KR940703806A - 20-메틸-치환된 비타민 D 유도체 (20-Methyl-Substituted Vitamin D Derivatives) - Google Patents
20-메틸-치환된 비타민 D 유도체 (20-Methyl-Substituted Vitamin D Derivatives)Info
- Publication number
- KR940703806A KR940703806A KR1019940702001A KR19940702001A KR940703806A KR 940703806 A KR940703806 A KR 940703806A KR 1019940702001 A KR1019940702001 A KR 1019940702001A KR 19940702001 A KR19940702001 A KR 19940702001A KR 940703806 A KR940703806 A KR 940703806A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- methyl
- vitamin
- dihydroxy
- hydroxy
- Prior art date
Links
- 150000003710 vitamin D derivatives Chemical class 0.000 title claims abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims abstract 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 6
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract 4
- 229930195733 hydrocarbon Natural products 0.000 claims abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000002252 acyl group Chemical group 0.000 claims abstract 3
- 125000003277 amino group Chemical group 0.000 claims abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 239000001301 oxygen Substances 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 239000011593 sulfur Substances 0.000 claims abstract 3
- 239000003814 drug Substances 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- DCROKXXPZPPINM-YHJXBONMSA-N (1r,3z)-3-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-6-methylhept-5-en-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCC=C(C)C)C)=C\C=C1\C[C@H](O)CCC1=C DCROKXXPZPPINM-YHJXBONMSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000011710 vitamin D Substances 0.000 claims 1
- 229940046009 vitamin E Drugs 0.000 claims 1
- 239000011709 vitamin E Substances 0.000 claims 1
- 229940046008 vitamin d Drugs 0.000 claims 1
- 125000004429 atom Chemical group 0.000 abstract 3
- -1 benzoyloxyl group Chemical group 0.000 abstract 1
- 235000020964 calcitriol Nutrition 0.000 abstract 1
- 239000011612 calcitriol Substances 0.000 abstract 1
- GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 abstract 1
- 229960005084 calcitriol Drugs 0.000 abstract 1
- 230000024245 cell differentiation Effects 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000006698 induction Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
본 발명은 하기 일반식(I)의 신규 20-메틸-치환된 비타민 D 유도체 및 그의 제조 방법에 관한 것이다.
상기 식 중, R1은 수소 원자, 히드록실기 또는 탄소 원자수 1 내지 12의 알카노일옥실기 또는 벤조일옥실기를 나타내고, R2는 수소 원자 또는 탄소 원자수 1 내지 12의 알카노일기 또는 벤조일기를 나타내고, R3은 임의로 1 이상의 탄소 고리 구조(C3-10-시클로알킬 또는 2개 이하의 이중 결합을 갖는 C3-10-시클로 알케닐 라디칼)에 의해 중단 및(또는) 치환되고, 임의로 1 이상의 히드록시기, 옥소기, 아미노기 및(또는) 1 이상의 할로겐 원자에 의해 치환되며, 필요한 경우 탄화 수소 라디칼에 연쇄 구성원으로서 1 이상의 산소, 황 및(또는) 질소(NH로서) 원자를 갖는, 탄소 원자수 18이하의 포화 또는 불포화된 직쇄 또는 분지쇄 탄화수소 라디칼이다. 본 발명에 따른 신규 화합물은 칼시트리올에 비하여 세포 분화(HL-60)의 현저히 증가된 유도를 보이며, 의약품 제조에 적합하다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- 하기 일반식(I)의 20-메틸-치환된 비타민 D 유도체.식 중, R1은 수소 원자, 히드록시기 또는 탄소 원자수 1 내지 12의 알카노일옥시기 또는 벤조일옥시기를 나타내고, R2는 수소 원자 또는 탄소 원자수 1 내지 12의 알카노일기 또는 벤조일기를 의미하고, R3은, 임의로 1 이상의 탄소 고리 구조(C3-10-시클로알킬 라디칼 또는 2개 이하의 이중 결합을 갖는 C3-10-시클로알케닐 라디칼)에 의해 중단 및(또는) 치환되고, 임의로 1 이상의 히드록시기, 옥소기, 아미노기 및(또는) 1 이상의 할로겐 원자에 의해 치환되며, 임의로 탄화수소 라디칼에 연쇄 구성원으로서 1 이상의 산소, 황 및(또는) 질소(NH로서) 원자를 갖는, 탄소 원자수 18 이하의 포화 또는 불포화된 직쇄 또는 분지쇄 탄화수소 라디칼을 의미한다.
- 제1항에 있어서, R3가 하기하는 라디칼인 비타민 D 유도체.식 중, R은 C1-C4-알킬, -히드록시알킬, -O-알킬(-알콕시)이다.
- 1α,25-디히드록시-20,26,27-트리메틸-23-옥사-비타민 D3, 1(S), 3(R)-디히드록시-20-(5-히드록시-5-메틸-헥사-1E,3E-디엔-1-일)-20-메틸-9,10-세코프레그나-5Z,7E,10(19)-트리엔, 1α,25-디히드록시-20-메틸-비타민 D3, 1α,25-디히드록시-20-메틸-24-호모-비타민 D3, 1α, 24(S)-디히드록시-20-메틸-비타민 D3, 1α,25-디히드록시-20-메틸-23-옥사-비타민 D3, 1α,24(R),25-트리히드록시-20-메틸-비타민 D3, 1α,24(S),25-트리히드록시-20-메틸-비타민 D3, 1α,25-디히드록시-20-메틸-24-옥소-비타민 D3, (5Z,7E)-(1S,3R)-20-메틸-20-비닐-9,10-세코-프레그나-5,7,10(19-트리엔-1,3-디올, (5Z,7E)-(1S,3R)-20-에틸-20-메틸-9,10-세코-프레그나-5,7,10(19)-트리엔-1,3-디올, (5Z,7E)-(1S,3R)-20-히드록시메틸-20-메틸-9,10-세코-프레그나-5,7,10(19)-트리엔-1,3-디올, 1α,25-디히드록시-20-메틸-23,24-데히드로-비타민 D3, 1α,25-디히드록시-20,26,27-트리메틸-23,24-데히드로-비타민 D3.
- 하기 일반식(Ⅱ)의 화합물의 존재하는 히드록시 보호기를 절단하고, 필요한 경우 히드록시기(들)의 일부 또는 전부를 에스테르화하여, 하기 일반식(Ⅰ)의 화합물로 전환시키는 것을 특징으로 하는 하기 일반식(I)의 20-메틸-치환 비타민 D 유도체의 제조 방법.식 중, R1은 수소 원자, 히드록시기 또는 탄소 원자수 1 내지 12의 알카노일옥시기 또는 벤조일옥시기를 나타내고, R2는 수소 원자 또는 탄소 원자수 1 내지 12의 알카노일기 또는 벤조일기를 의미하고, R3은, 임의로 1 이상의 탄소 고리 구조(C3-10-시클로알킬 라디칼 또는 2개 이하의 이중 결합을 갖는 C3-10-시클로알케닐 라디칼)에 의해 중단 및(또는) 치환되고, 임의로 1 이상의 히드록시기, 옥소기, 아미노기 및(또는) 1 이상의 할로겐 원자에 의해 치환되며, 임의로 탄화수소 라디칼에 연쇄 구성원으로서 1 이상의 산소, 황 및(또는) 질소(NH로서) 원자를 갖는, 탄소 원자수 18 이하의 포화 또는 불포화된 직쇄 또는 분지쇄 탄화수소 라디칼을 의미하고, R1'은 수소 원자 또는 보호된 히드록시기를 의미하고,2'는 내알칼리성 히드록시 보호기를 의미하고,3'은 임의로 존재하는 히드록시기가 보호되는, 일반식(I)의 최종 목적 화합물에서의 R3과 동일한 의미를 갖는다.
- 하기 일반식(Ⅴ)의 화합물.식 중, R1'은 수소 원자 또는 보호된 히드록시기를 의미하고, R2'는 내알칼리성 히드록시 보호기를 의미한다.
- 제1항 내지 제3항의 화합물과 제약학적으로 허용되는 부형제로 이루어지는 것을 특징으로 하는 제약학적 제제.
- 제1항 내지 제3항의 화합물의 약제 제조를 위한 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4141746.1 | 1991-12-13 | ||
| DE4141746A DE4141746A1 (de) | 1991-12-13 | 1991-12-13 | 20-methyl-substituierte vitamin d-derivate |
| PCT/EP1992/002887 WO1993012081A1 (de) | 1991-12-13 | 1992-12-14 | 20-methyl-substituierte vitamin d-derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR940703806A true KR940703806A (ko) | 1994-12-12 |
| KR100271462B1 KR100271462B1 (ko) | 2000-11-15 |
Family
ID=6447341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019940702001A KR100271462B1 (ko) | 1991-12-13 | 1992-12-14 | 20-메틸-치환된 비타민 d 유도체 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5446035A (ko) |
| EP (1) | EP0637299B1 (ko) |
| JP (1) | JP3280975B2 (ko) |
| KR (1) | KR100271462B1 (ko) |
| CN (1) | CN1035177C (ko) |
| AT (1) | ATE138366T1 (ko) |
| AU (1) | AU670585B2 (ko) |
| CA (1) | CA2125476C (ko) |
| CZ (1) | CZ286579B6 (ko) |
| DE (2) | DE4141746A1 (ko) |
| DK (1) | DK0637299T3 (ko) |
| ES (1) | ES2089585T3 (ko) |
| FI (1) | FI108226B (ko) |
| GR (1) | GR3020097T3 (ko) |
| HU (1) | HUT68263A (ko) |
| IL (1) | IL104074A (ko) |
| MX (1) | MX9207101A (ko) |
| NO (1) | NO305949B1 (ko) |
| NZ (1) | NZ246052A (ko) |
| PL (1) | PL171403B1 (ko) |
| SK (1) | SK280450B6 (ko) |
| TW (1) | TW275060B (ko) |
| WO (1) | WO1993012081A1 (ko) |
| ZA (1) | ZA929650B (ko) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4220757A1 (de) * | 1992-06-24 | 1994-01-05 | Schering Ag | Derivate in der Vitamin D-Reihe mit Modifikationen in der 20-Position, Verfahren zu ihrer Herstellung, Zwischenprodukte für dieses Verfahren, diese Derivate enthaltende pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln |
| GB9220272D0 (en) * | 1992-09-25 | 1992-11-11 | Leo Pharm Prod Ltd | Chemical compounds |
| IL107185A (en) * | 1992-10-06 | 1998-02-22 | Schering Ag | History of 52-carboxylic acid, processes for their preparation and pharmaceutical preparations containing them |
| US20040167106A1 (en) * | 1993-06-04 | 2004-08-26 | Rodriguez Gustavo C. | Prevention of ovarian cancer by administration of a Vitamin D compound |
| US6407082B1 (en) * | 1996-09-13 | 2002-06-18 | New Life Pharmaceuticals Inc. | Prevention of ovarian cancer by administration of a vitamin D compound |
| GB9315253D0 (en) * | 1993-07-23 | 1993-09-08 | Res Inst Medicine Chem | Chemical compounds |
| US5428029A (en) * | 1993-11-24 | 1995-06-27 | Hoffmann-La Roche Inc. | Vitamin D3 fluorinated analogs |
| US5981597A (en) * | 1995-02-13 | 1999-11-09 | Trustees Of The University Of Pennsylvania | Differentiating agents for the treatment of inflammatory intestinal diseases |
| DE69733338T2 (de) * | 1996-02-13 | 2006-03-16 | G.D. Searle & Co., Chicago | Zubereitungen, enthaltend einen cyclooxygenase-2-inhibitor und einen leukotrien-b4-rezeptor-antagonisten |
| DE19619036A1 (de) | 1996-04-30 | 1997-11-13 | Schering Ag | Neue Vitamin D-Derivate mit carbo- oder heterocyclischen Substituenten an C-25, Verfahren zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln |
| SG70010A1 (en) * | 1996-05-23 | 2000-01-25 | Hoffmann La Roche | Fluorinated vitamin d3 analogs |
| US6511970B1 (en) | 1996-09-13 | 2003-01-28 | New Life Pharmaceuticals Inc. | Prevention of ovarian cancer by administration of products that induce transforming growth factor-beta and/or apoptosis in the ovarian epithelium |
| US6765002B2 (en) | 2000-03-21 | 2004-07-20 | Gustavo Rodriguez | Prevention of ovarian cancer by administration of products that induce transforming growth factor-β and/or apoptosis in the ovarian epithelium |
| US6034074A (en) | 1996-09-13 | 2000-03-07 | New Life Pharmaceuticals Inc. | Prevention of ovarian cancer by administration of a Vitamin D compound |
| US6028064A (en) | 1996-09-13 | 2000-02-22 | New Life Pharmaceuticals Inc. | Prevention of ovarian cancer by administration of progestin products |
| ATE238986T1 (de) | 1997-09-08 | 2003-05-15 | Hoffmann La Roche | 1,3-dihydroxy-20,20-dialkyl-vitamin d3 analoga |
| JP2002509888A (ja) | 1998-03-27 | 2002-04-02 | オレゴン ヘルス サイエンシーズ ユニバーシティー | 腫瘍および他の過増殖性疾患の治療におけるビタミンｄおよびその類似体 |
| US20030188756A1 (en) * | 2002-08-19 | 2003-10-09 | Cantorna Margherita T | Treatment of inflammatory bowel disease with vitamin d compounds |
| US6358939B1 (en) | 1999-12-21 | 2002-03-19 | Northern Lights Pharmaceuticals, Llc | Use of biologically active vitamin D compounds for the prevention and treatment of inflammatory bowel disease |
| US6989377B2 (en) | 1999-12-21 | 2006-01-24 | Wisconsin Alumni Research Foundation | Treating vitamin D responsive diseases |
| US20010044431A1 (en) * | 2000-03-21 | 2001-11-22 | Rodriguez Gustavo C. | Prevention of ovarian cancer by administration of products that induce biologic effects in the ovarian epithelium |
| EP1314427A4 (en) * | 2000-08-17 | 2006-05-03 | Chugai Pharmaceutical Co Ltd | THERAPEUTIC AGENT FOR THE TREATMENT OF OSTEOPOROSIS |
| TWI329105B (en) * | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| PL1656372T3 (pl) | 2003-07-30 | 2013-08-30 | Rigel Pharmaceuticals Inc | Związki 2,4-pirymidynodiaminy do stosowania w leczeniu lub zapobieganiu chorobom autoimmunologicznym |
| CN101217868A (zh) * | 2005-05-10 | 2008-07-09 | 德米普瑟尔有限公司 | 用于皮肤护理的组合物和方法 |
| JP2008540514A (ja) | 2005-05-10 | 2008-11-20 | ダーミプソル リミテッド | 過剰増殖表皮疾患の治療用組成物及び方法 |
| JP2008543855A (ja) | 2005-06-13 | 2008-12-04 | ライジェル ファーマシューティカルズ， インコーポレイテッド | 変形性骨疾患を処置するための方法および組成物 |
| ATE352714T1 (de) * | 2005-06-17 | 2007-02-15 | Magneti Marelli Powertrain Spa | Brennstoffeinspritzventil |
| MX2008012674A (es) * | 2006-04-10 | 2008-10-15 | Wisconsin Alumni Res Found | Compuestos de 1 a-hidroxi-2-(3'-hidroxipropiliden)-19-nor-vitamina d con una cadena lateral 1,1-dimetilpropilo. |
| EP2063963A2 (en) | 2006-08-25 | 2009-06-03 | Cougar Biotechnology, Inc. | Methods for treating cancer comprising the administration of a vitamin d compound and an additional therapeutic agent |
| US20080051380A1 (en) * | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| US20080051375A1 (en) * | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods for treating cancer comprising the administration of a vitamin d compound and an additional therapeutic agent, and compositions containing the same |
| WO2009009132A1 (en) * | 2007-07-12 | 2009-01-15 | Cougar Biotechnology, Inc. | Use of 17alpha-hydroxylase/c17, 20-lyase inhibitors for the treatment of cancer |
| SG173119A1 (en) * | 2009-01-27 | 2011-08-29 | Berg Biosystems Llc | Vitamin d3 and analogs thereof for alleviating side effects associated with chemotherapy |
| CN106265695B (zh) | 2009-08-14 | 2021-05-07 | 博格有限责任公司 | 用于治疗脱发的维生素d3及其类似物 |
| US20190183908A1 (en) | 2016-05-13 | 2019-06-20 | Case Western Reserve University | Autophagy activators for treating or preventing skin injury |
| JP2019522032A (ja) | 2016-07-29 | 2019-08-08 | ヤンセン ファーマシューティカ エヌ．ベー． | 前立腺癌の治療方法 |
| US10548908B2 (en) * | 2016-09-15 | 2020-02-04 | Nostopharma, LLC | Compositions and methods for preventing and treating heterotopic ossification and pathologic calcification |
| US11903952B2 (en) | 2020-05-27 | 2024-02-20 | Northwestern University | Vitamin D as an immune modulator to prevent immune-related complication from COVID-19 infection |
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1991
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1992
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- 1992-12-14 HU HU9401456A patent/HUT68263A/hu unknown
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- 1992-12-14 KR KR1019940702001A patent/KR100271462B1/ko not_active IP Right Cessation
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1993
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1994
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