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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| ES3055185T3 (en) | 2014-03-28 | 2026-02-10 | Univ Duke | Treatment of an estrogen receptor positive breast cancer using a selective estrogen receptor modulator |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | 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 |
| AU2015266654A1 (en) * | 2014-05-30 | 2016-12-01 | British Columbia Cancer Agency Branch | Androgen receptor modulators and methods for their use |
| MX389702B (es) | 2016-06-22 | 2025-03-20 | Ellipses Pharma Ltd | Compuestos para usarse en el tratamiento de cancer de mama que expresa el receptor de androgenos (ar+). |
| JP7481115B2 (ja) | 2017-01-05 | 2024-05-10 | ラジウス ファーマシューティカルズ，インコーポレイテッド | Ｒａｄ１９０１－２ｈｃｌの多形性形態 |
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| MX2020013713A (es) | 2018-07-04 | 2021-03-02 | Radius Pharmaceuticals Inc | Formas polimorficas de rad1901-2hcl. |
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| US12552806B2 (en) | 2020-03-20 | 2026-02-17 | University Of Southern California | Androgen receptor regulation by small molecule enantiomers |
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Family Cites Families (158)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1547758A (en) | 1975-07-29 | 1979-06-27 | Shell Int Research | Herbicidal composition |
| JPH01261381A (ja) | 1988-04-12 | 1989-10-18 | Nippon Soda Co Ltd | オキサ（チア）ジアゾール誘導体、その製造方法及び殺ダニ剤 |
| FR2693461B1 (fr) | 1992-07-08 | 1994-09-02 | Roussel Uclaf | Nouvelles phénylimidazolidines substituées, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant. |
| US5411981A (en) | 1991-01-09 | 1995-05-02 | Roussel Uclaf | Phenylimidazolidines having antiandrogenic activity |
| US5589452A (en) | 1992-07-14 | 1996-12-31 | Syntex (U.S.A.) Inc. | Analogs of parathyroid hormone and parathyroid hormone related peptide: synthesis and use for the treatment of osteoporosis |
| GB9310635D0 (en) | 1993-05-21 | 1993-07-07 | Glaxo Group Ltd | Chemical compounds |
| DE19517430A1 (de) | 1995-05-12 | 1996-11-14 | Boehringer Mannheim Gmbh | Pharmazeutische Darreichungsform von Parathormon mit einer zwei- bis sechsstündigen Wirkstoff-Freisetzungsperiode |
| UA51652C2 (uk) | 1995-06-08 | 2002-12-16 | Новартіс Аг | Спосіб гідрування імінів |
| US6544949B1 (en) | 1995-07-13 | 2003-04-08 | Societe De Conseils De Recherches Et D'applications Scientifiques, S.A.S. | Analogs of parathyroid hormone |
| US5723577A (en) | 1995-07-13 | 1998-03-03 | Biomeasure Inc. | Analogs of parathyroid hormone |
| US5955574A (en) | 1995-07-13 | 1999-09-21 | Societe De Conseils De Recherches Et D'applications Scientifiques, S.A. | Analogs of parathyroid hormone |
| US5969095A (en) | 1995-07-13 | 1999-10-19 | Biomeasure, Inc. | Analogs of parathyroid hormone |
| US7410948B2 (en) | 1995-07-13 | 2008-08-12 | Societe De Conseils De Recherches Et D'applications Scientifiques, Sas | Analogs of parathyroid hormone |
| PT918774E (pt) | 1996-06-27 | 2002-05-31 | Ligand Pharm Inc | Compostos moduladores do receptor para androgenio e metodos |
| US20090264534A1 (en) | 1996-11-27 | 2009-10-22 | Dalton James T | Selective androgen receptor modulators |
| FR2770842B1 (fr) | 1997-11-13 | 1999-12-17 | Oreal | Nouveaux composes derives de n-aryl 2-hydroxy alkylamides |
| EP0922467A3 (en) | 1997-12-12 | 2000-05-24 | Takeda Chemical Industries, Ltd. | Iontophoretic drug delivery |
| JP4154017B2 (ja) | 1997-12-30 | 2008-09-24 | 久光製薬株式会社 | イオントフォレーシス装置および薬物ユニット |
| US6159959A (en) | 1999-05-06 | 2000-12-12 | American Home Products Corporation | Combined estrogen and antiestrogen therapy |
| US6566372B1 (en) * | 1999-08-27 | 2003-05-20 | Ligand Pharmaceuticals Incorporated | Bicyclic androgen and progesterone receptor modulator compounds and methods |
| WO2001036039A2 (en) | 1999-11-17 | 2001-05-25 | Novartis Ag | Iontophoretic transdermal delivery of peptides |
| US6544553B1 (en) | 1999-12-28 | 2003-04-08 | Watson Pharmaceuticals, Inc. | Dosage forms and methods for oral delivery of progesterone |
| IL150463A0 (en) | 1999-12-30 | 2002-12-01 | Signal Pharm Inc | Compounds and methods for modulation of estrogen receptors |
| MXPA02012605A (es) | 2000-06-28 | 2003-05-14 | Squibb Bristol Myers Co | Moduladores selectivos del receptor androgeno y metodo para su identificacion, dise°o y uso. |
| ATE485837T1 (de) | 2000-08-03 | 2010-11-15 | Antares Pharma Ipl Ag | Zusammensetzung zur transdermalen und/oder transmukosalen verabreichung von wirkstoffen, die ausreichende therapeutische spiegel garantiert |
| AU2006201538B2 (en) | 2000-08-24 | 2008-02-21 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| DE60137728D1 (de) | 2000-08-24 | 2009-04-02 | Univ Tennessee Res Foundation | Selektive Modulatoren des Androgenrezeptors und Methoden zu deren Verwendung |
| US7371721B2 (en) | 2000-09-18 | 2008-05-13 | Sanos Bioscience A/S | Use of GLP-2 and related compounds for the treatment, prevention, diagnosis, and prognosis of bone-related disorders and calcium homeostasis related syndromes |
| US7186683B2 (en) | 2000-09-18 | 2007-03-06 | Sanos Bioscience A/S | Use of GLP for the treatment, prevention, diagnosis, and prognosis of bone-related and nutrition-related disorders |
| NZ525551A (en) | 2000-10-26 | 2005-09-30 | Alza Corp | Transdermal drug delivery devices having coated microprotrusions |
| WO2003011824A1 (en) | 2001-07-31 | 2003-02-13 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| WO2003015761A1 (en) | 2001-08-13 | 2003-02-27 | Merck & Co., Inc. | Selective estrogen receptor modulators |
| US8853266B2 (en) | 2001-12-06 | 2014-10-07 | University Of Tennessee Research Foundation | Selective androgen receptor modulators for treating diabetes |
| JP2005524630A (ja) | 2002-01-14 | 2005-08-18 | ノルディック・ビオサイエンス・エー／エス | エストロゲン受容体を介する軟骨破壊の抑制 |
| US6933321B2 (en) | 2002-02-15 | 2005-08-23 | Endorecherche, Inc. | Antiandrogenic biphenyls |
| US7772433B2 (en) | 2002-02-28 | 2010-08-10 | University Of Tennessee Research Foundation | SARMS and method of use thereof |
| DK1501819T3 (da) | 2002-04-24 | 2011-01-10 | Merck Sharp & Dohme | Østrogenreceptormodulatorer |
| ITMI20020934A1 (it) * | 2002-05-03 | 2003-11-03 | Danimite Dipharma S P A | Processo per la sintesi di benazepril cloridrato |
| TW200407324A (en) | 2002-05-17 | 2004-05-16 | Bristol Myers Squibb Co | Bicyclic modulators of androgen receptor function |
| TW200307553A (en) | 2002-05-24 | 2003-12-16 | Akzo Nobel Nv | Treatment of post-menopausal complaints in breast cancer patients |
| AU2003248052A1 (en) | 2002-07-12 | 2004-02-02 | Yamanouchi Pharmaceutical Co., Ltd. | N-phenyl-(2r,5s)dimethylpiperadine derivative |
| PL375042A1 (en) | 2002-08-12 | 2005-11-14 | Takeda Pharmaceutical Company Limited | Fused benzene derivative and use |
| US7662404B2 (en) | 2002-10-31 | 2010-02-16 | Transpharma Medical Ltd. | Transdermal delivery system for dried particulate or lyophilized peptides and polypeptides |
| US8133505B2 (en) | 2002-10-31 | 2012-03-13 | Transpharma Medical Ltd. | Transdermal delivery system for dried particulate or lyophilized medications |
| IL152574A (en) | 2002-10-31 | 2009-09-22 | Transpharma Medical Ltd | A system for passing through the skin of dry items or dried medicines |
| US7383084B2 (en) | 2002-10-31 | 2008-06-03 | Transpharma Medical Ltd. | Transdermal delivery system for dried particulate or lyophilized medications |
| US7622592B2 (en) | 2002-11-01 | 2009-11-24 | Merck & Co., Inc. | Carbonylamino-benzimidazole derivatives as androgen receptor modulators |
| UA79504C2 (en) | 2002-11-07 | 2007-06-25 | Organon Nv | Indols for treating diseases associated with androgen receptors |
| WO2004045518A2 (en) | 2002-11-15 | 2004-06-03 | Bristol-Myers Squibb Company | Open chain prolyl urea-related modulators of androgen receptor function |
| CA2512000C (en) | 2002-12-26 | 2011-08-09 | Eisai Co., Ltd. | Selective estrogen receptor modulator |
| EP1603858A2 (en) | 2003-03-11 | 2005-12-14 | NeuroSearch A/S | Kcnq channel modulating compounds and their pharmaceutical use |
| WO2004110978A2 (en) | 2003-06-10 | 2004-12-23 | Smithkline Beecham Corporation | 1-aminonaphthalenes as modulators of androgen, glucocorticoid, mineralocorticoid and progesterone receptors |
| JP2007500245A (ja) | 2003-06-10 | 2007-01-11 | スミスクライン ビーチャム コーポレーション | 化合物 |
| FI20030958A0 (fi) | 2003-06-27 | 2003-06-27 | Orion Corp | Uusia yhdisteitä |
| WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
| KR20060038407A (ko) | 2003-06-30 | 2006-05-03 | 알자 코포레이션 | 비휘발성 반대이온을 포함하는 코팅된 미세돌출부용 제제 |
| CN1816324A (zh) | 2003-07-04 | 2006-08-09 | 尼克麦德丹麦公司 | 口服用的含甲状旁腺激素(pth)的药物组合物 |
| MXPA06001751A (es) * | 2003-08-22 | 2006-05-12 | Ligand Pharm Inc | Derivados de 6-cicloamino-2-quinolinona como compuestos moduladores de receptor de androgeno. |
| US7446110B2 (en) | 2003-09-10 | 2008-11-04 | Merck & Co., Inc. | 17-Heterocyclic-4-azasteroid derivatives as androgen receptor modulators |
| GB0324551D0 (en) | 2003-10-21 | 2003-11-26 | Karobio Ab | Novel compounds |
| US20050124625A1 (en) | 2003-10-21 | 2005-06-09 | Salvati Mark E. | Piperazine derivatives and their use as modulators of nuclear hormone receptor function |
| ES2377647T3 (es) | 2003-10-31 | 2012-03-29 | Alza Corporation | Aplicador auto-actuado para ordenamiento de microproyecciones |
| US7256208B2 (en) | 2003-11-13 | 2007-08-14 | Bristol-Myers Squibb Company | Monocyclic N-Aryl hydantoin modulators of androgen receptor function |
| KR20070010115A (ko) | 2003-11-13 | 2007-01-22 | 알자 코포레이션 | 경피전달용 조성물 및 장치 |
| EP1687274A1 (en) | 2003-11-20 | 2006-08-09 | Warner-Lambert Company LLC | Androgen receptor modulators |
| IL159273A0 (en) | 2003-12-09 | 2004-06-01 | Transpharma Medical Ltd | Transdermal delivery system for sustained release of polypeptides |
| US20070196395A1 (en) | 2003-12-12 | 2007-08-23 | Mackerell Alexander | Immunomodulatory compounds that target and inhibit the py'binding site of tyrosene kinase p56 lck sh2 domain |
| RU2397176C2 (ru) | 2004-01-07 | 2010-08-20 | Эндорешерш, Инк. | Стероидные фармацевтические продукты, направленные на спираль 12 |
| KR100849559B1 (ko) | 2004-01-22 | 2008-07-31 | 일라이 릴리 앤드 캄파니 | 혈관운동 증상의 치료를 위한 선택적 에스트로겐 수용체조절제 |
| IL160033A0 (en) | 2004-01-25 | 2004-06-20 | Transpharma Medical Ltd | Transdermal delivery system for polynucleotides |
| US20050182105A1 (en) | 2004-02-04 | 2005-08-18 | Nirschl Alexandra A. | Method of using 3-cyano-4-arylpyridine derivatives as modulators of androgen receptor function |
| US7820702B2 (en) | 2004-02-04 | 2010-10-26 | Bristol-Myers Squibb Company | Sulfonylpyrrolidine modulators of androgen receptor function and method |
| US7514470B2 (en) | 2004-03-03 | 2009-04-07 | Smithkline Beecham Corporation | Aniline derivatives as selective androgen receptor modulators |
| US7625923B2 (en) | 2004-03-04 | 2009-12-01 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| US7696241B2 (en) | 2004-03-04 | 2010-04-13 | Bristol-Myers Squibb Company | Bicyclic compounds as modulators of androgen receptor function and method |
| US7388027B2 (en) | 2004-03-04 | 2008-06-17 | Bristol-Myers Squibb Company | Bicyclic compounds as modulators of androgen receptor function and method |
| GB0405033D0 (en) | 2004-03-05 | 2004-04-07 | Karobio Ab | Novel pharmaceutical compositions |
| US8519158B2 (en) | 2004-03-12 | 2013-08-27 | Ligand Pharmaceuticals Incorporated | Androgen receptor modulator compounds and methods |
| JP2007223901A (ja) | 2004-03-24 | 2007-09-06 | Takeda Chem Ind Ltd | 複素環化合物およびその用途 |
| CA2562132A1 (en) | 2004-04-08 | 2005-10-27 | Merck & Co., Inc. | 17 beta-acetamide-4-azasteroids as androgen receptor modulators |
| TW200602317A (en) | 2004-04-23 | 2006-01-16 | Akzo Nobel Nv | Novel androgens |
| CN1980891B (zh) | 2004-05-03 | 2011-03-09 | 詹森药业有限公司 | 作为选择性雄激素受体调节剂(sarms)的吲哚、苯并呋喃和苯并噻吩衍生物 |
| JP5070042B2 (ja) | 2004-05-03 | 2012-11-07 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 選択的アンドローゲン受容体モジュレーター（ｓａｒｍｓ）としての新規インドール化合物 |
| MXPA06013115A (es) | 2004-05-11 | 2007-02-28 | Pfizer Prod Inc | Derivados de benzonitrilo para tratar la fragilidad musculoesqueletica. |
| US7556821B2 (en) | 2004-05-13 | 2009-07-07 | Alza Corporation | Apparatus and method for transdermal delivery of parathyroid hormone agents |
| EP1756101A2 (en) | 2004-05-17 | 2007-02-28 | Acadia Pharmaceuticals Inc. | Androgen receptor modulators and method of treating disease using the same |
| EP1758874A1 (en) | 2004-05-29 | 2007-03-07 | 7TM Pharma A/S | Substituted thiazoleacetic acids as crth2 ligands |
| PL1753417T3 (pl) | 2004-06-07 | 2012-09-28 | Univ Tennessee Res Found | Selektywny modulator receptora androgenowego i jego zastosowania medyczne |
| CA2579514A1 (en) * | 2004-09-10 | 2006-03-23 | Janssen Pharmaceutica N.V. | Novel imidazolidin-2-one derivatives as selective androgen receptor modulators (sarms) |
| US7338973B2 (en) | 2004-09-20 | 2008-03-04 | Janssen Pharmaceutica N.V. | Tetracyclic heteroatom containing derivatives useful as sex steroid hormone receptor modulators |
| EP1805147B1 (en) | 2004-09-30 | 2014-08-13 | Janssen Pharmaceutica NV | Novel benzimidazole derivatives useful as selective androgen receptor modulators (sarms) |
| US8143425B2 (en) | 2004-10-12 | 2012-03-27 | Bristol-Myers Squibb Company | Heterocyclic aromatic compounds useful as growth hormone secretagogues |
| EP1809275A1 (en) | 2004-10-13 | 2007-07-25 | Smithkline Beecham Corporation | Chemical compounds |
| JP2008518968A (ja) | 2004-10-29 | 2008-06-05 | メルク エンド カムパニー インコーポレーテッド | アンドロゲン受容体モジュレーターとしてのｎ−（ピリジン−３−イル）−２−フェニルブタンアミド |
| WO2006055184A2 (en) | 2004-11-16 | 2006-05-26 | Janssen Pharmaceutica N.V. | Novel heterocycle derivatives useful as selective androgen receptor modulators (sarms) |
| CA2587780A1 (en) | 2004-11-18 | 2006-05-26 | Transpharma Medical Ltd. | Combined micro-channel generation and iontophoresis for transdermal delivery of pharmaceutical agents |
| WO2006058088A2 (en) | 2004-11-23 | 2006-06-01 | Ptc Therapeutics, Inc. | Carbazole, carboline and indole derivatives useful in the inhibition of vegf production |
| CN101119993B (zh) | 2005-01-10 | 2015-03-04 | 阿卡蒂亚药品公司 | 作为选择性雄激素受体调节剂的氨基苯基衍生物 |
| JP2008536868A (ja) | 2005-04-15 | 2008-09-11 | スミスクライン・ビーチャム・コーポレイション | シアノアリールアミン |
| PL1891038T3 (pl) | 2005-05-13 | 2009-04-30 | Lilly Co Eli | Podstawione n-arylopirolidyny jako selektywne modulatory receptora androgenowego |
| EP1888512A2 (en) | 2005-06-06 | 2008-02-20 | Smithkline Beecham Corporation | Chemical compounds |
| US7829589B2 (en) | 2005-06-10 | 2010-11-09 | Elixir Pharmaceuticals, Inc. | Sulfonamide compounds and uses thereof |
| US7709516B2 (en) | 2005-06-17 | 2010-05-04 | Endorecherche, Inc. | Helix 12 directed non-steroidal antiandrogens |
| CA2612723A1 (en) | 2005-06-24 | 2007-01-04 | Eli Lilly And Company | Tetrahydrocarbazole derivatives useful as androgen receptor modulators |
| AR057656A1 (es) | 2005-07-01 | 2007-12-12 | Ligand Pharm Inc | Compuestos moduladores de receptores de androgeno y metodods relacionados |
| JP5070054B2 (ja) * | 2005-08-01 | 2012-11-07 | 武田薬品工業株式会社 | 環状アミン化合物 |
| JP2008303145A (ja) | 2005-09-22 | 2008-12-18 | Takeda Chem Ind Ltd | Ｇｒｋ阻害剤からなる強心薬 |
| US7776859B2 (en) | 2005-10-14 | 2010-08-17 | Bristol-Myers Squibb Company | Hexahydroimidazopyrazin-3-one compounds useful as modulators of androgen receptor function |
| CA2629193C (en) | 2005-11-18 | 2016-03-29 | 3M Innovative Properties Company | Coatable compositions, coatings derived therefrom and microarrays having such coatings |
| TW200730505A (en) | 2005-12-07 | 2007-08-16 | Merck & Co Inc | Polymorphs of an androgen receptor modulator |
| US8632801B2 (en) | 2005-12-28 | 2014-01-21 | Alza Corporation | Stable therapeutic formulations |
| EP1984343B1 (en) | 2006-01-24 | 2013-02-27 | Janssen Pharmaceutica N.V. | 2-substituted benzimidazoles as selective androgen receptor modulators (sarms) |
| AU2007220419B2 (en) | 2006-03-03 | 2012-03-15 | Orion Corporation | Selective androgen receptor modulators |
| AU2007225056A1 (en) | 2006-03-15 | 2007-09-20 | Alza Corporation | Apparatus and method for transdermal delivery of parathyroid hormone agents to prevent or treat osteopenia |
| US9119945B2 (en) | 2006-04-20 | 2015-09-01 | 3M Innovative Properties Company | Device for applying a microneedle array |
| WO2008002490A2 (en) | 2006-06-23 | 2008-01-03 | Radius Health, Inc. | Treatment of vasomotor symptoms with selective estrogen receptor modulators |
| MX2009000385A (es) | 2006-07-12 | 2009-04-06 | Univ Tennessee Res Foundation | Acil-anilidas sustituidas y metodos de uso de las mismas. |
| BRPI0713198A2 (pt) | 2006-07-19 | 2012-10-16 | Osurf Ohio State University Res Foundation | modulares seletivos de receptores de androgênio, seus análogos e derivados, e seus usos |
| TW200815428A (en) * | 2006-08-15 | 2008-04-01 | Wyeth Corp | Oxazolidone derivatives as PR modulators |
| ES2581765T3 (es) | 2006-08-24 | 2016-09-07 | University Of Tennessee Research Foundation | Acilanilidas sustituidas y métodos de uso de las mismas |
| JP5275236B2 (ja) | 2006-09-29 | 2013-08-28 | スミスクライン ビーチャム コーポレーション | 置換されたインドール化合物 |
| BRPI0719821B8 (pt) | 2006-10-03 | 2021-05-25 | Ipsen Pharma Sas | composição estável na armazenagem apropriada para administração a pacientes |
| US7803770B2 (en) | 2006-10-03 | 2010-09-28 | Radius Health, Inc. | Method of treating osteoporosis comprising administration of PTHrP analog |
| WO2008044033A1 (en) | 2006-10-11 | 2008-04-17 | Astrazeneca Ab | Amide derivatives |
| UA98777C2 (en) | 2006-11-20 | 2012-06-25 | Эли Лилли Энд Компани | Tetrahydrocyclopenta[b]indole compounds as androgen receptor modulators |
| WO2008121602A1 (en) | 2007-03-29 | 2008-10-09 | Smithkline Beecham Corporation | Chemical compounds |
| WO2008124000A2 (en) | 2007-04-02 | 2008-10-16 | Ligand Pharmaceuticals Incorporated | Thiazole derivatives as androgen receptor modulator compounds |
| US9284345B2 (en) | 2007-04-12 | 2016-03-15 | Endorecherche, Inc. | 17alpha-substituted steroids as systemic antiandrogens and selective androgen receptor modulators |
| WO2008128100A1 (en) | 2007-04-13 | 2008-10-23 | The Regents Of The University Of California | Small-molecule inhibitors of the androgen receptor |
| ES2817249T3 (es) | 2007-04-16 | 2021-04-06 | Corium Inc | Matrices de microagujas obtenidas mediante disolución y colada que contienen un principio activo |
| GB0712099D0 (en) | 2007-06-22 | 2007-08-01 | Wivenhoe Technology Ltd | Transmission Of Audio Information |
| ME01579B (me) | 2007-08-07 | 2014-09-20 | Takeda Pharmaceuticals Co | Derivati pirolidin-2-ona kao modulatori androgenskih receptora |
| WO2009054988A1 (en) | 2007-10-23 | 2009-04-30 | Alza Corporation | Transdermal sustained release drug delivery |
| EP2277124B1 (en) | 2007-11-21 | 2016-11-09 | Medizinische Hochschule Hannover | Means for treating myosin-related diseases |
| CA2709514A1 (en) | 2007-12-21 | 2009-07-02 | Astrazeneca Ab | Bicyclic derivatives for use in the treatment of androgen receptor associated conditions |
| EP2222636B1 (en) * | 2007-12-21 | 2013-04-10 | Ligand Pharmaceuticals Inc. | Selective androgen receptor modulators (sarms) and uses thereof |
| CA2716320C (en) | 2008-02-22 | 2014-01-28 | Radius Health, Inc. | Selective androgen receptor modulators |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| WO2009133861A1 (ja) * | 2008-04-28 | 2009-11-05 | 武田薬品工業株式会社 | 環状アミン化合物 |
| US20110124617A1 (en) | 2008-05-09 | 2011-05-26 | Lyttle C Richard | Combination Therapy for BreastCancer Comprising an Antiestrogenic Agent |
| EA019713B1 (ru) | 2008-05-16 | 2014-05-30 | Эли Лилли Энд Компани | ТЕТРАГИДРОЦИКЛОПЕНТА[b]ИНДОЛЬНЫЕ МОДУЛЯТОРЫ РЕЦЕПТОРОВ АНДРОГЕНОВ |
| WO2010022176A1 (en) | 2008-08-19 | 2010-02-25 | Ferring International Center S.A. | Methods of treatment for skeletal conditons |
| KR101634836B1 (ko) | 2008-12-26 | 2016-06-29 | 히사미쓰 세이야꾸 가부시키가이샤 | 마이크로 니들 디바이스 |
| US8629157B2 (en) * | 2009-01-05 | 2014-01-14 | Boehringer Ingelheim International Gmbh | Pyrrolidine compounds which modulate the CB2 receptor |
| US20100226966A1 (en) | 2009-03-03 | 2010-09-09 | Daddona Peter E | Method for transdermal controlled release drug delivery |
| WO2010118287A1 (en) | 2009-04-10 | 2010-10-14 | Radius Health, Inc. | Selective androgen receptor modulators |
| ES2525353T3 (es) * | 2009-04-28 | 2014-12-22 | Chugai Seiyaku Kabushiki Kaisha | Derivado de espiroimidazolona |
| US20110172609A1 (en) | 2010-01-08 | 2011-07-14 | Ratio, Inc. | Microneedle component assembly for drug delivery device |
| AU2011212813B2 (en) | 2010-02-04 | 2014-10-23 | Radius Health, Inc. | Selective androgen receptor modulators |
| IE20100174A1 (en) | 2010-03-25 | 2012-02-29 | Trinity College Dublin | Transdermal administration of peptides |
| EP2566501B1 (en) | 2010-05-04 | 2019-03-13 | Corium International, Inc. | Method and device for transdermal delivery of parathyroid hormone using a microprojection array |
| HUE030072T2 (en) | 2010-05-12 | 2017-04-28 | Radius Health Inc | Therapeutic prescriptions |
| EP2575845B1 (en) | 2010-05-28 | 2017-02-15 | 3M Innovative Properties Company | Aqueous formulations for coating microneedle arrays |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| US9133182B2 (en) | 2010-09-28 | 2015-09-15 | Radius Health, Inc. | Selective androgen receptor modulators |
| WO2012075375A1 (en) | 2010-12-02 | 2012-06-07 | Lanco Biosciences, Inc. | Delivery of parathyroid hormones by microinjection systems |
| EP2699252B1 (en) | 2011-04-22 | 2017-10-25 | Radius Health, Inc. | Method of drug delivery for pth, pthrp and related peptides |
| KR102143482B1 (ko) | 2011-11-30 | 2020-08-11 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 펩티드 치료제 및 아미노산을 포함하는 마이크로니들 장치, 이의 제조 및 사용 방법 |
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- 2011-09-27 EP EP11767355.8A patent/EP2621901B1/en active Active
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- 2011-09-27 WO PCT/US2011/053375 patent/WO2012047617A1/en not_active Ceased
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