JP2005518404A5 - - Google Patents
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- Publication number
- JP2005518404A5 JP2005518404A5 JP2003559458A JP2003559458A JP2005518404A5 JP 2005518404 A5 JP2005518404 A5 JP 2005518404A5 JP 2003559458 A JP2003559458 A JP 2003559458A JP 2003559458 A JP2003559458 A JP 2003559458A JP 2005518404 A5 JP2005518404 A5 JP 2005518404A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- methyl
- aza
- androst
- alkyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 285
- -1 (2) naphthyl Chemical group 0.000 claims 247
- 125000003118 aryl group Chemical group 0.000 claims 200
- 229910052739 hydrogen Inorganic materials 0.000 claims 76
- 239000001257 hydrogen Substances 0.000 claims 76
- 125000003545 alkoxy group Chemical group 0.000 claims 50
- 150000002431 hydrogen Chemical class 0.000 claims 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 34
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 34
- 239000000203 mixture Substances 0.000 claims 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 30
- 125000003342 alkenyl group Chemical group 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 26
- 229910052799 carbon Inorganic materials 0.000 claims 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 23
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 21
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims 21
- 125000003282 alkyl amino group Chemical group 0.000 claims 21
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 21
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 21
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 21
- 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 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 125000004432 carbon atom Chemical group C* 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 125000005842 heteroatom Chemical group 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 18
- 229910052717 sulfur Inorganic materials 0.000 claims 18
- 229940011871 estrogen Drugs 0.000 claims 17
- 239000000262 estrogen Substances 0.000 claims 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 16
- 229910052731 fluorine Inorganic materials 0.000 claims 16
- 239000011737 fluorine Substances 0.000 claims 16
- 125000004043 oxo group Chemical group O=* 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 239000011647 vitamin D3 Substances 0.000 claims 16
- 229940021056 vitamin d3 Drugs 0.000 claims 16
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 14
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 14
- 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 14
- 125000004442 acylamino group Chemical group 0.000 claims 14
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims 14
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 14
- 125000001153 fluoro group Chemical group F* 0.000 claims 14
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 13
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 13
- 125000004414 alkyl thio group Chemical group 0.000 claims 13
- 150000003710 vitamin D derivatives Chemical class 0.000 claims 12
- 235000005282 vitamin D3 Nutrition 0.000 claims 12
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound 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-YRZJJWOYSA-N 0.000 claims 12
- 229940122361 Bisphosphonate Drugs 0.000 claims 11
- 239000000199 parathyroid hormone Substances 0.000 claims 11
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 9
- 102000003982 Parathyroid hormone Human genes 0.000 claims 9
- 108090000445 Parathyroid hormone Proteins 0.000 claims 9
- 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 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 125000002541 furyl group Chemical group 0.000 claims 9
- 125000002883 imidazolyl group Chemical group 0.000 claims 9
- 229960001319 parathyroid hormone Drugs 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000000335 thiazolyl group Chemical group 0.000 claims 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 8
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 8
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 8
- 210000000988 bone and bone Anatomy 0.000 claims 8
- 210000002997 osteoclast Anatomy 0.000 claims 8
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 7
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 7
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 7
- 102000055006 Calcitonin Human genes 0.000 claims 7
- 108060001064 Calcitonin Proteins 0.000 claims 7
- 229930003316 Vitamin D Natural products 0.000 claims 7
- 229940046836 anti-estrogen Drugs 0.000 claims 7
- 230000001833 anti-estrogenic effect Effects 0.000 claims 7
- 150000004663 bisphosphonates Chemical class 0.000 claims 7
- 229960004015 calcitonin Drugs 0.000 claims 7
- 239000000328 estrogen antagonist Substances 0.000 claims 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 7
- 125000002971 oxazolyl group Chemical group 0.000 claims 7
- 239000000583 progesterone congener Substances 0.000 claims 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 7
- 229940095743 selective estrogen receptor modulator Drugs 0.000 claims 7
- 239000000333 selective estrogen receptor modulator Substances 0.000 claims 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 7
- 125000001544 thienyl group Chemical group 0.000 claims 7
- 125000001425 triazolyl group Chemical group 0.000 claims 7
- 235000019166 vitamin D Nutrition 0.000 claims 7
- 239000011710 vitamin D Substances 0.000 claims 7
- 229940046008 vitamin d Drugs 0.000 claims 7
- 125000001769 aryl amino group Chemical group 0.000 claims 6
- 150000003721 vitamin K derivatives Chemical class 0.000 claims 6
- 229940121819 ATPase inhibitor Drugs 0.000 claims 5
- 102100032187 Androgen receptor Human genes 0.000 claims 5
- 108010007726 Bone Morphogenetic Proteins Proteins 0.000 claims 5
- 102000007350 Bone Morphogenetic Proteins Human genes 0.000 claims 5
- 229940122156 Cathepsin K inhibitor Drugs 0.000 claims 5
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 5
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 claims 5
- 102000014429 Insulin-like growth factor Human genes 0.000 claims 5
- 108010047852 Integrin alphaVbeta3 Proteins 0.000 claims 5
- 102000008108 Osteoprotegerin Human genes 0.000 claims 5
- 108010035042 Osteoprotegerin Proteins 0.000 claims 5
- 102000011731 Vacuolar Proton-Translocating ATPases Human genes 0.000 claims 5
- 108010037026 Vacuolar Proton-Translocating ATPases Proteins 0.000 claims 5
- 239000000362 adenosine triphosphatase inhibitor Substances 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 108010080146 androgen receptors Proteins 0.000 claims 5
- 229940112869 bone morphogenetic protein Drugs 0.000 claims 5
- 229940069978 calcium supplement Drugs 0.000 claims 5
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 150000004673 fluoride salts Chemical class 0.000 claims 5
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 5
- XXUPLYBCNPLTIW-UHFFFAOYSA-N octadec-7-ynoic acid Chemical compound CCCCCCCCCCC#CCCCCCC(O)=O XXUPLYBCNPLTIW-UHFFFAOYSA-N 0.000 claims 5
- 150000003180 prostaglandins Chemical class 0.000 claims 5
- 229940044551 receptor antagonist Drugs 0.000 claims 5
- 239000002464 receptor antagonist Substances 0.000 claims 5
- 238000005728 strengthening Methods 0.000 claims 5
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 4
- 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 4
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 4
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 4
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 4
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 4
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 4
- 125000000173 4-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC(F)(F)F)C([H])([H])* 0.000 claims 4
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical group [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 4
- 208000001132 Osteoporosis Diseases 0.000 claims 4
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 4
- 125000005002 aryl methyl group Chemical group 0.000 claims 4
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 4
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 4
- 229960002797 pitavastatin Drugs 0.000 claims 4
- 229960002855 simvastatin Drugs 0.000 claims 4
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims 4
- 206010002261 Androgen deficiency Diseases 0.000 claims 3
- 102100033367 Appetite-regulating hormone Human genes 0.000 claims 3
- 101710111255 Appetite-regulating hormone Proteins 0.000 claims 3
- 229940123613 Calcium receptor antagonist Drugs 0.000 claims 3
- 102000002265 Human Growth Hormone Human genes 0.000 claims 3
- 108010000521 Human Growth Hormone Proteins 0.000 claims 3
- 239000000854 Human Growth Hormone Substances 0.000 claims 3
- 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 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 108010016731 PPAR gamma Proteins 0.000 claims 3
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims 3
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims 3
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims 3
- 229930003448 Vitamin K Natural products 0.000 claims 3
- 239000012190 activator Substances 0.000 claims 3
- 230000001668 ameliorated effect Effects 0.000 claims 3
- 239000003098 androgen Substances 0.000 claims 3
- 230000008485 antagonism Effects 0.000 claims 3
- 239000005557 antagonist Substances 0.000 claims 3
- 239000003324 growth hormone secretagogue Substances 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 229960005431 ipriflavone Drugs 0.000 claims 3
- 229940043355 kinase inhibitor Drugs 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 3
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims 3
- 208000028169 periodontal disease Diseases 0.000 claims 3
- 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 3
- 239000003909 protein kinase inhibitor Substances 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- 235000019168 vitamin K Nutrition 0.000 claims 3
- 239000011712 vitamin K Substances 0.000 claims 3
- 229940046010 vitamin k Drugs 0.000 claims 3
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims 2
- PMXAPNNYCFBALB-UHFFFAOYSA-N (1-hydroxy-1-phosphono-3-pyrrolidin-1-ylpropyl)phosphonic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CCN1CCCC1 PMXAPNNYCFBALB-UHFFFAOYSA-N 0.000 claims 2
- NGMZSXZBZNXBGX-UHFFFAOYSA-N (1-phosphono-2-pyridin-2-ylethyl)phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)CC1=CC=CC=N1 NGMZSXZBZNXBGX-UHFFFAOYSA-N 0.000 claims 2
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims 2
- BFPYWIDHMRZLRN-SWBPCFCJSA-N (8r,9s,13s,14s,17s)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SWBPCFCJSA-N 0.000 claims 2
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- JWUBBDSIWDLEOM-UHFFFAOYSA-N 25-Hydroxycholecalciferol Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CCC1=C JWUBBDSIWDLEOM-UHFFFAOYSA-N 0.000 claims 2
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 claims 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims 2
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims 2
- 102100024506 Bone morphogenetic protein 2 Human genes 0.000 claims 2
- 102100024504 Bone morphogenetic protein 3 Human genes 0.000 claims 2
- 102100022526 Bone morphogenetic protein 5 Human genes 0.000 claims 2
- 102100022525 Bone morphogenetic protein 6 Human genes 0.000 claims 2
- 102100022544 Bone morphogenetic protein 7 Human genes 0.000 claims 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 claims 2
- 241000283073 Equus caballus Species 0.000 claims 2
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims 2
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 claims 2
- 102000018233 Fibroblast Growth Factor Human genes 0.000 claims 2
- 108050007372 Fibroblast Growth Factor Proteins 0.000 claims 2
- 108090000386 Fibroblast Growth Factor 1 Proteins 0.000 claims 2
- 102100031706 Fibroblast growth factor 1 Human genes 0.000 claims 2
- 102100024785 Fibroblast growth factor 2 Human genes 0.000 claims 2
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 claims 2
- 102100035379 Growth/differentiation factor 5 Human genes 0.000 claims 2
- 208000003577 HIV wasting syndrome Diseases 0.000 claims 2
- 101000762366 Homo sapiens Bone morphogenetic protein 2 Proteins 0.000 claims 2
- 101000762375 Homo sapiens Bone morphogenetic protein 3 Proteins 0.000 claims 2
- 101000899388 Homo sapiens Bone morphogenetic protein 5 Proteins 0.000 claims 2
- 101000899390 Homo sapiens Bone morphogenetic protein 6 Proteins 0.000 claims 2
- 101000899361 Homo sapiens Bone morphogenetic protein 7 Proteins 0.000 claims 2
- 101001023988 Homo sapiens Growth/differentiation factor 5 Proteins 0.000 claims 2
- 101001135770 Homo sapiens Parathyroid hormone Proteins 0.000 claims 2
- 101001135995 Homo sapiens Probable peptidyl-tRNA hydrolase Proteins 0.000 claims 2
- MPBVHIBUJCELCL-UHFFFAOYSA-N Ibandronate Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 0.000 claims 2
- JJKOTMDDZAJTGQ-DQSJHHFOSA-N Idoxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN2CCCC2)=CC=1)/C1=CC=C(I)C=C1 JJKOTMDDZAJTGQ-DQSJHHFOSA-N 0.000 claims 2
- 102100037852 Insulin-like growth factor I Human genes 0.000 claims 2
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| US8309544B2 (en) * | 2007-05-16 | 2012-11-13 | Merck Sharp & Dohme Corp. | Spiroindalones |
| US8623909B2 (en) * | 2008-05-09 | 2014-01-07 | Aska Pharmaceutical Co., Ltd. | Prophylactic/therapeutic agents for lifestyle-related diseases |
| US8461102B2 (en) | 2010-03-02 | 2013-06-11 | George E. Royster, JR. | Methods and compositions for treating and preventing symptoms of hormonal variations |
| PT3691620T (pt) | 2017-10-05 | 2022-10-06 | Fulcrum Therapeutics Inc | Os inibidores da quinase p38 reduzem a expressão de dux4 e genes a jusante para o tratamento de fshd |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
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| AU527030B2 (en) | 1978-04-13 | 1983-02-10 | Merck & Co., Inc. | 4-aza-17-substituted-5a-androstan-3-ones |
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| AU4251993A (en) * | 1992-05-20 | 1993-12-13 | Merck & Co., Inc. | Substituted 4-aza-5A-androstan-ones as 5A-reductase inhibitors |
| US5710275A (en) | 1992-05-20 | 1998-01-20 | Merck & Co., Inc. | 7β-substituted-4-aza-5α-androstan-3-ones as 5α-reductase inhibitors |
| AU680818B2 (en) * | 1992-05-21 | 1997-08-14 | Endorecherche Inc. | Improved antiandrogens |
| AU4258493A (en) * | 1992-05-21 | 1993-12-13 | Endorecherche Inc. | Inhibitors of testosterone 5alpha-reductase activity |
| JP2741286B2 (ja) * | 1993-05-17 | 1998-04-15 | アンドルシェルシュ・インコーポレイテッド | 改良された抗アンドロゲン |
| US5550134A (en) * | 1995-05-10 | 1996-08-27 | Eli Lilly And Company | Methods for inhibiting bone loss |
| AU5369198A (en) * | 1996-12-09 | 1998-07-03 | Merck & Co., Inc. | Methods and compositions for preventing and treating bone loss |
| US5945412A (en) * | 1996-12-09 | 1999-08-31 | Merck & Co., Inc. | Methods and compositions for preventing and treating bone loss |
| AU5791698A (en) * | 1996-12-09 | 1998-07-03 | Merck & Co., Inc. | Methods and compositions for preventing and treating bone loss |
| WO1998025623A1 (en) * | 1996-12-09 | 1998-06-18 | Merck & Co., Inc. | Methods and compositions for preventing and treating bone loss |
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