FR2475048A1 - 17a-acyloxy-5b-corticoides et 17a-acyloxy-5a-corticoides, leur preparation et leur utilisation - Google Patents
17a-acyloxy-5b-corticoides et 17a-acyloxy-5a-corticoides, leur preparation et leur utilisation Download PDFInfo
- Publication number
- FR2475048A1 FR2475048A1 FR8101828A FR8101828A FR2475048A1 FR 2475048 A1 FR2475048 A1 FR 2475048A1 FR 8101828 A FR8101828 A FR 8101828A FR 8101828 A FR8101828 A FR 8101828A FR 2475048 A1 FR2475048 A1 FR 2475048A1
- Authority
- FR
- France
- Prior art keywords
- dione
- methyl
- pregnane
- fluoro
- dihydroxy
- 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.)
- Granted
Links
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- 238000000034 method Methods 0.000 claims description 92
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- 150000003431 steroids Chemical class 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- -1 p-carboxyphenyl Chemical group 0.000 claims description 34
- XMRPGKVKISIQBV-BJMCWZGWSA-N 5alpha-pregnane-3,20-dione Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 XMRPGKVKISIQBV-BJMCWZGWSA-N 0.000 claims description 29
- 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 claims description 27
- 229910052801 chlorine Chemical group 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 238000005984 hydrogenation reaction Methods 0.000 claims description 22
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- 239000011737 fluorine Chemical group 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 230000000903 blocking effect Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
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- 125000004429 atom Chemical group 0.000 claims description 2
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- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical class [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 210000000613 ear canal Anatomy 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940079360 enema for constipation Drugs 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000001969 hypertrophic effect Effects 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 210000001117 keloid Anatomy 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 201000011486 lichen planus Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229960002509 miconazole Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- LCXMRSLFWMMCAS-WRJHFWDFSA-N pregna-4,9(11)-diene-3,20-dione Chemical compound O=C1CC[C@]2(C)C3=CC[C@]4(C)[C@@H](C(=O)C)CC[C@H]4[C@@H]3CCC2=C1 LCXMRSLFWMMCAS-WRJHFWDFSA-N 0.000 description 1
- JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane group Chemical group [C@@H]12CC[C@H](CC)[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical class [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- C07J5/0046—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 substituted in position 17 alfa
- C07J5/0053—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 substituted in position 17 alfa not substituted in position 16
-
- 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
- C07J5/0046—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 substituted in position 17 alfa
- C07J5/0061—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 substituted in position 17 alfa substituted in position 16
- C07J5/0069—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
- C07J5/0076—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- 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
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
-
- 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
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16
- C07J7/0055—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
-
- 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
- C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
- C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom
-
- 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
- C07J71/0015—Oxiranes at position 9(11)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/117,401 US4318853A (en) | 1980-01-31 | 1980-01-31 | 9β,11β-Epoxy-5β-corticoids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2475048A1 true FR2475048A1 (fr) | 1981-08-07 |
| FR2475048B1 FR2475048B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-11-16 |
Family
ID=22372732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8101828A Granted FR2475048A1 (fr) | 1980-01-31 | 1981-01-30 | 17a-acyloxy-5b-corticoides et 17a-acyloxy-5a-corticoides, leur preparation et leur utilisation |
Country Status (18)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0665238A1 (en) * | 1994-01-28 | 1995-08-02 | Senju Pharmaceutical Co., Ltd. | Corticoid derivatives and pharmaceutical and cosmetic compositions |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3243482A1 (de) * | 1982-11-22 | 1984-05-24 | Schering AG, 1000 Berlin und 4709 Bergkamen | Neue 6(alpha)-methylkortikoide, ihre herstellung und verwendung |
| EP0221705A1 (en) * | 1985-10-23 | 1987-05-13 | The Upjohn Company | Tetrahydro angiostatic steroids |
| NL8900507A (nl) * | 1989-03-02 | 1990-10-01 | Philips Nv | Versterkerschakeling met verzadigingsdetectie. |
| GB2302807A (en) * | 1995-07-04 | 1997-02-05 | Surtech Int Ltd | Method and composition for treating atopic eczema |
| DE19737348C2 (de) * | 1997-08-27 | 2002-07-25 | Dan-Gabriel Vulpescu | Neue Clindamycin und Clotrimazol enthaltende pharmazeutische Zusammensetzung |
| ITMI20071616A1 (it) | 2007-08-03 | 2009-02-04 | Cosmo Spa | Processo enzimatico per l'ottenimento di 17-alfa monoesteri del cortexolone e/o suoi 9,11-deidroderivati. |
| NZ603107A (en) | 2008-05-28 | 2014-03-28 | Validus Biopharma Inc | Non-hormonal steroid modulators of nf-kb for treatment of disease |
| WO2011127048A2 (en) | 2010-04-05 | 2011-10-13 | Validus Biopharma | NON-HORMONAL STEROID MODULATORS OF NF-ĸB FOR TREATMENT OF DISEASE |
| CN102225959B (zh) * | 2011-04-29 | 2012-11-07 | 中国科学院上海有机化学研究所 | 一种16β-甲基-17α-羟基孕甾-3,20-二酮化合物及其合成方法 |
| WO2017004205A1 (en) | 2015-06-29 | 2017-01-05 | Reveragen Biopharma, Inc. | NON-HORMONAL STEROID MODULATORS OF NF-κB FOR TREATMENT OF DISEASE |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831874A (en) * | 1954-04-20 | 1958-04-22 | Gnrd Patent Holdings Ltd | Improvements in the preparation of 17:21-diacyloxy-2:4-dibromo-3:11:20-triketoallopregnanes |
| US2854465A (en) * | 1955-02-18 | 1958-09-30 | Ciba Pharm Prod Inc | Process for the manufacture of halogen-pregnanes and dehalogenation products thereof |
| US3152154A (en) * | 1961-06-24 | 1964-10-06 | Vismara Francesco Spa | 17-monoesters of 17alpha, 21-dihydroxy steroids and process for the preparation thereof |
| US3681410A (en) * | 1970-08-07 | 1972-08-01 | Syntex Corp | Process for preparing 17{60 -hydroxy-20-keto and 17{60 ,21-dihydroxy-20-keto pregnanes and derivatives and intermediates thereof |
-
1980
- 1980-01-31 US US06/117,401 patent/US4318853A/en not_active Expired - Lifetime
-
1981
- 1981-01-02 ZA ZA00810018A patent/ZA8118B/xx unknown
- 1981-01-16 GB GB8101407A patent/GB2070016B/en not_active Expired
- 1981-01-16 CA CA000368713A patent/CA1155108A/en not_active Expired
- 1981-01-21 AU AU66513/81A patent/AU538883B2/en not_active Ceased
- 1981-01-24 PH PH25134A patent/PH16525A/en unknown
- 1981-01-26 GR GR63960A patent/GR73511B/el unknown
- 1981-01-26 DE DE3102397A patent/DE3102397A1/de not_active Withdrawn
- 1981-01-27 IT IT19360/81A patent/IT1193576B/it active
- 1981-01-28 SE SE8100563A patent/SE8100563L/ not_active Application Discontinuation
- 1981-01-29 ES ES498938A patent/ES498938A0/es active Granted
- 1981-01-29 DK DK39281A patent/DK39281A/da not_active Application Discontinuation
- 1981-01-30 CH CH62681A patent/CH644614A5/de not_active IP Right Cessation
- 1981-01-30 JP JP1178381A patent/JPS56122398A/ja active Pending
- 1981-01-30 FR FR8101828A patent/FR2475048A1/fr active Granted
- 1981-01-30 NL NL8100467A patent/NL8100467A/nl not_active Application Discontinuation
- 1981-01-30 KR KR1019810000285A patent/KR850001208B1/ko not_active Expired
- 1981-01-30 BE BE0/203661A patent/BE887323A/fr not_active IP Right Cessation
-
1983
- 1983-06-21 PH PH29092A patent/PH19579A/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831874A (en) * | 1954-04-20 | 1958-04-22 | Gnrd Patent Holdings Ltd | Improvements in the preparation of 17:21-diacyloxy-2:4-dibromo-3:11:20-triketoallopregnanes |
| US2854465A (en) * | 1955-02-18 | 1958-09-30 | Ciba Pharm Prod Inc | Process for the manufacture of halogen-pregnanes and dehalogenation products thereof |
| US3152154A (en) * | 1961-06-24 | 1964-10-06 | Vismara Francesco Spa | 17-monoesters of 17alpha, 21-dihydroxy steroids and process for the preparation thereof |
| US3681410A (en) * | 1970-08-07 | 1972-08-01 | Syntex Corp | Process for preparing 17{60 -hydroxy-20-keto and 17{60 ,21-dihydroxy-20-keto pregnanes and derivatives and intermediates thereof |
Non-Patent Citations (4)
| Title |
|---|
| CA1967-1971 * |
| CA1971 * |
| EXBK/56 * |
| EXBK/79 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0665238A1 (en) * | 1994-01-28 | 1995-08-02 | Senju Pharmaceutical Co., Ltd. | Corticoid derivatives and pharmaceutical and cosmetic compositions |
| US5776922A (en) * | 1994-01-28 | 1998-07-07 | Senju Pharmaceutical Co., Ltd. | Corticoid derivatives and pharmaceutical and cosmetic compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2070016A (en) | 1981-09-03 |
| JPS56122398A (en) | 1981-09-25 |
| PH19579A (en) | 1986-05-26 |
| KR850001208B1 (ko) | 1985-08-20 |
| KR830005263A (ko) | 1983-08-03 |
| ES8300342A1 (es) | 1982-11-01 |
| GB2070016B (en) | 1983-09-14 |
| PH16525A (en) | 1983-11-10 |
| CA1155108A (en) | 1983-10-11 |
| AU6651381A (en) | 1981-08-06 |
| FR2475048B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-11-16 |
| CH644614A5 (de) | 1984-08-15 |
| IT1193576B (it) | 1988-07-08 |
| SE8100563L (sv) | 1981-08-01 |
| ZA8118B (en) | 1982-01-27 |
| GR73511B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-03-07 |
| US4318853A (en) | 1982-03-09 |
| NL8100467A (nl) | 1981-09-01 |
| DE3102397A1 (de) | 1981-12-24 |
| IT8119360A0 (it) | 1981-01-27 |
| ES498938A0 (es) | 1982-11-01 |
| AU538883B2 (en) | 1984-08-30 |
| BE887323A (fr) | 1981-07-30 |
| DK39281A (da) | 1981-08-01 |
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