JP2014532622A5 - - Google Patents
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- Publication number
- JP2014532622A5 JP2014532622A5 JP2014537120A JP2014537120A JP2014532622A5 JP 2014532622 A5 JP2014532622 A5 JP 2014532622A5 JP 2014537120 A JP2014537120 A JP 2014537120A JP 2014537120 A JP2014537120 A JP 2014537120A JP 2014532622 A5 JP2014532622 A5 JP 2014532622A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrogen
- methylene
- alkyl
- hydroxy
- 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
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 239000001257 hydrogen Substances 0.000 claims description 83
- 150000002431 hydrogen Chemical class 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 229930003316 Vitamin D Natural products 0.000 claims description 16
- 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 16
- 235000019166 vitamin D Nutrition 0.000 claims description 16
- 239000011710 vitamin D Substances 0.000 claims description 16
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 16
- 229940046008 vitamin d Drugs 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 208000001132 Osteoporosis Diseases 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052805 deuterium 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
- 125000004433 nitrogen atom Chemical group N* 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
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 4
- 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
- 208000030136 Marchiafava-Bignami Disease 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
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 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
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims 1
- 229940088594 vitamin Drugs 0.000 claims 1
- 229930003231 vitamin Natural products 0.000 claims 1
- 239000011782 vitamin Substances 0.000 claims 1
- 235000013343 vitamin Nutrition 0.000 claims 1
- 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 1
- 230000000699 topical effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161550172P | 2011-10-21 | 2011-10-21 | |
| US61/550,172 | 2011-10-21 | ||
| PCT/US2012/059667 WO2013059060A1 (en) | 2011-10-21 | 2012-10-11 | 2-methylene-vitamin d analogs and their uses |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014532622A JP2014532622A (ja) | 2014-12-08 |
| JP2014532622A5 true JP2014532622A5 (https=) | 2015-11-26 |
| JP6114292B2 JP6114292B2 (ja) | 2017-04-12 |
Family
ID=47143292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014537120A Expired - Fee Related JP6114292B2 (ja) | 2011-10-21 | 2012-10-11 | ２−メチレン−ビタミンｄ類似体およびそれらの使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8410080B1 (https=) |
| EP (1) | EP2768804B1 (https=) |
| JP (1) | JP6114292B2 (https=) |
| AU (1) | AU2012326485B2 (https=) |
| CA (1) | CA2851283C (https=) |
| WO (1) | WO2013059060A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 (21)
| 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 |
| US5843928A (en) | 1997-03-17 | 1998-12-01 | Wisconsin Alumni Research Foundation | 2-alkylidene-19-nor-vitamin D compounds |
| US6392071B1 (en) | 1997-03-17 | 2002-05-21 | Wisconsin Alumni: Research Foundation | 26,27-homologated-20-EPI-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 |
| JPH11171859A (ja) * | 1997-09-19 | 1999-06-29 | Chugai Pharmaceut Co Ltd | ビタミンｄ誘導体およびその製造方法 |
| US6080879A (en) * | 1998-05-19 | 2000-06-27 | Tetrionics, Inc. | Hexafluoro-vitamin synthesis and crystallization method, solvent and product |
| US6114317A (en) * | 1998-05-21 | 2000-09-05 | Wisconsin Alumni Research Foundation | Method of locking 1α-OH of vitamin D compounds in axial orientation |
| CA2390859A1 (en) * | 1999-12-02 | 2001-06-14 | The Penn State Research Foundation | Treatment of inflammatory bowel disease with 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 |
| US7259143B2 (en) * | 2002-09-05 | 2007-08-21 | Wisconsin Alumni Research Foundation | Method of extending the dose range of vitamin D compounds |
| US20080249068A1 (en) * | 2002-09-05 | 2008-10-09 | Deluca Hector F | Method of Extending the Dose Range of Vitamin D Compounds |
| MX2007006261A (es) * | 2004-11-22 | 2007-07-10 | Wisconsin Alumni Res Found | Analogos de 17,20(z)-deshidro vitamina d y sus usos. |
| RU2440980C2 (ru) * | 2006-06-02 | 2012-01-27 | Ниппон Синяку Ко., Лтд. | 9,10-секопрегнановое производное и фармацевтические средства |
| AU2007300214A1 (en) * | 2006-09-28 | 2008-04-03 | Wisconsin Alumni Research Foundation | 2-methylene-(20R,25S)-19,27-dinor-(22E)-vitamin D analogs |
| US8377913B2 (en) * | 2007-11-20 | 2013-02-19 | Abbvie Inc. | Vitamin D receptor activators and methods of making |
-
2012
- 2012-10-11 CA CA2851283A patent/CA2851283C/en not_active Expired - Fee Related
- 2012-10-11 JP JP2014537120A patent/JP6114292B2/ja not_active Expired - Fee Related
- 2012-10-11 EP EP12781531.4A patent/EP2768804B1/en not_active Not-in-force
- 2012-10-11 WO PCT/US2012/059667 patent/WO2013059060A1/en not_active Ceased
- 2012-10-11 AU AU2012326485A patent/AU2012326485B2/en not_active Ceased
- 2012-10-11 US US13/649,240 patent/US8410080B1/en not_active Expired - Fee Related
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