JP2006528686A5 - - Google Patents
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- JP2006528686A5 JP2006528686A5 JP2006532555A JP2006532555A JP2006528686A5 JP 2006528686 A5 JP2006528686 A5 JP 2006528686A5 JP 2006532555 A JP2006532555 A JP 2006532555A JP 2006532555 A JP2006532555 A JP 2006532555A JP 2006528686 A5 JP2006528686 A5 JP 2006528686A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- aryl
- androst
- aza
- 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 486
- 125000003118 aryl group Chemical group 0.000 claims 386
- -1 perfluoro Chemical group 0.000 claims 190
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 119
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 119
- 125000003545 alkoxy group Chemical group 0.000 claims 117
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 66
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 51
- 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 48
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 48
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 48
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 42
- 125000001424 substituent group Chemical group 0.000 claims 42
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 36
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 36
- 229910052736 halogen Inorganic materials 0.000 claims 36
- 150000002367 halogens Chemical class 0.000 claims 36
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 33
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims 33
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 33
- 125000004414 alkyl thio group Chemical group 0.000 claims 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 30
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 24
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 24
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 24
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 24
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 24
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 24
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 24
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 24
- 125000003282 alkyl amino group Chemical group 0.000 claims 24
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 24
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 24
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 24
- 125000004043 oxo group Chemical group O=* 0.000 claims 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 24
- 239000004202 carbamide Substances 0.000 claims 21
- 150000002148 esters Chemical class 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 125000004442 acylamino group Chemical group 0.000 claims 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 12
- 125000001153 fluoro group Chemical group F* 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 12
- 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 10
- 239000002253 acid Substances 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 9
- 229940080818 propionamide Drugs 0.000 claims 9
- 102100032187 Androgen receptor Human genes 0.000 claims 8
- 108010080146 androgen receptors Proteins 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 239000011647 vitamin D3 Substances 0.000 claims 8
- 229940021056 vitamin d3 Drugs 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 229940011871 estrogen Drugs 0.000 claims 7
- 239000000262 estrogen Substances 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 210000002997 osteoclast Anatomy 0.000 claims 7
- 150000003710 vitamin D derivatives Chemical class 0.000 claims 7
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 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 6
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 6
- 210000000988 bone and bone Anatomy 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 235000005282 vitamin D3 Nutrition 0.000 claims 6
- 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 6
- 102000003982 Parathyroid hormone Human genes 0.000 claims 5
- 108090000445 Parathyroid hormone Proteins 0.000 claims 5
- 239000000199 parathyroid hormone Substances 0.000 claims 5
- 229960001319 parathyroid hormone Drugs 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 229940122361 Bisphosphonate Drugs 0.000 claims 4
- 229930003316 Vitamin D Natural products 0.000 claims 4
- 239000005557 antagonist Substances 0.000 claims 4
- 150000004663 bisphosphonates Chemical class 0.000 claims 4
- 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 4
- 102000005962 receptors Human genes 0.000 claims 4
- 108020003175 receptors Proteins 0.000 claims 4
- 239000011710 vitamin D Substances 0.000 claims 4
- 235000019166 vitamin D Nutrition 0.000 claims 4
- 150000003721 vitamin K derivatives Chemical class 0.000 claims 4
- 229940046008 vitamin d Drugs 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 3
- ZSVOTZROTNEVNK-UHFFFAOYSA-N 2-(3,5-difluorophenyl)acetamide Chemical compound NC(=O)CC1=CC(F)=CC(F)=C1 ZSVOTZROTNEVNK-UHFFFAOYSA-N 0.000 claims 3
- QBAYIBZITZBSFO-UHFFFAOYSA-N 2-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=CC=C1C(F)(F)F QBAYIBZITZBSFO-UHFFFAOYSA-N 0.000 claims 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- MZBSJLAGBUNNLH-UHFFFAOYSA-N 3,3,3-trifluoropropanamide Chemical compound NC(=O)CC(F)(F)F MZBSJLAGBUNNLH-UHFFFAOYSA-N 0.000 claims 3
- FYNMXNGAHZKQFP-UHFFFAOYSA-N 3-(2-chlorophenyl)propanamide Chemical compound NC(=O)CCC1=CC=CC=C1Cl FYNMXNGAHZKQFP-UHFFFAOYSA-N 0.000 claims 3
- LRLAQGDEVIXGSU-UHFFFAOYSA-N 3-(4-chlorophenyl)propanamide Chemical compound NC(=O)CCC1=CC=C(Cl)C=C1 LRLAQGDEVIXGSU-UHFFFAOYSA-N 0.000 claims 3
- XBGXGCOLWCMVOI-UHFFFAOYSA-N 3-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(F)(F)F)=C1 XBGXGCOLWCMVOI-UHFFFAOYSA-N 0.000 claims 3
- HYRHTTXQOTWOLR-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]propanamide Chemical compound NC(=O)CCC1=CC=C(C(F)(F)F)C=C1 HYRHTTXQOTWOLR-UHFFFAOYSA-N 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- VKPLPDIMEREJJF-UHFFFAOYSA-N 3-methoxybenzamide Chemical compound COC1=CC=CC(C(N)=O)=C1 VKPLPDIMEREJJF-UHFFFAOYSA-N 0.000 claims 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 3
- KJWMBTLFHATURL-UHFFFAOYSA-N 4-(2-nitrophenyl)butanamide Chemical compound NC(=O)CCCC1=CC=CC=C1[N+]([O-])=O KJWMBTLFHATURL-UHFFFAOYSA-N 0.000 claims 3
- DUIWVCASVUBFSH-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)butanamide Chemical compound COC1=CC=C(CCCC(N)=O)C=C1OC DUIWVCASVUBFSH-UHFFFAOYSA-N 0.000 claims 3
- XYHHQIWETDSNOP-UHFFFAOYSA-N 4-bromobutanamide Chemical compound NC(=O)CCCBr XYHHQIWETDSNOP-UHFFFAOYSA-N 0.000 claims 3
- XYOXIERJKILWCG-UHFFFAOYSA-N 4-chlorobutanamide Chemical compound NC(=O)CCCCl XYOXIERJKILWCG-UHFFFAOYSA-N 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 3
- 102000055006 Calcitonin Human genes 0.000 claims 3
- 108060001064 Calcitonin Proteins 0.000 claims 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 3
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 claims 3
- 102000014429 Insulin-like growth factor Human genes 0.000 claims 3
- 208000001132 Osteoporosis Diseases 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000003368 amide group Chemical group 0.000 claims 3
- 229940046836 anti-estrogen Drugs 0.000 claims 3
- 230000001833 anti-estrogenic effect Effects 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 3
- 229960004015 calcitonin Drugs 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000000328 estrogen antagonist Substances 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 150000004673 fluoride salts Chemical class 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 3
- 229940125798 integrin inhibitor Drugs 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 239000000583 progesterone congener Substances 0.000 claims 3
- 150000003180 prostaglandins Chemical class 0.000 claims 3
- 229940095743 selective estrogen receptor modulator Drugs 0.000 claims 3
- 239000000333 selective estrogen receptor modulator Substances 0.000 claims 3
- CAKRAHQRJGUPIG-UHFFFAOYSA-M sodium;[4-azaniumyl-1-hydroxy-1-[hydroxy(oxido)phosphoryl]butyl]-hydroxyphosphinate Chemical compound [Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O CAKRAHQRJGUPIG-UHFFFAOYSA-M 0.000 claims 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 210000001519 tissue Anatomy 0.000 claims 3
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims 3
- 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
- 206010002261 Androgen deficiency Diseases 0.000 claims 2
- 208000032467 Aplastic anaemia Diseases 0.000 claims 2
- 102100033367 Appetite-regulating hormone Human genes 0.000 claims 2
- 101710111255 Appetite-regulating hormone Proteins 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000010392 Bone Fractures Diseases 0.000 claims 2
- 108010007726 Bone Morphogenetic Proteins Proteins 0.000 claims 2
- 102000007350 Bone Morphogenetic Proteins Human genes 0.000 claims 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical group [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- 229940123613 Calcium receptor antagonist Drugs 0.000 claims 2
- 229940122156 Cathepsin K inhibitor Drugs 0.000 claims 2
- 206010057671 Female sexual dysfunction Diseases 0.000 claims 2
- 206010017076 Fracture Diseases 0.000 claims 2
- 102000002265 Human Growth Hormone Human genes 0.000 claims 2
- 108010000521 Human Growth Hormone Proteins 0.000 claims 2
- 239000000854 Human Growth Hormone Substances 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 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 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- 206010027304 Menopausal symptoms Diseases 0.000 claims 2
- 208000029725 Metabolic bone disease Diseases 0.000 claims 2
- 206010049088 Osteopenia Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- 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 2
- 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 2
- 208000025865 Ulcer Diseases 0.000 claims 2
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims 2
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims 2
- 229930003448 Vitamin K Natural products 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 230000001668 ameliorated effect Effects 0.000 claims 2
- 239000003098 androgen Substances 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 229940112869 bone morphogenetic protein Drugs 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 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 2
- 235000015872 dietary supplement Nutrition 0.000 claims 2
- 201000003585 eunuchism Diseases 0.000 claims 2
- 201000003617 glucocorticoid-induced osteoporosis Diseases 0.000 claims 2
- 239000003324 growth hormone secretagogue Substances 0.000 claims 2
- 208000018706 hematopoietic system disease Diseases 0.000 claims 2
- 229960005431 ipriflavone Drugs 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 229940043355 kinase inhibitor Drugs 0.000 claims 2
- 208000037106 male hypogonadism Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 210000003205 muscle Anatomy 0.000 claims 2
- 201000006938 muscular dystrophy Diseases 0.000 claims 2
- 208000015124 ovarian disease Diseases 0.000 claims 2
- 201000004535 ovarian dysfunction Diseases 0.000 claims 2
- 231100000543 ovarian dysfunction Toxicity 0.000 claims 2
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 2
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 208000028169 periodontal disease Diseases 0.000 claims 2
- 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 2
- 229960002797 pitavastatin Drugs 0.000 claims 2
- 230000002028 premature Effects 0.000 claims 2
- 239000003909 protein kinase inhibitor Substances 0.000 claims 2
- 229960002855 simvastatin Drugs 0.000 claims 2
- 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 2
- 230000009759 skin aging Effects 0.000 claims 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 238000005728 strengthening Methods 0.000 claims 2
- 231100000397 ulcer Toxicity 0.000 claims 2
- 235000019168 vitamin K Nutrition 0.000 claims 2
- 239000011712 vitamin K Substances 0.000 claims 2
- 229940046010 vitamin k Drugs 0.000 claims 2
- 230000003313 weakening effect Effects 0.000 claims 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims 1
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| US5359071A (en) * | 1993-03-12 | 1994-10-25 | Merck & Co., Inc. | 15-substituted 4-azasteroids |
| AU681585B2 (en) | 1993-06-24 | 1997-09-04 | Richter Gedeon Vegyeszeti Gyar Rt. | Novel process for preparing 17beta -substituted 4-azaandrostane derivatives |
| WO1995000532A1 (en) * | 1993-06-24 | 1995-01-05 | Richter Gedeon Vegyészeti Gyár Rt. | 17-halogeno-4-azaandrostene derivatives and process for the preparation thereof |
| US6001844A (en) * | 1995-09-15 | 1999-12-14 | Merck & Co., Inc. | 4-Azasteroids for treatment of hyperandrogenic conditions |
| CA2233966A1 (en) * | 1995-10-26 | 1997-05-01 | Merck & Co., Inc. | 4-oxa and 4-thia steroids |
| BR9708301A (pt) | 1996-02-14 | 1999-08-03 | Hoechst Marion Roussel Inc | Esteróides de 17-beta-ciclopropil (amino/óxi) 4-aza como inibidores ativos de 5-alfa-redutase e liase de c17-20 de testosterona |
| WO1998025622A1 (en) * | 1996-12-09 | 1998-06-18 | Merck & Co., Inc. | Methods and compositions for preventing and treating bone loss |
-
2004
- 2004-05-03 EP EP04751257.9A patent/EP1622567B1/en not_active Expired - Lifetime
- 2004-05-03 WO PCT/US2004/013787 patent/WO2004100874A2/en not_active Ceased
- 2004-05-03 US US10/551,975 patent/US7351698B2/en not_active Expired - Lifetime
- 2004-05-03 AU AU2004238238A patent/AU2004238238C1/en not_active Ceased
- 2004-05-03 CN CNA2004800122535A patent/CN1784236A/zh active Pending
- 2004-05-03 JP JP2006532555A patent/JP4832303B2/ja not_active Expired - Fee Related
- 2004-05-03 CA CA2524409A patent/CA2524409C/en not_active Expired - Fee Related
-
2008
- 2008-01-16 US US12/009,113 patent/US20080119503A1/en not_active Abandoned
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