Title:
AKR1C3 INHIBITOR AND MEDICAL USE
Document Type and Number:
WIPO Patent Application WO/2021/000862
Kind Code:
A1
Abstract:
The present invention provides an AKR1C3 inhibitor of compounds of the following formulas and pharmaceutically acceptable salts or solvates or isotopically substituted compounds thereof and medical use.
Inventors:
DUAN JIANXIN (CN)
LI ANRONG (CN)
MENG FANYING (US)
CAI XIAOHONG (CN)
LI ANRONG (CN)
MENG FANYING (US)
CAI XIAOHONG (CN)
Application Number:
PCT/CN2020/099353
Publication Date:
January 07, 2021
Filing Date:
June 30, 2020
Export Citation:
Assignee:
ASCENTAWITS PHARMACEUTICALS LTD (CN)
International Classes:
C07C33/20; A61K31/04; A61K31/06; A61K31/664; A61P35/00; C07B55/00; C07C205/38; C07F9/22; C07F9/564
Domestic Patent References:
| WO2019062919A1 | 2019-04-04 | |||
| WO2016145092A1 | 2016-09-15 | |||
| WO2017087428A1 | 2017-05-26 | |||
| WO2016161342A2 | 2016-10-06 | |||
| WO2017202817A1 | 2017-11-30 |
Foreign References:
| CN110693892A | 2020-01-17 | |||
| CN108136214A | 2018-06-08 | |||
| CN107530556A | 2018-01-02 | |||
| CN108290911A | 2018-07-17 | |||
| US20040214798A1 | 2004-10-28 | |||
| CN102924507A | 2013-02-13 | |||
| CN109897085A | 2019-06-18 | |||
| US20160021581W | 2016-03-09 | |||
| US20160062114W | 2016-11-15 | |||
| US20160025665W | 2016-04-01 | |||
| TW201742868A | 2017-12-16 | |||
| AU2017269871A1 | 2018-11-15 | |||
| US20180319807A2 | 2018-11-08 | |||
| US20170342082A1 | 2017-11-30 |
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BARAN NKONOPLEVA M: "Molecular Pathways:Hypoxia-activated prodrugs in cancer therapy[J", CLINICAL CANCER RESEARCH, 2017
CINDY CAZARES-KORNERISABEL M.PIRESI.DIANE SWALLOW ET AL.: "CH-01 is a Hypoxia-Activated Prodrug That Sensitizes Cells to Hypoxia/Reoxygenation Through Inhibition of Chkl and Aurora A[J", ACS CHEM.BIOL., vol. 8, no. 7, 2013, pages 1451
"Potent and Highly Selective Hypoxia-Activated Achiral Phosphoramidate Mustards as Anticancer Drugs[J", JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, no. 8, 2008, pages 2412 - 2420
JAMESON M BRISCHIN DPEGRAM M ET AL.: "A phase I trial of PR-104, a nitrogen mustard prodrug activated by both hypoxia and aldo-keto reductase 1C3, in patients with solid tumors[J", CANCER CHEMOTHERAPY & PHARMACOLOGY, vol. 65, no. 4, 2010, pages 791 - 801, XP019779243
HUNTER F WWOUTERS B GWILSON W R: "Hypoxia-activated prodrugs: paths forward in the era of personalised medicine[J", BRITISH JOURNAL OF CANCER, 2016
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BAINS O SGRIGLIATTI T AREID R E ET AL.: "Naturally occurring variants of human aldo-keto reductases with reduced in vitro metabolism of daunorubicin and doxorubicin.[J", JOURNAL OF PHARMACOLOGY & EXPERIMENTAL THERAPEUTICS, vol. 335, no. 3, 2010, pages 533 - 545
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LEGRORICHARD SBRZYSKI ROBERT GDIAMOND MICHAE P: "Letrozole versus Clomiphene for Infertility in the Polycystic Ovary Syndrome[J", NEW ENGLAND JOURNAL OF MEDICINE, vol. 371, no. 2, 2014, pages 119 - 129
TAPONEN SMARTIKAINEN HJARVELIN M R: "Metabolic Cardiovascular Disease Risk Factors in Women With Self-Reported Symptoms of Oligomenorrhea and/or Hirsutism: Northern Finland Birth Cohort 1966 Study[J", JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM, vol. 89, no. 5, 2004, pages 2114 - 8
MANI HLEVY MJDAVIES MJ ET AL.: "Diabetes and cardiovascular events in women with polycystic ovary syndrome; a 20-year retrospective cohort study[J", CLIN ENDOCRINOL, vol. 78, no. 6, 2013, pages 926 - 934
O'REILLYMICHAEL WTAYLOR A ECRABTREE N J ET AL.: "Hyperandrogenemia predicts metabolic phenotype in polycystic ovary syndrome: the utility of serum androstenedione[J", THE JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM, 2014
FRANKS SGHARANI NGILLING-SMITH C: "Polycystic ovary syndrome: evidence for a primary disorder of ovarian steroidogenesis[J", JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, vol. 69, 1999, pages 269 - 272, XP027377507
QUINKLER MSINHA BTOMLINSON JWBUJALSKA IJSTEWART PM: "Arlt W(2004) Androgen generation in adipose tissue in women with simple obesity a site-specific role for 17{beta}-hydroxysteroid dehydrogenase type 5. [J", J ENDOCRINOL, vol. 183, 2004, pages 331 - 342
CAPPER F ET AL.: "Effect of insulin on AKR1C3 expression in female adipose tissue: in-vivo and in-vitro study of adipose androgen generation in polycystic ovary syndrome[J", THE LANCET, 2015, pages 385
LAN QMUMFORD JLSHEN MDEMARINI DMBONNER MRHE XYEAGER MWELCH RCHANOCK STIAN L: "Oxidative damage-related genes AKR1C3 and OGG1 modulate risks for lung cancer due to exposure to PAH-rich coal combustion emissions", CARCINOGENESIS, vol. 25, no. 11, 2004, pages 2177 - 2181
LAN QZHENG TSHEN M ET AL.: "Genetic polymorphisms in the oxidative stress pathway and susceptibility to non-Hodgkin lymphoma", HUM GENET, vol. 121, 2007, pages 161 - 168, XP019492043
FIGUEROA J DNURIA MALATSMONTSERRAT GARCIA-CLOSAS ET AL.: "Bladder cancer risk and genetic variation in AKR1C3 and other metabolizing genes [J", CARCINOGENESIS, vol. 29, no. 10, 2008, pages 1955 - 62
BIRTWISTLE JHAYDEN R EKHANIM F L ET AL.: "The aldo-keto reductase AKR1C3 contributes to 7, 12-dimethylbenz(a)anthracene-3, 4-dihydrodiol mediated oxidative DNA damage in myeloid cells: Implications for leukemogenesis[J", MUTATION RESEARCH, vol. 662, no. 1-2, 2009, pages 67 - 74, XP025963214, DOI: 10.1016/j.mrfmmm.2008.12.010
BYRNS M CDUAN LLEE S H ET AL.: "Aldo-keto reductase 1C3 expression in MCF-7 cells reveals roles in steroid hormone and prostaglandin metabolism that may explain its over-expression in breast cancer[J", J STEROID BIOCHEM MOL BIOL, vol. 118, no. 3, 2010, pages 0 - 187, XP026866600
GHEREZGHIHER A ET AL.: "Expression of AKR1C3 in renal cell carcinoma, papillary urothelial carcinoma, and Wilms' tumor[J", INTERNATIONAL JOURNAL OF CLINICAL & EXPERIMENTAL PATHOLOGY, vol. 3, no. 2, 2010, pages 147
MILLER: "Aldo-keto reductase family 1 member C3 (AKR1C3) is expressed in adenocarcinoma and squamous cell carcinoma but not small cell carcinoma. [J", INT. J. CLIN. EXP. PATH., vol. 5, 2012, pages 278 - 289
STANBROUGH M: "Increased expression of genes converting in androgen-independent prostate cancer[J", CANCER RES, vol. 66, 2006, pages 2815 - 25, XP002639099, DOI: 10.1158/0008-5472.CAN-05-4000
WAKO KKAWASAKI TYAMANA K ET AL.: "Expression of androgen receptor through androgen-converting enzymes is associated with biological aggressiveness in prostate cancer", J CLIN PATHOL, vol. 61, no. 4, April 2008 (2008-04-01), pages 448 - 54
PENNING T MSTECKELBROECK SBAUMAN D R ET AL.: "Aldo-keto reductase (AKR) 1C3: role in prostate disease and the development of specific inhibitors.[J", MOLECULAR & CELLULAR ENDOCRINOLOGY, vol. 248, 2006, pages 182 - 191, XP025020590, DOI: 10.1016/j.mce.2005.12.009
LIU CLOU WZHU Y ET AL.: "Intracrine Androgens and AKR1C3 Activation Confer Resistance to Enzalutamide in Prostate Cancer[J", CANCER RESEARCH, vol. 75, no. 7, 2015, pages 1413 - 1422
FUNG, K-M: "Increased expression of type 2 3-hydroxysteroid dehydrogenase/type 5 17-hydroxysteroid dehydrogenase (AKR1C3) and its relationship with androgen receptor in prostate carcinoma[J", ENDOCRINE RELATED CANCER, vol. 13, no. 1, 2006, pages 169 - 180
STANBROUGH, CANCER RES, vol. 66, 2006, pages 2815 - 2825
HAMID ARPFEIFFER MJVERHAEGH GWSCHAAFSMA EBRANDT ASWEEP FCSEDELAAR JPSCHALKEN JA.: "Aldo-keto reductase family 1 member C3 (AKR1C3) is a biomarker and therapeutic target for castration-resistant prostate cancer", MOL. MED., vol. 18, 2012, pages 1449 - 1455, XP055296681, DOI: 10.2119/molmed.2012.00296
PFEIFFER MJSMIT FPSEDELAAR JP ET AL.: "Steroidogenic enzymes and stem cell markers are upregulated during androgen deprivation in prostate cancer", MOL MED, vol. 17, 2011, pages 657 - 664
MOSTAGHEL, CLIN CANCER RES, vol. 17, 2011, pages 5913 - 5925
CAI, CANCER RES, vol. 71, 2011, pages 6503 - 6513
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LORIOT, INVEST NEW DRUGS, vol. 32, 2014, pages 995 - 1004
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HEIBEIN, BMC CANCER, vol. 12, 2012, pages 381
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HOFMAN, TOXICOLOGY AND APPLIED PHARMACOLOGY, vol. 278, 2014, pages 238 - 248
SUN ET AL.: "Overexpression of AKR1C3 significantly enhances human prostate cancer cells resistance to radiation", ONCOTARGET, vol. 7, no. 30, 26 July 2016 (2016-07-26), pages 48050 - 48058
XIONG ET AL.: "Elevated Expression of AKR1C3 Increases Resistance of Cancer Cells to Ionizing Radiation via Modulation of Oxidative Stress", PLOS ONE, vol. 9, no. 11, 2014, pages e111911
XIE ET AL.: "Aldo-keto reductase 1C3 may be a new radioresistance marker in non-small-cell lung cancer", CANCER GENE THER, vol. 20, no. 4, April 2013 (2013-04-01), pages 260 - 6
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ROGER M. PHILLIPS: "Targeting the hypoxic fraction of tumours using hypoxia-activated prodrugs[J", CANCER CHEMOTHER PHARMACOL, vol. 77, 2016, pages 441 - 457, XP035872944, DOI: 10.1007/s00280-015-2920-7
BARAN NKONOPLEVA M: "Molecular Pathways:Hypoxia-activated prodrugs in cancer therapy[J", CLINICAL CANCER RESEARCH, 2017
CINDY CAZARES-KORNERISABEL M.PIRESI.DIANE SWALLOW ET AL.: "CH-01 is a Hypoxia-Activated Prodrug That Sensitizes Cells to Hypoxia/Reoxygenation Through Inhibition of Chkl and Aurora A[J", ACS CHEM.BIOL., vol. 8, no. 7, 2013, pages 1451
"Potent and Highly Selective Hypoxia-Activated Achiral Phosphoramidate Mustards as Anticancer Drugs[J", JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, no. 8, 2008, pages 2412 - 2420
JAMESON M BRISCHIN DPEGRAM M ET AL.: "A phase I trial of PR-104, a nitrogen mustard prodrug activated by both hypoxia and aldo-keto reductase 1C3, in patients with solid tumors[J", CANCER CHEMOTHERAPY & PHARMACOLOGY, vol. 65, no. 4, 2010, pages 791 - 801, XP019779243
HUNTER F WWOUTERS B GWILSON W R: "Hypoxia-activated prodrugs: paths forward in the era of personalised medicine[J", BRITISH JOURNAL OF CANCER, 2016
"Pre-clinical activity of PR-104 as monotherapy and in combination with sorafenib in hepatocellular carcinoma[J", CANCER BIOLOGY & THERAPY, vol. 16, no. 4, 2015, pages 610 - 622
LABRIE FLUU-THE VLABRIE C ET AL.: "DHEA and Its Transformation into Androgens and Estrogens in Peripheral Target Tissues: Intracrinology[J", FRONTIERS IN NEUROENDOCRINOLOGY, vol. 22, no. 3, 2001, pages 185 - 212, XP002247732
BAINS O SGRIGLIATTI T AREID R E ET AL.: "Naturally occurring variants of human aldo-keto reductases with reduced in vitro metabolism of daunorubicin and doxorubicin.[J", JOURNAL OF PHARMACOLOGY & EXPERIMENTAL THERAPEUTICS, vol. 335, no. 3, 2010, pages 533 - 545
NOVOTNA RWSOL VXIONG G ET AL.: "Inactivation of the anticancer drugs doxorubicin and oracin by aldo-keto reductase (AKR) 1C3[J", TOXICOLOGY LETTERS, vol. 181, no. l, 2008, pages 1 - 6, XP024525175, DOI: 10.1016/j.toxlet.2008.06.858
HOFMAN JMALCEKOVA BSKARKA A ET AL.: "Anthracycline resistance mediated by reductive metabolism in cancer cells: The role of aldo-keto reductase 1C3[J", TOXICOLOGY AND APPLIED PHARMACOLOGY, vol. 278, no. 3, 2014, pages 238 - 248, XP028854644, DOI: 10.1016/j.taap.2014.04.027
HUHTINEN KDESAI RSTAHLEE M ET AL.: "Endometrial and Endometriotic Concentrations of Estrone and Estradiol Are Determined by Local Metabolism Rather than Circulating Levels[J", THE JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM, vol. 97, no. 11, 2012, pages 4228 - 4235
TINA SMUCHEVIR NMARTINA RIBICPUCELJ ET AL.: "Disturbed estrogen and progesterone action in ovarian endometriosis[J", MOLECULAR & CELLULAR ENDOCRINOLOGY, vol. 301, no. 1, 2009, pages 59 - 64, XP025953147, DOI: 10.1016/j.mce.2008.07.020
FANG Y: "Insulin resistance and the polycystic ovary syndrome: Mechanism and implications for pathogenesis[J", ENDOCRINE REVIEWS, vol. 18, no. 6, 1998, pages 774 - 800, XP055434584, DOI: 10.1210/er.18.6.774
AZZIZ RCARMINA EDEWAILLY DDIAMANTI-KANDARAKIS EESCOBAR-MORREALE HFFUTTERWEIT W ET AL.: "Position statement: criteria for defining polycystic ovary syndrome as a predominantly hyperandrogenic syndrome: an Androgen Excess Society.[J", CLIN ENDOCRINOL METAB, vol. 91, 2006, pages 4237 - 45
LEGRORICHARD SBRZYSKI ROBERT GDIAMOND MICHAE P: "Letrozole versus Clomiphene for Infertility in the Polycystic Ovary Syndrome[J", NEW ENGLAND JOURNAL OF MEDICINE, vol. 371, no. 2, 2014, pages 119 - 129
TAPONEN SMARTIKAINEN HJARVELIN M R: "Metabolic Cardiovascular Disease Risk Factors in Women With Self-Reported Symptoms of Oligomenorrhea and/or Hirsutism: Northern Finland Birth Cohort 1966 Study[J", JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM, vol. 89, no. 5, 2004, pages 2114 - 8
MANI HLEVY MJDAVIES MJ ET AL.: "Diabetes and cardiovascular events in women with polycystic ovary syndrome; a 20-year retrospective cohort study[J", CLIN ENDOCRINOL, vol. 78, no. 6, 2013, pages 926 - 934
O'REILLYMICHAEL WTAYLOR A ECRABTREE N J ET AL.: "Hyperandrogenemia predicts metabolic phenotype in polycystic ovary syndrome: the utility of serum androstenedione[J", THE JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM, 2014
FRANKS SGHARANI NGILLING-SMITH C: "Polycystic ovary syndrome: evidence for a primary disorder of ovarian steroidogenesis[J", JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, vol. 69, 1999, pages 269 - 272, XP027377507
QUINKLER MSINHA BTOMLINSON JWBUJALSKA IJSTEWART PM: "Arlt W(2004) Androgen generation in adipose tissue in women with simple obesity a site-specific role for 17{beta}-hydroxysteroid dehydrogenase type 5. [J", J ENDOCRINOL, vol. 183, 2004, pages 331 - 342
CAPPER F ET AL.: "Effect of insulin on AKR1C3 expression in female adipose tissue: in-vivo and in-vitro study of adipose androgen generation in polycystic ovary syndrome[J", THE LANCET, 2015, pages 385
LAN QMUMFORD JLSHEN MDEMARINI DMBONNER MRHE XYEAGER MWELCH RCHANOCK STIAN L: "Oxidative damage-related genes AKR1C3 and OGG1 modulate risks for lung cancer due to exposure to PAH-rich coal combustion emissions", CARCINOGENESIS, vol. 25, no. 11, 2004, pages 2177 - 2181
LAN QZHENG TSHEN M ET AL.: "Genetic polymorphisms in the oxidative stress pathway and susceptibility to non-Hodgkin lymphoma", HUM GENET, vol. 121, 2007, pages 161 - 168, XP019492043
FIGUEROA J DNURIA MALATSMONTSERRAT GARCIA-CLOSAS ET AL.: "Bladder cancer risk and genetic variation in AKR1C3 and other metabolizing genes [J", CARCINOGENESIS, vol. 29, no. 10, 2008, pages 1955 - 62
BIRTWISTLE JHAYDEN R EKHANIM F L ET AL.: "The aldo-keto reductase AKR1C3 contributes to 7, 12-dimethylbenz(a)anthracene-3, 4-dihydrodiol mediated oxidative DNA damage in myeloid cells: Implications for leukemogenesis[J", MUTATION RESEARCH, vol. 662, no. 1-2, 2009, pages 67 - 74, XP025963214, DOI: 10.1016/j.mrfmmm.2008.12.010
BYRNS M CDUAN LLEE S H ET AL.: "Aldo-keto reductase 1C3 expression in MCF-7 cells reveals roles in steroid hormone and prostaglandin metabolism that may explain its over-expression in breast cancer[J", J STEROID BIOCHEM MOL BIOL, vol. 118, no. 3, 2010, pages 0 - 187, XP026866600
GHEREZGHIHER A ET AL.: "Expression of AKR1C3 in renal cell carcinoma, papillary urothelial carcinoma, and Wilms' tumor[J", INTERNATIONAL JOURNAL OF CLINICAL & EXPERIMENTAL PATHOLOGY, vol. 3, no. 2, 2010, pages 147
MILLER: "Aldo-keto reductase family 1 member C3 (AKR1C3) is expressed in adenocarcinoma and squamous cell carcinoma but not small cell carcinoma. [J", INT. J. CLIN. EXP. PATH., vol. 5, 2012, pages 278 - 289
STANBROUGH M: "Increased expression of genes converting in androgen-independent prostate cancer[J", CANCER RES, vol. 66, 2006, pages 2815 - 25, XP002639099, DOI: 10.1158/0008-5472.CAN-05-4000
WAKO KKAWASAKI TYAMANA K ET AL.: "Expression of androgen receptor through androgen-converting enzymes is associated with biological aggressiveness in prostate cancer", J CLIN PATHOL, vol. 61, no. 4, April 2008 (2008-04-01), pages 448 - 54
PENNING T MSTECKELBROECK SBAUMAN D R ET AL.: "Aldo-keto reductase (AKR) 1C3: role in prostate disease and the development of specific inhibitors.[J", MOLECULAR & CELLULAR ENDOCRINOLOGY, vol. 248, 2006, pages 182 - 191, XP025020590, DOI: 10.1016/j.mce.2005.12.009
LIU CLOU WZHU Y ET AL.: "Intracrine Androgens and AKR1C3 Activation Confer Resistance to Enzalutamide in Prostate Cancer[J", CANCER RESEARCH, vol. 75, no. 7, 2015, pages 1413 - 1422
FUNG, K-M: "Increased expression of type 2 3-hydroxysteroid dehydrogenase/type 5 17-hydroxysteroid dehydrogenase (AKR1C3) and its relationship with androgen receptor in prostate carcinoma[J", ENDOCRINE RELATED CANCER, vol. 13, no. 1, 2006, pages 169 - 180
STANBROUGH, CANCER RES, vol. 66, 2006, pages 2815 - 2825
HAMID ARPFEIFFER MJVERHAEGH GWSCHAAFSMA EBRANDT ASWEEP FCSEDELAAR JPSCHALKEN JA.: "Aldo-keto reductase family 1 member C3 (AKR1C3) is a biomarker and therapeutic target for castration-resistant prostate cancer", MOL. MED., vol. 18, 2012, pages 1449 - 1455, XP055296681, DOI: 10.2119/molmed.2012.00296
PFEIFFER MJSMIT FPSEDELAAR JP ET AL.: "Steroidogenic enzymes and stem cell markers are upregulated during androgen deprivation in prostate cancer", MOL MED, vol. 17, 2011, pages 657 - 664
MOSTAGHEL, CLIN CANCER RES, vol. 17, 2011, pages 5913 - 5925
CAI, CANCER RES, vol. 71, 2011, pages 6503 - 6513
ADENIJI, J STEROID BIOCHEM MOL BIOL, vol. 137, 2013, pages 136 - 149
LORIOT, INVEST NEW DRUGS, vol. 32, 2014, pages 995 - 1004
THOMA, NATURE REVIEWS UROLOGY, vol. 12, 2015, pages 124
FUJIWARA: "Streptomyces bacterium Streptomyces peucetius var", CAESIUS, CRITICAL REVIEWS IN BIOTECHNOLOGY, vol. 3, no. 2, 1985, pages 133
GAVELOVA, CHEM. BIOL. INTERACT, vol. 176, 2008, pages 9 - 18
HEIBEIN, BMC CANCER, vol. 12, 2012, pages 381
NOVOTNA, TOXICOL. LETTER, vol. 181, 2008, pages 1 - 6
VOON, BRITISH J OF CLIN PHARMACOLOGY, vol. 75, 2012, pages 1497 - 1505
HOFMAN, TOXICOLOGY AND APPLIED PHARMACOLOGY, vol. 278, 2014, pages 238 - 248
SUN ET AL.: "Overexpression of AKR1C3 significantly enhances human prostate cancer cells resistance to radiation", ONCOTARGET, vol. 7, no. 30, 26 July 2016 (2016-07-26), pages 48050 - 48058
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