GB814000A - Steroid compounds and the preparation thereof - Google Patents
Steroid compounds and the preparation thereofInfo
- Publication number
- GB814000A GB814000A GB1694/56A GB169456A GB814000A GB 814000 A GB814000 A GB 814000A GB 1694/56 A GB1694/56 A GB 1694/56A GB 169456 A GB169456 A GB 169456A GB 814000 A GB814000 A GB 814000A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- acid
- hydrocortisone
- hydroxy
- dione
- 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
- -1 Steroid compounds Chemical class 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 12
- 229960000890 hydrocortisone Drugs 0.000 abstract 9
- 150000002148 esters Chemical class 0.000 abstract 8
- DKVSUQWCZQBWCP-QAGGRKNESA-N (8R,9S,10R,13S,14S)-10,13-dimethyl-9,10,11,12,13,14,15,16-octahydro-3H-cyclopenta[alpha]phenanthrene-3,17(8H)-dione Natural products O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C=CC2=C1 DKVSUQWCZQBWCP-QAGGRKNESA-N 0.000 abstract 6
- JYGXADMDTFJGBT-VWUMJDOOSA-N Hydrocortisone Natural products O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 abstract 6
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 abstract 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 abstract 4
- 229960001067 hydrocortisone acetate Drugs 0.000 abstract 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 abstract 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 3
- 229960004719 nandrolone Drugs 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- VRRHHTISESGZFN-RKFFNLMFSA-N 16,17-didehydroprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 VRRHHTISESGZFN-RKFFNLMFSA-N 0.000 abstract 2
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 abstract 2
- 241000186359 Mycobacterium Species 0.000 abstract 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 abstract 2
- 239000001768 carboxy methyl cellulose 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
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract 2
- 238000002347 injection Methods 0.000 abstract 2
- 239000007924 injection Substances 0.000 abstract 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 abstract 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 abstract 2
- 229960002216 methylparaben Drugs 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 abstract 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 2
- 229920000136 polysorbate Polymers 0.000 abstract 2
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 abstract 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 abstract 2
- 229960003415 propylparaben Drugs 0.000 abstract 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 abstract 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 abstract 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 abstract 2
- 239000011780 sodium chloride Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- YEWSFUFGMDJFFG-QAGGRKNESA-N (8r,9s,10r,13s,14s)-10,13-dimethyl-2,8,9,11,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C=CC2=C1 YEWSFUFGMDJFFG-QAGGRKNESA-N 0.000 abstract 1
- QQCBOIWDENXRLP-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 QQCBOIWDENXRLP-BYZMTCBYSA-N 0.000 abstract 1
- BLCAJJQPGLGJDA-DVFHKXEWSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-1,3-dione Chemical compound C1CC2=CC(=O)CC(=O)[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 BLCAJJQPGLGJDA-DVFHKXEWSA-N 0.000 abstract 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 abstract 1
- QRRSHRVKVLSFQS-UHFFFAOYSA-N 1-ethylcyclohexane-1-carboxylic acid Chemical compound CCC1(C(O)=O)CCCCC1 QRRSHRVKVLSFQS-UHFFFAOYSA-N 0.000 abstract 1
- DIZKLZKLNKQFGB-UHFFFAOYSA-N 1-methylcyclopropane-1-carboxylic acid Chemical class OC(=O)C1(C)CC1 DIZKLZKLNKQFGB-UHFFFAOYSA-N 0.000 abstract 1
- WKAVAGKRWFGIEA-UHFFFAOYSA-N 11-Ketoprogesterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2=O WKAVAGKRWFGIEA-UHFFFAOYSA-N 0.000 abstract 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 abstract 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- LCZBQMKVFQNSJR-CZUPSRJTSA-N 21-deoxycortisol Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)C[C@H]2O LCZBQMKVFQNSJR-CZUPSRJTSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 abstract 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- 229920003091 Methocel™ Polymers 0.000 abstract 1
- 241001139337 Mycobacterium lacticola Species 0.000 abstract 1
- 241000187481 Mycobacterium phlei Species 0.000 abstract 1
- 241000187480 Mycobacterium smegmatis Species 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Natural products C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004141 Sodium laurylsulphate Substances 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000001506 calcium phosphate Substances 0.000 abstract 1
- 229910000389 calcium phosphate Inorganic materials 0.000 abstract 1
- 235000011010 calcium phosphates Nutrition 0.000 abstract 1
- 229960000541 cetyl alcohol Drugs 0.000 abstract 1
- 235000012000 cholesterol Nutrition 0.000 abstract 1
- 235000015165 citric acid Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229960004544 cortisone Drugs 0.000 abstract 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 abstract 1
- GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000000796 flavoring agent Substances 0.000 abstract 1
- 235000013355 food flavoring agent Nutrition 0.000 abstract 1
- 235000003599 food sweetener Nutrition 0.000 abstract 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000391 magnesium silicate Substances 0.000 abstract 1
- 235000019359 magnesium stearate Nutrition 0.000 abstract 1
- 229940099273 magnesium trisilicate Drugs 0.000 abstract 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 abstract 1
- 235000019793 magnesium trisilicate Nutrition 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 239000001630 malic acid Substances 0.000 abstract 1
- 235000011090 malic acid Nutrition 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 abstract 1
- 229940100654 ophthalmic suspension Drugs 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 235000019271 petrolatum Nutrition 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 abstract 1
- 229950008882 polysorbate Drugs 0.000 abstract 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 abstract 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 abstract 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 abstract 1
- 229920001592 potato starch Polymers 0.000 abstract 1
- 229960003387 progesterone Drugs 0.000 abstract 1
- 239000000186 progesterone Substances 0.000 abstract 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- 239000003765 sweetening agent Substances 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 229940100615 topical ointment Drugs 0.000 abstract 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 abstract 1
- 239000003871 white petrolatum Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises D 1,4,6-androstatrien-3,17 - dione, D 1,9(11) - Compound S, a 21-ester thereof with a monocarboxylic acid, a 21-acid ester thereof with a polycarboxylic acid, or a salt of such an acid ester, 14-hydroxy- D 1-cortisone, 14 - hydroxy - D 1 - hydrocortisone, 21-esters thereof with a monocarboxylic acid, 21-acid esters thereof with a polycarboxylic acid and salts of said acid esters and a process according to the parent Specification for the preparation of a 3-keto- D 1,4-steroid compound by contacting a 3-keto- D 4-steroid compound with the oxidizing activity of an organism of the genus Mycobacterium, characterized by the fact that the steroid starting material is an 11-oxygenated 3-keto- D 1-steroid compound or one of the following other 3-keto- D 4-steroid compounds: nortestosterone, 17a - hydroxyprogesterone, D 4,6 - androstadien - 3,17 - dione, 16 - dehydroprogesterone and D 9(11) - compound S. As the micro-organism there may be used Mycobacterium species 607, M. berolinense, M. lacticola, M. thamnopheos, M. smegmatis, and M. phlei. Starting compounds mentioned are hydrocortisone, cortisone, D 4-pregnadiene-11b , 21 - diol-3,20 - dione, nortestosterone, 17a -hydroxyprogesterone, 1 - ketoprogesterone, 9a -fluorohydrocortisone, 14a - hydroxy - hydrocortisone, 1 - epihydrocortisone, D 4,6 - andostadien - 3,17 - dione, 11b ,17a - dihydroxyprogesterone, D 14 - dehydro - Compound S, 16-dehydroprogesterone, and D 9,11 - dehydro-Compound S. The 21-hydroxy group may be esterified by means of acetic anhydride or the acid halides of propanoic, butanoic, hexanoic, heptanoic, octanoic, nonanoic, decanoic, o-toluic, benzoic, 1-ethyl cyclohexane carboxylic, cyclohexane carboxylic, 1-methyl cyclopropane carboxylic acids, maleic anhydride, glutaric anhydride, phthalic anhydride, phthaloyl chloride, malic acid, citric acid, tartaric acid, succinic anhydride and pyromellitic acid. The acid esters may be converted to ammonium or alkali metal salts. Examples describe the production of D 1-hydrocortisone, D 1 - cortisone, D 1 - 14a - hydroxy - hydrocortisone, D 1 - 14a - hydroxycortisone, D 1,4 - pregnadiene - 11a ,21 - diol-3,20 - dione D 1 - 9a - fluoro - compound F, D 1,4,6 - androstatriene - 3,17 - dione, D 1 - 11b , 17a - dihydroxyprogesteron, D 1,14 - compound S, D 1 - 19 - nortestosterone, D 1,16 - progesterone, D 1 - 11 - keto - progesterone, D 1,9(11)-compound S, D 1 - 14a ,15a - epoxido - Compound S, D 1 - 14a ,15a - epoxido - Compound F, D 1-hydrocortisone acetate, formate, propionate, phthalate and succinate, &c.ALSO:The invention comprises a therapeutic composition comprising one of the following compounds: D 1-cortisone, D 1-hydrocortisone, 14-hydroxy - D 1 - cortisone, 14 - hydroxy - D 1 - hydrocortisone, D 1,4,6 - androstatriene - 3,17 - dione, D 1,9(11)-compound S, 21-esters thereof with a monocarboxylic acid, 21-acid esters thereof with a polycarboxylic acid, and salts of said acid esters, incorporated with a pharmaceutical carrier, or in the case of a salt of an acid ester, in sterile aqueous solution. Excipients such as starch and milk sugar may be used to prepare tablets for oral administration. Elixirs containing flavouring and sweetening agents may also be used. Solutions for injection are made isotonic with saline or glucose. Examples describe (1) a tablet for oral usage comprising D 1-hydrocortisone, calcium phosphate, milk sugar, potato starch, magnesium stearate, and magnesium trisilicate; (2) a topical ointment comprising D 1-hydrocortisone acetate, sodium lauryl sulphate, propylene glycol, stearyl alcohol, cetyl alcohol, cholesterol, white petrolatum, mineral oil, water, methyl paraben, and propyl paraben; (3) a solution for intra-articular injection comprising D 1-hydrocortisone acetate, sodium chloride, sodium carboxymethylcellulose, methocel, "Tween" (Registered Trade Mark), methyl paraben, propyl paraben and water; (4) an ophthalmic suspension comprising D 1-hydrocortisone acetate, sodium carboxymethylcellulose, polyvinyl pyrrolidone, benzyl alcohol polysorbate and water. In the above compositions the D 1-hydrocortisone may be replaced by D 1-cortisone or the corresponding 14-hydroxy compounds.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US787410XA | 1954-05-21 | 1954-05-21 | |
| US814000XA | 1955-01-24 | 1955-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB814000A true GB814000A (en) | 1959-05-27 |
Family
ID=35229790
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14569/55A Expired GB787410A (en) | 1954-05-21 | 1955-05-20 | Improvements in or relating to steroid compounds and the preparation thereof |
| GB1694/56A Expired GB814000A (en) | 1954-05-21 | 1956-01-18 | Steroid compounds and the preparation thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14569/55A Expired GB787410A (en) | 1954-05-21 | 1955-05-20 | Improvements in or relating to steroid compounds and the preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| GB (2) | GB787410A (en) |
| NL (1) | NL98445C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8207151B2 (en) | 2008-05-28 | 2012-06-26 | Validus Biopharma Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US9198921B2 (en) | 2010-04-05 | 2015-12-01 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US10799514B2 (en) | 2015-06-29 | 2020-10-13 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kappa beta for treatment of disease |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
-
1955
- 1955-05-20 GB GB14569/55A patent/GB787410A/en not_active Expired
-
1956
- 1956-01-18 GB GB1694/56A patent/GB814000A/en not_active Expired
- 1956-01-23 NL NL203850A patent/NL98445C/nl active
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10857161B2 (en) | 2008-05-28 | 2020-12-08 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kB for treatment of disease |
| US8334279B2 (en) | 2008-05-28 | 2012-12-18 | Validus Genetics | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US8673887B2 (en) | 2008-05-28 | 2014-03-18 | Reveragen Biopharma, Inc | Non-hormonal steroid modulators of NF-kB for treatment of disease |
| US8207151B2 (en) | 2008-05-28 | 2012-06-26 | Validus Biopharma Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US9434758B2 (en) | 2008-05-28 | 2016-09-06 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US9649320B2 (en) | 2008-05-28 | 2017-05-16 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US11833159B2 (en) | 2008-05-28 | 2023-12-05 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kB for treatment of disease |
| US10206933B2 (en) | 2008-05-28 | 2019-02-19 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kB for treatment of disease |
| US9198921B2 (en) | 2010-04-05 | 2015-12-01 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US10000525B2 (en) | 2010-04-05 | 2018-06-19 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US10799514B2 (en) | 2015-06-29 | 2020-10-13 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kappa beta for treatment of disease |
| US11690853B2 (en) | 2015-06-29 | 2023-07-04 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κβ for treatment of disease |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
| US11471471B2 (en) | 2019-03-07 | 2022-10-18 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
| US12201639B2 (en) | 2019-03-07 | 2025-01-21 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| GB787410A (en) | 1957-12-11 |
| NL98445C (en) | 1961-07-17 |
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