JP2005529897A5 - - Google Patents
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- Publication number
- JP2005529897A5 JP2005529897A5 JP2004500773A JP2004500773A JP2005529897A5 JP 2005529897 A5 JP2005529897 A5 JP 2005529897A5 JP 2004500773 A JP2004500773 A JP 2004500773A JP 2004500773 A JP2004500773 A JP 2004500773A JP 2005529897 A5 JP2005529897 A5 JP 2005529897A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxo
- androst
- aza
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 cyano, carboxy Chemical group 0.000 claims 370
- 125000000217 alkyl group Chemical group 0.000 claims 63
- 150000001875 compounds Chemical class 0.000 claims 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 239000008194 pharmaceutical composition Substances 0.000 claims 17
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 9
- 229940011871 estrogen Drugs 0.000 claims 9
- 239000000262 estrogen Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 8
- 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 8
- 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 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 150000003710 vitamin D derivatives Chemical class 0.000 claims 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- 229940122361 Bisphosphonate Drugs 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 150000004663 bisphosphonates Chemical class 0.000 claims 6
- 239000011647 vitamin D3 Substances 0.000 claims 6
- 229940021056 vitamin d3 Drugs 0.000 claims 6
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 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 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 210000002997 osteoclast Anatomy 0.000 claims 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 4
- 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 claims 4
- 102000055006 Calcitonin Human genes 0.000 claims 4
- 108060001064 Calcitonin Proteins 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 229930003316 Vitamin D Natural products 0.000 claims 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 4
- 229940046836 anti-estrogen Drugs 0.000 claims 4
- 230000001833 anti-estrogenic effect Effects 0.000 claims 4
- 229960004015 calcitonin Drugs 0.000 claims 4
- 239000000328 estrogen antagonist Substances 0.000 claims 4
- 229940088597 hormone Drugs 0.000 claims 4
- 239000005556 hormone Substances 0.000 claims 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000000583 progesterone congener Substances 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 229940095743 selective estrogen receptor modulator Drugs 0.000 claims 4
- 239000000333 selective estrogen receptor modulator Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- SAAQXAKXAHPXJR-UHFFFAOYSA-N tert-butyl 3-[[(5,6,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,8,9,9b,10,11-decahydro-1h-indeno[5,4-f]quinoline-1-carbonyl)amino]methyl]indole-1-carboxylate Chemical compound C1=CC=C2C(CNC(=O)C3CCC4C3(C)CCC3C5(C)CCC(=O)N(C5=C(C)CC34)C)=CN(C(=O)OC(C)(C)C)C2=C1 SAAQXAKXAHPXJR-UHFFFAOYSA-N 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 239000011710 vitamin D Substances 0.000 claims 4
- 235000019166 vitamin D Nutrition 0.000 claims 4
- 235000005282 vitamin D3 Nutrition 0.000 claims 4
- 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 4
- 150000003721 vitamin K derivatives Chemical class 0.000 claims 4
- 229940046008 vitamin d Drugs 0.000 claims 4
- 229940121819 ATPase inhibitor Drugs 0.000 claims 3
- 102100032187 Androgen receptor Human genes 0.000 claims 3
- 108010007726 Bone Morphogenetic Proteins Proteins 0.000 claims 3
- 102000007350 Bone Morphogenetic Proteins Human genes 0.000 claims 3
- 229940122156 Cathepsin K inhibitor Drugs 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
- 108010047852 Integrin alphaVbeta3 Proteins 0.000 claims 3
- 208000001132 Osteoporosis Diseases 0.000 claims 3
- 102000008108 Osteoprotegerin Human genes 0.000 claims 3
- 108010035042 Osteoprotegerin Proteins 0.000 claims 3
- 239000000362 adenosine triphosphatase inhibitor Substances 0.000 claims 3
- 108010080146 androgen receptors Proteins 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 210000000988 bone and bone Anatomy 0.000 claims 3
- 229940112869 bone morphogenetic protein Drugs 0.000 claims 3
- 229940069978 calcium supplement Drugs 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 150000004673 fluoride salts Chemical class 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims 3
- XXUPLYBCNPLTIW-UHFFFAOYSA-N octadec-7-ynoic acid Chemical compound CCCCCCCCCCC#CCCCCCC(O)=O XXUPLYBCNPLTIW-UHFFFAOYSA-N 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 150000003180 prostaglandins Chemical class 0.000 claims 3
- 125000005493 quinolyl group Chemical group 0.000 claims 3
- 229940044551 receptor antagonist Drugs 0.000 claims 3
- 239000002464 receptor antagonist Substances 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 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
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000005871 1,3-benzodioxolyl group Chemical group 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
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- JQDGXMUAJCVGKB-UHFFFAOYSA-N 3-[(5,6,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,8,9,9b,10,11-decahydro-1h-indeno[5,4-f]quinoline-1-carbonyl)amino]-4-chlorobenzoic acid Chemical compound C12CC(C)=C3N(C)C(=O)CCC3(C)C2CCC2(C)C1CCC2C(=O)NC1=CC(C(O)=O)=CC=C1Cl JQDGXMUAJCVGKB-UHFFFAOYSA-N 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- 102100033367 Appetite-regulating hormone Human genes 0.000 claims 2
- 101710111255 Appetite-regulating hormone Proteins 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 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
- 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
- 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
- 108010016731 PPAR gamma Proteins 0.000 claims 2
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 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
- 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
- 239000012190 activator Substances 0.000 claims 2
- DCSBSVSZJRSITC-UHFFFAOYSA-M alendronate sodium trihydrate Chemical group O.O.O.[Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O DCSBSVSZJRSITC-UHFFFAOYSA-M 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 2
- 230000008485 antagonism Effects 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 239000003324 growth hormone secretagogue Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 229960005431 ipriflavone Drugs 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 229940043355 kinase inhibitor Drugs 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 210000003205 muscle Anatomy 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 239000003909 protein kinase inhibitor Substances 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 229920006395 saturated elastomer Polymers 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
- DUYCFMAOEDAKDN-UHFFFAOYSA-M sodium (4-amino-1-hydroxy-1-phosphonobutyl)-hydroxyphosphinate hydrate Chemical compound O.[Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O DUYCFMAOEDAKDN-UHFFFAOYSA-M 0.000 claims 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims 2
- AWYTZXPRDUDYBI-UHFFFAOYSA-N tert-butyl 3-[2-[(5,6,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,8,9,9b,10,11-decahydro-1h-indeno[5,4-f]quinoline-1-carbonyl)amino]ethyl]indole-1-carboxylate Chemical compound C1=CC=C2C(CCNC(=O)C3CCC4C3(C)CCC3C5(C)CCC(=O)N(C5=C(C)CC34)C)=CN(C(=O)OC(C)(C)C)C2=C1 AWYTZXPRDUDYBI-UHFFFAOYSA-N 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 229940088594 vitamin Drugs 0.000 claims 2
- 229930003231 vitamin Natural products 0.000 claims 2
- 235000013343 vitamin Nutrition 0.000 claims 2
- 239000011782 vitamin Substances 0.000 claims 2
- 235000019168 vitamin K Nutrition 0.000 claims 2
- 239000011712 vitamin K Substances 0.000 claims 2
- 150000003722 vitamin derivatives Chemical class 0.000 claims 2
- 229940046010 vitamin k Drugs 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
- 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 1
- 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 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
- 206010002261 Androgen deficiency Diseases 0.000 claims 1
- 208000032467 Aplastic anaemia Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 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 1
- 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 1
- 206010003694 Atrophy Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000010392 Bone Fractures Diseases 0.000 claims 1
- 102100024506 Bone morphogenetic protein 2 Human genes 0.000 claims 1
- 102100024504 Bone morphogenetic protein 3 Human genes 0.000 claims 1
- 102100022526 Bone morphogenetic protein 5 Human genes 0.000 claims 1
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| KR101536701B1 (ko) | 2004-01-07 | 2015-07-14 | 앙도르쉐르슈 인코포레이티드 | 헬릭스 12 배향형 스테로이드계 약학 제품 |
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| EP1824495A2 (en) * | 2004-12-03 | 2007-08-29 | ProteoSys AG | Finasteride, dutasteride and related compounds for preventing/treating neurologically-associated disorders |
| JP2008525381A (ja) | 2004-12-23 | 2008-07-17 | ノボ ノルディスク ヘルス ケア アクチェンゲゼルシャフト | 関心のあるビタミンｋ依存性タンパク質を含んでなる組成物中におけるタンパク質混入物の量の減少 |
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| TW408127B (en) * | 1993-09-17 | 2000-10-11 | Glaxo Inc | Androstenones |
| TW369521B (en) * | 1993-09-17 | 1999-09-11 | Smithkline Beecham Corp | Androstenone derivative |
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-
2003
- 2003-04-25 US US10/512,800 patent/US20050131005A1/en not_active Abandoned
- 2003-04-25 CA CA002484173A patent/CA2484173A1/en not_active Abandoned
- 2003-04-25 WO PCT/US2003/013120 patent/WO2003092588A2/en not_active Ceased
- 2003-04-25 JP JP2004500773A patent/JP4516839B2/ja not_active Expired - Fee Related
- 2003-04-25 AU AU2003223754A patent/AU2003223754B2/en not_active Ceased
- 2003-04-25 EP EP03719957A patent/EP1501512A4/en not_active Withdrawn
-
2006
- 2006-08-14 US US11/504,325 patent/US7625919B2/en not_active Expired - Fee Related
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