NL192343C - 17Ó-gesubstitueerde androsta-(1,)4-(di)een-3-on-17ß-carbonzuurverbindingen met een ontstekingswerende werkzaamheid en farmaceutische preparaten, die deze verbindingen bevatten. - Google Patents
17Ó-gesubstitueerde androsta-(1,)4-(di)een-3-on-17ß-carbonzuurverbindingen met een ontstekingswerende werkzaamheid en farmaceutische preparaten, die deze verbindingen bevatten. Download PDFInfo
- Publication number
- NL192343C NL192343C NL8103315A NL8103315A NL192343C NL 192343 C NL192343 C NL 192343C NL 8103315 A NL8103315 A NL 8103315A NL 8103315 A NL8103315 A NL 8103315A NL 192343 C NL192343 C NL 192343C
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- Netherlands
- Prior art keywords
- formula
- hydroxy
- carboxylate
- chloromethyl
- compound
- Prior art date
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- 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 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic 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
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 231100001038 reduction in thymus weight Toxicity 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940096017 silver fluoride Drugs 0.000 description 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000024891 symptom Diseases 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000021195 test diet Nutrition 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000002992 thymic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 201000009482 yaws Diseases 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16845380A | 1980-07-10 | 1980-07-10 | |
| US16845380 | 1980-07-10 | ||
| US26578581A | 1981-05-21 | 1981-05-21 | |
| US26578581 | 1981-05-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL8103315A NL8103315A (nl) | 1982-02-01 |
| NL192343B NL192343B (nl) | 1997-02-03 |
| NL192343C true NL192343C (nl) | 1997-06-04 |
Family
ID=26864131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8103315A NL192343C (nl) | 1980-07-10 | 1981-07-10 | 17Ó-gesubstitueerde androsta-(1,)4-(di)een-3-on-17ß-carbonzuurverbindingen met een ontstekingswerende werkzaamheid en farmaceutische preparaten, die deze verbindingen bevatten. |
Country Status (17)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2137206B (en) * | 1980-02-15 | 1985-04-03 | Glaxo Group Ltd | Androstane 17-carbothioc acid derivatives |
| JPS6041607A (ja) * | 1983-08-12 | 1985-03-05 | Otsuka Pharmaceut Co Ltd | 軟膏基剤 |
| 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 |
| WO1989003390A1 (en) * | 1987-10-13 | 1989-04-20 | Bodor Nicholas S | Soft steroids having anti-inflammatory activity |
| DE4025342A1 (de) * | 1990-08-10 | 1992-02-13 | Hoechst Ag | In 17-stellung substituierte corticoid-17-alkylcarbonate, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| EP0998484B1 (en) * | 1997-06-30 | 2004-03-03 | Glaxo Group Limited | Method of identifying compounds having reduced systemic effects |
| CA2634715A1 (en) | 2000-08-05 | 2002-02-14 | Glaxo Group Limited | 6.alpha.,9.alpha.-difluoro-17.alpha.-[(2-furanylcarboxyl)oxy}-11.beta.-hydroxy-16.alpha-methyl-3-oxo-androsta-1,4-diene-17.beta.carbothioic acids-fluoromethyl ester as an anti-inflammatory agent |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| GB0019172D0 (en) | 2000-08-05 | 2000-09-27 | Glaxo Group Ltd | Novel compounds |
| US6777400B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6787532B2 (en) | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
| UA77656C2 (en) | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
| CA2445839A1 (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 |
| GB2389530B (en) | 2002-06-14 | 2007-01-10 | Cipla Ltd | Pharmaceutical compositions |
| UA82323C2 (uk) * | 2002-08-09 | 2008-04-10 | Меда Фарма Гмбх & Ко. Кг | Нова комбінація глюкокортикоїду та pde-інгібітору для лікування респіраторних захворювань, алергічних захворювань, астми та хронічних обструктивних легеневих захворювань |
| GB0316290D0 (en) | 2003-07-11 | 2003-08-13 | Glaxo Group Ltd | Novel compounds |
| ATE517908T1 (de) | 2005-01-10 | 2011-08-15 | Glaxo Group Ltd | Androstan-17-alpha-carbonat-derivate zur verwendung bei der behandlung allergischer und entzündlicher zustände |
| TWI374147B (en) * | 2006-01-27 | 2012-10-11 | Sun Pharma Advance Res Company Ltd | Novel 11β-hydroxyandrosta-4-ene-3-ones |
| US7687484B2 (en) * | 2006-05-25 | 2010-03-30 | Bodor Nicholas S | Transporter enhanced corticosteroid activity |
| US7691811B2 (en) * | 2006-05-25 | 2010-04-06 | Bodor Nicholas S | Transporter-enhanced corticosteroid activity and methods and compositions for treating dry eye |
| CN101942001B (zh) * | 2010-08-24 | 2013-02-06 | 山东省医药工业研究所 | 一种氯替泼诺的提纯方法 |
| CN103183714A (zh) * | 2011-12-29 | 2013-07-03 | 山东方明药业集团股份有限公司 | 一种氯替泼诺的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1384372A (en) * | 1971-01-20 | 1975-02-19 | Glaxo Lab Ltd | Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids |
| GB1438940A (en) * | 1972-07-19 | 1976-06-09 | Glaxo Lab Ltd | 17beta-haloalkoxycarbonyl-17alpha-oxysteroids |
| GB1514476A (en) * | 1974-08-30 | 1978-06-14 | Glaxo Lab Ltd | Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates |
| DE2735110A1 (de) * | 1977-08-04 | 1979-02-15 | Hoechst Ag | Corticoid-17-alkylcarbonate und verfahren zu ihrer herstellung |
| IT1114534B (it) * | 1978-02-08 | 1986-01-27 | Glaxo Group Ltd | Steroide anti-infiammatorio della serie dell'androstano composizioni che lo contengono e procedimento per produrlo |
| US4188385A (en) * | 1978-04-05 | 1980-02-12 | Syntex (U.S.A.) Inc. | Thioetianic acid derivatives |
| DE2817988A1 (de) * | 1978-04-25 | 1979-11-08 | Hoechst Ag | Corticoid 17-alkylcarbonate und verfahren zu deren herstellung |
-
1981
- 1981-07-02 SE SE8104132A patent/SE449106B/sv not_active IP Right Cessation
- 1981-07-06 GB GB8120864A patent/GB2079755B/en not_active Expired
- 1981-07-06 AU AU72591/81A patent/AU540898B2/en not_active Expired
- 1981-07-07 DE DE3126732A patent/DE3126732C2/de not_active Expired
- 1981-07-08 PH PH25877A patent/PH25874A/en unknown
- 1981-07-08 DK DK302181A patent/DK165837C/da not_active IP Right Cessation
- 1981-07-08 CA CA000381293A patent/CA1174667A/en not_active Expired
- 1981-07-08 CH CH4497/81A patent/CH648856A5/de not_active IP Right Cessation
- 1981-07-09 FI FI812175A patent/FI71748C/fi not_active IP Right Cessation
- 1981-07-09 NO NO812344A patent/NO163285C/no unknown
- 1981-07-09 IT IT05186/81A patent/IT1205446B/it active
- 1981-07-10 ES ES504340A patent/ES8300785A1/es not_active Expired
- 1981-07-10 AT AT0307081A patent/AT379816B/de not_active IP Right Cessation
- 1981-07-10 NL NL8103315A patent/NL192343C/nl not_active IP Right Cessation
- 1981-07-10 FR FR8113607A patent/FR2486529A1/fr active Granted
- 1981-07-10 PT PT73348A patent/PT73348B/pt unknown
- 1981-07-10 KR KR1019810002502A patent/KR860000266B1/ko not_active Expired
-
1982
- 1982-08-02 ES ES514633A patent/ES514633A0/es active Granted
-
1984
- 1984-09-25 KR KR1019840005874A patent/KR860000452B1/ko not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| A85 | Still pending on 85-01-01 | ||
| BC | A request for examination has been filed | ||
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: BODOR. DR. NICHOLAS STEPHEN - |
|
| V4 | Discontinued because of reaching the maximum lifetime of a patent |
Free format text: 20010710 |