JP2013537919A5 - - Google Patents
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- JP2013537919A5 JP2013537919A5 JP2013530412A JP2013530412A JP2013537919A5 JP 2013537919 A5 JP2013537919 A5 JP 2013537919A5 JP 2013530412 A JP2013530412 A JP 2013530412A JP 2013530412 A JP2013530412 A JP 2013530412A JP 2013537919 A5 JP2013537919 A5 JP 2013537919A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoro
- hydroxyethyl
- methyl
- benzonitrile
- oxo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 206010006895 Cachexia Diseases 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 206010060800 Hot flush Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 206010022489 Insulin Resistance Diseases 0.000 claims 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims 4
- 208000027418 Wounds and injury Diseases 0.000 claims 4
- 208000029078 coronary artery disease Diseases 0.000 claims 4
- 230000006378 damage Effects 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 238000002657 hormone replacement therapy Methods 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 208000014674 injury Diseases 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- 102000001307 androgen receptors Human genes 0.000 claims 3
- 108010080146 androgen receptors Proteins 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
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- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims 2
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- 206010047791 Vulvovaginal dryness Diseases 0.000 claims 2
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- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 206010000496 acne Diseases 0.000 claims 2
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- 208000015294 blood coagulation disease Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 230000009852 coagulant defect Effects 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
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- 230000003247 decreasing effect Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 238000000502 dialysis Methods 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000016253 exhaustion Diseases 0.000 claims 2
- 208000010706 fatty liver disease Diseases 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 208000024963 hair loss Diseases 0.000 claims 2
- 230000003676 hair loss Effects 0.000 claims 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 2
- 201000008980 hyperinsulinism Diseases 0.000 claims 2
- 201000001881 impotence Diseases 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 208000000509 infertility Diseases 0.000 claims 2
- 230000036512 infertility Effects 0.000 claims 2
- 231100000535 infertility Toxicity 0.000 claims 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 208000027202 mammary Paget disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 206010051747 multiple endocrine neoplasia Diseases 0.000 claims 2
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- 201000006938 muscular dystrophy Diseases 0.000 claims 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
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- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 208000001076 sarcopenia Diseases 0.000 claims 2
- 208000008742 seborrheic dermatitis Diseases 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 2
- 201000003120 testicular cancer Diseases 0.000 claims 2
- 229960003604 testosterone Drugs 0.000 claims 2
- 206010043554 thrombocytopenia Diseases 0.000 claims 2
- 201000002510 thyroid cancer Diseases 0.000 claims 2
- 238000002054 transplantation Methods 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- 206010048828 underweight Diseases 0.000 claims 2
- 230000001457 vasomotor Effects 0.000 claims 2
- WTJSJWCRLSCIGQ-MWLCHTKSSA-N (5r)-1-(3,4-dichlorophenyl)-5-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]pyrrolidin-2-one Chemical compound FC(F)(F)[C@H](O)[C@H]1CCC(=O)N1C1=CC=C(Cl)C(Cl)=C1 WTJSJWCRLSCIGQ-MWLCHTKSSA-N 0.000 claims 1
- WTJSJWCRLSCIGQ-KOLCDFICSA-N (5r)-1-(3,4-dichlorophenyl)-5-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]pyrrolidin-2-one Chemical compound FC(F)(F)[C@@H](O)[C@H]1CCC(=O)N1C1=CC=C(Cl)C(Cl)=C1 WTJSJWCRLSCIGQ-KOLCDFICSA-N 0.000 claims 1
- YWXUYRCPRZSNBK-GZMMTYOYSA-N (5s)-1-(1,2,3-benzothiadiazol-6-yl)-5-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]pyrrolidin-2-one Chemical compound FC(F)(F)[C@H](O)[C@@H]1CCC(=O)N1C1=CC=C(N=NS2)C2=C1 YWXUYRCPRZSNBK-GZMMTYOYSA-N 0.000 claims 1
- YWXUYRCPRZSNBK-KWQFWETISA-N (5s)-1-(1,2,3-benzothiadiazol-6-yl)-5-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]pyrrolidin-2-one Chemical compound FC(F)(F)[C@@H](O)[C@@H]1CCC(=O)N1C1=CC=C(N=NS2)C2=C1 YWXUYRCPRZSNBK-KWQFWETISA-N 0.000 claims 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- YDGDWJFCZMDSDW-MWLCHTKSSA-N 2-chloro-3-methyl-4-[(4r)-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound CC1=C(Cl)C(C#N)=CC=C1N1C(=O)OC[C@@H]1[C@@H](O)C(F)(F)F YDGDWJFCZMDSDW-MWLCHTKSSA-N 0.000 claims 1
- YDGDWJFCZMDSDW-KOLCDFICSA-N 2-chloro-3-methyl-4-[(4r)-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound CC1=C(Cl)C(C#N)=CC=C1N1C(=O)OC[C@@H]1[C@H](O)C(F)(F)F YDGDWJFCZMDSDW-KOLCDFICSA-N 0.000 claims 1
- AJSPBOQQLUICJK-NZXMKCKXSA-N 2-chloro-3-methyl-4-[(4s,5r)-5-methyl-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound FC(F)(F)[C@H](O)[C@H]1[C@@H](C)OC(=O)N1C1=CC=C(C#N)C(Cl)=C1C AJSPBOQQLUICJK-NZXMKCKXSA-N 0.000 claims 1
- AJSPBOQQLUICJK-HFKOZYHYSA-N 2-chloro-3-methyl-4-[(4s,5r)-5-methyl-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound FC(F)(F)[C@@H](O)[C@H]1[C@@H](C)OC(=O)N1C1=CC=C(C#N)C(Cl)=C1C AJSPBOQQLUICJK-HFKOZYHYSA-N 0.000 claims 1
- AJSPBOQQLUICJK-UPZJHPNMSA-N 2-chloro-3-methyl-4-[(4s,5s)-5-methyl-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound FC(F)(F)[C@H](O)[C@H]1[C@H](C)OC(=O)N1C1=CC=C(C#N)C(Cl)=C1C AJSPBOQQLUICJK-UPZJHPNMSA-N 0.000 claims 1
- AJSPBOQQLUICJK-BPTDKIDVSA-N 2-chloro-3-methyl-4-[(4s,5s)-5-methyl-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound FC(F)(F)[C@@H](O)[C@H]1[C@H](C)OC(=O)N1C1=CC=C(C#N)C(Cl)=C1C AJSPBOQQLUICJK-BPTDKIDVSA-N 0.000 claims 1
- QHEPWISZBKIPMN-ZWNOBZJWSA-N 2-chloro-3-methyl-4-[(5r)-2-oxo-5-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]pyrrolidin-1-yl]benzonitrile Chemical compound CC1=C(Cl)C(C#N)=CC=C1N1C(=O)CC[C@@H]1[C@@H](O)C(F)(F)F QHEPWISZBKIPMN-ZWNOBZJWSA-N 0.000 claims 1
- QHEPWISZBKIPMN-MFKMUULPSA-N 2-chloro-3-methyl-4-[(5r)-2-oxo-5-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]pyrrolidin-1-yl]benzonitrile Chemical compound CC1=C(Cl)C(C#N)=CC=C1N1C(=O)CC[C@@H]1[C@H](O)C(F)(F)F QHEPWISZBKIPMN-MFKMUULPSA-N 0.000 claims 1
- OCLUFVULSBZQOP-VHSXEESVSA-N 2-chloro-4-[(4s)-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound FC(F)(F)[C@H](O)[C@@H]1COC(=O)N1C1=CC=C(C#N)C(Cl)=C1 OCLUFVULSBZQOP-VHSXEESVSA-N 0.000 claims 1
- OCLUFVULSBZQOP-UWVGGRQHSA-N 2-chloro-4-[(4s)-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound FC(F)(F)[C@@H](O)[C@@H]1COC(=O)N1C1=CC=C(C#N)C(Cl)=C1 OCLUFVULSBZQOP-UWVGGRQHSA-N 0.000 claims 1
- GHAJKXVXLNSRDU-DIMCTHFVSA-N 2-chloro-4-[(4s,5r)-5-methyl-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound FC(F)(F)[C@H](O)[C@H]1[C@@H](C)OC(=O)N1C1=CC=C(C#N)C(Cl)=C1 GHAJKXVXLNSRDU-DIMCTHFVSA-N 0.000 claims 1
- GHAJKXVXLNSRDU-PFZYVWIYSA-N 2-chloro-4-[(4s,5r)-5-methyl-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound FC(F)(F)[C@@H](O)[C@H]1[C@@H](C)OC(=O)N1C1=CC=C(C#N)C(Cl)=C1 GHAJKXVXLNSRDU-PFZYVWIYSA-N 0.000 claims 1
- GHAJKXVXLNSRDU-MQOMDTIOSA-N 2-chloro-4-[(4s,5s)-5-methyl-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound FC(F)(F)[C@H](O)[C@H]1[C@H](C)OC(=O)N1C1=CC=C(C#N)C(Cl)=C1 GHAJKXVXLNSRDU-MQOMDTIOSA-N 0.000 claims 1
- GHAJKXVXLNSRDU-FZYJTZEISA-N 2-chloro-4-[(4s,5s)-5-methyl-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]benzonitrile Chemical compound FC(F)(F)[C@@H](O)[C@H]1[C@H](C)OC(=O)N1C1=CC=C(C#N)C(Cl)=C1 GHAJKXVXLNSRDU-FZYJTZEISA-N 0.000 claims 1
- GIPXIANWYFSQAU-ZYHUDNBSSA-N 2-chloro-4-[(5r)-2-oxo-5-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]pyrrolidin-1-yl]benzonitrile Chemical compound FC(F)(F)[C@H](O)[C@H]1CCC(=O)N1C1=CC=C(C#N)C(Cl)=C1 GIPXIANWYFSQAU-ZYHUDNBSSA-N 0.000 claims 1
- GIPXIANWYFSQAU-PWSUYJOCSA-N 2-chloro-4-[(5r)-2-oxo-5-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]pyrrolidin-1-yl]benzonitrile Chemical compound FC(F)(F)[C@@H](O)[C@H]1CCC(=O)N1C1=CC=C(C#N)C(Cl)=C1 GIPXIANWYFSQAU-PWSUYJOCSA-N 0.000 claims 1
- DCTYIEQDJSQQKS-MWLCHTKSSA-N 3-methyl-4-[(4r)-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=CC(C#N)=C(C(F)(F)F)C(C)=C1N1C(=O)OC[C@@H]1[C@@H](O)C(F)(F)F DCTYIEQDJSQQKS-MWLCHTKSSA-N 0.000 claims 1
- DCTYIEQDJSQQKS-KOLCDFICSA-N 3-methyl-4-[(4r)-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=CC(C#N)=C(C(F)(F)F)C(C)=C1N1C(=O)OC[C@@H]1[C@H](O)C(F)(F)F DCTYIEQDJSQQKS-KOLCDFICSA-N 0.000 claims 1
- CDCCUYIGQVCZGD-NZXMKCKXSA-N 3-methyl-4-[(4s,5r)-5-methyl-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)[C@H](O)[C@H]1[C@@H](C)OC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1C CDCCUYIGQVCZGD-NZXMKCKXSA-N 0.000 claims 1
- CDCCUYIGQVCZGD-HFKOZYHYSA-N 3-methyl-4-[(4s,5r)-5-methyl-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)[C@@H](O)[C@H]1[C@@H](C)OC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1C CDCCUYIGQVCZGD-HFKOZYHYSA-N 0.000 claims 1
- CDCCUYIGQVCZGD-UPZJHPNMSA-N 3-methyl-4-[(4s,5s)-5-methyl-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)[C@H](O)[C@H]1[C@H](C)OC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1C CDCCUYIGQVCZGD-UPZJHPNMSA-N 0.000 claims 1
- CDCCUYIGQVCZGD-BPTDKIDVSA-N 3-methyl-4-[(4s,5s)-5-methyl-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)[C@@H](O)[C@H]1[C@H](C)OC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1C CDCCUYIGQVCZGD-BPTDKIDVSA-N 0.000 claims 1
- GLGCTWNFYQFEIR-MFKMUULPSA-N 3-methyl-4-[(5r)-2-oxo-5-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]pyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=CC(C#N)=C(C(F)(F)F)C(C)=C1N1C(=O)CC[C@@H]1[C@H](O)C(F)(F)F GLGCTWNFYQFEIR-MFKMUULPSA-N 0.000 claims 1
- GLGCTWNFYQFEIR-GWCFXTLKSA-N 3-methyl-4-[(5s)-2-oxo-5-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]pyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=CC(C#N)=C(C(F)(F)F)C(C)=C1N1C(=O)CC[C@H]1[C@H](O)C(F)(F)F GLGCTWNFYQFEIR-GWCFXTLKSA-N 0.000 claims 1
- LPHQOQIPNPHGQA-NXEZZACHSA-N 4-[(4r)-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)[C@H](O)[C@H]1COC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 LPHQOQIPNPHGQA-NXEZZACHSA-N 0.000 claims 1
- LPHQOQIPNPHGQA-ZJUUUORDSA-N 4-[(4r)-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)[C@@H](O)[C@H]1COC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 LPHQOQIPNPHGQA-ZJUUUORDSA-N 0.000 claims 1
- CGPSIOMHVIIIGV-DIMCTHFVSA-N 4-[(4s,5r)-5-methyl-2-oxo-4-[(1r)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)[C@H](O)[C@H]1[C@@H](C)OC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 CGPSIOMHVIIIGV-DIMCTHFVSA-N 0.000 claims 1
- CGPSIOMHVIIIGV-PFZYVWIYSA-N 4-[(4s,5r)-5-methyl-2-oxo-4-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-1,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)[C@@H](O)[C@H]1[C@@H](C)OC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 CGPSIOMHVIIIGV-PFZYVWIYSA-N 0.000 claims 1
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| CA2943611A1 (en) | 2014-03-28 | 2015-10-01 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| KR101597327B1 (ko) * | 2014-04-24 | 2016-02-24 | 동아에스티 주식회사 | 옥사졸리딘계 화합물 및 이를 포함하는 선택적 안드로겐 수용체 효능제 |
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-
2011
- 2011-09-27 US US13/876,809 patent/US9133182B2/en active Active
- 2011-09-27 BR BR112013007685-2A patent/BR112013007685B1/pt active IP Right Grant
- 2011-09-27 AU AU2011312490A patent/AU2011312490B2/en active Active
- 2011-09-27 ES ES11767355.8T patent/ES2550319T3/es active Active
- 2011-09-27 EP EP11767355.8A patent/EP2621901B1/en active Active
- 2011-09-27 WO PCT/US2011/053375 patent/WO2012047617A1/en not_active Ceased
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2015
- 2015-07-22 US US14/806,360 patent/US9920044B2/en active Active
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