JP2008501800A5 - - Google Patents
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- Publication number
- JP2008501800A5 JP2008501800A5 JP2007527597A JP2007527597A JP2008501800A5 JP 2008501800 A5 JP2008501800 A5 JP 2008501800A5 JP 2007527597 A JP2007527597 A JP 2007527597A JP 2007527597 A JP2007527597 A JP 2007527597A JP 2008501800 A5 JP2008501800 A5 JP 2008501800A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- hydroxy
- methyl
- trifluoro
- phenylbutanamide
- 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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- -1 Perfluoro Chemical group 0.000 claims 32
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 11
- SEXSZNASUHPUPT-OAHLLOKOSA-N (2r)-3,3,3-trifluoro-n-[(2-fluoro-5-methylpyridin-3-yl)methyl]-2-hydroxy-2-phenylpropanamide Chemical compound CC1=CN=C(F)C(CNC(=O)[C@](O)(C=2C=CC=CC=2)C(F)(F)F)=C1 SEXSZNASUHPUPT-OAHLLOKOSA-N 0.000 claims 6
- YSMGNNKNGUPHCD-OAHLLOKOSA-N (2r)-3,3,3-trifluoro-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-hydroxy-2-phenylpropanamide Chemical compound O=C([C@](O)(C=1C=CC=CC=1)C(F)(F)F)NCC1=CC(C(F)(F)F)=CC=C1F YSMGNNKNGUPHCD-OAHLLOKOSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- UAJUEDTYIVUMKP-GOSISDBHSA-N (2r)-n-[(5-cyclopropyl-2-fluorophenyl)methyl]-3,3,3-trifluoro-2-(4-fluorophenyl)-2-hydroxypropanamide Chemical compound O=C([C@](O)(C=1C=CC(F)=CC=1)C(F)(F)F)NCC(C(=CC=1)F)=CC=1C1CC1 UAJUEDTYIVUMKP-GOSISDBHSA-N 0.000 claims 3
- USHFGOGPBYRMNY-OAHLLOKOSA-N (2r)-n-[[3-bromo-2-fluoro-5-(trifluoromethyl)phenyl]methyl]-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide Chemical compound O=C([C@](O)(C=1C=CC=CC=1)C(F)(F)F)NCC1=CC(C(F)(F)F)=CC(Br)=C1F USHFGOGPBYRMNY-OAHLLOKOSA-N 0.000 claims 3
- UAJUEDTYIVUMKP-SFHVURJKSA-N (2s)-n-[(5-cyclopropyl-2-fluorophenyl)methyl]-3,3,3-trifluoro-2-(4-fluorophenyl)-2-hydroxypropanamide Chemical compound O=C([C@@](O)(C=1C=CC(F)=CC=1)C(F)(F)F)NCC(C(=CC=1)F)=CC=1C1CC1 UAJUEDTYIVUMKP-SFHVURJKSA-N 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- JNDQWCQWQFGZGJ-SFHVURJKSA-N (2r)-2-cyclopropyl-n-[(2-fluoro-5-methylpyridin-3-yl)methyl]-2-hydroxy-2-phenylacetamide Chemical compound CC1=CN=C(F)C(CNC(=O)[C@@](O)(C2CC2)C=2C=CC=CC=2)=C1 JNDQWCQWQFGZGJ-SFHVURJKSA-N 0.000 claims 2
- JNDQWCQWQFGZGJ-GOSISDBHSA-N (2s)-2-cyclopropyl-n-[(2-fluoro-5-methylpyridin-3-yl)methyl]-2-hydroxy-2-phenylacetamide Chemical compound CC1=CN=C(F)C(CNC(=O)[C@](O)(C2CC2)C=2C=CC=CC=2)=C1 JNDQWCQWQFGZGJ-GOSISDBHSA-N 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 229940122361 Bisphosphonate Drugs 0.000 claims 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 230000002917 arthritic effect Effects 0.000 claims 2
- 150000004663 bisphosphonates Chemical class 0.000 claims 2
- 210000000988 bone and bone Anatomy 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229940011871 estrogen Drugs 0.000 claims 2
- 239000000262 estrogen Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 210000002997 osteoclast Anatomy 0.000 claims 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 2
- 150000003710 vitamin D derivatives Chemical class 0.000 claims 2
- 150000003721 vitamin K derivatives Chemical class 0.000 claims 2
- XSJFQSRYOWBLNY-QGZVFWFLSA-N (2r)-2-(3-chlorophenyl)-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-hydroxybutanamide Chemical compound O=C([C@@](O)(CC)C=1C=C(Cl)C=CC=1)NCC1=CC(C(F)(F)F)=CC=C1F XSJFQSRYOWBLNY-QGZVFWFLSA-N 0.000 claims 1
- HNNCNBYDSNFDDX-OAHLLOKOSA-N (2r)-2-(4-chloro-3-fluorophenyl)-3,3,3-trifluoro-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-hydroxypropanamide Chemical compound O=C([C@](O)(C=1C=C(F)C(Cl)=CC=1)C(F)(F)F)NCC1=CC(C(F)(F)F)=CC=C1F HNNCNBYDSNFDDX-OAHLLOKOSA-N 0.000 claims 1
- IEWWEFAALLOHSC-OAHLLOKOSA-N (2r)-3,3,3-trifluoro-2-hydroxy-2-phenyl-n-[(2,3,5-trifluorophenyl)methyl]propanamide Chemical compound O=C([C@](O)(C=1C=CC=CC=1)C(F)(F)F)NCC1=CC(F)=CC(F)=C1F IEWWEFAALLOHSC-OAHLLOKOSA-N 0.000 claims 1
- NSGNSPYQGXAFSN-OAHLLOKOSA-N (2r)-3,3,4,4,4-pentafluoro-n-[(2-fluoro-5-methylpyridin-3-yl)methyl]-2-hydroxy-2-phenylbutanamide Chemical compound CC1=CN=C(F)C(CNC(=O)[C@](O)(C=2C=CC=CC=2)C(F)(F)C(F)(F)F)=C1 NSGNSPYQGXAFSN-OAHLLOKOSA-N 0.000 claims 1
- RZNKQBAQPJKVOI-OAHLLOKOSA-N (2r)-3,3,4,4,4-pentafluoro-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-hydroxy-2-phenylbutanamide Chemical compound O=C([C@](O)(C=1C=CC=CC=1)C(F)(F)C(F)(F)F)NCC1=CC(C(F)(F)F)=CC=C1F RZNKQBAQPJKVOI-OAHLLOKOSA-N 0.000 claims 1
- LJURUBHTNOKMEK-QGZVFWFLSA-N (2r)-n-[(2-fluoro-5-methylpyridin-3-yl)methyl]-2-hydroxy-2-phenylbutanamide Chemical compound O=C([C@@](O)(CC)C=1C=CC=CC=1)NCC1=CC(C)=CN=C1F LJURUBHTNOKMEK-QGZVFWFLSA-N 0.000 claims 1
- VBKZMLMVKRNZOP-GOSISDBHSA-N (2r)-n-[(4-cyano-5-ethyl-2-fluorophenyl)methyl]-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide Chemical compound C1=C(C#N)C(CC)=CC(CNC(=O)[C@](O)(C=2C=CC=CC=2)C(F)(F)F)=C1F VBKZMLMVKRNZOP-GOSISDBHSA-N 0.000 claims 1
- UYYWXNVYNNWNPN-OAHLLOKOSA-N (2r)-n-[(5-bromo-2-fluorophenyl)methyl]-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide Chemical compound O=C([C@](O)(C=1C=CC=CC=1)C(F)(F)F)NCC1=CC(Br)=CC=C1F UYYWXNVYNNWNPN-OAHLLOKOSA-N 0.000 claims 1
- YDLZMUBWZZTBLG-OAHLLOKOSA-N (2r)-n-[(5-chloro-2-fluorophenyl)methyl]-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide Chemical compound O=C([C@](O)(C=1C=CC=CC=1)C(F)(F)F)NCC1=CC(Cl)=CC=C1F YDLZMUBWZZTBLG-OAHLLOKOSA-N 0.000 claims 1
- UQEYXVNFJCKIET-GOSISDBHSA-N (2r)-n-[(5-cyclopropyl-2-fluorophenyl)methyl]-3,3,4,4,4-pentafluoro-2-hydroxy-2-phenylbutanamide Chemical compound O=C([C@](O)(C=1C=CC=CC=1)C(F)(F)C(F)(F)F)NCC(C(=CC=1)F)=CC=1C1CC1 UQEYXVNFJCKIET-GOSISDBHSA-N 0.000 claims 1
- COLQLWGKRZOYFC-OAHLLOKOSA-N (2r)-n-[(5-cyclopropyl-2-fluoropyridin-3-yl)methyl]-2-(3,4-dichlorophenyl)butanamide Chemical compound O=C([C@H](CC)C=1C=C(Cl)C(Cl)=CC=1)NCC(C(=NC=1)F)=CC=1C1CC1 COLQLWGKRZOYFC-OAHLLOKOSA-N 0.000 claims 1
- ABYCQYBNFPENTN-QGZVFWFLSA-N (2r)-n-[(5-ethyl-2-fluorophenyl)methyl]-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide Chemical compound CCC1=CC=C(F)C(CNC(=O)[C@](O)(C=2C=CC=CC=2)C(F)(F)F)=C1 ABYCQYBNFPENTN-QGZVFWFLSA-N 0.000 claims 1
- OOWJHBQWBMZGBJ-GOSISDBHSA-N (2r)-n-[(5-ethyl-2-fluoropyridin-3-yl)methyl]-2-hydroxy-2-phenylbutanamide Chemical compound CCC1=CN=C(F)C(CNC(=O)[C@@](O)(CC)C=2C=CC=CC=2)=C1 OOWJHBQWBMZGBJ-GOSISDBHSA-N 0.000 claims 1
- BTUSAGMRJFOYJG-QGZVFWFLSA-N (2r)-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-hydroxy-2-phenylbutanamide Chemical compound O=C([C@@](O)(CC)C=1C=CC=CC=1)NCC1=CC(C(F)(F)F)=CC=C1F BTUSAGMRJFOYJG-QGZVFWFLSA-N 0.000 claims 1
- ABSVKUQMEMAYBO-MRXNPFEDSA-N (2r)-n-[[3-cyano-2-fluoro-5-(trifluoromethyl)phenyl]methyl]-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide Chemical compound O=C([C@](O)(C=1C=CC=CC=1)C(F)(F)F)NCC1=CC(C(F)(F)F)=CC(C#N)=C1F ABSVKUQMEMAYBO-MRXNPFEDSA-N 0.000 claims 1
- XSJFQSRYOWBLNY-KRWDZBQOSA-N (2s)-2-(3-chlorophenyl)-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-hydroxybutanamide Chemical compound O=C([C@](O)(CC)C=1C=C(Cl)C=CC=1)NCC1=CC(C(F)(F)F)=CC=C1F XSJFQSRYOWBLNY-KRWDZBQOSA-N 0.000 claims 1
- HNNCNBYDSNFDDX-HNNXBMFYSA-N (2s)-2-(4-chloro-3-fluorophenyl)-3,3,3-trifluoro-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-hydroxypropanamide Chemical compound O=C([C@@](O)(C=1C=C(F)C(Cl)=CC=1)C(F)(F)F)NCC1=CC(C(F)(F)F)=CC=C1F HNNCNBYDSNFDDX-HNNXBMFYSA-N 0.000 claims 1
- SEXSZNASUHPUPT-HNNXBMFYSA-N (2s)-3,3,3-trifluoro-n-[(2-fluoro-5-methylpyridin-3-yl)methyl]-2-hydroxy-2-phenylpropanamide Chemical compound CC1=CN=C(F)C(CNC(=O)[C@@](O)(C=2C=CC=CC=2)C(F)(F)F)=C1 SEXSZNASUHPUPT-HNNXBMFYSA-N 0.000 claims 1
- NSGNSPYQGXAFSN-HNNXBMFYSA-N (2s)-3,3,4,4,4-pentafluoro-n-[(2-fluoro-5-methylpyridin-3-yl)methyl]-2-hydroxy-2-phenylbutanamide Chemical compound CC1=CN=C(F)C(CNC(=O)[C@@](O)(C=2C=CC=CC=2)C(F)(F)C(F)(F)F)=C1 NSGNSPYQGXAFSN-HNNXBMFYSA-N 0.000 claims 1
- RZNKQBAQPJKVOI-HNNXBMFYSA-N (2s)-3,3,4,4,4-pentafluoro-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-hydroxy-2-phenylbutanamide Chemical compound O=C([C@@](O)(C=1C=CC=CC=1)C(F)(F)C(F)(F)F)NCC1=CC(C(F)(F)F)=CC=C1F RZNKQBAQPJKVOI-HNNXBMFYSA-N 0.000 claims 1
- ROROYOIYWUWEAJ-HNNXBMFYSA-N (2s)-n-[(2-fluoro-5-methylpyridin-3-yl)methyl]-2-phenylbutanamide Chemical compound O=C([C@@H](CC)C=1C=CC=CC=1)NCC1=CC(C)=CN=C1F ROROYOIYWUWEAJ-HNNXBMFYSA-N 0.000 claims 1
- VLNKNIFVOBPSMC-HNNXBMFYSA-N (2s)-n-[(5-bromo-2-fluorophenyl)methyl]-2-phenylbutanamide Chemical compound O=C([C@@H](CC)C=1C=CC=CC=1)NCC1=CC(Br)=CC=C1F VLNKNIFVOBPSMC-HNNXBMFYSA-N 0.000 claims 1
- UQEYXVNFJCKIET-SFHVURJKSA-N (2s)-n-[(5-cyclopropyl-2-fluorophenyl)methyl]-3,3,4,4,4-pentafluoro-2-hydroxy-2-phenylbutanamide Chemical compound O=C([C@@](O)(C=1C=CC=CC=1)C(F)(F)C(F)(F)F)NCC(C(=CC=1)F)=CC=1C1CC1 UQEYXVNFJCKIET-SFHVURJKSA-N 0.000 claims 1
- COLQLWGKRZOYFC-HNNXBMFYSA-N (2s)-n-[(5-cyclopropyl-2-fluoropyridin-3-yl)methyl]-2-(3,4-dichlorophenyl)butanamide Chemical compound O=C([C@@H](CC)C=1C=C(Cl)C(Cl)=CC=1)NCC(C(=NC=1)F)=CC=1C1CC1 COLQLWGKRZOYFC-HNNXBMFYSA-N 0.000 claims 1
- HXIAUKFEZJLDIT-KRWDZBQOSA-N (2s)-n-[(5-cyclopropyl-2-fluoropyridin-3-yl)methyl]-2-phenylbutanamide Chemical compound O=C([C@@H](CC)C=1C=CC=CC=1)NCC(C(=NC=1)F)=CC=1C1CC1 HXIAUKFEZJLDIT-KRWDZBQOSA-N 0.000 claims 1
- PXZKOPPVRIJGGB-KRWDZBQOSA-N (2s)-n-[(5-ethyl-2-fluorophenyl)methyl]-2-phenylbutanamide Chemical compound O=C([C@@H](CC)C=1C=CC=CC=1)NCC1=CC(CC)=CC=C1F PXZKOPPVRIJGGB-KRWDZBQOSA-N 0.000 claims 1
- OOWJHBQWBMZGBJ-SFHVURJKSA-N (2s)-n-[(5-ethyl-2-fluoropyridin-3-yl)methyl]-2-hydroxy-2-phenylbutanamide Chemical compound CCC1=CN=C(F)C(CNC(=O)[C@](O)(CC)C=2C=CC=CC=2)=C1 OOWJHBQWBMZGBJ-SFHVURJKSA-N 0.000 claims 1
- DTLORZJLDDAITP-INIZCTEOSA-N (2s)-n-[(5-ethyl-2-fluoropyridin-3-yl)methyl]-2-phenylbutanamide Chemical compound O=C([C@@H](CC)C=1C=CC=CC=1)NCC1=CC(CC)=CN=C1F DTLORZJLDDAITP-INIZCTEOSA-N 0.000 claims 1
- BTUSAGMRJFOYJG-KRWDZBQOSA-N (2s)-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-hydroxy-2-phenylbutanamide Chemical compound O=C([C@](O)(CC)C=1C=CC=CC=1)NCC1=CC(C(F)(F)F)=CC=C1F BTUSAGMRJFOYJG-KRWDZBQOSA-N 0.000 claims 1
- JOJCMUGQTZHAFQ-HNNXBMFYSA-N (2s)-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-phenylbutanamide Chemical compound O=C([C@@H](CC)C=1C=CC=CC=1)NCC1=CC(C(F)(F)F)=CC=C1F JOJCMUGQTZHAFQ-HNNXBMFYSA-N 0.000 claims 1
- FUTXZOUYRWNGAO-AWEZNQCLSA-N (2s)-n-[[2-fluoro-5-(trifluoromethyl)pyridin-3-yl]methyl]-2-phenylbutanamide Chemical compound O=C([C@@H](CC)C=1C=CC=CC=1)NCC1=CC(C(F)(F)F)=CN=C1F FUTXZOUYRWNGAO-AWEZNQCLSA-N 0.000 claims 1
- USHFGOGPBYRMNY-HNNXBMFYSA-N (2s)-n-[[3-bromo-2-fluoro-5-(trifluoromethyl)phenyl]methyl]-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide Chemical compound O=C([C@@](O)(C=1C=CC=CC=1)C(F)(F)F)NCC1=CC(C(F)(F)F)=CC(Br)=C1F USHFGOGPBYRMNY-HNNXBMFYSA-N 0.000 claims 1
- SEXSZNASUHPUPT-UHFFFAOYSA-N 3,3,3-trifluoro-n-[(2-fluoro-5-methylpyridin-3-yl)methyl]-2-hydroxy-2-phenylpropanamide Chemical compound CC1=CN=C(F)C(CNC(=O)C(O)(C=2C=CC=CC=2)C(F)(F)F)=C1 SEXSZNASUHPUPT-UHFFFAOYSA-N 0.000 claims 1
- 229940121819 ATPase inhibitor Drugs 0.000 claims 1
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000032467 Aplastic anaemia Diseases 0.000 claims 1
- 102100033367 Appetite-regulating hormone Human genes 0.000 claims 1
- 101710111255 Appetite-regulating hormone Proteins 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 208000010392 Bone Fractures Diseases 0.000 claims 1
- 102000007350 Bone Morphogenetic Proteins Human genes 0.000 claims 1
- 108010007726 Bone Morphogenetic Proteins Proteins 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 102000055006 Calcitonin Human genes 0.000 claims 1
- 108060001064 Calcitonin Proteins 0.000 claims 1
- 229940123613 Calcium receptor antagonist Drugs 0.000 claims 1
- 229940122156 Cathepsin K inhibitor Drugs 0.000 claims 1
- 206010017076 Fracture Diseases 0.000 claims 1
- 208000036119 Frailty Diseases 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 102000002265 Human Growth Hormone Human genes 0.000 claims 1
- 108010000521 Human Growth Hormone Proteins 0.000 claims 1
- 239000000854 Human Growth Hormone Substances 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 claims 1
- 108010047852 Integrin alphaVbeta3 Proteins 0.000 claims 1
- SFBODOKJTYAUCM-UHFFFAOYSA-N Ipriflavone Chemical compound C=1C(OC(C)C)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 SFBODOKJTYAUCM-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010027304 Menopausal symptoms Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 208000029725 Metabolic bone disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010049088 Osteopenia Diseases 0.000 claims 1
- 102000008108 Osteoprotegerin Human genes 0.000 claims 1
- 108010035042 Osteoprotegerin Proteins 0.000 claims 1
- 108010016731 PPAR gamma Proteins 0.000 claims 1
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 102000013275 Somatomedins Human genes 0.000 claims 1
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 claims 1
- 102000011731 Vacuolar Proton-Translocating ATPases Human genes 0.000 claims 1
- 108010037026 Vacuolar Proton-Translocating ATPases Proteins 0.000 claims 1
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims 1
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims 1
- 229930003316 Vitamin D Natural products 0.000 claims 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims 1
- 229930003448 Vitamin K Natural products 0.000 claims 1
- LXCFTLNNPFEIHC-INIZCTEOSA-N [(2r)-3-[(2-fluoro-5-methylpyridin-3-yl)methylamino]-3-oxo-2-phenylpropyl] n,n-dimethylcarbamate Chemical compound O=C([C@@H](COC(=O)N(C)C)C=1C=CC=CC=1)NCC1=CC(C)=CN=C1F LXCFTLNNPFEIHC-INIZCTEOSA-N 0.000 claims 1
- CDGGBWJOZAQXAV-SFHVURJKSA-N [(2r)-3-[(2-fluoro-5-methylpyridin-3-yl)methylamino]-3-oxo-2-phenylpropyl] pyrrolidine-1-carboxylate Chemical compound CC1=CN=C(F)C(CNC(=O)[C@@H](COC(=O)N2CCCC2)C=2C=CC=CC=2)=C1 CDGGBWJOZAQXAV-SFHVURJKSA-N 0.000 claims 1
- GJOGLIRTUXJPBH-INIZCTEOSA-N [(2r)-3-[[2-fluoro-5-(trifluoromethyl)phenyl]methylamino]-3-oxo-2-phenylpropyl] n,n-dimethylcarbamate Chemical compound O=C([C@@H](COC(=O)N(C)C)C=1C=CC=CC=1)NCC1=CC(C(F)(F)F)=CC=C1F GJOGLIRTUXJPBH-INIZCTEOSA-N 0.000 claims 1
- KSSALMVCYLZVPI-SFHVURJKSA-N [(2r)-3-[[2-fluoro-5-(trifluoromethyl)phenyl]methylamino]-3-oxo-2-phenylpropyl] pyrrolidine-1-carboxylate Chemical compound FC1=CC=C(C(F)(F)F)C=C1CNC(=O)[C@H](C=1C=CC=CC=1)COC(=O)N1CCCC1 KSSALMVCYLZVPI-SFHVURJKSA-N 0.000 claims 1
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| WO2015048246A1 (en) * | 2013-09-27 | 2015-04-02 | The Board Of Trustees Of The University Of Illinois | Tetra-aryl cyclobutane inhibitors of androgen receptor action for the treatment of hormone refractory cancer |
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| US10806720B2 (en) | 2015-04-21 | 2020-10-20 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US11230523B2 (en) | 2016-06-10 | 2022-01-25 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
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| US12202815B2 (en) | 2018-09-05 | 2025-01-21 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
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-
2005
- 2005-03-06 UA UAA200700165A patent/UA87854C2/ru unknown
- 2005-05-31 MY MYPI20052469A patent/MY147997A/en unknown
- 2005-06-03 MX MXPA06014235A patent/MXPA06014235A/es active IP Right Grant
- 2005-06-03 SG SG201100895-0A patent/SG169398A1/en unknown
- 2005-06-03 NZ NZ551738A patent/NZ551738A/en not_active IP Right Cessation
- 2005-06-03 AT AT05756622T patent/ATE545631T1/de active
- 2005-06-03 RU RU2006146678/04A patent/RU2378255C2/ru not_active IP Right Cessation
- 2005-06-03 CA CA2569124A patent/CA2569124C/en not_active Expired - Fee Related
- 2005-06-03 PE PE2005000631A patent/PE20060401A1/es not_active Application Discontinuation
- 2005-06-03 TW TW094118475A patent/TW200610755A/zh unknown
- 2005-06-03 AU AU2005251766A patent/AU2005251766B9/en not_active Ceased
- 2005-06-03 WO PCT/US2005/019554 patent/WO2005120477A2/en not_active Ceased
- 2005-06-03 CN CNA2005800185774A patent/CN1976902A/zh active Pending
- 2005-06-03 BR BRPI0511862-0A patent/BRPI0511862A/pt not_active IP Right Cessation
- 2005-06-03 AR ARP050102284A patent/AR049140A1/es not_active Application Discontinuation
- 2005-06-03 US US11/145,490 patent/US7268153B2/en not_active Expired - Fee Related
- 2005-06-03 US US11/628,685 patent/US7629367B2/en not_active Expired - Fee Related
- 2005-06-03 JP JP2007527597A patent/JP4881865B2/ja not_active Expired - Fee Related
- 2005-06-03 EP EP05756622A patent/EP1755572B1/en not_active Expired - Lifetime
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2006
- 2006-11-21 ZA ZA200609673A patent/ZA200609673B/xx unknown
- 2006-12-01 CR CR8777A patent/CR8777A/es not_active Application Discontinuation
- 2006-12-04 EC EC2006007061A patent/ECSP067061A/es unknown
- 2006-12-05 IL IL179843A patent/IL179843A0/en unknown
- 2006-12-25 MA MA29551A patent/MA28677B1/fr unknown
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- 2007-01-05 NO NO20070085A patent/NO20070085L/no not_active Application Discontinuation
- 2007-03-01 US US11/712,727 patent/US7763659B2/en not_active Expired - Fee Related
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