JP2005526082A5 - - Google Patents
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- JP2005526082A5 JP2005526082A5 JP2003575972A JP2003575972A JP2005526082A5 JP 2005526082 A5 JP2005526082 A5 JP 2005526082A5 JP 2003575972 A JP2003575972 A JP 2003575972A JP 2003575972 A JP2003575972 A JP 2003575972A JP 2005526082 A5 JP2005526082 A5 JP 2005526082A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxo
- aza
- carboxamide
- fluoro
- 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 description 125
- -1 (2) naphthyl Chemical group 0.000 claims description 115
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 5
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 5
- 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 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000005602 azabenzimidazolyl group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims 35
- 238000000034 method Methods 0.000 claims 12
- 229940011871 estrogen Drugs 0.000 claims 11
- 239000000262 estrogen Substances 0.000 claims 11
- 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 10
- 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
- 239000000199 parathyroid hormone Substances 0.000 claims 9
- 241000124008 Mammalia Species 0.000 claims 8
- 102000003982 Parathyroid hormone Human genes 0.000 claims 8
- 108090000445 Parathyroid hormone Proteins 0.000 claims 8
- 229960001319 parathyroid hormone Drugs 0.000 claims 8
- 239000011647 vitamin D3 Substances 0.000 claims 8
- 229940021056 vitamin d3 Drugs 0.000 claims 8
- 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 7
- 229940122361 Bisphosphonate Drugs 0.000 claims 7
- 150000004663 bisphosphonates Chemical class 0.000 claims 7
- 210000000988 bone and bone Anatomy 0.000 claims 7
- 210000002997 osteoclast Anatomy 0.000 claims 7
- 150000003710 vitamin D derivatives Chemical class 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 229940046836 anti-estrogen Drugs 0.000 claims 5
- 230000001833 anti-estrogenic effect Effects 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
- 239000000328 estrogen antagonist Substances 0.000 claims 5
- 239000000583 progesterone congener Substances 0.000 claims 5
- 229940095743 selective estrogen receptor modulator Drugs 0.000 claims 5
- 239000000333 selective estrogen receptor modulator Substances 0.000 claims 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 4
- 229940121819 ATPase inhibitor Drugs 0.000 claims 4
- 102000055006 Calcitonin Human genes 0.000 claims 4
- 108060001064 Calcitonin Proteins 0.000 claims 4
- 229940122156 Cathepsin K inhibitor Drugs 0.000 claims 4
- 108010047852 Integrin alphaVbeta3 Proteins 0.000 claims 4
- 102000011731 Vacuolar Proton-Translocating ATPases Human genes 0.000 claims 4
- 108010037026 Vacuolar Proton-Translocating ATPases Proteins 0.000 claims 4
- 229930003316 Vitamin D Natural products 0.000 claims 4
- 239000000362 adenosine triphosphatase inhibitor Substances 0.000 claims 4
- 229960004015 calcitonin Drugs 0.000 claims 4
- 229940044551 receptor antagonist Drugs 0.000 claims 4
- 239000002464 receptor antagonist Substances 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
- 102100032187 Androgen receptor Human genes 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
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims 3
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims 3
- 108010080146 androgen receptors Proteins 0.000 claims 3
- 239000005557 antagonist Substances 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 150000004673 fluoride salts Chemical class 0.000 claims 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 230000000921 morphogenic effect Effects 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 150000003180 prostaglandins Chemical class 0.000 claims 3
- 102000004169 proteins and genes Human genes 0.000 claims 3
- 108090000623 proteins and genes Proteins 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- 208000024891 symptom Diseases 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
- 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
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 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
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 claims 2
- 102100033367 Appetite-regulating hormone Human genes 0.000 claims 2
- 101710111255 Appetite-regulating hormone Proteins 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
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- 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
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- 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
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- 239000003909 protein kinase inhibitor Substances 0.000 claims 2
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- 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
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims 2
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- 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
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- 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
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| CA2478186C (en) * | 2002-03-13 | 2011-08-23 | Merck & Co., Inc. | Fluorinated 4-azasteroid derivatives as androgen receptor modulators |
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| TW200730505A (en) * | 2005-12-07 | 2007-08-16 | Merck & Co Inc | Polymorphs of an androgen receptor modulator |
| US9844528B2 (en) | 2006-08-24 | 2017-12-19 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
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| US10010521B2 (en) | 2006-08-24 | 2018-07-03 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| US8183286B2 (en) | 2006-11-16 | 2012-05-22 | Gemmus Pharma Inc. | EP2 and EP4 agonists as agents for the treatment of influenza a viral infection |
| US7968603B2 (en) | 2007-09-11 | 2011-06-28 | University Of Tennessee Research Foundation | Solid forms of selective androgen receptor modulators |
| CA2709677C (en) | 2007-12-21 | 2017-03-14 | Lin Zhi | Selective androgen receptor modulators (sarms) and uses thereof |
| EP2247597A1 (en) * | 2008-02-07 | 2010-11-10 | Bristol-Myers Squibb Company | Fused heteroaryl modulators of glucocorticoid receptor, ap-1, and/or nf-kb activity and use thereof |
| EP2149554A1 (de) | 2008-07-30 | 2010-02-03 | Bayer Schering Pharma Aktiengesellschaft | Indolylamide als Modulatoren des EP2-Rezeptors |
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| EP2149552A1 (de) | 2008-07-30 | 2010-02-03 | Bayer Schering Pharma AG | 5,6 substituierte Benzamid-Derivate als Modulatoren des EP2-Rezeptors |
| JP2013528223A (ja) | 2010-06-10 | 2013-07-08 | アラゴン ファーマシューティカルズ，インク． | エストロゲン受容体モジュレーターおよびその用途 |
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2003
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- 2003-03-07 PL PL03372920A patent/PL372920A1/xx not_active Application Discontinuation
- 2003-03-07 US US10/507,239 patent/US7186838B2/en not_active Expired - Fee Related
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