BE889563A - Steroides doux exercant une activite anti-inflammatoire - Google Patents
Steroides doux exercant une activite anti-inflammatoire Download PDFInfo
- Publication number
- BE889563A BE889563A BE2/59253A BE2059253A BE889563A BE 889563 A BE889563 A BE 889563A BE 2/59253 A BE2/59253 A BE 2/59253A BE 2059253 A BE2059253 A BE 2059253A BE 889563 A BE889563 A BE 889563A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- group
- carbon atoms
- lower alkyl
- alkyl
- Prior art date
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- 230000003110 anti-inflammatory effect Effects 0.000 title claims description 14
- 150000003431 steroids Chemical class 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 132
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
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- 230000003000 nontoxic effect Effects 0.000 claims description 5
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
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- 229910052737 gold Inorganic materials 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 230000008569 process Effects 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000012360 testing method Methods 0.000 description 27
- 230000000875 corresponding effect Effects 0.000 description 23
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound 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 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
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- 239000003153 chemical reaction reagent Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
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- SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 description 8
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
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- 150000003839 salts Chemical class 0.000 description 8
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
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- 238000004061 bleaching Methods 0.000 description 5
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- 238000003379 elimination reaction Methods 0.000 description 5
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 235000019698 starch Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 231100000057 systemic toxicity Toxicity 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 230000003096 thymolvtic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- 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
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J33/002—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16845380A | 1980-07-10 | 1980-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE889563A true BE889563A (fr) | 1981-11-03 |
Family
ID=22611544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE2/59253A BE889563A (fr) | 1980-07-10 | 1981-07-09 | Steroides doux exercant une activite anti-inflammatoire |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5745200A (en(2012)) |
| BE (1) | BE889563A (en(2012)) |
| SU (1) | SU1318169A3 (en(2012)) |
| ZA (1) | ZA814440B (en(2012)) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002088167A1 (en) * | 2001-04-30 | 2002-11-07 | Glaxo Group Limited | Anti-inflammatory 17.beta.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.alpha |
| US7101866B2 (en) | 2000-08-05 | 2006-09-05 | Glaxo Group Limited | Anti-inflammatory androstane derivative |
| US7125985B2 (en) | 2000-08-05 | 2006-10-24 | Glaxo Group Limited | Compounds useful in the manufacture of an anti-inflammatory androstane derivative |
| WO2007099548A3 (en) * | 2006-01-27 | 2008-10-09 | Sun Pharmaceutical Ind Ltd | Novel 11 beta - hydroxyandrosta-4-ene-3-ones |
| US7541350B2 (en) | 2000-08-05 | 2009-06-02 | Glaxo Group Limited | Formulation containing anti-inflammatory androstane derivative |
| US7592329B2 (en) | 2002-02-04 | 2009-09-22 | Glaxo Group Limited | Crystalline complexes of fluticasone-2-furoate |
| US8163723B2 (en) | 2002-06-14 | 2012-04-24 | Cipla Limited | Combination of azelastine and steroids |
| WO2018232007A1 (en) | 2017-06-13 | 2018-12-20 | Bodor Laboratories, Inc. | Potent soft anti-inflammatory corticosteroid compounds and uses therof |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4607028A (en) * | 1983-08-18 | 1986-08-19 | Ciba-Geigy Corporation | Novel carboxylic acid esters |
| IL78144A0 (en) * | 1985-04-04 | 1986-07-31 | Draco Ab | Novel androstane-17beta-carboxylic acid esters |
| SE8501693D0 (sv) * | 1985-04-04 | 1985-04-04 | Draco Ab | Novel 16,17-acetalsubstituted androstane-17beta-carboxylic acid esters |
| DE19947235A1 (de) * | 1999-09-30 | 2001-04-05 | Asta Medica Ag | Neue Kombination von Loteprednol und beta¶2¶-Adrenorezeptor-Agonisten |
| CN1838960A (zh) * | 2003-06-19 | 2006-09-27 | 尼古拉斯·S·博多尔 | 局部应用的温和抗炎类固醇的活性和/或作用时间的增强 |
| GB0523251D0 (en) * | 2005-11-15 | 2005-12-21 | Glaxo Group Ltd | Novel compounds |
| US7687484B2 (en) * | 2006-05-25 | 2010-03-30 | Bodor Nicholas S | Transporter enhanced corticosteroid activity |
-
1981
- 1981-06-30 ZA ZA814440A patent/ZA814440B/xx unknown
- 1981-07-09 SU SU813306552A patent/SU1318169A3/ru active
- 1981-07-09 BE BE2/59253A patent/BE889563A/fr not_active IP Right Cessation
- 1981-07-10 JP JP56108755A patent/JPS5745200A/ja active Granted
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7498321B2 (en) | 2000-08-05 | 2009-03-03 | Glaxo Group Limited | 17β-carbothioate 17α-arylcarbonyloxyloxy androstane derivative as anti-inflammatory agents |
| US7101866B2 (en) | 2000-08-05 | 2006-09-05 | Glaxo Group Limited | Anti-inflammatory androstane derivative |
| US7125985B2 (en) | 2000-08-05 | 2006-10-24 | Glaxo Group Limited | Compounds useful in the manufacture of an anti-inflammatory androstane derivative |
| US7144845B2 (en) | 2000-08-05 | 2006-12-05 | Glaxo Group Limited | Compounds useful in the manufacture of an anti-inflammatory androstane derivative |
| US7629335B2 (en) | 2000-08-05 | 2009-12-08 | Glaxo Group Limited | Anti-inflammatory androstane derivative |
| US7541350B2 (en) | 2000-08-05 | 2009-06-02 | Glaxo Group Limited | Formulation containing anti-inflammatory androstane derivative |
| US7531528B2 (en) | 2000-08-05 | 2009-05-12 | Glaxo Group Limited | Formulation containing anti-inflammatory androstane derivatives |
| US7291608B2 (en) | 2001-04-30 | 2007-11-06 | Glaxo Group Limited | Anti-inflammatory 17.β.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.α |
| CN1302007C (zh) * | 2001-04-30 | 2007-02-28 | 葛兰素集团有限公司 | 具有抗炎性的在17.α位上具有环酯基的雄甾烷的17.β.－硫代羧酸酯衍生物 |
| KR100831534B1 (ko) * | 2001-04-30 | 2008-05-22 | 글락소 그룹 리미티드 | 17.알파 위치에 시클릭 에스테르기를 지닌 항염증성의안드로스탄의 17.베타.-카르보티오에이트 에스테르 유도체 |
| WO2002088167A1 (en) * | 2001-04-30 | 2002-11-07 | Glaxo Group Limited | Anti-inflammatory 17.beta.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.alpha |
| US7592329B2 (en) | 2002-02-04 | 2009-09-22 | Glaxo Group Limited | Crystalline complexes of fluticasone-2-furoate |
| US8168620B2 (en) | 2002-06-14 | 2012-05-01 | Cipla Limited | Combination of azelastine and steroids |
| US8163723B2 (en) | 2002-06-14 | 2012-04-24 | Cipla Limited | Combination of azelastine and steroids |
| US8304405B2 (en) | 2002-06-14 | 2012-11-06 | Cipla Limited | Combination of azelastine and ciclesonide for nasal administration |
| US8318709B2 (en) | 2002-06-14 | 2012-11-27 | Cipla Limited | Combination of azelastine and mometasone for nasal administration |
| US9901585B2 (en) | 2002-06-14 | 2018-02-27 | Cipla Limited | Combination of azelastine and fluticasone for nasal administration |
| WO2007099548A3 (en) * | 2006-01-27 | 2008-10-09 | Sun Pharmaceutical Ind Ltd | Novel 11 beta - hydroxyandrosta-4-ene-3-ones |
| AP2642A (en) * | 2006-01-27 | 2013-04-15 | Sun Pharma Advanced Res Co Ltd | Novel 11 beta-hydroxyandrosta-4-ene-3-ones |
| WO2018232007A1 (en) | 2017-06-13 | 2018-12-20 | Bodor Laboratories, Inc. | Potent soft anti-inflammatory corticosteroid compounds and uses therof |
| US11447522B2 (en) | 2017-06-13 | 2022-09-20 | Bodor Laboratories, Inc. | Potent soft anti-inflammatory corticosteroid compounds and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA814440B (en) | 1982-10-27 |
| JPS5745200A (en) | 1982-03-13 |
| SU1318169A3 (ru) | 1987-06-15 |
| JPS6411037B2 (en(2012)) | 1989-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE20 | Patent expired |
Owner name: BODOR NICHOLAS STEPHEN Effective date: 20010709 |