GB1503941A - Cholecalciferol derivative and process for preparing it - Google Patents
Cholecalciferol derivative and process for preparing itInfo
- Publication number
- GB1503941A GB1503941A GB17314/75A GB1731475A GB1503941A GB 1503941 A GB1503941 A GB 1503941A GB 17314/75 A GB17314/75 A GB 17314/75A GB 1731475 A GB1731475 A GB 1731475A GB 1503941 A GB1503941 A GB 1503941A
- Authority
- GB
- United Kingdom
- Prior art keywords
- give
- deoxy
- acetoxy
- ene
- cholestan
- 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
- 150000003704 vitamin D3 derivatives Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- YUGCAAVRZWBXEQ-UHFFFAOYSA-N Precholecalciferol Natural products C=1CCC2(C)C(C(C)CCCC(C)C)CCC2C=1C=CC1=C(C)CCC(O)C1 YUGCAAVRZWBXEQ-UHFFFAOYSA-N 0.000 abstract 3
- 229960002535 alfacalcidol Drugs 0.000 abstract 3
- 230000031709 bromination Effects 0.000 abstract 3
- 238000005893 bromination reaction Methods 0.000 abstract 3
- WCXVWNCXXVGIIA-PVYPBFNKSA-N (1s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-1-ol Chemical compound C1C=C2CCC[C@H](O)[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 WCXVWNCXXVGIIA-PVYPBFNKSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 230000000397 acetylating effect Effects 0.000 abstract 2
- 125000000746 allylic group Chemical group 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract 2
- 238000007269 dehydrobromination reaction Methods 0.000 abstract 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- 150000004678 hydrides Chemical class 0.000 abstract 2
- 230000001678 irradiating effect Effects 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 230000005855 radiation Effects 0.000 abstract 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 abstract 2
- WCTZGGUYTPOTQA-LPUHQQPYSA-N (1's,5's,8's,9's,10'r,13'r,14's,17'r)-10',13'-dimethyl-17'-[(2r)-6-methylheptan-2-yl]spiro[1,3-dioxolane-2,6'-1,4,5,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene]-1'-ol Chemical compound C([C@H]1[C@@H]2CC[C@@H]([C@]2(CC[C@@H]1[C@@]1(C)[C@@H](O)C=CC[C@@H]11)C)[C@H](C)CCCC(C)C)C21OCCO2 WCTZGGUYTPOTQA-LPUHQQPYSA-N 0.000 abstract 1
- UXFVRWPSABSGRQ-AFWJMSMISA-N (1s,3r,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-1,3-diol Chemical compound C1C=C2C[C@@H](O)C[C@H](O)[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 UXFVRWPSABSGRQ-AFWJMSMISA-N 0.000 abstract 1
- AQTOMKDXLNYMMP-LPUHQQPYSA-N (1s,5s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]spiro[1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-6,2'-1,3-dioxolane]-1-ol Chemical compound C([C@H]1[C@@H]2CC[C@@H]([C@]2(CC[C@@H]1[C@@]1(C)[C@@H](O)CCC[C@@H]11)C)[C@H](C)CCCC(C)C)C21OCCO2 AQTOMKDXLNYMMP-LPUHQQPYSA-N 0.000 abstract 1
- SFKSZNDXMPANHH-ARILJOLPSA-N (5's,8's,9's,10'r,13'r,14's,17'r)-10',13'-dimethyl-17'-[(2r)-6-methylheptan-2-yl]spiro[1,3-dioxolane-2,6'-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene]-3'-one Chemical compound C([C@H]1[C@@H]2CC[C@@H]([C@]2(CC[C@@H]1[C@@]1(C)CCC(=O)C[C@@H]11)C)[C@H](C)CCCC(C)C)C21OCCO2 SFKSZNDXMPANHH-ARILJOLPSA-N 0.000 abstract 1
- JIQSIDGRMVAOIA-ARILJOLPSA-N (5's,8's,9's,10'r,13'r,14's,17'r)-10',13'-dimethyl-17'-[(2r)-6-methylheptan-2-yl]spiro[1,3-dioxolane-2,6'-5,7,8,9,11,12,14,15,16,17-decahydro-4h-cyclopenta[a]phenanthrene]-3'-one Chemical compound C([C@H]1[C@@H]2CC[C@@H]([C@]2(CC[C@@H]1[C@@]1(C)C=CC(=O)C[C@@H]11)C)[C@H](C)CCCC(C)C)C21OCCO2 JIQSIDGRMVAOIA-ARILJOLPSA-N 0.000 abstract 1
- HTCJGXGLMIWOCW-UHFFFAOYSA-N 1alpha-hydroxycholesterol Natural products C1C=C2CC(O)CC(O)C2(C)C2C1C1CCC(C(C)CCC(=C)C(C)C)C1(C)CC2 HTCJGXGLMIWOCW-UHFFFAOYSA-N 0.000 abstract 1
- PESKGJQREUXSRR-UHFFFAOYSA-N 5beta-cholestanone Natural products C1CC2CC(=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 PESKGJQREUXSRR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- JYNNMAXNSSDBJP-DIVAVJABSA-N [(1s,3r,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-3-(4-methylphenyl)sulfonyloxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl] acetate Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)[C@@H](OC(C)=O)C1)C)[C@H](C)CCCC(C)C)S(=O)(=O)C1=CC=C(C)C=C1 JYNNMAXNSSDBJP-DIVAVJABSA-N 0.000 abstract 1
- -1 acetoxy compound Chemical class 0.000 abstract 1
- GGCLNOIGPMGLDB-GYKMGIIDSA-N cholest-5-en-3-one Chemical compound C1C=C2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 GGCLNOIGPMGLDB-GYKMGIIDSA-N 0.000 abstract 1
- NYOXRYYXRWJDKP-UHFFFAOYSA-N cholestenone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 NYOXRYYXRWJDKP-UHFFFAOYSA-N 0.000 abstract 1
- 235000012000 cholesterol Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J11/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US480211A US3906014A (en) | 1974-06-17 | 1974-06-17 | 3-Deoxy-1{60 -hydroxycholecalciferol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1503941A true GB1503941A (en) | 1978-03-15 |
Family
ID=23907099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17314/75A Expired GB1503941A (en) | 1974-06-17 | 1975-04-25 | Cholecalciferol derivative and process for preparing it |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3906014A (enExample) |
| DE (1) | DE2518843C3 (enExample) |
| FR (1) | FR2274311A1 (enExample) |
| GB (1) | GB1503941A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK261278A (da) * | 1977-06-13 | 1979-12-15 | Merck & Co Inc | Fremgangsmaade til fremstilling af 24-dehydrovitamin d-3-derivater |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3833622A (en) * | 1969-03-17 | 1974-09-03 | Upjohn Co | Crystalline 25-hydroxycholecalciferol hydrate and structurally related compounds |
| US3585221A (en) * | 1969-03-24 | 1971-06-15 | Wisconsin Alumni Res Found | 25-hydroxyergocalciferol |
| US3847955A (en) * | 1973-07-16 | 1974-11-12 | Wisconsin Alumni Res Found | 1,24,25-trihydroxycholecalciferol |
-
1974
- 1974-06-17 US US480211A patent/US3906014A/en not_active Expired - Lifetime
-
1975
- 1975-04-25 GB GB17314/75A patent/GB1503941A/en not_active Expired
- 1975-04-28 DE DE2518843A patent/DE2518843C3/de not_active Expired
- 1975-04-28 FR FR7513244A patent/FR2274311A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2274311B1 (enExample) | 1978-11-17 |
| DE2518843B2 (de) | 1979-02-08 |
| US3906014A (en) | 1975-09-16 |
| DE2518843C3 (de) | 1979-10-11 |
| FR2274311A1 (fr) | 1976-01-09 |
| DE2518843A1 (de) | 1976-01-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |