GB1508043A - Trihydroxycholesta-5,7-dienes - Google Patents
Trihydroxycholesta-5,7-dienesInfo
- Publication number
- GB1508043A GB1508043A GB44013/76A GB4401376A GB1508043A GB 1508043 A GB1508043 A GB 1508043A GB 44013/76 A GB44013/76 A GB 44013/76A GB 4401376 A GB4401376 A GB 4401376A GB 1508043 A GB1508043 A GB 1508043A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cholesta
- epimers
- protected
- groups
- prepared
- 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.)
- Expired
Links
- BYKJMKQYVPSYFK-UVBSCRANSA-N (6R)-6-[(9S,10R,13R,14R,17R)-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptane-1,1,1-triol Chemical class OC(C(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CCCC[C@]4(C)[C@H]3CC[C@]12C)(O)O BYKJMKQYVPSYFK-UVBSCRANSA-N 0.000 title 1
- 230000031709 bromination Effects 0.000 abstract 3
- 238000005893 bromination reaction Methods 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 125000006239 protecting group Chemical group 0.000 abstract 3
- 239000004593 Epoxy Substances 0.000 abstract 2
- 229910004298 SiO 2 Inorganic materials 0.000 abstract 2
- 238000007269 dehydrobromination reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000003431 steroids Chemical class 0.000 abstract 2
- OSELKOCHBMDKEJ-UHFFFAOYSA-N (10R)-3c-Hydroxy-10r.13c-dimethyl-17c-((R)-1-methyl-4-isopropyl-hexen-(4c)-yl)-(8cH.9tH.14tH)-Delta5-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 OSELKOCHBMDKEJ-UHFFFAOYSA-N 0.000 abstract 1
- PGLNLCWHYQYRGQ-UHFFFAOYSA-N (3beta,20S)-3-Hydroxycholest-5-en-24-one Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=O)C(C)C)C1(C)CC2 PGLNLCWHYQYRGQ-UHFFFAOYSA-N 0.000 abstract 1
- XQZBMHQJFYYJTQ-REEZCCHISA-N (8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methyl-5-oxoheptan-2-yl]-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC(=O)C(C)C)C)[C@@]1(C)CC2 XQZBMHQJFYYJTQ-REEZCCHISA-N 0.000 abstract 1
- LXUJBCFZDYDKMN-OXIFXYDNSA-N (9S,10R,13R,14R,17R)-17-[(2R)-5-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-1,3-diol Chemical class OC1CC(CC2=CC=C3[C@@H]4CC[C@H]([C@@H](CCC(C(C)C)O)C)[C@]4(CC[C@@H]3[C@@]12C)C)O LXUJBCFZDYDKMN-OXIFXYDNSA-N 0.000 abstract 1
- PGLNLCWHYQYRGQ-ZHHJOTBYSA-N 24-oxocholest-5-en-3beta-ol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCC(=O)C(C)C)[C@@]1(C)CC2 PGLNLCWHYQYRGQ-ZHHJOTBYSA-N 0.000 abstract 1
- CQSRUKJFZKVYCY-UHFFFAOYSA-N 5alpha-isofucostan-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 CQSRUKJFZKVYCY-UHFFFAOYSA-N 0.000 abstract 1
- GBBBJSKVBYJMBG-QTWVXCTBSA-N Fucosterol Natural products CC=C(CC[C@@H](C)[C@@H]1CC[C@@H]2[C@H]3C=C[C@@H]4C[C@H](O)CC[C@@]4(C)[C@@H]3CC[C@@]12C)C(C)C GBBBJSKVBYJMBG-QTWVXCTBSA-N 0.000 abstract 1
- OSELKOCHBMDKEJ-VRUYXKNBSA-N Isofucosterol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@@H]2[C@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C OSELKOCHBMDKEJ-VRUYXKNBSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000746 allylic group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000006480 benzoylation reaction Methods 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 239000000356 contaminant Substances 0.000 abstract 1
- OSELKOCHBMDKEJ-JUGJNGJRSA-N fucosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC\C(=C/C)C(C)C)[C@@]1(C)CC2 OSELKOCHBMDKEJ-JUGJNGJRSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/174—Vitamins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6866474A JPS539222B2 (en, 2012) | 1974-06-18 | 1974-06-18 | |
| JP14133074A JPS5168557A (en) | 1974-12-09 | 1974-12-09 | 1 arufua 244 jihidorokishikorekarushifuerooruno seizoho |
| JP49141332A JPS5168560A (en) | 1974-12-09 | 1974-12-09 | 1 arufua 244 jihidorokishikorekarushifuerooruno bunriho |
| JP14132974A JPS5168556A (en) | 1974-12-09 | 1974-12-09 | 1 arufua 244 jihidorokishikorekarushifuerooruno seizohoho |
| JP14133174A JPS5320989B2 (en, 2012) | 1974-12-09 | 1974-12-09 | |
| JP14901774A JPS5176252A (en) | 1974-12-27 | 1974-12-27 | 1 arufua *24 * r * jihidorokishikorekarushifueroorunoseizoho |
| JP14902174A JPS5176255A (en) | 1974-12-27 | 1974-12-27 | 1 arufua * 24 * s * jihidorokishikorekarushifueroorunoseizohoho |
| JP14902074A JPS5176254A (en) | 1974-12-27 | 1974-12-27 | 1 arufua * 24 * s * jihidorokishikorekarushifueroorunoseizoho |
| JP14901874A JPS5176253A (en) | 1974-12-27 | 1974-12-27 | 1 arufua *24 * r * jihidorokishikorekarushifueroorunoseizohoho |
| JP14902274A JPS5176259A (en) | 1974-12-27 | 1974-12-27 | 244 benzoiruokishikoresuteroorujudotaino 24 iepimaanobunriho |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1508043A true GB1508043A (en) | 1978-04-19 |
Family
ID=27580092
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB44013/76A Expired GB1508043A (en) | 1974-06-18 | 1975-06-04 | Trihydroxycholesta-5,7-dienes |
| GB24138/75A Expired GB1508042A (en) | 1974-06-18 | 1975-06-04 | Dihydroxycalciferols |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24138/75A Expired GB1508042A (en) | 1974-06-18 | 1975-06-04 | Dihydroxycalciferols |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4022891A (en, 2012) |
| CA (1) | CA1051442A (en, 2012) |
| CH (1) | CH618669A5 (en, 2012) |
| DE (1) | DE2526981C3 (en, 2012) |
| DK (1) | DK142410B (en, 2012) |
| FR (1) | FR2275196A1 (en, 2012) |
| GB (2) | GB1508043A (en, 2012) |
| NL (1) | NL7507268A (en, 2012) |
| NO (1) | NO145162C (en, 2012) |
| SE (1) | SE413096B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4305881A (en) * | 1978-11-17 | 1981-12-15 | Hoffmann-La Roche Inc. | Process for 1α,3β-dihydroxy-Δ5 -steroids |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1088094B (it) * | 1976-10-14 | 1985-06-04 | Hoffmann La Roche | Derivati del pregnano |
| JPS53147051A (en) * | 1977-05-24 | 1978-12-21 | Teijin Ltd | 1alpha-hydroxy-24-dehydro-vitamin d3 and its preparation |
| JPS5822479B2 (ja) * | 1977-09-07 | 1983-05-09 | 帝人株式会社 | １α−ヒドロキシ−２４−オキソ−ビタミンＤ↓３およびその製造法 |
| US4225596A (en) * | 1978-10-13 | 1980-09-30 | Wisconsin Alumni Research Foundation | Method for treating calcium imbalance and improving calcium absorption in mammals |
| US4230701A (en) * | 1979-03-21 | 1980-10-28 | Hoffmann-La Roche Inc. | Administration of biologically active vitamin D3 and vitamin D2 materials |
| US4335120A (en) * | 1979-03-21 | 1982-06-15 | Hoffmann-La Roche Inc. | Administration of biologically active vitamin D3 and vitamin D2 materials |
| JPS55136229A (en) * | 1979-04-10 | 1980-10-23 | Teijin Ltd | Adjustment of bone metabolism in warm-blooded animal and drug for it |
| JPS5626820A (en) * | 1979-08-10 | 1981-03-16 | Chugai Pharmaceut Co Ltd | Immunosuppressing agent |
| US4338250A (en) * | 1981-04-27 | 1982-07-06 | Wisconsin Alumni Research Foundation | 1-Hydroxylation process |
| CA1272953A (en) | 1984-10-08 | 1990-08-21 | Yuji Makino | Pharmaceutical composition for external use containing active-type vitamin d.sub.3 |
| JPH0749435B2 (ja) * | 1988-07-04 | 1995-05-31 | 帝人株式会社 | １α，３β，２４−トリヒドロキシ−△▲上５▼−ステロイド類の製造方法 |
| 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 |
| US6538037B2 (en) | 1991-01-08 | 2003-03-25 | Bone Care International, Inc. | Methods for preparation and use of 1α,24(S)-dihydroxyvitamin D2 |
| US5786348A (en) * | 1991-01-08 | 1998-07-28 | Bone Care International, Inc. | Methods for preparation and use of 1α,24(S)-dihydroxy vitamin D2 |
| US20040009958A1 (en) * | 1991-01-08 | 2004-01-15 | Bone Care International, Inc. | Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2 |
| ES2200238T3 (es) * | 1991-01-08 | 2004-03-01 | Bone Care International, Inc. | Procedimiento para la preparacion de la 1-alpha-24-dihidroxi vitamina d2. |
| US6251883B1 (en) | 1991-01-08 | 2001-06-26 | Bone Care International, Inc. | Methods for preparation and use of 1α,24(S)-dihydroxy vitamin D2 |
| US6166000A (en) * | 1991-01-08 | 2000-12-26 | Bone Care International, Inc. | Methods for preparation and use of 1α,24(S)-Dihydroxy vitamin . D.sub2 |
| EP0614456B1 (en) * | 1992-08-28 | 1999-06-09 | Bone Care International, Inc. | 1alpha,24(s)-dihydroxy vitamin d2, its formation and use |
| IL107185A (en) * | 1992-10-06 | 1998-02-22 | Schering Ag | Vitamin d, 25-carboxylic acid derivatives and pharmaceutical compositions containing the same |
| US5869472A (en) * | 1994-07-18 | 1999-02-09 | Bone Care International, Inc. | Synthesis of 1α-hydroxy vitamin D |
| US6362350B1 (en) | 1999-07-01 | 2002-03-26 | Wisconsin Alumni Research Foundation | Crystalline 1α, 24(S)-dihydroxyvitamin D2 and method of purification thereof |
| US7129230B2 (en) | 2001-03-12 | 2006-10-31 | Nestec S.A. | Method and product for treating cancer in pets |
| US7094775B2 (en) * | 2004-06-30 | 2006-08-22 | Bone Care International, Llc | Method of treating breast cancer using a combination of vitamin D analogues and other agents |
| US20060003950A1 (en) * | 2004-06-30 | 2006-01-05 | Bone Care International, Inc. | Method of treating prostatic diseases using a combination of vitamin D analogues and other agents |
| TW200714580A (en) * | 2005-10-14 | 2007-04-16 | Formosa Lab Inc | Process for preparing vitamin D analogs |
| JP5492099B2 (ja) * | 2008-03-12 | 2014-05-14 | シトクロマ インコーポレイテッド | 安定化１，２５−ジヒドロキシビタミンｄ２及びその製造方法 |
| KR102300311B1 (ko) | 2017-04-18 | 2021-09-10 | 연성정밀화학(주) | 타칼시톨의 제조방법 및 그를 위한 중간체 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3901928A (en) * | 1973-01-10 | 1975-08-26 | Robert Henry Hesse | 1' ,3' -dihydroxy steroid-5-enes method of preparing same and their use for preparing 1' -hydroxy-25-hydrogen vitamin d compounds |
| US3928397A (en) * | 1973-03-02 | 1975-12-23 | Eisai Co Ltd | New 5-cholestene derivatives and preparation thereof |
-
1975
- 1975-06-02 US US05/583,115 patent/US4022891A/en not_active Expired - Lifetime
- 1975-06-04 GB GB44013/76A patent/GB1508043A/en not_active Expired
- 1975-06-04 GB GB24138/75A patent/GB1508042A/en not_active Expired
- 1975-06-09 SE SE7506560A patent/SE413096B/xx not_active IP Right Cessation
- 1975-06-17 CA CA229,466A patent/CA1051442A/en not_active Expired
- 1975-06-17 DK DK273375AA patent/DK142410B/da not_active IP Right Cessation
- 1975-06-17 NO NO752150A patent/NO145162C/no unknown
- 1975-06-18 NL NL7507268A patent/NL7507268A/xx unknown
- 1975-06-18 FR FR7519074A patent/FR2275196A1/fr active Granted
- 1975-06-18 DE DE752526981A patent/DE2526981C3/de not_active Expired
- 1975-06-18 CH CH793875A patent/CH618669A5/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4305881A (en) * | 1978-11-17 | 1981-12-15 | Hoffmann-La Roche Inc. | Process for 1α,3β-dihydroxy-Δ5 -steroids |
Also Published As
| Publication number | Publication date |
|---|---|
| NO145162C (no) | 1982-01-27 |
| DE2526981A1 (de) | 1976-01-15 |
| DE2526981B2 (de) | 1978-06-29 |
| GB1508042A (en) | 1978-04-19 |
| NL7507268A (nl) | 1975-12-22 |
| SE413096B (sv) | 1980-04-14 |
| DE2526981C3 (de) | 1979-03-01 |
| DK273375A (en, 2012) | 1975-12-19 |
| NO752150L (en, 2012) | 1975-12-19 |
| NO145162B (no) | 1981-10-19 |
| DK142410B (da) | 1980-10-27 |
| SE7506560L (sv) | 1975-12-19 |
| CH618669A5 (en, 2012) | 1980-08-15 |
| CA1051442A (en) | 1979-03-27 |
| FR2275196B1 (en, 2012) | 1978-10-06 |
| FR2275196A1 (fr) | 1976-01-16 |
| US4022891A (en) | 1977-05-10 |
| DK142410C (en, 2012) | 1981-03-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1508043A (en) | Trihydroxycholesta-5,7-dienes | |
| KR930003496B1 (ko) | 1α-히드록시비타민 D화합물의 제조방법 | |
| GB1503965A (en) | Production of isocyanates from lower alkyl esters of mononuclear aromatic carbamic acids | |
| Tanida et al. | Acetolyses of 6-substituted syn-9-benzonorbornenyl and 9-methyl-anti (and syn)-9-benzonorbornenyl arenesulfonates. Anti-syn rate ratios as a test for participation. Substituent effects and variation from secondary to tertiary systems | |
| Kotera | (—) β-Lycorane | |
| Wakamatsu et al. | Stereocontrolled total synthesis of (+)-tutin and (+)-asteromurin A, toxic picrotoxane sesquiterpenes | |
| GB1492746A (en) | Androstane derivatives and compositions containing them | |
| GB1206872A (en) | 6beta-HYDROXY-7alpha-METHYL-ANDROSTANE COMPOUNDS | |
| DE3060195D1 (en) | Process for obtaining a conjugated diolefin from a mixture containing c 4- or c 5-hydrocarbons | |
| GB1200916A (en) | Improved organic compositions | |
| See | Trifluoromethylfluorosulfane and 1, 2-Bis (trifluorornethyl) disulf ane 1, l ‘-Difluoride | |
| JPS525733A (en) | Process for separation and purification of cyclohexene | |
| Whitlock Jr et al. | The enzymatic requirement for “concerted” backbone rearrangement | |
| ES428049A1 (es) | Procedimiento para aislar 1,5-dinitroantraquinona a partir de mezclas de dinitroantraquinonas. | |
| Cambie et al. | Solanum alkaloids. XVIII. Utilization of solasodine for the preparation of nitrogen analogues of ecdysones | |
| GB1324381A (en) | 9alpha-methyl steroids | |
| Nagasawa et al. | Absolute Configuration of (+)-l-Acetoxy-p-menth-3-one Isolated from Essential Oil of Mentha gentilis (L.) | |
| Masamune | The stereochemistry of ring A of gibberellic acid | |
| JPS543019A (en) | Preparation of 4-nitrosodiphenylamine hydrochliride | |
| JPS51127043A (en) | Process for purification of cyclohexene | |
| GB1431616A (en) | Process for separating diolefins | |
| GB1419299A (en) | Process for separating an alcohol mixture | |
| GB1265446A (en, 2012) | ||
| US3080391A (en) | 6alpha-chloro-delta1, 4-androstadien-17beta-ol-3-one derivatives | |
| JPS52144650A (en) | Separation and purification of cyclohexene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19950603 |