GB952085A - 16-methylene-steroids and processes for the manufacture thereof - Google Patents
16-methylene-steroids and processes for the manufacture thereofInfo
- Publication number
- GB952085A GB952085A GB32677/60A GB3267760A GB952085A GB 952085 A GB952085 A GB 952085A GB 32677/60 A GB32677/60 A GB 32677/60A GB 3267760 A GB3267760 A GB 3267760A GB 952085 A GB952085 A GB 952085A
- Authority
- GB
- United Kingdom
- Prior art keywords
- steroid
- treating
- hydroxy
- compound
- acid
- 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 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 abstract 5
- 150000003431 steroids Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 230000018044 dehydration Effects 0.000 abstract 3
- 238000006297 dehydration reaction Methods 0.000 abstract 3
- 238000005805 hydroxylation reaction Methods 0.000 abstract 3
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 abstract 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 3
- 244000005700 microbiome Species 0.000 abstract 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 abstract 1
- 241000228212 Aspergillus Species 0.000 abstract 1
- 241000193830 Bacillus <bacterium> Species 0.000 abstract 1
- 241000223208 Curvularia Species 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 241000223218 Fusarium Species 0.000 abstract 1
- 241000193386 Lysinibacillus sphaericus Species 0.000 abstract 1
- 241000235395 Mucor Species 0.000 abstract 1
- 241000235388 Mucorales Species 0.000 abstract 1
- 238000006036 Oppenauer oxidation reaction Methods 0.000 abstract 1
- 241000228143 Penicillium Species 0.000 abstract 1
- 241000203720 Pimelobacter simplex Species 0.000 abstract 1
- 241000235527 Rhizopus Species 0.000 abstract 1
- 241000187747 Streptomyces Species 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 229910052731 fluorine Chemical group 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 230000002906 microbiologic effect Effects 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229960003387 progesterone Drugs 0.000 abstract 1
- 239000000186 progesterone Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 230000001225 therapeutic 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
Classifications
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM42831A DE1130805B (de) | 1959-09-23 | 1959-09-23 | Verfahren zur Herstellung von 16-Methylen-steroiden |
| DEM44703A DE1156804B (de) | 1960-03-18 | 1960-03-18 | Verfahren zur Herstellung von 16-Methylen-steroiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB952085A true GB952085A (en) | 1964-03-11 |
Family
ID=25986910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32677/60A Expired GB952085A (en) | 1959-09-23 | 1960-09-22 | 16-methylene-steroids and processes for the manufacture thereof |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH432516A (enrdf_load_stackoverflow) |
| DK (1) | DK107290C (enrdf_load_stackoverflow) |
| FR (1) | FR676M (enrdf_load_stackoverflow) |
| GB (1) | GB952085A (enrdf_load_stackoverflow) |
-
1960
- 1960-08-10 CH CH1780465A patent/CH432516A/de unknown
- 1960-08-10 CH CH903360A patent/CH417583A/de unknown
- 1960-09-22 GB GB32677/60A patent/GB952085A/en not_active Expired
- 1960-09-22 FR FR839249A patent/FR676M/fr active Active
- 1960-09-23 DK DK375560AA patent/DK107290C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| FR676M (enrdf_load_stackoverflow) | 1961-07-17 |
| DK107290C (da) | 1967-05-16 |
| CH432516A (de) | 1967-03-31 |
| CH417583A (de) | 1966-07-31 |
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