AU2003220169B2 - Use of carbon-2-modified-19-nor-vitamin D analogs to induce the formation of new bone - Google Patents
Use of carbon-2-modified-19-nor-vitamin D analogs to induce the formation of new bone Download PDFInfo
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- AU2003220169B2 AU2003220169B2 AU2003220169A AU2003220169A AU2003220169B2 AU 2003220169 B2 AU2003220169 B2 AU 2003220169B2 AU 2003220169 A AU2003220169 A AU 2003220169A AU 2003220169 A AU2003220169 A AU 2003220169A AU 2003220169 B2 AU2003220169 B2 AU 2003220169B2
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- 108090000623 proteins and genes Proteins 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
- A61K31/593—9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Prostheses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/105,826 | 2002-03-25 | ||
| US10/105,826 US20030195175A1 (en) | 2002-03-25 | 2002-03-25 | Use of carbon-2-modified-vitamin D analogs to induce the formation of new bone |
| PCT/US2003/007443 WO2003082300A1 (en) | 2002-03-25 | 2003-03-12 | Use of carbon-2-modified-vitamin d analogs to induce the formation of new bone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003220169A1 AU2003220169A1 (en) | 2003-10-13 |
| AU2003220169B2 true AU2003220169B2 (en) | 2008-09-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| AU2003220169A Ceased AU2003220169B2 (en) | 2002-03-25 | 2003-03-12 | Use of carbon-2-modified-19-nor-vitamin D analogs to induce the formation of new bone |
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| Country | Link |
|---|---|
| US (3) | US20030195175A1 (https=) |
| EP (1) | EP1494680B1 (https=) |
| JP (1) | JP2005527558A (https=) |
| KR (1) | KR100983953B1 (https=) |
| CN (1) | CN100531739C (https=) |
| AT (1) | ATE406901T1 (https=) |
| AU (1) | AU2003220169B2 (https=) |
| BR (1) | BR0308701A (https=) |
| CA (1) | CA2480125C (https=) |
| DE (1) | DE60323351D1 (https=) |
| DK (1) | DK1494680T3 (https=) |
| ES (1) | ES2312764T3 (https=) |
| HK (1) | HK1079996B (https=) |
| IL (1) | IL164275A0 (https=) |
| MX (1) | MXPA04009288A (https=) |
| NZ (1) | NZ535843A (https=) |
| PL (1) | PL372346A1 (https=) |
| PT (1) | PT1494680E (https=) |
| WO (1) | WO2003082300A1 (https=) |
| ZA (1) | ZA200408153B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100413507C (zh) * | 2003-09-19 | 2008-08-27 | 威斯康星州男校友研究基金会 | 治疗骨质稀少或雄性骨质疏松的2-亚烷基-19-去甲-维生素d衍生物 |
| RU2326674C2 (ru) * | 2003-09-19 | 2008-06-20 | Пфайзер Продактс Инк. | Производные 2-алкилиден-19-нор-витамина d для лечения слабости, поражения мышц или саркопении |
| BRPI0414448A (pt) * | 2003-09-19 | 2006-11-14 | Pfizer Prod Inc | composições farmacêuticas e métodos compreendendo combinações de derivados de 2-alquilideno-19-nor-vitamina d e um agonista/antagonista de estrogênio |
| WO2005027928A1 (en) * | 2003-09-19 | 2005-03-31 | Pfizer Products Inc. | 2-alkylidene-19-nor-vit amin d derivatives for the treatment of hypocalcemic tetany or hyproparathyroidism |
| WO2005027919A1 (en) * | 2003-09-19 | 2005-03-31 | Pfizer Products Inc. | 2-alkylidene-19-nor-vitamin d derivatives for the treatment of a second hip fracture |
| US7214671B2 (en) * | 2004-02-19 | 2007-05-08 | Wisconsin Alumni Research Foundation | Use of 2-methylene-19-nor-20(S)-1α,25-dihydroxyvitamin D3 for the prophylaxis of bone diseases |
| KR20070015588A (ko) | 2004-05-07 | 2007-02-05 | 위스콘신 얼럼나이 리서어치 화운데이션 | 배아 줄기 세포로부터 중간엽 줄기 세포를 형성하는 방법 |
| WO2006061683A1 (en) * | 2004-12-09 | 2006-06-15 | Pfizer Products Inc. | 2-alkylidene-19-nor-vitamin d derivatives for the treatment of osteogenesis imperfecta |
| US7803789B2 (en) * | 2006-02-02 | 2010-09-28 | Wisconsin Alumni Research Foundation | Vitamin D analog—RAK, methods and uses thereof |
| US7528122B2 (en) | 2006-02-02 | 2009-05-05 | Wisconsin Alumni Research Foundation | Vitamin D analog—NEL, methods and uses thereof |
| WO2010120698A1 (en) * | 2009-04-17 | 2010-10-21 | Vidasym, Llc | Vitamin d receptor agonists and uses thereof |
| 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 |
| CN111588506B (zh) * | 2020-01-02 | 2022-01-25 | 南京医科大学 | 一种含维生素c的钛种植体存储液的应用 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997011053A1 (en) * | 1995-09-21 | 1997-03-27 | Wisconsin Alumni Research Foundation | Calcitriol derivatives and their uses |
| WO1998041500A1 (en) * | 1997-03-17 | 1998-09-24 | Wisconsin Alumni Research Foundation | 2-alkyl-19-nor-vitamin d compounds |
| WO1998041501A1 (en) * | 1997-03-17 | 1998-09-24 | Wisconsin Alumni Research Foundation | 2-alkylidene-19-nor-vitamin d compounds |
| WO2001074766A1 (en) * | 2000-03-31 | 2001-10-11 | Wisconsin Alumni Research Foundation | 2-alkylidene-19-nor-vitamin d compounds and their therapeutic uses |
| WO2002005823A2 (en) * | 2000-07-14 | 2002-01-24 | Wisconsin Alumni Research Foundation | USE OF 2-METHYLENE-19-NOR-20(S)-1α,25-DIHYDROXYVITAMIN D3 TO INCREASE BONE STRENGTH |
| WO2002005824A1 (en) * | 2000-07-14 | 2002-01-24 | Wisconsin Alumni Research Foundation | USE OF 2α-METHYL-19-NOR-20(S)-1α,25-DIHYDROXYVITAMIN D3 TO INCREASE BONE STRENGTH |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US584928A (en) * | 1897-06-22 | Schlag | ||
| US4666634A (en) * | 1984-12-05 | 1987-05-19 | Chugai Seiyaku Kabushiki Kaisha | vitamin D3 derivatives having a substituent at 2-position |
| IL74617A (en) * | 1985-03-15 | 1988-11-15 | Yeda Res & Dev | Compositions comprising a vitamin d derivative and method for the local treatment of bone fractures in animals |
| US5246925A (en) * | 1989-03-09 | 1993-09-21 | Wisconsin Alumni Research Foundation | 19-nor-vitamin D compounds for use in treating hyperparathyroidism |
| CA1333616C (en) * | 1989-03-09 | 1994-12-20 | Hector F. Deluca | 19-nor-vitamin d compounds |
| US5556645A (en) * | 1990-01-12 | 1996-09-17 | Bockman; Richard | Methods of enhancing wound healing and tissue repair |
| 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 |
| US5565589A (en) * | 1993-11-03 | 1996-10-15 | Wisconsin Alumni Research Foundation | 17-formyl-5,6-trans-vitamin D compounds |
| US5428029A (en) * | 1993-11-24 | 1995-06-27 | Hoffmann-La Roche Inc. | Vitamin D3 fluorinated analogs |
| US5976142A (en) * | 1996-10-16 | 1999-11-02 | Chin; Martin | Apparatus and method for distraction osteogenesis of small alveolar bone |
| ATE417927T1 (de) * | 1997-07-30 | 2009-01-15 | Univ Emory | Neue knochenmineralisierungsproteine, dna, vektoren, expressionssysteme |
-
2002
- 2002-03-25 US US10/105,826 patent/US20030195175A1/en not_active Abandoned
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2003
- 2003-03-12 AU AU2003220169A patent/AU2003220169B2/en not_active Ceased
- 2003-03-12 PL PL03372346A patent/PL372346A1/xx unknown
- 2003-03-12 BR BR0308701-8A patent/BR0308701A/pt not_active Application Discontinuation
- 2003-03-12 PT PT03716465T patent/PT1494680E/pt unknown
- 2003-03-12 JP JP2003579837A patent/JP2005527558A/ja active Pending
- 2003-03-12 AT AT03716465T patent/ATE406901T1/de active
- 2003-03-12 CN CNB038119684A patent/CN100531739C/zh not_active Expired - Fee Related
- 2003-03-12 EP EP03716465A patent/EP1494680B1/en not_active Expired - Lifetime
- 2003-03-12 CA CA002480125A patent/CA2480125C/en not_active Expired - Fee Related
- 2003-03-12 KR KR1020047015427A patent/KR100983953B1/ko not_active Expired - Fee Related
- 2003-03-12 NZ NZ535843A patent/NZ535843A/xx not_active IP Right Cessation
- 2003-03-12 DK DK03716465T patent/DK1494680T3/da active
- 2003-03-12 DE DE60323351T patent/DE60323351D1/de not_active Expired - Lifetime
- 2003-03-12 US US10/509,065 patent/US20050203071A1/en not_active Abandoned
- 2003-03-12 HK HK06100147.6A patent/HK1079996B/zh not_active IP Right Cessation
- 2003-03-12 MX MXPA04009288A patent/MXPA04009288A/es active IP Right Grant
- 2003-03-12 ES ES03716465T patent/ES2312764T3/es not_active Expired - Lifetime
- 2003-03-12 IL IL16427503A patent/IL164275A0/xx not_active IP Right Cessation
- 2003-03-12 WO PCT/US2003/007443 patent/WO2003082300A1/en not_active Ceased
-
2004
- 2004-10-08 ZA ZA200408153A patent/ZA200408153B/xx unknown
-
2010
- 2010-12-02 US US12/958,879 patent/US20110112056A1/en not_active Abandoned
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997011053A1 (en) * | 1995-09-21 | 1997-03-27 | Wisconsin Alumni Research Foundation | Calcitriol derivatives and their uses |
| WO1998041500A1 (en) * | 1997-03-17 | 1998-09-24 | Wisconsin Alumni Research Foundation | 2-alkyl-19-nor-vitamin d compounds |
| WO1998041501A1 (en) * | 1997-03-17 | 1998-09-24 | Wisconsin Alumni Research Foundation | 2-alkylidene-19-nor-vitamin d compounds |
| WO2001074766A1 (en) * | 2000-03-31 | 2001-10-11 | Wisconsin Alumni Research Foundation | 2-alkylidene-19-nor-vitamin d compounds and their therapeutic uses |
| WO2002005823A2 (en) * | 2000-07-14 | 2002-01-24 | Wisconsin Alumni Research Foundation | USE OF 2-METHYLENE-19-NOR-20(S)-1α,25-DIHYDROXYVITAMIN D3 TO INCREASE BONE STRENGTH |
| WO2002005824A1 (en) * | 2000-07-14 | 2002-01-24 | Wisconsin Alumni Research Foundation | USE OF 2α-METHYL-19-NOR-20(S)-1α,25-DIHYDROXYVITAMIN D3 TO INCREASE BONE STRENGTH |
Non-Patent Citations (1)
| Title |
|---|
| Journal of Medicinal Chemistry 41 (22 Oct 1998) pp 4662-4674 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110112056A1 (en) | 2011-05-12 |
| WO2003082300A1 (en) | 2003-10-09 |
| ATE406901T1 (de) | 2008-09-15 |
| HK1079996A1 (zh) | 2006-04-21 |
| EP1494680A1 (en) | 2005-01-12 |
| JP2005527558A (ja) | 2005-09-15 |
| DK1494680T3 (da) | 2008-11-17 |
| BR0308701A (pt) | 2005-01-18 |
| US20030195175A1 (en) | 2003-10-16 |
| ES2312764T3 (es) | 2009-03-01 |
| CN1655797A (zh) | 2005-08-17 |
| PT1494680E (pt) | 2008-10-21 |
| IL164275A0 (en) | 2005-12-18 |
| KR100983953B1 (ko) | 2010-09-27 |
| AU2003220169A1 (en) | 2003-10-13 |
| CA2480125C (en) | 2009-12-29 |
| PL372346A1 (en) | 2005-07-11 |
| ZA200408153B (en) | 2006-03-29 |
| HK1079996B (zh) | 2010-04-01 |
| NZ535843A (en) | 2006-03-31 |
| EP1494680B1 (en) | 2008-09-03 |
| CN100531739C (zh) | 2009-08-26 |
| MXPA04009288A (es) | 2005-06-08 |
| DE60323351D1 (de) | 2008-10-16 |
| CA2480125A1 (en) | 2003-10-09 |
| US20050203071A1 (en) | 2005-09-15 |
| KR20040095346A (ko) | 2004-11-12 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |