JP2008501800A5 - - Google Patents
Download PDFInfo
- 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
Links
- -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
- LXCFTLNNPFEIHC-MRXNPFEDSA-N [(2s)-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-MRXNPFEDSA-N 0.000 claims 1
- CDGGBWJOZAQXAV-GOSISDBHSA-N [(2s)-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-GOSISDBHSA-N 0.000 claims 1
- GJOGLIRTUXJPBH-MRXNPFEDSA-N [(2s)-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-MRXNPFEDSA-N 0.000 claims 1
- KSSALMVCYLZVPI-GOSISDBHSA-N [(2s)-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-GOSISDBHSA-N 0.000 claims 1
- 230000003187 abdominal effect Effects 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000362 adenosine triphosphatase inhibitor Substances 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 229940062527 alendronate Drugs 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 206010003549 asthenia Diseases 0.000 claims 1
- 229940112869 bone morphogenetic protein Drugs 0.000 claims 1
- 229960004015 calcitonin Drugs 0.000 claims 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims 1
- 229940069978 calcium supplement Drugs 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 230000006999 cognitive decline Effects 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 235000005911 diet Nutrition 0.000 claims 1
- 230000000378 dietary effect Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000328 estrogen antagonist Substances 0.000 claims 1
- 201000003585 eunuchism Diseases 0.000 claims 1
- 150000004673 fluoride salts Chemical class 0.000 claims 1
- 201000003617 glucocorticoid-induced osteoporosis Diseases 0.000 claims 1
- 239000003324 growth hormone secretagogue Substances 0.000 claims 1
- 208000018706 hematopoietic system disease Diseases 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 229960005431 ipriflavone Drugs 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 208000037106 male hypogonadism Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 201000006938 muscular dystrophy Diseases 0.000 claims 1
- HXCCXUWPISVJRA-UHFFFAOYSA-N n-[(2-fluoro-5-methylphenyl)methyl]-2-phenylbutanamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)NCC1=CC(C)=CC=C1F HXCCXUWPISVJRA-UHFFFAOYSA-N 0.000 claims 1
- ROROYOIYWUWEAJ-UHFFFAOYSA-N n-[(2-fluoro-5-methylpyridin-3-yl)methyl]-2-phenylbutanamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)NCC1=CC(C)=CN=C1F ROROYOIYWUWEAJ-UHFFFAOYSA-N 0.000 claims 1
- VLNKNIFVOBPSMC-UHFFFAOYSA-N n-[(5-bromo-2-fluorophenyl)methyl]-2-phenylbutanamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)NCC1=CC(Br)=CC=C1F VLNKNIFVOBPSMC-UHFFFAOYSA-N 0.000 claims 1
- YLBXEYCFAGJNOW-UHFFFAOYSA-N n-[(5-cyclopropyl-2-fluorophenyl)methyl]-2-phenylbutanamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)NCC(C(=CC=1)F)=CC=1C1CC1 YLBXEYCFAGJNOW-UHFFFAOYSA-N 0.000 claims 1
- UAJUEDTYIVUMKP-UHFFFAOYSA-N n-[(5-cyclopropyl-2-fluorophenyl)methyl]-3,3,3-trifluoro-2-(4-fluorophenyl)-2-hydroxypropanamide Chemical compound C=1C=C(F)C=CC=1C(C(F)(F)F)(O)C(=O)NCC(C(=CC=1)F)=CC=1C1CC1 UAJUEDTYIVUMKP-UHFFFAOYSA-N 0.000 claims 1
- ISKVQYWSYZQLPU-UHFFFAOYSA-N n-[(5-ethenyl-2-fluorophenyl)methyl]-2-phenylbutanamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)NCC1=CC(C=C)=CC=C1F ISKVQYWSYZQLPU-UHFFFAOYSA-N 0.000 claims 1
- PXZKOPPVRIJGGB-UHFFFAOYSA-N n-[(5-ethyl-2-fluorophenyl)methyl]-2-phenylbutanamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)NCC1=CC(CC)=CC=C1F PXZKOPPVRIJGGB-UHFFFAOYSA-N 0.000 claims 1
- JOJCMUGQTZHAFQ-UHFFFAOYSA-N n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-phenylbutanamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)NCC1=CC(C(F)(F)F)=CC=C1F JOJCMUGQTZHAFQ-UHFFFAOYSA-N 0.000 claims 1
- USHFGOGPBYRMNY-UHFFFAOYSA-N n-[[3-bromo-2-fluoro-5-(trifluoromethyl)phenyl]methyl]-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide Chemical compound C=1C=CC=CC=1C(C(F)(F)F)(O)C(=O)NCC1=CC(C(F)(F)F)=CC(Br)=C1F USHFGOGPBYRMNY-UHFFFAOYSA-N 0.000 claims 1
- GLWLJRFLFJLVGZ-UHFFFAOYSA-N n-[[5-(1,1-difluoroethyl)-2-fluorophenyl]methyl]-2-phenylbutanamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)NCC1=CC(C(C)(F)F)=CC=C1F GLWLJRFLFJLVGZ-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- XXUPLYBCNPLTIW-UHFFFAOYSA-N octadec-7-ynoic acid Chemical compound CCCCCCCCCCC#CCCCCCC(O)=O XXUPLYBCNPLTIW-UHFFFAOYSA-N 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 1
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 208000028169 periodontal disease Diseases 0.000 claims 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 claims 1
- 206010036601 premature menopause Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000583 progesterone congener Substances 0.000 claims 1
- 239000003909 protein kinase inhibitor Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 238000002278 reconstructive surgery Methods 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000001076 sarcopenia Diseases 0.000 claims 1
- 239000000333 selective estrogen receptor modulator Substances 0.000 claims 1
- 229940095743 selective estrogen receptor modulator Drugs 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 201000002859 sleep apnea Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000005495 thyroid hormone Substances 0.000 claims 1
- 229940036555 thyroid hormone Drugs 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 235000019166 vitamin D Nutrition 0.000 claims 1
- 239000011710 vitamin D Substances 0.000 claims 1
- 235000019168 vitamin K Nutrition 0.000 claims 1
- 239000011712 vitamin K Substances 0.000 claims 1
- 229940046008 vitamin d Drugs 0.000 claims 1
- 229940046010 vitamin k Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57769804P | 2004-06-07 | 2004-06-07 | |
| US60/577,698 | 2004-06-07 | ||
| PCT/US2005/019554 WO2005120477A2 (en) | 2004-06-07 | 2005-06-03 | N- (2-benzyl) -2-phenylbutanamides as androgen receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008501800A JP2008501800A (ja) | 2008-01-24 |
| JP2008501800A5 true JP2008501800A5 (enExample) | 2008-04-10 |
| JP4881865B2 JP4881865B2 (ja) | 2012-02-22 |
Family
ID=35415107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007527597A Expired - Fee Related JP4881865B2 (ja) | 2004-06-07 | 2005-06-03 | アンドロゲン受容体調節剤としてのｎ−（２−ベンジル）−２−フェニルブタンアミド |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US7629367B2 (enExample) |
| EP (1) | EP1755572B1 (enExample) |
| JP (1) | JP4881865B2 (enExample) |
| CN (1) | CN1976902A (enExample) |
| AR (1) | AR049140A1 (enExample) |
| AT (1) | ATE545631T1 (enExample) |
| AU (1) | AU2005251766B9 (enExample) |
| BR (1) | BRPI0511862A (enExample) |
| CA (1) | CA2569124C (enExample) |
| CR (1) | CR8777A (enExample) |
| EC (1) | ECSP067061A (enExample) |
| IL (1) | IL179843A0 (enExample) |
| MA (1) | MA28677B1 (enExample) |
| MX (1) | MXPA06014235A (enExample) |
| MY (1) | MY147997A (enExample) |
| NO (1) | NO20070085L (enExample) |
| NZ (1) | NZ551738A (enExample) |
| PE (1) | PE20060401A1 (enExample) |
| RU (1) | RU2378255C2 (enExample) |
| SG (1) | SG169398A1 (enExample) |
| TW (1) | TW200610755A (enExample) |
| UA (1) | UA87854C2 (enExample) |
| WO (1) | WO2005120477A2 (enExample) |
| ZA (1) | ZA200609673B (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA87854C2 (en) * | 2004-06-07 | 2009-08-25 | Мерк Энд Ко., Инк. | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators |
| AU2005310238A1 (en) * | 2004-10-29 | 2006-06-08 | Merck Sharp & Dohme Corp. | N-(pyridin-3-yl)-2-phenylbutanamides as androgen receptor modulators |
| EP1912945A4 (en) * | 2005-08-02 | 2010-06-16 | Merck Sharp & Dohme | N- (PYRIDIN-4-YL) -2-PHENYLBUTANAMIDES AS ANDROGEN RECEPTOR MODULATORS |
| WO2007077510A2 (en) * | 2005-12-30 | 2007-07-12 | Ranbaxy Laboratories Limited | Muscarinic receptor antagonists |
| CA2666769A1 (en) * | 2006-10-18 | 2008-04-24 | Merck & Co., Inc. | 2-hydroxy-2-phenyl/thiophenyl propionamides as androgen receptor modulators |
| CN101945853B (zh) | 2007-12-21 | 2014-08-20 | 配体药物公司 | 选择性雄激素受体调节剂(sarm)及其应用 |
| US20090197947A1 (en) * | 2008-02-01 | 2009-08-06 | The Research Foundation Of State University Of New York | Medicaments and methods for lowering plasma lipid levels and screening drugs |
| WO2009136629A1 (ja) * | 2008-05-09 | 2009-11-12 | あすか製薬株式会社 | 生活習慣病予防・治療剤 |
| EP3205648A1 (en) | 2010-06-10 | 2017-08-16 | Seragon Pharmaceuticals, Inc. | Estrogen receptor modulators and uses thereof |
| US9763678B2 (en) | 2010-06-24 | 2017-09-19 | DePuy Synthes Products, Inc. | Multi-segment lateral cage adapted to flex substantially in the coronal plane |
| FR2982261B1 (fr) * | 2011-11-04 | 2014-06-13 | Galderma Res & Dev | Nouveaux amides, et leur utilisation pharmaceutique ou cosmetique |
| EP2791132A4 (en) | 2011-12-14 | 2015-08-05 | Seragon Pharmaceuticals Inc | ESTROGEN RECEPTOR MODULATORS AND USES THEREOF |
| CN103288669B (zh) * | 2013-07-01 | 2015-06-24 | 南开大学 | 一种阿卓乳酸酰胺衍生物及应用 |
| US9868705B2 (en) | 2013-09-27 | 2018-01-16 | The Board Of Trustees Of The University Of Illinois | Tetra-aryl cyclobutane inhibitors of androgen receptor action for the treatment of hormone refractory cancer |
| EP3613418A1 (en) | 2014-01-17 | 2020-02-26 | Ligand Pharmaceuticals, Inc. | Methods and compositions for modulating hormone levels |
| US10441570B2 (en) | 2015-04-21 | 2019-10-15 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) Ligands and methods of use thereof |
| CA2983426C (en) * | 2015-04-21 | 2023-10-17 | Gtx, Inc. | Selective androgen receptor degrader (sard) ligands and methods of use thereof |
| US10865184B2 (en) | 2015-04-21 | 2020-12-15 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US10806720B2 (en) | 2015-04-21 | 2020-10-20 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US10654809B2 (en) | 2016-06-10 | 2020-05-19 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US10093613B2 (en) | 2015-04-21 | 2018-10-09 | Gtx, Inc. | 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 |
| ES2927715T3 (es) | 2017-10-05 | 2022-11-10 | Fulcrum Therapeutics Inc | Inhibidores de la quinasa p38 reducen la expresión de dux4 y de los genes que le siguen para el tratamiento de la FSHD |
| BR112020023136A2 (pt) | 2018-05-14 | 2021-02-09 | Nuvation Bio Inc. | compostos de alvo de receptor de hormônio nuclear anticâncer |
| WO2020048826A1 (en) | 2018-09-03 | 2020-03-12 | Bayer Aktiengesellschaft | 5-substituted 1-oxa-3,9-diazaspiro[5.5]undecan-2-one compounds |
| US12202815B2 (en) | 2018-09-05 | 2025-01-21 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| AU2020257397B2 (en) | 2019-04-19 | 2026-02-26 | Ligand Pharmaceuticals Inc. | Crystalline forms and methods of producing crystalline forms of a compound |
| CN113811333B (zh) | 2019-05-14 | 2024-03-12 | 诺维逊生物股份有限公司 | 靶向抗癌核激素受体的化合物 |
| WO2021021708A1 (en) * | 2019-07-26 | 2021-02-04 | Chemistyrx | Compositions for treating sexual dysfunction |
| EP4058464A1 (en) | 2019-11-13 | 2022-09-21 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| EP4313991A1 (en) | 2021-03-23 | 2024-02-07 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| WO2022235585A1 (en) | 2021-05-03 | 2022-11-10 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| CN113816900B (zh) * | 2021-10-18 | 2024-06-25 | 宁夏瑞泰科技股份有限公司 | 一种2-氯-5-甲基吡啶-3-甲醛的合成方法 |
Family Cites Families (139)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809965A (en) | 1956-04-30 | 1957-10-15 | Dow Chemical Co | Phthalides |
| CA777769A (en) | 1963-03-18 | 1968-02-06 | H. Roy Clarence | Substituted methylene diphosphonic acid compounds and detergent compositions |
| US3239345A (en) | 1965-02-15 | 1966-03-08 | Estrogenic compounds and animal growth promoters | |
| US4411890A (en) | 1981-04-14 | 1983-10-25 | Beckman Instruments, Inc. | Synthetic peptides having pituitary growth hormone releasing activity |
| US4036979A (en) | 1974-01-25 | 1977-07-19 | American Cyanamid Company | Compositions containing 4,5,6,7-tetrahydrobenz[b]thien-4-yl-ureas or derivatives and methods of enhancing growth rate |
| US4342767A (en) | 1980-01-23 | 1982-08-03 | Merck & Co., Inc. | Hypocholesteremic fermentation products |
| US4444784A (en) | 1980-08-05 | 1984-04-24 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| MX7065E (es) | 1980-06-06 | 1987-04-10 | Sankyo Co | Un procedimiento microbiologico para preparar derivados de ml-236b |
| FR2531088B1 (fr) | 1982-07-29 | 1987-08-28 | Sanofi Sa | Produits anti-inflammatoires derives de l'acide methylenediphosphonique et leur procede de preparation |
| US5354772A (en) | 1982-11-22 | 1994-10-11 | Sandoz Pharm. Corp. | Indole analogs of mevalonolactone and derivatives thereof |
| GB8332704D0 (en) | 1983-12-07 | 1984-01-11 | Pfizer Ltd | Growth promotants for animals |
| US4761406A (en) | 1985-06-06 | 1988-08-02 | The Procter & Gamble Company | Regimen for treating osteoporosis |
| DE3623397A1 (de) | 1986-07-11 | 1988-01-14 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| GB8726179D0 (en) * | 1987-11-09 | 1987-12-16 | Fujisawa Pharmaceutical Co | Heterocyclic derivatives |
| CA1339805C (en) | 1988-01-20 | 1998-04-07 | Yasuo Isomura | (cycloalkylamino)methylenebis(phosphonic acid) and medicines containing the same as an active |
| US4922007A (en) | 1989-06-09 | 1990-05-01 | Merck & Co., Inc. | Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid or salts thereof |
| FI94339C (fi) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| US5019651A (en) | 1990-06-20 | 1991-05-28 | Merck & Co., Inc. | Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (ABP) or salts thereof |
| US5177080A (en) | 1990-12-14 | 1993-01-05 | Bayer Aktiengesellschaft | Substituted pyridyl-dihydroxy-heptenoic acid and its salts |
| US5206235A (en) | 1991-03-20 | 1993-04-27 | Merck & Co., Inc. | Benzo-fused lactams that promote the release of growth hormone |
| JP2648897B2 (ja) | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
| US5283241A (en) | 1992-08-28 | 1994-02-01 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
| US5583130A (en) | 1992-09-25 | 1996-12-10 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
| US5317017A (en) | 1992-09-30 | 1994-05-31 | Merck & Co., Inc. | N-biphenyl-3-amido substituted benzolactams stimulate growth hormone release |
| US5374721A (en) | 1992-10-14 | 1994-12-20 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
| CA2147503A1 (en) | 1992-11-06 | 1994-05-26 | Judith M. Pisano | Substituted dipeptide analogs promote release of growth hormone |
| US5578593A (en) | 1992-12-11 | 1996-11-26 | Merck & Co., Inc. | Spiro piperidines and homologs promote release of growth hormone |
| SK282166B6 (sk) | 1992-12-11 | 2001-11-06 | Merck & Co., Inc. | Spiropiperidínové deriváty, spôsob ich výroby a farmaceutický prostriedok s ich obsahom |
| US5284841A (en) | 1993-02-04 | 1994-02-08 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
| US5430144A (en) | 1993-07-26 | 1995-07-04 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
| US5434261A (en) | 1993-07-26 | 1995-07-18 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
| US5952281A (en) | 1993-08-04 | 1999-09-14 | Colgate Palmolive Company | Aqueous cleaning composition which may be in microemulsion form containing a silicone antifoam agent |
| TW257765B (enExample) | 1993-08-25 | 1995-09-21 | Merck & Co Inc | |
| US5510517A (en) | 1993-08-25 | 1996-04-23 | Merck & Co., Inc. | Process for producing N-amino-1-hydroxy-alkylidene-1,1-bisphosphonic acids |
| US5631365A (en) | 1993-09-21 | 1997-05-20 | Schering Corporation | Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents |
| DE4332384A1 (de) | 1993-09-23 | 1995-03-30 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten III |
| US5545735A (en) | 1993-10-04 | 1996-08-13 | Merck & Co., Inc. | Benzo-Fused Lactams promote release of growth hormone |
| AU8083694A (en) | 1993-10-19 | 1995-05-08 | Merck & Co., Inc. | Combination of bisphosphonates and growth hormone secretagogues |
| US5438136A (en) | 1993-11-02 | 1995-08-01 | Merck & Co., Inc. | Benzo-fused macrocycles promote release of growth hormone |
| US5492916A (en) | 1993-12-23 | 1996-02-20 | Merck & Co., Inc. | Di- and tri-substituted piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone |
| US5494919A (en) | 1993-11-09 | 1996-02-27 | Merck & Co., Inc. | 2-substituted piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone |
| BR9408019A (pt) | 1993-11-09 | 1997-08-26 | Merck & Co Inc | Composto composição util para aumentar a produção endógena ou a liberaçao de hormonio do crescimento em ser humano ou um animal e para o tratamento da osteoporose processos para aumentar os niveis de hormônio do crescimento em um ser humano ou um animal e a eficácia de alimentação promover o crescimento aumentar a produçao de leite e melhorar a qualidade da carcaça de gado para tratar ou previnir uma condição selecionada para tratar osteoporose e para preparar um composto |
| WO1995014666A1 (en) | 1993-11-24 | 1995-06-01 | Merck & Co., Inc. | Indolyl group containing compounds and the use thereof to promote the release of growth hormone(s) |
| AU1371895A (en) | 1993-12-13 | 1995-07-03 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
| US5606054A (en) | 1993-12-14 | 1997-02-25 | Merck & Co., Inc. | Heterocyclic-fused lactams promote release of growth hormone |
| CA2179597A1 (en) | 1993-12-23 | 1995-06-29 | Nils Langeland Johansen | Compounds with growth hormone releasing properties |
| US5854211A (en) | 1993-12-23 | 1998-12-29 | Novo Nordisk A/S | Compounds with growth hormone releasing properties |
| US5501969A (en) | 1994-03-08 | 1996-03-26 | Human Genome Sciences, Inc. | Human osteoclast-derived cathepsin |
| ATE227567T1 (de) | 1994-05-27 | 2002-11-15 | Merck & Co Inc | Präparate zur hemmung der durch osteoklasten vermittelten knochenresorption |
| US5777112A (en) | 1994-06-13 | 1998-07-07 | Merck & Co., Inc | Piperazine compounds promote release of growth hormone |
| WO1996000730A1 (en) | 1994-06-29 | 1996-01-11 | Smithkline Beecham Corporation | Vitronectin receptor antagonists |
| ZA955391B (en) | 1994-06-29 | 1996-02-09 | Smithkline Beecham Corp | Vitronectin receptor antagonists |
| WO1996002530A1 (en) | 1994-07-20 | 1996-02-01 | Merck & Co., Inc. | Piperidines and hexahydro-1h-azepines spiro substituted at the 4-position promote release of growth hormone |
| JPH10504825A (ja) | 1994-08-22 | 1998-05-12 | スミスクライン・ビーチャム・コーポレイション | 二環式化合物 |
| US5494920A (en) | 1994-08-22 | 1996-02-27 | Eli Lilly And Company | Methods of inhibiting viral replication |
| US5736357A (en) | 1994-10-27 | 1998-04-07 | Arris Pharmaceutical | Cathespin O protease |
| US6544767B1 (en) | 1994-10-27 | 2003-04-08 | Axys Pharmaceuticals, Inc. | Cathespin O2 protease |
| DE19504379A1 (de) | 1995-02-10 | 1996-08-14 | Hoechst Ag | Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Präparate sowie sie enthaltende pharmazeutische Präparate |
| WO1996026190A1 (en) | 1995-02-22 | 1996-08-29 | Smithkline Beecham Corporation | Integrin receptor antagonists |
| US5710159A (en) | 1996-05-09 | 1998-01-20 | The Dupont Merck Pharmaceutical Company | Integrin receptor antagonists |
| US6008213A (en) | 1995-06-29 | 1999-12-28 | Smithkline Beecham Corporation | Integrin receptor antagonists |
| SI0910563T1 (en) | 1995-06-29 | 2003-10-31 | Smithkline Beecham Corporation | Integrin receptor antagonists |
| MX9801716A (es) | 1995-08-30 | 1998-05-31 | Searle & Co | Derivados de meta-guanidina, urea, tiourea o acido aminobenzoico azaciclico, como antagonistas de integrina. |
| US6204293B1 (en) | 1995-11-06 | 2001-03-20 | University Of Pittsburgh | Inhibitors of protein isoprenyl transferases |
| DK0814782T3 (da) | 1995-12-22 | 2002-12-16 | Nissan Chemical Ind Ltd | Farmaceutisk præparat stabiliseret med et basisk middel |
| US5760028A (en) | 1995-12-22 | 1998-06-02 | The Dupont Merck Pharmaceutical Company | Integrin receptor antagonists |
| WO1997024124A1 (en) | 1995-12-29 | 1997-07-10 | Smithkline Beecham Corporation | Vitronectin receptor antagonists |
| CN1209744A (zh) | 1995-12-29 | 1999-03-03 | 史密丝克莱恩比彻姆公司 | 玻连蛋白受体拮抗剂 |
| TR199801255T2 (xx) | 1995-12-29 | 1998-10-21 | Smithkline Beecham Corporation | Vitronektin resept�r antagonistleri. |
| EA002271B1 (ru) | 1996-03-20 | 2002-02-28 | Хехст Марион Руссель | ТРИЦИКЛИЧЕСКИЕ СОЕДИНЕНИЯ, ОБЛАДАЮЩИЕ АКТИВНОСТЬЮ В ОТНОШЕНИИ ИНТЕГРИНОВ, В ЧАСТНОСТИ В ОТНОШЕНИИ ИНТЕГРИНА АЛЬФАvБЕТА 3, СПОСОБ ИХ ПОЛУЧЕНИЯ И ПРОМЕЖУТОЧНЫЕ СОЕДИНЕНИЯ, ИСПОЛЬЗУЕМЫЕ В ЭТОМ СПОСОБЕ, ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ МЕДИКАМЕНТОВ И СОДЕРЖАЩИЕ ИХ ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ |
| ATE212990T1 (de) | 1996-03-20 | 2002-02-15 | Hoechst Ag | Inhibitoren der knochenresorption und vitronectinrezeptor-antagonisten |
| DE69713582T2 (de) | 1996-03-29 | 2003-01-09 | G.D. Searle & Co., Chicago | Zimtsäurederivate und deren verwendung als integrin-antagonisten |
| DE69706407T2 (de) | 1996-03-29 | 2002-05-29 | G.D. Searle & Co., Chicago | META-SUBSTITUIERTE PHENYLENDERIVATE UND IHRE VERWENDUNG ALS ALPHAvBETA3 INTERGRIN-ANTAGONISTEN ODER INHIBITOREN |
| JP2000507575A (ja) | 1996-03-29 | 2000-06-20 | ジー．ディー．サール アンド カンパニー | シクロプロピルアルカノイック酸誘導体 |
| JP2000507952A (ja) | 1996-03-29 | 2000-06-27 | ジー．ディー．サール アンド カンパニー | ｍｅｔａ―置換フェニレンスルホンアミド誘導体 |
| US5925655A (en) | 1996-04-10 | 1999-07-20 | Merck & Co., Inc. | αv β3 antagonists |
| EP0907637A1 (de) | 1996-06-28 | 1999-04-14 | MERCK PATENT GmbH | Phenylalanin-derivate als integrin-inhibitoren |
| DE19629816A1 (de) | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Cycloalkyl-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| DE19629817A1 (de) | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Imino-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| US5981546A (en) | 1996-08-29 | 1999-11-09 | Merck & Co., Inc. | Integrin antagonists |
| UA60311C2 (uk) | 1996-10-02 | 2003-10-15 | Смітклайн Бічам Корпорейшн | Антагоністи рецептора вітронектину, спосіб одержання цих сполук та фармацевтична композиція |
| EP0946180A4 (en) | 1996-10-07 | 2003-07-23 | Smithkline Beecham Corp | METHODS FOR STIMULATING BONE FORMATION |
| US5919792A (en) | 1996-10-30 | 1999-07-06 | Merck & Co., Inc. | Integrin antagonists |
| PT944619E (pt) | 1996-11-27 | 2007-01-31 | Bristol Myers Squibb Pharma Co | Novos antagonistas dos receptores da integrina |
| DE19653646A1 (de) | 1996-12-20 | 1998-06-25 | Hoechst Ag | Substituierte Purinderivate, Verfahren zu deren Herstellung, sie enthaltende Mittel und deren Verwendung |
| CO4920232A1 (es) | 1997-01-08 | 2000-05-29 | Smithkline Beecham Corp | Acidos aceticos dibenzo [a,d] cicloheptano con actividad antagonista del receptor de vitronectin |
| DE19705450A1 (de) | 1997-02-13 | 1998-08-20 | Merck Patent Gmbh | Bicyclische aromatische Aminosäuren |
| US6239138B1 (en) | 1997-07-25 | 2001-05-29 | Smithkline Beecham Corporation | Vitronectin receptor antagonist |
| WO1999006049A1 (en) | 1997-08-04 | 1999-02-11 | Smithkline Beecham Corporation | Integrin receptor antagonists |
| WO1999011626A1 (en) | 1997-09-04 | 1999-03-11 | Smithkline Beecham Corporation | Integrin receptor antagonists |
| PE122699A1 (es) | 1997-09-19 | 2000-02-12 | Smithkline Beecham Corp | Antagonistas de receptores de vitronectina |
| FR2768736B1 (fr) | 1997-09-24 | 2000-05-26 | Roussel Uclaf | Nouveaux composes tricycliques, leur procede de preparation et les intermediaires de ce procede, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
| JP2002500162A (ja) | 1997-09-24 | 2002-01-08 | スミスクライン・ビーチャム・コーポレイション | ビトロネクチン受容体アンタゴニスト |
| IL135189A0 (en) | 1997-09-24 | 2001-05-20 | Smithkline Beecham Corp | Vitronectin receptor antagonist |
| JP2001524481A (ja) | 1997-11-26 | 2001-12-04 | デュポン ファーマシューティカルズ カンパニー | αＶβ３アンタゴニストとしての１，３，４−チアジアゾール類および１，３，４−オキサジアゾール類 |
| US6066648A (en) | 1997-12-17 | 2000-05-23 | Merck & Co., Inc. | Integrin receptor antagonists |
| ES2243016T3 (es) | 1997-12-17 | 2005-11-16 | MERCK & CO., INC. | Antagonistas de receptores de integrinas. |
| US6017926A (en) | 1997-12-17 | 2000-01-25 | Merck & Co., Inc. | Integrin receptor antagonists |
| DE69830806T2 (de) | 1997-12-17 | 2006-04-27 | Merck & Co., Inc. | Integrinrezeptor antagonisten |
| EP1047425A4 (en) | 1997-12-17 | 2009-04-22 | Merck & Co Inc | INTEGRIN RECEPTOR ANTAGONISTS |
| EP0933367A1 (en) | 1997-12-19 | 1999-08-04 | Hoechst Marion Roussel Deutschland GmbH | Novel acylguanidine derivates as inhibitors of bone resorption and as vitronectin receptor antagonists |
| WO1999033798A1 (en) | 1997-12-25 | 1999-07-08 | Yamanouchi Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic derivatives |
| SI0928793T1 (en) | 1998-01-02 | 2002-10-31 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
| EP0928790B1 (en) | 1998-01-02 | 2003-03-05 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
| BR9907735A (pt) | 1998-01-23 | 2000-10-17 | Aventis Pharma Gmbh | Derivados de sulfonamida como inibidores da reabsorção óssea e como inibidores da aderência celular |
| ZA994406B (en) | 1998-03-04 | 2000-02-11 | Searle & Co | Meta-azacyclic amino benzoic acid and derivatives thereof. |
| IL138245A0 (en) | 1998-03-10 | 2001-10-31 | Smithkline Beecham Corp | Vitronectin receptor antagonists |
| WO1999052872A1 (en) | 1998-04-09 | 1999-10-21 | Meiji Seika Kaisha, Ltd. | AMINOPIPERIDINE DERIVATIVES AS INTEGRIN αvβ3 ANTAGONISTS |
| KR20010042614A (ko) | 1998-04-10 | 2001-05-25 | 윌리암스 로저 에이 | 비트로넥틴 길항제로서 복소환식 글리실 베타-알라닌 유도체 |
| WO1999052879A1 (en) | 1998-04-14 | 1999-10-21 | American Home Products Corporation | Acylresorcinol derivatives as selective vitronectin receptor inhibitors |
| EP0960882A1 (en) | 1998-05-19 | 1999-12-01 | Hoechst Marion Roussel Deutschland GmbH | Thienyl substituted acylguanidines as inhibitors of bone resorption and vitronectin receptor antagonists |
| DE69912432D1 (de) | 1998-06-29 | 2003-12-04 | Iaf Biochem Int | Zur behandlung von krebs nützliche thiophen- und furan-2,5-dicarboxamide |
| AR019190A1 (es) | 1998-07-08 | 2001-12-26 | Sod Conseils Rech Applic | Derivados de 2-aminopiridinas, productos intermedios para su preparacion, medicamentos y composiciones farmaceuticas que los contienen y su uso para preparar medicamentos |
| WO2000006169A1 (en) | 1998-07-29 | 2000-02-10 | Merck & Co., Inc. | Integrin receptor antagonists |
| AU748621B2 (en) | 1998-08-13 | 2002-06-06 | Merck & Co., Inc. | Integrin receptor antagonists |
| GB9828442D0 (en) | 1998-12-24 | 1999-02-17 | Karobio Ab | Novel thyroid receptor ligands and method II |
| AU7278500A (en) | 1999-08-18 | 2001-03-13 | Aventis Cropscience Gmbh | Fungicides |
| WO2001017562A1 (fr) | 1999-09-02 | 2001-03-15 | Yamanouchi Pharmaceutical Co., Ltd. | Agents promoteurs de l'osteogenese |
| DE60132975T2 (de) | 2000-01-06 | 2009-02-26 | Merck Frosst Canada Inc., Kirkland | Neue substanzen und verbindungen als protease-inhibitoren |
| JP2003530384A (ja) | 2000-04-06 | 2003-10-14 | メルク フロスト カナダ アンド カンパニー | カテプシンシステインプロテアーゼ阻害薬 |
| ES2353020T3 (es) | 2000-05-31 | 2011-02-24 | Santen Pharmaceutical Co., Ltd. | (piridinil)alquil-amidas o -ureas como inhibidores de la producción del tnf-alfa. |
| EP1193248A1 (en) | 2000-09-30 | 2002-04-03 | Aventis Pharma Deutschland GmbH | Malonamid and malonamic ester derivatives with antithrombotic activity, their preparation and their use |
| US7214690B2 (en) * | 2001-02-23 | 2007-05-08 | Ligand Pharmaceuticals Incorporated | Tricyclic quinolinone and tricyclic quinoline androgen receptor modulator compounds and methods |
| WO2003030937A1 (en) * | 2001-10-05 | 2003-04-17 | Ono Pharmaceutical Co., Ltd. | Remedies for stress diseases comprising mitochondrial benzodiazepine receptor antagonists |
| CA2689080C (en) * | 2002-02-07 | 2011-07-05 | University Of Tennessee Research Foundation | Treating benign prostate hyperplasia with sarms |
| WO2003074473A2 (en) * | 2002-02-28 | 2003-09-12 | University Of Tennessee Research Foundation | Irreversible selective androgen receptor modulators and methods of use thereof |
| WO2003092588A2 (en) * | 2002-04-30 | 2003-11-13 | Merck & Co., Inc. | 4-azasteroid derivatives as androgen receptor modulators |
| JP2006518328A (ja) * | 2002-10-15 | 2006-08-10 | ユニバーシティ・オブ・テネシー・リサーチ・ファウンデーション | 複素環選択的アンドロゲン受容体調節剤及びその使用方法 |
| US20040087810A1 (en) | 2002-10-23 | 2004-05-06 | Dalton James T. | Irreversible selective androgen receptor modulators and methods of use thereof |
| TW200410921A (en) | 2002-11-25 | 2004-07-01 | Hoffmann La Roche | Mandelic acid derivatives |
| US7217794B2 (en) | 2003-04-02 | 2007-05-15 | Daiamed, Inc. | Compounds and methods for treatment of thrombosis |
| US7268147B2 (en) | 2003-05-15 | 2007-09-11 | Pfizer Inc | Compounds useful for the treatment of diseases |
| EP1477167A1 (en) | 2003-05-15 | 2004-11-17 | Pfizer Limited | [(2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)-ethylamino)-propyl] phenyl derivatives as beta2 agonists |
| GB0312832D0 (en) | 2003-06-04 | 2003-07-09 | Pfizer Ltd | 2-amino-pyridine derivatives useful for the treatment of diseases |
| US7375100B2 (en) | 2003-06-04 | 2008-05-20 | Pfizer Inc | 2-amino-pyridine derivatives useful for the treatment of diseases |
| WO2005063690A1 (en) | 2003-12-22 | 2005-07-14 | Merck & Co., Inc. | Alpha-hydroxy amides as bradykinin antagonists or inverse agonists |
| EA200601510A1 (ru) * | 2004-03-17 | 2007-04-27 | Пфайзер Инк. | Производные фенилэтаноламина в качестве бета-2-агонистов |
| US7629358B2 (en) | 2004-03-17 | 2009-12-08 | Pfizer Inc | Compounds useful for the treatment of diseases |
| UA87854C2 (en) | 2004-06-07 | 2009-08-25 | Мерк Энд Ко., Инк. | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators |
-
2005
- 2005-03-06 UA UAA200700165A patent/UA87854C2/ru unknown
- 2005-05-31 MY MYPI20052469A patent/MY147997A/en unknown
- 2005-06-03 CN CNA2005800185774A patent/CN1976902A/zh active Pending
- 2005-06-03 US US11/628,685 patent/US7629367B2/en not_active Expired - Fee Related
- 2005-06-03 MX MXPA06014235A patent/MXPA06014235A/es active IP Right Grant
- 2005-06-03 EP EP05756622A patent/EP1755572B1/en not_active Expired - Lifetime
- 2005-06-03 CA CA2569124A patent/CA2569124C/en not_active Expired - Fee Related
- 2005-06-03 WO PCT/US2005/019554 patent/WO2005120477A2/en not_active Ceased
- 2005-06-03 SG SG201100895-0A patent/SG169398A1/en unknown
- 2005-06-03 TW TW094118475A patent/TW200610755A/zh unknown
- 2005-06-03 JP JP2007527597A patent/JP4881865B2/ja not_active Expired - Fee Related
- 2005-06-03 AT AT05756622T patent/ATE545631T1/de active
- 2005-06-03 AR ARP050102284A patent/AR049140A1/es not_active Application Discontinuation
- 2005-06-03 AU AU2005251766A patent/AU2005251766B9/en not_active Ceased
- 2005-06-03 PE PE2005000631A patent/PE20060401A1/es not_active Application Discontinuation
- 2005-06-03 RU RU2006146678/04A patent/RU2378255C2/ru not_active IP Right Cessation
- 2005-06-03 BR BRPI0511862-0A patent/BRPI0511862A/pt not_active IP Right Cessation
- 2005-06-03 NZ NZ551738A patent/NZ551738A/en not_active IP Right Cessation
- 2005-06-03 US US11/145,490 patent/US7268153B2/en not_active Expired - Fee Related
-
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
-
2007
- 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2006146678A (ru) | N-(2-бензил)-2-фенилбутанамиды в качестве модуляторов рецептора андрогена | |
| RU2345067C2 (ru) | Ингибиторы дпп-iv | |
| JP2009505962A5 (enExample) | ||
| RU2009118254A (ru) | Фенилацетамиды в качестве ингибиторов протеинкиназ | |
| JP2006525276A5 (enExample) | ||
| JP2010090173A (ja) | Ｄｐｐｉｖ阻害剤および心臓血管化合物の組み合わせ | |
| JP2015528471A5 (enExample) | ||
| NZ597241A (en) | Pharmaceutical dosage form for oral administration of a bcl-2 family inhibitor | |
| RU2004134564A (ru) | Химические соединения | |
| JP2005518337A5 (enExample) | ||
| JP2007519754A5 (enExample) | ||
| RU2016146826A (ru) | Производные карбонитрилов как селективные модуляторы андрогенового рецептора | |
| JP2004525179A5 (enExample) | ||
| JP2016523923A5 (enExample) | ||
| RU2006116887A (ru) | Производные n-[гетероарил(пиперидин-2-ил)метил]бензамида, способ получения указанных соединений и их применение в терапии | |
| JP2008540554A5 (enExample) | ||
| UA84146C2 (ru) | Амиды пирролопиридин-2-карбоновой кислоты как ингибиторы гликогенфосфорилазы, способ их получения, фармацевтическая композиция и их применение как терапевтических агентов для лечения заболеваний | |
| PL1735278T3 (pl) | Związki receptora histaminowego H3, wytwarzanie i zastosowania terapeutyczne | |
| CA2660529A1 (en) | Benzimidazole derivatives useful in treatment of vallinoid receptor trpv1 related disorders | |
| JP2016514141A5 (enExample) | ||
| EA016687B8 (ru) | Производные циклопропиламида | |
| JP2003528861A5 (enExample) | ||
| JP2004509857A5 (enExample) | ||
| JP2010533131A5 (enExample) | ||
| RU2000131184A (ru) | Соединения, обладающие свойствами, способствующими выделению гормона роста |