LT3912B - Novel 16,17-acetal-substituted derivatives of pregnan-21-oic acid, process for preparing thereof, pharmaceutical preparations containing them - Google Patents
Novel 16,17-acetal-substituted derivatives of pregnan-21-oic acid, process for preparing thereof, pharmaceutical preparations containing them Download PDFInfo
- Publication number
- LT3912B LT3912B LTIP1682A LTIP1682A LT3912B LT 3912 B LT3912 B LT 3912B LT IP1682 A LTIP1682 A LT IP1682A LT IP1682 A LTIP1682 A LT IP1682A LT 3912 B LT3912 B LT 3912B
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- compound
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- acid
- alcohol
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- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 7
- GWZUYOSMTQIJMY-DIKHCDEOSA-N 2-[(8s,9s,10s,13r,14s,17r)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]acetic acid Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)CC(O)=O)[C@@H]4[C@@H]3CCC21 GWZUYOSMTQIJMY-DIKHCDEOSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 31
- 230000008569 process Effects 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims abstract description 10
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- 208000010668 atopic eczema Diseases 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 230000003647 oxidation Effects 0.000 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 12
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 230000000241 respiratory effect Effects 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 1
- 125000004036 acetal group Chemical group 0.000 claims 1
- 238000006149 azo coupling reaction Methods 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 14
- 230000002757 inflammatory effect Effects 0.000 abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
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- 150000003431 steroids Chemical class 0.000 description 22
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- 239000003862 glucocorticoid Substances 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
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- 239000012507 Sephadex™ Substances 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 13
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 150000001879 copper Chemical class 0.000 description 9
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 8
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 229960004436 budesonide Drugs 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 206010037423 Pulmonary oedema Diseases 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
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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
- 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
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8506015A SE8506015D0 (sv) | 1985-12-19 | 1985-12-19 | Novel 16,17-acetalsubstituted pregnane 21-oic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1682A LTIP1682A (en) | 1995-07-25 |
| LT3912B true LT3912B (en) | 1996-04-25 |
Family
ID=20362521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1682A LT3912B (en) | 1985-12-19 | 1993-12-28 | Novel 16,17-acetal-substituted derivatives of pregnan-21-oic acid, process for preparing thereof, pharmaceutical preparations containing them |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP0232690B1 (cs) |
| JP (1) | JPH0780900B2 (cs) |
| KR (1) | KR940004067B1 (cs) |
| CN (1) | CN1016508B (cs) |
| AR (1) | AR242797A1 (cs) |
| AT (1) | ATE57935T1 (cs) |
| AU (1) | AU591950B2 (cs) |
| CA (1) | CA1318664C (cs) |
| CS (1) | CS266597B2 (cs) |
| DD (1) | DD256703A5 (cs) |
| DE (1) | DE3675378D1 (cs) |
| DK (1) | DK168601B1 (cs) |
| ES (1) | ES2018656B3 (cs) |
| FI (1) | FI84488C (cs) |
| GR (1) | GR3001052T3 (cs) |
| HU (1) | HU196831B (cs) |
| IE (1) | IE59241B1 (cs) |
| IL (1) | IL80679A (cs) |
| IS (1) | IS1559B (cs) |
| JO (1) | JO1499B1 (cs) |
| LT (1) | LT3912B (cs) |
| LV (1) | LV10959B (cs) |
| MY (1) | MY100750A (cs) |
| NO (1) | NO164243C (cs) |
| NZ (1) | NZ218614A (cs) |
| PH (1) | PH23237A (cs) |
| PL (1) | PL151627B1 (cs) |
| PT (1) | PT83984B (cs) |
| RU (1) | RU1839673C (cs) |
| SE (1) | SE8506015D0 (cs) |
| ZA (1) | ZA868750B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU203769B (en) * | 1989-03-09 | 1991-09-30 | Richter Gedeon Vegyeszet | Process for producing new steroide derivatives and pharmaceutical compositions containing them |
| SE8903914D0 (sv) | 1989-11-22 | 1989-11-22 | Draco Ab | Oral composition for the treatment of inflammatory bowel diseases |
| US5643602A (en) * | 1989-11-22 | 1997-07-01 | Astra Aktiebolag | Oral composition for the treatment of inflammatory bowel disease |
| US6166024A (en) * | 1995-03-30 | 2000-12-26 | Mayo Foundation For Medical Education And Research | Use of topical azathioprine and thioguanine to treat colorectal adenomas |
| CA2902911C (en) | 2014-10-31 | 2017-06-27 | Purdue Pharma | Methods and compositions particularly for treatment of attention deficit disorder |
| US10722473B2 (en) | 2018-11-19 | 2020-07-28 | Purdue Pharma L.P. | Methods and compositions particularly for treatment of attention deficit disorder |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2150268C3 (de) * | 1971-10-04 | 1980-11-06 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Pregnansäure-Derivate, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel |
| DE2204360C2 (de) * | 1972-01-27 | 1982-11-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue Pregnansäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
| DD95565B1 (de) * | 1971-10-04 | 1986-10-29 | Schering Ag | Verfahren zur herstellung neuer pregnansaeurederivate |
| SE378109B (cs) * | 1972-05-19 | 1975-08-18 | Bofors Ab | |
| DE2264003C2 (de) * | 1972-12-22 | 1982-11-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue Pregnansäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
| DK135380C (da) * | 1972-12-22 | 1977-10-03 | Schering Ag | Analogifremgangsmade til fremstilling af pregnan-21-syrederivater |
| SE8403905D0 (sv) * | 1984-07-30 | 1984-07-30 | Draco Ab | Liposomes and steroid esters |
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1985
- 1985-12-19 SE SE8506015A patent/SE8506015D0/xx unknown
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1986
- 1986-11-18 ZA ZA868750A patent/ZA868750B/xx unknown
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- 1986-12-11 NO NO865004A patent/NO164243C/no unknown
- 1986-12-11 IE IE324586A patent/IE59241B1/en not_active IP Right Cessation
- 1986-12-12 AU AU66448/86A patent/AU591950B2/en not_active Ceased
- 1986-12-12 AT AT86850436T patent/ATE57935T1/de not_active IP Right Cessation
- 1986-12-12 EP EP86850436A patent/EP0232690B1/en not_active Expired - Lifetime
- 1986-12-12 DE DE8686850436T patent/DE3675378D1/de not_active Expired - Lifetime
- 1986-12-12 ES ES86850436T patent/ES2018656B3/es not_active Expired - Lifetime
- 1986-12-12 NZ NZ218614A patent/NZ218614A/xx unknown
- 1986-12-15 PH PH34590A patent/PH23237A/en unknown
- 1986-12-15 JO JO19861499A patent/JO1499B1/en active
- 1986-12-16 FI FI865128A patent/FI84488C/fi not_active IP Right Cessation
- 1986-12-16 DK DK605186A patent/DK168601B1/da not_active IP Right Cessation
- 1986-12-17 MY MYPI86000221A patent/MY100750A/en unknown
- 1986-12-17 PL PL1986263041A patent/PL151627B1/pl unknown
- 1986-12-18 KR KR1019860010870A patent/KR940004067B1/ko not_active Expired - Fee Related
- 1986-12-18 HU HU865302A patent/HU196831B/hu not_active IP Right Cessation
- 1986-12-18 AR AR86306261A patent/AR242797A1/es active
- 1986-12-18 JP JP61300242A patent/JPH0780900B2/ja not_active Expired - Lifetime
- 1986-12-18 CA CA000525677A patent/CA1318664C/en not_active Expired - Fee Related
- 1986-12-18 DD DD86297902A patent/DD256703A5/de unknown
- 1986-12-18 RU SU864028689A patent/RU1839673C/ru active
- 1986-12-19 IS IS3179A patent/IS1559B/is unknown
- 1986-12-19 CS CS869604A patent/CS266597B2/cs unknown
- 1986-12-19 CN CN86108634A patent/CN1016508B/zh not_active Expired
- 1986-12-19 PT PT83984A patent/PT83984B/pt not_active IP Right Cessation
-
1990
- 1990-11-06 GR GR90400871T patent/GR3001052T3/el unknown
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1993
- 1993-08-27 LV LVP-93-1046A patent/LV10959B/lv unknown
- 1993-12-28 LT LTIP1682A patent/LT3912B/lt not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
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| TOOGOOD JH ET AL.: "Influence of dosing frequency and schedule on the response of chronic asthmatics to the aerosol steroid, budesonide.", J ALLERGY CLIN IMMUNOL., 1982, pages 288 - 298 |
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Effective date: 19971228 |