CA2296145A1 - Dihomo-seco-cholestanes with two unsaturated bonds in the side chain - Google Patents
Dihomo-seco-cholestanes with two unsaturated bonds in the side chain Download PDFInfo
- Publication number
- CA2296145A1 CA2296145A1 CA002296145A CA2296145A CA2296145A1 CA 2296145 A1 CA2296145 A1 CA 2296145A1 CA 002296145 A CA002296145 A CA 002296145A CA 2296145 A CA2296145 A CA 2296145A CA 2296145 A1 CA2296145 A1 CA 2296145A1
- Authority
- CA
- Canada
- Prior art keywords
- seco
- cholesta
- triol
- dihomo
- compounds
- 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.)
- Abandoned
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- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- OBTIDFCSHQLONE-UHFFFAOYSA-N diphenylphosphane;lithium Chemical compound [Li].C=1C=CC=CC=1PC1=CC=CC=C1 OBTIDFCSHQLONE-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
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- 238000011067 equilibration Methods 0.000 description 1
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- 229920001249 ethyl cellulose Polymers 0.000 description 1
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- 238000004817 gas chromatography Methods 0.000 description 1
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- 229940100242 glycol stearate Drugs 0.000 description 1
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- 239000008241 heterogeneous mixture Substances 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
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- 239000011981 lindlar catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- NDNSKOGZQRSQJS-ZRSFQXBVSA-N methyl (2e,4e,7r)-7-[(1r,4ar,5s,8ar)-5-[tert-butyl(dimethyl)silyl]oxy-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1h-naphthalen-1-yl]octa-2,4-dienoate Chemical compound CC(C)(C)[Si](C)(C)O[C@H]1CCC[C@]2(C)[C@@H]([C@H](C)C/C=C/C=C/C(=O)OC)CCC[C@H]21 NDNSKOGZQRSQJS-ZRSFQXBVSA-N 0.000 description 1
- ZWMLOCKDLNHMJX-LLNVDQSOSA-N methyl (2e,4e,7r)-7-[(4ar,5s,8as)-5-[tert-butyl(dimethyl)silyl]oxy-8a-methyl-4,4a,5,6,7,8-hexahydro-3h-naphthalen-1-yl]octa-2,4-dienoate Chemical compound CC(C)(C)[Si](C)(C)O[C@H]1CCC[C@]2(C)C([C@H](C)C/C=C/C=C/C(=O)OC)=CCC[C@H]21 ZWMLOCKDLNHMJX-LLNVDQSOSA-N 0.000 description 1
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- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
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- RMCPHNCJKRHGCX-BXWFABGCSA-N o-[(2s,4as,5s)-4a-methyl-5-[(2-methylpropan-2-yl)oxy]-3,4,5,6,7,8-hexahydro-2h-naphthalen-2-yl] imidazole-1-carbothioate Chemical compound O([C@@H]1C=C2CCC[C@@H]([C@]2(CC1)C)OC(C)(C)C)C(=S)N1C=CN=C1 RMCPHNCJKRHGCX-BXWFABGCSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920000059 polyethylene glycol stearate Polymers 0.000 description 1
- 229940068917 polyethylene glycols Drugs 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010405 reoxidation reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- OTAWXJIJOFAKJE-JZXIEBOPSA-N tert-butyl-[(1s,3s)-3-[tert-butyl(diphenyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-diphenylsilane Chemical compound O([C@H]1C[C@H](CC(C1=C)=CCP(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)O[Si](C(C)(C)C)(C=1C=CC=CC=1)C=1C=CC=CC=1)[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 OTAWXJIJOFAKJE-JZXIEBOPSA-N 0.000 description 1
- OTAWXJIJOFAKJE-GFMVVXEMSA-N tert-butyl-[(1s,3s,5z)-3-[tert-butyl(diphenyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-diphenylsilane Chemical compound O([C@H]1C[C@H](CC(/C1=C)=C/CP(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)O[Si](C(C)(C)C)(C=1C=CC=CC=1)C=1C=CC=CC=1)[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 OTAWXJIJOFAKJE-GFMVVXEMSA-N 0.000 description 1
- OFSDSMTXHBTJEI-GUHCFGCBSA-N tert-butyl-[(1s,3z)-3-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)CCC(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 OFSDSMTXHBTJEI-GUHCFGCBSA-N 0.000 description 1
- SNTQADHOIZWIDT-ZCSJDZNHSA-N tert-butyl-[(3s,5s)-3-[tert-butyl(diphenyl)silyl]oxy-9-(oxan-2-yloxy)non-1-en-7-yn-5-yl]oxy-diphenylsilane Chemical compound C([C@H](O[Si](C(C)(C)C)(C=1C=CC=CC=1)C=1C=CC=CC=1)C[C@H](O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C(C)(C)C)C=C)C#CCOC1CCCCO1 SNTQADHOIZWIDT-ZCSJDZNHSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- DVFXLNFDWATPMW-IWOKLKJTSA-N tert-butyldiphenylsilyl Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C(C)(C)C)[C@@H](OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](CC(O2)N2C3=NC=NC(N)=C3N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 DVFXLNFDWATPMW-IWOKLKJTSA-N 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- ULYLMHUHFUQKOE-UHFFFAOYSA-N trimethyl(prop-2-ynyl)silane Chemical compound C[Si](C)(C)CC#C ULYLMHUHFUQKOE-UHFFFAOYSA-N 0.000 description 1
- XDOXFRFLKQBNNT-XRVBUDJMSA-N trimethyl-[(z)-4-[(2r)-oxiran-2-yl]but-2-enyl]silane Chemical compound C[Si](C)(C)C\C=C/C[C@@H]1CO1 XDOXFRFLKQBNNT-XRVBUDJMSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 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
- 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
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Nutrition Science (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97112225.4 | 1997-07-17 | ||
| EP97112225 | 1997-07-17 | ||
| PCT/EP1998/004293 WO1999003828A1 (en) | 1997-07-17 | 1998-07-10 | Dihomo-seco-cholestanes with two unsaturated bones in the side chain |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2296145A1 true CA2296145A1 (en) | 1999-01-28 |
Family
ID=8227074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002296145A Abandoned CA2296145A1 (en) | 1997-07-17 | 1998-07-10 | Dihomo-seco-cholestanes with two unsaturated bonds in the side chain |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5994569A (enExample) |
| EP (1) | EP0998455B1 (enExample) |
| JP (1) | JP2001510183A (enExample) |
| AR (1) | AR013217A1 (enExample) |
| AU (1) | AU8860298A (enExample) |
| CA (1) | CA2296145A1 (enExample) |
| DE (1) | DE69818673T2 (enExample) |
| ES (1) | ES2206981T3 (enExample) |
| WO (1) | WO1999003828A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117018000A (zh) * | 2023-08-29 | 2023-11-10 | 东莞市东南部中心医院(东莞市东南部中医医疗服务中心) | 4-胆甾烯-3-酮在制备预防或治疗炎症性肠病药物中的应用 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0957098A1 (en) * | 1998-05-14 | 1999-11-17 | F. Hoffmann-La Roche Ag | Intermediates for the synthesis of 3-epi vitamin D3 metabolites and analogs |
| ES2251248T3 (es) * | 1998-12-09 | 2006-04-16 | Protein Design Labs, Inc. | Uso de anticuerpos contra il-12 para tratar la psoriasis. |
| WO2001042205A2 (en) * | 1999-12-02 | 2001-06-14 | The Penn State Research Foundation | Treatment of inflammatory bowel disease with vitamin d compounds |
| TW200838544A (en) * | 2007-01-25 | 2008-10-01 | Bioxell Spa | Synthesis of 1 α-fluoro-25-hydroxy-16-23E-diene-26, 27-bishomo-20-epi-cholecalciferol |
| CN114276284A (zh) * | 2021-12-30 | 2022-04-05 | 正大制药（青岛）有限公司 | 一种氟骨化醇的制备方法 |
| CN114957068A (zh) * | 2022-04-19 | 2022-08-30 | 正大制药（青岛）有限公司 | 一种氟骨化醇20s异构体的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8915770D0 (en) * | 1989-07-10 | 1989-08-31 | Leo Pharm Prod Ltd | Chemical compounds |
| ES2055521T3 (es) * | 1990-02-06 | 1994-08-16 | Schering Ag | Derivados de vitamina d que son homologos en la cadena lateral, procedimiento para su preparacion, preparados farmaceuticos que contienen estos derivados asi como su utilizacion como medicamentos. |
| US5532228A (en) * | 1990-02-06 | 1996-07-02 | Schering Aktiengesellschaft | Side-chain homologous vitamin D derivatives, process for their production, pharmaceutical preparations containing these derivatives and their use as pharmaceutical agents |
| GB9017890D0 (en) * | 1990-08-15 | 1990-09-26 | Leo Pharm Prod Ltd | Chemical compounds i |
| GB9314400D0 (en) * | 1993-07-12 | 1993-08-25 | Leo Pharm Prod Ltd | Produktionsaktieselskab) chemical compounds |
| CA2175881A1 (en) * | 1995-05-09 | 1996-11-10 | Andrzej Kutner | Vitamin d compounds and methods of preparing these compounds |
| EP0771789B1 (en) * | 1995-10-30 | 2000-02-16 | F. Hoffmann-La Roche Ag | 1 alpha, 26-dihydroxy-D-homo-vitamin D3 |
| WO1998018754A1 (en) * | 1996-10-28 | 1998-05-07 | Versicor, Inc. | Methods for solid-phase synthesis of hydroxylamine compounds and derivatives, and combinatorial libraries thereof |
| GB9622590D0 (en) * | 1996-10-30 | 1997-01-08 | Leo Pharm Prod Ltd | Chemical compounds |
-
1998
- 1998-07-10 DE DE69818673T patent/DE69818673T2/de not_active Expired - Fee Related
- 1998-07-10 EP EP98940201A patent/EP0998455B1/en not_active Expired - Lifetime
- 1998-07-10 WO PCT/EP1998/004293 patent/WO1999003828A1/en not_active Ceased
- 1998-07-10 ES ES98940201T patent/ES2206981T3/es not_active Expired - Lifetime
- 1998-07-10 AU AU88602/98A patent/AU8860298A/en not_active Abandoned
- 1998-07-10 JP JP2000503057A patent/JP2001510183A/ja active Pending
- 1998-07-10 CA CA002296145A patent/CA2296145A1/en not_active Abandoned
- 1998-07-14 US US09/115,188 patent/US5994569A/en not_active Expired - Fee Related
- 1998-07-15 AR ARP980103432A patent/AR013217A1/es unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117018000A (zh) * | 2023-08-29 | 2023-11-10 | 东莞市东南部中心医院(东莞市东南部中医医疗服务中心) | 4-胆甾烯-3-酮在制备预防或治疗炎症性肠病药物中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001510183A (ja) | 2001-07-31 |
| AR013217A1 (es) | 2000-12-13 |
| DE69818673T2 (de) | 2004-08-05 |
| ES2206981T3 (es) | 2004-05-16 |
| WO1999003828A1 (en) | 1999-01-28 |
| EP0998455B1 (en) | 2003-10-01 |
| US5994569A (en) | 1999-11-30 |
| EP0998455A1 (en) | 2000-05-10 |
| DE69818673D1 (de) | 2003-11-06 |
| AU8860298A (en) | 1999-02-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |