DE2222491C3 - Steroid-21-salpetersäureester der Pregnanreihe, solche enthaltende Arzneimittel und Verfahren zur Herstellung derselben - Google Patents
Steroid-21-salpetersäureester der Pregnanreihe, solche enthaltende Arzneimittel und Verfahren zur Herstellung derselbenInfo
- Publication number
- DE2222491C3 DE2222491C3 DE2222491A DE2222491A DE2222491C3 DE 2222491 C3 DE2222491 C3 DE 2222491C3 DE 2222491 A DE2222491 A DE 2222491A DE 2222491 A DE2222491 A DE 2222491A DE 2222491 C3 DE2222491 C3 DE 2222491C3
- Authority
- DE
- Germany
- Prior art keywords
- nitric acid
- steroid
- acid esters
- acid ester
- 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 Pregnan series steroid Chemical class 0.000 title description 11
- 238000000034 method Methods 0.000 title description 6
- 239000003814 drug Substances 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 27
- 150000003431 steroids Chemical class 0.000 claims description 25
- 150000003128 pregnanes Chemical class 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 12
- 230000003110 anti-inflammatory effect Effects 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000013558 reference substance Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical class BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000035935 pregnancy Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 206010018691 Granuloma Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 206010041277 Sodium retention Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000001426 cardiotropic effect Effects 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004121 glycogenesis Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000004041 inotropic agent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 230000003096 thymolvtic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000014616 translation Effects 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
- 229960005294 triamcinolone Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- 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)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
-
- 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
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI429A HU164115B (enExample) | 1971-05-07 | 1971-05-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2222491A1 DE2222491A1 (de) | 1972-11-16 |
| DE2222491B2 DE2222491B2 (de) | 1977-09-29 |
| DE2222491C3 true DE2222491C3 (de) | 1978-05-03 |
Family
ID=11000864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2222491A Expired DE2222491C3 (de) | 1971-05-07 | 1972-05-08 | Steroid-21-salpetersäureester der Pregnanreihe, solche enthaltende Arzneimittel und Verfahren zur Herstellung derselben |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5330707B1 (enExample) |
| AT (1) | AT316767B (enExample) |
| AU (1) | AU469581B2 (enExample) |
| CA (1) | CA975755A (enExample) |
| CS (2) | CS171259B2 (enExample) |
| DD (1) | DD98668A5 (enExample) |
| DE (1) | DE2222491C3 (enExample) |
| ES (1) | ES402230A1 (enExample) |
| FR (1) | FR2143664A1 (enExample) |
| HU (1) | HU164115B (enExample) |
| NL (1) | NL7206134A (enExample) |
| PL (1) | PL75494B1 (enExample) |
| SE (2) | SE385590B (enExample) |
| SU (1) | SU493963A3 (enExample) |
| YU (1) | YU34701B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2186781C2 (ru) * | 1996-10-04 | 2002-08-10 | Никокс С.А. | Нитроэфиры кортикоидных соединений |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5792758A (en) * | 1995-12-08 | 1998-08-11 | G. D. Searle & Co. | Steroid nitrite ester derivatives useful as anti-inflammatory drugs |
| US5707984A (en) * | 1995-12-08 | 1998-01-13 | G. D. Searle & Co. | Steroid nitrite/nitrate ester derivatives useful as anti-inflammatory drugs |
| US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| US5837698A (en) * | 1996-05-02 | 1998-11-17 | G. D. Searle & Co. | Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs |
| US5985862A (en) * | 1996-05-02 | 1999-11-16 | G.D. Searle & Co. | Pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs |
| ITMI20020148A1 (it) | 2002-01-29 | 2003-07-29 | Nicox Sa | Nuovi corticosteroidi |
| CN101652380A (zh) | 2007-02-05 | 2010-02-17 | 尼科克斯公司 | 释放一氧化氮的类固醇 |
| PT2805720T (pt) | 2008-05-28 | 2019-09-23 | Reveragen Biopharma Inc | Moduladores esteroides não hormonais de nf-kb para tratamento de uma doença |
| EP2556083A4 (en) | 2010-04-05 | 2013-12-04 | Validus Biopharma Inc | NONHORMONAL STEROID MODULATORS OF NF-KAPPA-B FOR DISEASE TREATMENT |
| US8716268B2 (en) | 2010-06-07 | 2014-05-06 | Chao Liu | Nitrate esters of corticoid compounds useful as diuretics |
| 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 |
-
1971
- 1971-05-07 HU HURI429A patent/HU164115B/hu unknown
-
1972
- 1972-04-20 AT AT345872A patent/AT316767B/de not_active IP Right Cessation
- 1972-04-22 ES ES402230A patent/ES402230A1/es not_active Expired
- 1972-04-26 YU YU1117/72A patent/YU34701B/xx unknown
- 1972-04-28 DD DD162651A patent/DD98668A5/xx unknown
- 1972-05-01 AU AU41722/72A patent/AU469581B2/en not_active Expired
- 1972-05-04 FR FR7215938A patent/FR2143664A1/fr active Granted
- 1972-05-04 JP JP4376772A patent/JPS5330707B1/ja active Pending
- 1972-05-05 PL PL15518272A patent/PL75494B1/pl unknown
- 1972-05-05 SU SU1783400A patent/SU493963A3/ru active
- 1972-05-05 NL NL7206134A patent/NL7206134A/xx not_active Application Discontinuation
- 1972-05-05 CS CS2266*[A patent/CS171259B2/cs unknown
- 1972-05-05 CA CA141,366A patent/CA975755A/en not_active Expired
- 1972-05-05 SE SE7205915A patent/SE385590B/xx unknown
- 1972-05-05 CS CS3050A patent/CS171258B2/cs unknown
- 1972-05-08 DE DE2222491A patent/DE2222491C3/de not_active Expired
-
1975
- 1975-03-21 SE SE7503290A patent/SE7503290L/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2186781C2 (ru) * | 1996-10-04 | 2002-08-10 | Никокс С.А. | Нитроэфиры кортикоидных соединений |
Also Published As
| Publication number | Publication date |
|---|---|
| AT316767B (de) | 1974-07-25 |
| PL75494B1 (enExample) | 1974-12-31 |
| CS171258B2 (enExample) | 1976-10-29 |
| YU34701B (en) | 1979-12-31 |
| FR2143664A1 (en) | 1973-02-09 |
| SE385590B (sv) | 1976-07-12 |
| SU493963A3 (ru) | 1975-11-28 |
| DE2222491A1 (de) | 1972-11-16 |
| DE2222491B2 (de) | 1977-09-29 |
| JPS5330707B1 (enExample) | 1978-08-29 |
| CA975755A (en) | 1975-10-07 |
| ES402230A1 (es) | 1975-03-16 |
| YU111772A (en) | 1979-07-10 |
| FR2143664B1 (enExample) | 1976-07-02 |
| AU469581B2 (en) | 1976-02-19 |
| NL7206134A (enExample) | 1972-11-09 |
| AU4172272A (en) | 1973-11-08 |
| DD98668A5 (enExample) | 1973-07-05 |
| CS171259B2 (enExample) | 1976-10-29 |
| SE7503290L (enExample) | 1975-03-21 |
| HU164115B (enExample) | 1973-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |