A61P31/10; A61P31/12; A61P33/00; A61P35/00; C07D215/38; C07D215/42; C07D215/48; C07D401/04; C07D401/12; C07D401/14; C07D405/12; C07D413/04; C07D471/04
Domestic Patent References:
| WO2003045313A2 | 2003-06-05 | |||
| WO2007093402A1 | 2007-08-23 | |||
| WO2012080284A2 | 2012-06-21 | |||
| WO2019067528A1 | 2019-04-04 | |||
| WO2011082270A2 | 2011-07-07 | |||
| WO2001053274A1 | 2001-07-26 | |||
| WO2003045920A1 | 2003-06-05 | |||
| WO2011119693A1 | 2011-09-29 | |||
| WO2004014860A2 | 2004-02-19 |
Foreign References:
| EP2727920A1 | 2014-05-07 | |||
| EP1072263A1 | 2001-01-31 | |||
| EP0507594A1 | 1992-10-07 | |||
| US2650226A | 1953-08-25 |
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MADAPA S ET AL: "Search for new pharmacophores for antimalarial activity. Part I: Synthesis and antimalarial activity of new 2-methyl-6-ureido-4-quinolinamides", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, NL, vol. 17, no. 1, 1 January 2009 (2009-01-01), pages 203 - 221, XP025875990, ISSN: 0968-0896, [retrieved on 20081118], DOI: 10.1016/J.BMC.2008.11.021
UPADHAYAYA RAM SHANKAR ET AL: "New antiprotozoal agents: Their synthesis and biological evaluations", BIORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 23, no. 9, 22 February 2013 (2013-02-22), pages 2750 - 2758, XP028546930, ISSN: 0960-894X, DOI: 10.1016/J.BMCL.2013.02.054
HIRONOBU MAEZAKI ET AL: "Discovery of potent, selective, and orally bioavailable quinoline-based dipeptidyl peptidase IV inhibitors targeting Lys554", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, NL, vol. 19, no. 15, 10 June 2011 (2011-06-10), pages 4482 - 4498, XP028241209, ISSN: 0968-0896, [retrieved on 20110618], DOI: 10.1016/J.BMC.2011.06.032
L V GYUL 'BUDAGYAN ET AL: "2-DICH LOROMETHYL-4-METHYL-2,3-DIHYDROFURO[3,2-c] - QUINOLINE DERIVATIVES", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 9, 1 January 1973 (1973-01-01), pages 73 - 75, XP055758844
L V GYUL 'BUDAGYAN ET AL: "QUINALDINE DERIVATIVES XXVI.* SYNTHESES OF SUBSTITUTED 3,4-DIHYDRO-2H- P YRANO [3,2-c ]QUINOLINES", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 8, 1 January 1972 (1972-01-01), pages 487 - 490, XP055758846
A K MALLAMS ET AL: "The Reaction between /3-Keto Esters and Arylamines in the Presence of Polyphosphoric Acid. II.1 Ethyl Acetoacetate and Its -Alkyl Derivatives and Arylamines", J. ORG. CHEM. CHEM. IND, 1 January 1961 (1961-01-01), pages 944 - 1649, XP055759136, Retrieved from the Internet
HEINRICH JENSCH: "Die Bedeutung von Kern-Methylgruppen in einigen chemotherapeutisch wirksamen Verbindungen der 4-Aminochinolin-Reihe", JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 568, no. 1, 20 April 1950 (1950-04-20), DE, pages 73 - 82, XP055666712, ISSN: 0075-4617, DOI: 10.1002/jlac.19505680107
GYUL'BUDAGYAN ET AL: "QUINALDINE DERIVATIVES XXII. 3- (m-DICHLORALLYL) -4.6-DIAMINOQUINALDINE", ARMYANSKII KHIMICHESKII ZHURNAL/ AIKAKAN HIMIAKAN AMSAGIR/ ARMENIAN CHEMICAL JOURNAL, AKADEMIYA NAUK ARMENII, EREVAN, AI, vol. 24, 1 January 1971 (1971-01-01), pages 537, XP009524556, ISSN: 0515-9628
GYUL'BUDAGYAN ET AL: "New derivatives of 4-quinaldinol - Communication VI. 3- (t-Chlorallyl) -6-amno-4-quina.1dinol and its transformations", INVESTI AKADEMIINAUK ARMANSKOJ SSR. HIMICESKIE NAUKI, EREVAN, AM, vol. 15, 1 January 1962 (1962-01-01), pages 199 - 203, XP009524560, ISSN: 0367-6846
GYUL'BUDAGYAN: "New derivatives of 4-quinaldinol -Communication V. 2-Methyl-3- (l-alkoxybenzyl) -4-hydroxy-6-aminoquinolines and their derivatives", INVESTI AKADEMIINAUK ARMANSKOJ SSR. HIMICESKIE NAUKI, EREVAN, AM, vol. 15, 1 January 1962 (1962-01-01), pages 191 - 197, XP009524561, ISSN: 0367-6846
NICKEL ET AL: "Antimalarial 6-aminoquinolines XI / Gegen Malaria wirksame 6-Aminochinoline", ARZNEIMITTEL FORSCHUNG. DRUG RESEARCH, ECV EDITIO CANTOR VERLAG, AULENDORF, DE, vol. 28, no. 5, 1 January 1978 (1978-01-01), pages 723 - 731, XP009524575, ISSN: 0004-4172
BATT D G ET AL: "Immunosuppressive structure-activity relationships of Brequinar and related cinchoninic acid derivatives", BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS,, vol. 5, no. 14, 20 July 1995 (1995-07-20), pages 1549 - 1554, XP004135444, ISSN: 0960-894X, DOI: 10.1016/0960-894X(95)00252-O
SESTILI I ET AL: "A new synthetic approach of N-(4-amino-2-methylquinolin-6-yl)-2-(4-ethylphenoxymethyl)benzamide (JTC-801) and its analogues and their pharmacological evaluation as nociceptin receptor (NOP) antagonists", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 39, no. 12, 1 December 2004 (2004-12-01), pages 1047 - 1057, XP004663680, ISSN: 0223-5234, DOI: 10.1016/J.EJMECH.2004.09.009
PETER NICKEL ET AL: "2-, 3-, 4-Mono-, Di- and Trimethylderivate von 6-(4-Diäthylamino-1-methylbutylamino)-5,6-dimethoxychinolin", JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 2, 1 January 1976 (1976-01-01), pages 367 - 382, XP055743510
JIA-CHEN XING ET AL: "Divergent Synthesis of Functionalized Quinolines from Aniline and Two Distinct Amino Acids", JOURNAL OF ORGANIC CHEMISTRY, vol. 82, no. 17, 1 January 2017 (2017-01-01), pages 9210 - 9216, XP055743514
JOHN D. WILLIAMS ET AL: "Small molecule inhibitors of anthrax lethal factor toxin", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 22, no. 1, 1 January 2014 (2014-01-01), NL, pages 419 - 434, XP055758696, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2013.11.009
BHAVIN MARVANIA ET AL: "The synthesis and biological evaluation of new DNA-directed alkylating agents, phenyl N-mustard-4-anilinoquinoline conjugates containing a urea linker", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 83, 1 August 2014 (2014-08-01), NL, pages 695 - 708, XP055334281, ISSN: 0223-5234, DOI: 10.1016/j.ejmech.2014.06.066
MADAPA S ET AL: "Search for new pharmacophores for antimalarial activity. Part I: Synthesis and antimalarial activity of new 2-methyl-6-ureido-4-quinolinamides", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, NL, vol. 17, no. 1, 1 January 2009 (2009-01-01), pages 203 - 221, XP025875990, ISSN: 0968-0896, [retrieved on 20081118], DOI: 10.1016/J.BMC.2008.11.021
UPADHAYAYA RAM SHANKAR ET AL: "New antiprotozoal agents: Their synthesis and biological evaluations", BIORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 23, no. 9, 22 February 2013 (2013-02-22), pages 2750 - 2758, XP028546930, ISSN: 0960-894X, DOI: 10.1016/J.BMCL.2013.02.054
HIRONOBU MAEZAKI ET AL: "Discovery of potent, selective, and orally bioavailable quinoline-based dipeptidyl peptidase IV inhibitors targeting Lys554", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, NL, vol. 19, no. 15, 10 June 2011 (2011-06-10), pages 4482 - 4498, XP028241209, ISSN: 0968-0896, [retrieved on 20110618], DOI: 10.1016/J.BMC.2011.06.032
L V GYUL 'BUDAGYAN ET AL: "2-DICH LOROMETHYL-4-METHYL-2,3-DIHYDROFURO[3,2-c] - QUINOLINE DERIVATIVES", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 9, 1 January 1973 (1973-01-01), pages 73 - 75, XP055758844
L V GYUL 'BUDAGYAN ET AL: "QUINALDINE DERIVATIVES XXVI.* SYNTHESES OF SUBSTITUTED 3,4-DIHYDRO-2H- P YRANO [3,2-c ]QUINOLINES", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 8, 1 January 1972 (1972-01-01), pages 487 - 490, XP055758846
A K MALLAMS ET AL: "The Reaction between /3-Keto Esters and Arylamines in the Presence of Polyphosphoric Acid. II.1 Ethyl Acetoacetate and Its -Alkyl Derivatives and Arylamines", J. ORG. CHEM. CHEM. IND, 1 January 1961 (1961-01-01), pages 944 - 1649, XP055759136, Retrieved from the Internet
HEINRICH JENSCH: "Die Bedeutung von Kern-Methylgruppen in einigen chemotherapeutisch wirksamen Verbindungen der 4-Aminochinolin-Reihe", JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 568, no. 1, 20 April 1950 (1950-04-20), DE, pages 73 - 82, XP055666712, ISSN: 0075-4617, DOI: 10.1002/jlac.19505680107
GYUL'BUDAGYAN ET AL: "QUINALDINE DERIVATIVES XXII. 3- (m-DICHLORALLYL) -4.6-DIAMINOQUINALDINE", ARMYANSKII KHIMICHESKII ZHURNAL/ AIKAKAN HIMIAKAN AMSAGIR/ ARMENIAN CHEMICAL JOURNAL, AKADEMIYA NAUK ARMENII, EREVAN, AI, vol. 24, 1 January 1971 (1971-01-01), pages 537, XP009524556, ISSN: 0515-9628
GYUL'BUDAGYAN ET AL: "New derivatives of 4-quinaldinol - Communication VI. 3- (t-Chlorallyl) -6-amno-4-quina.1dinol and its transformations", INVESTI AKADEMIINAUK ARMANSKOJ SSR. HIMICESKIE NAUKI, EREVAN, AM, vol. 15, 1 January 1962 (1962-01-01), pages 199 - 203, XP009524560, ISSN: 0367-6846
GYUL'BUDAGYAN: "New derivatives of 4-quinaldinol -Communication V. 2-Methyl-3- (l-alkoxybenzyl) -4-hydroxy-6-aminoquinolines and their derivatives", INVESTI AKADEMIINAUK ARMANSKOJ SSR. HIMICESKIE NAUKI, EREVAN, AM, vol. 15, 1 January 1962 (1962-01-01), pages 191 - 197, XP009524561, ISSN: 0367-6846
NICKEL ET AL: "Antimalarial 6-aminoquinolines XI / Gegen Malaria wirksame 6-Aminochinoline", ARZNEIMITTEL FORSCHUNG. DRUG RESEARCH, ECV EDITIO CANTOR VERLAG, AULENDORF, DE, vol. 28, no. 5, 1 January 1978 (1978-01-01), pages 723 - 731, XP009524575, ISSN: 0004-4172
Attorney, Agent or Firm:
GARG, Vidisha et al. (IN)
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