JP2014523419A5 - - Google Patents
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- Publication number
- JP2014523419A5 JP2014523419A5 JP2014515955A JP2014515955A JP2014523419A5 JP 2014523419 A5 JP2014523419 A5 JP 2014523419A5 JP 2014515955 A JP2014515955 A JP 2014515955A JP 2014515955 A JP2014515955 A JP 2014515955A JP 2014523419 A5 JP2014523419 A5 JP 2014523419A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrogen
- pharmaceutical composition
- compound
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000008194 pharmaceutical composition Substances 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 150000002431 hydrogen Chemical group 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 10
- 229930003316 Vitamin D Natural products 0.000 claims description 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 description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 235000019166 vitamin D Nutrition 0.000 claims description 10
- 239000011710 vitamin D Substances 0.000 claims description 10
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 10
- 229940046008 vitamin d Drugs 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 208000001132 Osteoporosis Diseases 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 208000013725 Chronic Kidney Disease-Mineral and Bone disease Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000029725 Metabolic bone disease Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 206010039984 Senile osteoporosis Diseases 0.000 claims description 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
- 230000008416 bone turnover Effects 0.000 claims description 2
- 125000005345 deuteroalkyl group Chemical group 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 208000005368 osteomalacia Diseases 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 208000001685 postmenopausal osteoporosis Diseases 0.000 claims description 2
- 201000006409 renal osteodystrophy Diseases 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- 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
- -1 and C 1-5 -alkyl Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 238000007911 parenteral administration Methods 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 12
- 125000001118 alkylidene group Chemical group 0.000 description 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 208000030136 Marchiafava-Bignami Disease Diseases 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161496777P | 2011-06-14 | 2011-06-14 | |
| US61/496,777 | 2011-06-14 | ||
| US201161550099P | 2011-10-21 | 2011-10-21 | |
| US61/550,099 | 2011-10-21 | ||
| PCT/US2012/042225 WO2012174095A1 (en) | 2011-06-14 | 2012-06-13 | 3-desoxy-2-methylene-19-nor-vitamin d analogs and their uses |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014523419A JP2014523419A (ja) | 2014-09-11 |
| JP2014523419A5 true JP2014523419A5 (https=) | 2015-07-16 |
| JP6035331B2 JP6035331B2 (ja) | 2016-11-30 |
Family
ID=46331719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014515955A Expired - Fee Related JP6035331B2 (ja) | 2011-06-14 | 2012-06-13 | ３−デスオキシ−２−メチレン−１９−ノル−ビタミンｄ類似体およびそれらの使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8993547B2 (https=) |
| EP (1) | EP2721004B1 (https=) |
| JP (1) | JP6035331B2 (https=) |
| AU (1) | AU2012271759B2 (https=) |
| CA (1) | CA2824870C (https=) |
| WO (1) | WO2012174095A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105143463A (zh) | 2013-02-25 | 2015-12-09 | 诺华股份有限公司 | 新的雄激素受体突变 |
| CA2991260A1 (en) | 2015-08-05 | 2017-02-09 | Wisconsin Alumni Research Foundation | Synthesis and biological activity of 2-methylene analogs of calcitriol and related compounds |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666634A (en) | 1984-12-05 | 1987-05-19 | Chugai Seiyaku Kabushiki Kaisha | vitamin D3 derivatives having a substituent at 2-position |
| US5086191A (en) | 1991-05-28 | 1992-02-04 | Wisconsin Alumni Research Foundation | Intermediates for the synthesis of 19-nor vitamin D compounds |
| EP0619306B1 (en) | 1993-04-05 | 1996-09-11 | Wisconsin Alumni Research Foundation | 19-Nor-vitamin D3 compounds with substituent at 2-position |
| US6392071B1 (en) * | 1997-03-17 | 2002-05-21 | Wisconsin Alumni: Research Foundation | 26,27-homologated-20-EPI-2-alkylidene-19-nor-vitamin D compounds |
| US5843928A (en) * | 1997-03-17 | 1998-12-01 | Wisconsin Alumni Research Foundation | 2-alkylidene-19-nor-vitamin D compounds |
| US5945410A (en) | 1997-03-17 | 1999-08-31 | Wisconsin Alumni Research Foundation | 2-alkyl-19-nor-vitamin D compounds |
| US6382071B1 (en) | 2000-08-07 | 2002-05-07 | Gilbert A. Bertani | Bola capturing apparatus |
| NZ524657A (en) * | 2000-09-08 | 2004-12-24 | Wisconsin Alumni Res Found | 1 alpha-hydroxy-2-methylene-19-nor-homopregnacalciferol and its therapeutic applications |
| NZ533424A (en) * | 2001-12-13 | 2006-08-31 | Wisconsin Alumni Res Found | Vitamin D derivative, methods of purifying and uses in treating psoriasis, cancer, autoimmune diseases, inflammatory diseases, skin conidtions and renal ostepdystrophy |
| US6627622B2 (en) | 2002-02-18 | 2003-09-30 | Wisconsin Alumni Research Foundation | (20S)-1α-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses |
| US6566352B1 (en) | 2002-02-18 | 2003-05-20 | Wisconsin Alumni Research Foudation | 1 α-hydroxy-2-methylene-19-nor-pregnacalciferol and its uses |
| HK1079766B (zh) * | 2002-03-29 | 2007-05-25 | 威斯康星校友研究基金会 | 合成1α-羟基-2-亚甲基-19-去甲-高孕钙化醇的方法 |
| CA2531294A1 (en) * | 2003-07-03 | 2005-02-10 | Wisconsin Alumni Research Foundation | 2-methylene-19-nor-20(s)-25-methyl-1.alpha.-hydroxycalciferol and its uses |
| US20050009792A1 (en) * | 2003-07-08 | 2005-01-13 | Deluca Hector F. | (20S)-1alpha-hydroxy-2-methylene-19-nor-vitamin D3 and its uses |
| AU2004266706B2 (en) * | 2003-08-20 | 2009-07-30 | Wisconsin Alumni Research Foundation | 2-methylene-19-nor-vitamin D2 compounds |
| EP1827452B1 (en) * | 2004-11-22 | 2011-03-02 | Wisconsin Alumni Research Foundation | 2-methylene-19,21-dinor-1alpha-hydroxy-bishomopregnacalciferol |
| DE602005021245D1 (de) * | 2004-11-22 | 2010-06-24 | Wisconsin Alumni Res Found | 2-methylen-19,26,27-trinor-(20s)-1-alpha-hydroxyvitamin d3 and dessen verwendungen |
| EP1828115A4 (en) * | 2004-11-22 | 2010-05-05 | Wisconsin Alumni Res Found | 2-METHYLENE-19-NOR (20S) -1ALPHA-HYDROXYTRISHOMOPREGNACALCIFEROL |
| WO2006086613A2 (en) * | 2005-02-11 | 2006-08-17 | Wisconsin Alumni Research Foundation | 2-METHYLENE-19-NOR- (20S-24S) - 1α, 25-D IHYDROXYVITAMIN-D2 |
| DK1848442T3 (da) * | 2005-02-11 | 2012-05-29 | Wisconsin Alumni Res Found | 2-methylene-19-nor-(20s-24epi)-1alfa,25-dihydroxyvitamine-d2 |
| MX2007013558A (es) * | 2005-05-03 | 2008-01-24 | Wisconsin Alumni Res Found | Compuestos de 19,26,27-trinor-1a,25-dihidroxivitamina d3. |
| US7803789B2 (en) * | 2006-02-02 | 2010-09-28 | Wisconsin Alumni Research Foundation | Vitamin D analog—RAK, methods and uses thereof |
| MX2008012912A (es) * | 2006-04-06 | 2008-11-26 | Wisconsin Alumni Res Found | Analogos de 2-metilen-1a,25-dihidroxi-19,21-dinorvitamina d3 y sus usos. |
| NZ570711A (en) * | 2006-04-06 | 2012-10-26 | Wisconsin Alumni Res Found | 2-Substituted-1alpha, 25-dihydroxy-19,26,27-trinor vitamin D analogs and uses thereof |
| WO2008035207A2 (en) * | 2006-04-06 | 2008-03-27 | Wisconsin Alumni Research Foundation | 2-methylene-1alpha-hydroxy-19,21-dinorvitamin d3 analogs and uses thereof |
| RU2440980C2 (ru) * | 2006-06-02 | 2012-01-27 | Ниппон Синяку Ко., Лтд. | 9,10-секопрегнановое производное и фармацевтические средства |
| EP2069296B1 (en) * | 2006-09-28 | 2012-04-04 | Wisconsin Alumni Research Foundation | 2-methylene-(20s,25s)-19,27-dinor-(22e)-vitamin d analogs |
| AU2007300214A1 (en) * | 2006-09-28 | 2008-04-03 | Wisconsin Alumni Research Foundation | 2-methylene-(20R,25S)-19,27-dinor-(22E)-vitamin D analogs |
| US20080171728A1 (en) * | 2007-01-12 | 2008-07-17 | Quatrx Pharmaceuticals Co. | Efficient Process for Preparing Steroids and Vitamin D Derivatives With the Unnatural Configuration at C20 (20 Alpha-Methyl) from Pregnenolone |
| US8377913B2 (en) * | 2007-11-20 | 2013-02-19 | Abbvie Inc. | Vitamin D receptor activators and methods of making |
| EP2240463A2 (en) * | 2007-12-28 | 2010-10-20 | Wisconsin Alumni Research Foundation | 2-methylene-(20s,25r)-19,26-dinor-vitamin d analogs |
| WO2009086439A2 (en) * | 2007-12-28 | 2009-07-09 | Wisconsin Alumni Research Foundation | 2-methylene-(20s,25s)-19,26-dinor-vitamin d analogs |
| WO2009086436A1 (en) * | 2007-12-28 | 2009-07-09 | Wisconsin Alumni Research Foundation | (20s)-23,23-difluoro-2-methylene-19-nor-bishomopregnacalciferol-vitamin d analogs |
| US8193170B2 (en) * | 2008-07-10 | 2012-06-05 | Wisconsin Alumni Research Foundation | 2-methylene-19,26-dinor-(20R,22E,25R)-vitamin D analogs |
| US8399439B2 (en) * | 2008-07-10 | 2013-03-19 | Wisconsin Alumni Research Foundation | 2-methylene-19,26-dinor-(20S,22E,25R)-vitamin D analogs |
| WO2010120698A1 (en) * | 2009-04-17 | 2010-10-21 | Vidasym, Llc | Vitamin d receptor agonists and uses thereof |
| US8642579B2 (en) * | 2009-10-02 | 2014-02-04 | Wisconsin Alumni Research Foundation | 1-desoxy-2-methylene-19-nor-vitamin D analogs and their uses |
| EP2525799B1 (en) * | 2009-10-02 | 2014-09-03 | Wisconsin Alumni Research Foundation | (20s,22e)-2-methylene-19-nor-22-ene-1alpha,25-dihydroxyvitamin d3 analogs |
| MX2012005936A (es) * | 2009-11-30 | 2012-09-07 | Wisconsin Alumni Res Found | 2-metilen-19,26-nor-(20s)-1a-hidroxivitamina d3. |
-
2012
- 2012-06-13 AU AU2012271759A patent/AU2012271759B2/en not_active Ceased
- 2012-06-13 JP JP2014515955A patent/JP6035331B2/ja not_active Expired - Fee Related
- 2012-06-13 EP EP12729302.5A patent/EP2721004B1/en not_active Not-in-force
- 2012-06-13 WO PCT/US2012/042225 patent/WO2012174095A1/en not_active Ceased
- 2012-06-13 US US13/495,548 patent/US8993547B2/en active Active
- 2012-06-13 CA CA2824870A patent/CA2824870C/en not_active Expired - Fee Related
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