GB898295A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB898295A GB898295A GB2909561A GB2909561A GB898295A GB 898295 A GB898295 A GB 898295A GB 2909561 A GB2909561 A GB 2909561A GB 2909561 A GB2909561 A GB 2909561A GB 898295 A GB898295 A GB 898295A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- hydroxy
- compound
- ketoprogesterone
- hydroxymethylene
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 3
- 229910052801 chlorine Chemical group 0.000 abstract 3
- 239000000460 chlorine Chemical group 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 239000011737 fluorine Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- -1 alkylene glycol Chemical compound 0.000 abstract 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 abstract 2
- XMRPGKVKISIQBV-UHFFFAOYSA-N (+-)-5- Pregnane-3,20-dione Natural products C1CC2CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2 XMRPGKVKISIQBV-UHFFFAOYSA-N 0.000 abstract 1
- HQIUNJOUAMNVLX-AQCKJBIYSA-N (6S,8S,9S,10R,11S,13S,14S,16S)-11-hydroxy-17-(2-hydroxyethylidene)-6,10,13,16-tetramethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one Chemical compound C[C@H]1C[C@H]2[C@@H]3C[C@@H](C(=CCO)[C@]3(C[C@@H]([C@@H]2[C@]2(CCC(C=C12)=O)C)O)C)C HQIUNJOUAMNVLX-AQCKJBIYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 229930193140 Neomycin Natural products 0.000 abstract 1
- YJQPYGGHQPGBLI-UHFFFAOYSA-N Novobiocin Natural products O1C(C)(C)C(OC)C(OC(N)=O)C(O)C1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-UHFFFAOYSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- 239000004133 Sodium thiosulphate Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001911 anti-progestational effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 229960005091 chloramphenicol Drugs 0.000 abstract 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 229960004927 neomycin Drugs 0.000 abstract 1
- 229960002950 novobiocin Drugs 0.000 abstract 1
- YJQPYGGHQPGBLI-KGSXXDOSSA-N novobiocin Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-N 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 abstract 1
- 235000019345 sodium thiosulphate Nutrition 0.000 abstract 1
- 239000000725 suspension Substances 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
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises compounds represented by the formulae <FORM:0898295/IV (b)/1> wherein X is hydrogen, fluorine or chlorine and Y is b -hydroxymethylene or carbonyl, process for the preparation of 6a , 16b -dimethyl-11-ketoprogesterone by (1) diketalising 11a -hydroxy-16b -methylprogesterone with a lower alkylene glycol; (2) epoxidising the 5(6)-double bond of the thus produced diketal with a peracid to produce a 5a , 6a -epoxide; (3) reacting the thus produced compound with a methyl Grignard reagent to produce a 5a -hydroxy-6b -methyl compound; (4) hydrolysing the ketal groups with acid to give 5a , 11a - dihydroxy - 6b , 16b - dimethylallo - pregnane-3,20-dione; (5) oxidising the 11-hydroxy group to an 11-keto group with an oxidising agent; and (6) dehydrating the 5a -hydroxy group, to produce 6a , 16b -dimethyl-11-ketoprogesterone; and a process for the preparation of a compound having the formula <FORM:0898295/IV (b)/2> wherein the dotted line in the 1,2-position represents an optional single bond, X is hydrogen, chlorine or fluorine and Y is carbonyl or b -hydroxymethylene by subjecting a compound having the formula <FORM:0898295/IV (b)/3> wherein the dotted line, X and Y are as defined above to reduction by known methods for the removal of iodine, e.g. with sodium thiosulphate. 3, 11 - Diketo - 6a , 16b - dimethyl - 4, 17 (20) - pregnadien-21-oic acid alkyl ester is obtained by diglyoxalating, trihalogenating, rearranging and dehydrating either 6a , 16b - dimethyl - 11 - ketoprogesterone or 5a -hydroxy-6b ,16b -dimethylallopregnane-3,11,20-trione. By protecting the 3-keto group, e.g. by forming a 3-enamine, the 21-carboxylic acid ester group may be reduced with lithium aluminium hydride to obtain 6a ,16b -dimethyl - 11b , 21 - dihydroxy - 4, 17 (20) - pregnadien-3-one into which a D 1-double bond may be introduced either microbiologically or with selenium dioxide. Specifications 749,195, 761,490, 761,527, 761,528, 779,001 and 779,002 also are referred to.ALSO:Pharmaceutical compositions having anti-inflammatory and progestational activity comprise compounds having the formulae <FORM:0898295/VI/1> wherein X is hydrogen, fluorine or chlorine, and Y is b -hydroxymethylene or carbonyl, antibiotics e.g. penicillin, neomycin, chloramphenicol and novobiocin, and a pharmaceutical carrier. They are administered orally, intramuscularly or topically in tablets, sterile suspensions and ointments. Specifications 749,195, 761,490, 761,527, 761,528, 779,001 and 779,002 also are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80009159A | 1959-03-18 | 1959-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB898295A true GB898295A (en) | 1962-06-06 |
Family
ID=25177459
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB892260A Expired GB898291A (en) | 1959-03-18 | 1960-03-14 | Improvements in or relating to steroids and the manufacture thereof |
| GB2909561A Expired GB898295A (en) | 1959-03-18 | 1960-03-14 | Improvements in or relating to steroids and the manufacture thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB892260A Expired GB898291A (en) | 1959-03-18 | 1960-03-14 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (2)
| Country | Link |
|---|---|
| CH (3) | CH396896A (en) |
| GB (2) | GB898291A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10711032B2 (en) | 2016-11-08 | 2020-07-14 | Regeneron Pharmaceuticals, Inc. | Steroids and protein-conjugates thereof |
| US11377502B2 (en) | 2018-05-09 | 2022-07-05 | Regeneron Pharmaceuticals, Inc. | Anti-MSR1 antibodies and methods of use thereof |
| US11491237B2 (en) | 2017-05-18 | 2022-11-08 | Regeneron Pharmaceuticals, Inc. | Cyclodextrin protein drug conjugates |
| US12070506B2 (en) | 2018-01-08 | 2024-08-27 | Regeneron Pharmaceuticals, Inc. | Steroids and antibody-conjugates thereof |
| US12134631B2 (en) | 2017-11-07 | 2024-11-05 | Regeneron Pharmaceuticals, Inc. | Hydrophilic linkers for antibody drug conjugates |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3227312A1 (en) * | 1982-07-19 | 1984-01-19 | Schering AG, 1000 Berlin und 4709 Bergkamen | NEW 6.16 DIMETHYL CORTICOIDS, THEIR PRODUCTION AND USE |
-
1960
- 1960-03-14 GB GB892260A patent/GB898291A/en not_active Expired
- 1960-03-14 GB GB2909561A patent/GB898295A/en not_active Expired
- 1960-03-15 CH CH230465A patent/CH396896A/en unknown
- 1960-03-15 CH CH230365A patent/CH396895A/en unknown
- 1960-03-15 CH CH291360A patent/CH397665A/en unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10711032B2 (en) | 2016-11-08 | 2020-07-14 | Regeneron Pharmaceuticals, Inc. | Steroids and protein-conjugates thereof |
| US11760775B2 (en) | 2016-11-08 | 2023-09-19 | Regeneron Pharmaceuticals, Inc. | Steroids and protein-conjugates thereof |
| US12377159B2 (en) | 2016-11-08 | 2025-08-05 | Regeneron Pharmaceuticals, Inc. | Steroids and protein-conjugates thereof |
| US11491237B2 (en) | 2017-05-18 | 2022-11-08 | Regeneron Pharmaceuticals, Inc. | Cyclodextrin protein drug conjugates |
| US12134631B2 (en) | 2017-11-07 | 2024-11-05 | Regeneron Pharmaceuticals, Inc. | Hydrophilic linkers for antibody drug conjugates |
| US12070506B2 (en) | 2018-01-08 | 2024-08-27 | Regeneron Pharmaceuticals, Inc. | Steroids and antibody-conjugates thereof |
| US11377502B2 (en) | 2018-05-09 | 2022-07-05 | Regeneron Pharmaceuticals, Inc. | Anti-MSR1 antibodies and methods of use thereof |
| US12497460B2 (en) | 2018-05-09 | 2025-12-16 | Regeneron Pharmaceuticals, Inc. | Anti-MSR1 antibodies and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| GB898291A (en) | 1962-06-06 |
| CH397665A (en) | 1965-08-31 |
| CH396896A (en) | 1965-08-15 |
| CH396895A (en) | 1965-08-15 |
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