GB994746A - 6ª‰:19-oxido-steroids and their oxidation products and process for their manufacture - Google Patents
6ª‰:19-oxido-steroids and their oxidation products and process for their manufactureInfo
- Publication number
- GB994746A GB994746A GB2589461A GB2589461A GB994746A GB 994746 A GB994746 A GB 994746A GB 2589461 A GB2589461 A GB 2589461A GB 2589461 A GB2589461 A GB 2589461A GB 994746 A GB994746 A GB 994746A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- groups
- steroid
- oxo
- oxido
- 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
- 238000000034 method Methods 0.000 title abstract 6
- 230000003647 oxidation Effects 0.000 title abstract 2
- 238000007254 oxidation reaction Methods 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 4
- 229910052740 iodine Inorganic materials 0.000 abstract 4
- 239000011630 iodine Substances 0.000 abstract 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- -1 cyanogen halides Chemical class 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002596 lactones Chemical class 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- INLFWQCRAJUDCR-LYLBMTSKSA-N spirostane Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 INLFWQCRAJUDCR-LYLBMTSKSA-N 0.000 abstract 2
- XIIAYQZJNBULGD-UHFFFAOYSA-N (5alpha)-cholestane Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XIIAYQZJNBULGD-UHFFFAOYSA-N 0.000 abstract 1
- YJDYCULVYZDESB-HQEMIIEJSA-N (8r,9s,10s,13s,14s)-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC21 YJDYCULVYZDESB-HQEMIIEJSA-N 0.000 abstract 1
- MSATYYBKPKURGO-DTDSOPBBSA-N 1-[(3R,5R,6R,8S,9S,10R,13S,14S,17S)-3,5,6-trihydroxy-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone Chemical compound O[C@H]1C[C@@]2([C@@H](C[C@H]3[C@@H]4CC[C@H](C(C)=O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C)O)O MSATYYBKPKURGO-DTDSOPBBSA-N 0.000 abstract 1
- GKBHKNPLNHLYHT-UHFFFAOYSA-N 5beta-Stigmastan Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 GKBHKNPLNHLYHT-UHFFFAOYSA-N 0.000 abstract 1
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 abstract 1
- QSHQKIURKJITMZ-OBUPQJQESA-N 5β-cholane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCC)[C@@]2(C)CC1 QSHQKIURKJITMZ-OBUPQJQESA-N 0.000 abstract 1
- JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 abstract 1
- WBEMLZMQSQWKQW-ROSJKRMUSA-N [(3S,6R,8R,9S,10R,13S,14S,17R)-17-acetyloxy-6-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)O[C@@H]1CC2[C@@H](C[C@H]3[C@@H]4CC[C@H]([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)OC(C)=O)O WBEMLZMQSQWKQW-ROSJKRMUSA-N 0.000 abstract 1
- OFPZQZUIEASWRB-KICKRKHOSA-N [(3S,8R,9S,10R,13S,14S,17R)-17-acetyloxy-10,13-dimethyl-6-oxo-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)O[C@@H]1CC2C(C[C@H]3[C@@H]4CC[C@H]([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)OC(C)=O)=O OFPZQZUIEASWRB-KICKRKHOSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 150000001737 cardanolides Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 abstract 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 238000007269 dehydrobromination reaction Methods 0.000 abstract 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 abstract 1
- 150000002249 furostenes Chemical class 0.000 abstract 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 125000000686 lactone group Chemical group 0.000 abstract 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 abstract 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 abstract 1
- 239000012454 non-polar solvent Substances 0.000 abstract 1
- 125000000369 oxido group Chemical group [*]=O 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 229910001927 ruthenium tetroxide Inorganic materials 0.000 abstract 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 abstract 1
- 229940071536 silver acetate Drugs 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- GKBHKNPLNHLYHT-LWQAOISPSA-N stigmastane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 GKBHKNPLNHLYHT-LWQAOISPSA-N 0.000 abstract 1
- LAGFCVRVICMFFF-UHFFFAOYSA-N stigmastane Natural products CCC(CCC(C)C1CCC2C3CCC4CC(=O)CC(C)C4C3CCC12C)C(C)C LAGFCVRVICMFFF-UHFFFAOYSA-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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- 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)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH813360A CH412874A (de) | 1960-07-15 | 1960-07-15 | Verfahren zur Herstellung neuer 6B,19-Oxido-steroide |
| CH1210760A CH454840A (de) | 1960-10-28 | 1960-10-28 | Verfahren zur Herstellung von Steroid-19-säuren |
| CH1439360A CH451925A (de) | 1960-12-23 | 1960-12-23 | Verfahren zur Herstellung von 19-Hydroxy-steroiden |
| CH398961 | 1961-04-05 | ||
| CH647961 | 1961-06-02 | ||
| CH689561 | 1961-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB994746A true GB994746A (en) | 1965-06-10 |
Family
ID=27543727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2589461A Expired GB994746A (en) | 1960-07-15 | 1961-07-17 | 6ª‰:19-oxido-steroids and their oxidation products and process for their manufacture |
Country Status (3)
| Country | Link |
|---|---|
| DK (1) | DK105644C (cs) |
| GB (1) | GB994746A (cs) |
| SE (1) | SE310671B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3515719A (en) * | 1967-03-15 | 1970-06-02 | Upjohn Co | 7-methyl-6,19-epoxy steroids of the androstane series |
-
1961
- 1961-07-13 SE SE728661A patent/SE310671B/xx unknown
- 1961-07-14 DK DK290961A patent/DK105644C/da active
- 1961-07-17 GB GB2589461A patent/GB994746A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3515719A (en) * | 1967-03-15 | 1970-06-02 | Upjohn Co | 7-methyl-6,19-epoxy steroids of the androstane series |
Also Published As
| Publication number | Publication date |
|---|---|
| SE310671B (cs) | 1969-05-12 |
| DK105644C (da) | 1966-10-24 |
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