IL42155A - 16alpha,17alpha-alkylidenedioxy-11beta,21-dihydroxy-pregna-1,4-diene-3,20-diones their manufacture and preparations containing same - Google Patents
16alpha,17alpha-alkylidenedioxy-11beta,21-dihydroxy-pregna-1,4-diene-3,20-diones their manufacture and preparations containing sameInfo
- Publication number
- IL42155A IL42155A IL42155A IL4215573A IL42155A IL 42155 A IL42155 A IL 42155A IL 42155 A IL42155 A IL 42155A IL 4215573 A IL4215573 A IL 4215573A IL 42155 A IL42155 A IL 42155A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- fluorine
- steroids
- hydroxyl
- formula
- Prior art date
Links
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- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000003431 steroids Chemical class 0.000 claims abstract description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052731 fluorine Chemical group 0.000 claims description 10
- 239000011737 fluorine Chemical group 0.000 claims description 10
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 6
- CILPHQCEVYJUDN-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-ylcyclohexyl)oxyacetic acid Chemical compound CC(C)C1CCC(C)CC1OCC(O)=O CILPHQCEVYJUDN-UHFFFAOYSA-N 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
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- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 claims description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
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- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 238000005303 weighing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C07J71/0026—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]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| SE7206644A SE378109B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-05-19 | 1972-05-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42155A0 IL42155A0 (en) | 1973-07-30 |
| IL42155A true IL42155A (en) | 1977-06-30 |
Family
ID=20269234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42155A IL42155A (en) | 1972-05-19 | 1973-05-01 | 16alpha,17alpha-alkylidenedioxy-11beta,21-dihydroxy-pregna-1,4-diene-3,20-diones their manufacture and preparations containing same |
Country Status (26)
Families Citing this family (144)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8004580L (sv) * | 1980-06-19 | 1981-12-20 | Draco Ab | Farmaceutisk beredning |
| SE8008524L (sv) * | 1980-12-04 | 1982-06-05 | Draco Ab | 4-pregnen-derivat, ett forfarande for deras framstellning, beredning och metod for behandling av inflammatoriska tillstand |
| IT1196142B (it) * | 1984-06-11 | 1988-11-10 | Sicor Spa | Procedimento per la preparazione di 16,17-acetali di derivati pregnanici e nuovi composti ottenuti |
| SE8403905D0 (sv) * | 1984-07-30 | 1984-07-30 | Draco Ab | Liposomes and steroid esters |
| SE8501693D0 (sv) * | 1985-04-04 | 1985-04-04 | Draco Ab | Novel 16,17-acetalsubstituted androstane-17beta-carboxylic acid esters |
| US5215979A (en) * | 1985-12-19 | 1993-06-01 | Aktiebolaget Draco | 16,17-acetalsubstituted pregnane 21-oic acid derivatives |
| SE8506015D0 (sv) * | 1985-12-19 | 1985-12-19 | Draco Ab | Novel 16,17-acetalsubstituted pregnane 21-oic acid derivatives |
| SE8604059D0 (sv) * | 1986-09-25 | 1986-09-25 | Astra Pharma Prod | A method of controlling the epimeric distribution in the preparation of 16,17-acetals of pregnane derivatives |
| LV5274A3 (lv) * | 1988-02-29 | 1993-10-10 | Richter Gedeon Vegyeszet | 22(R,S)-11 beta,21-dihidroksi-16 alpha,17-butilidenbisoksipregna-1,4-dien-3,20-diona iegusanas panemiens |
| HU203769B (en) * | 1989-03-09 | 1991-09-30 | Richter Gedeon Vegyeszet | Process for producing new steroide derivatives and pharmaceutical compositions containing them |
| SE8903219D0 (sv) * | 1989-10-02 | 1989-10-02 | Astra Ab | Process for the manufacture of budesonide |
| 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 |
| GR1001529B (el) * | 1990-09-07 | 1994-03-31 | Elmuquimica Farm Sl | Μέ?οδος για την λήψη νέων 21-εστέρων της 16-17-ακετάλης της πρ να-1,4-διενο-3,20-διόνης. |
| SE9100342D0 (sv) * | 1991-02-04 | 1991-02-04 | Astra Ab | Novel steroid esters |
| US5888995A (en) * | 1991-02-04 | 1999-03-30 | Astra Aktiebolag | Steroid esters |
| SE9100341D0 (sv) * | 1991-02-04 | 1991-02-04 | Astra Ab | Novel steroids |
| IE67345B1 (en) * | 1991-03-12 | 1996-03-20 | Akzo Nv | Low dose dry pharmaceutical preparations |
| FR2675146A1 (fr) * | 1991-04-10 | 1992-10-16 | Roussel Uclaf | Nouveaux derives sterouides de la pregna-1,4-diene-3,20-dione, leur preparation, leur application a la preparation de derives 16,17-methylene dioxy substitues et nouveaux intermediaires. |
| MD24B1 (ro) * | 1991-07-09 | 1994-05-31 | Parfumerii Si Cosmetice Vioric | Compozitie de substante odorante |
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|---|---|---|---|---|
| US3126375A (en) * | 1964-03-24 | Chioacyl | ||
| US3133940A (en) * | 1956-04-10 | 1964-05-19 | Glaxo Group Ltd | Process for the separation of delta-1, 4-3-keto steroid compounds from mixtures thereof with other 3-keto steroids |
| US2990401A (en) * | 1958-06-18 | 1961-06-27 | American Cyanamid Co | 11-substituted 16alpha, 17alpha-substituted methylenedioxy steroids |
| US3197469A (en) * | 1958-08-06 | 1965-07-27 | Pharmaceutical Res Products In | 16, 17-acetals and ketals of 6-halo-16, 17-dihydroxy steroids of the pregnane seriesand intermediates therefor |
| US3048581A (en) * | 1960-04-25 | 1962-08-07 | Olin Mathieson | Acetals and ketals of 16, 17-dihydroxy steroids |
| US3128238A (en) * | 1962-09-14 | 1964-04-07 | Lilly Co Eli | delta1-dehydrogenation of steroids by fermentation with actinoplanaceae |
| JPS4843910A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-10-08 | 1973-06-25 |
-
1972
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-
1973
- 1973-05-01 ZA ZA732955A patent/ZA732955B/xx unknown
- 1973-05-01 IL IL42155A patent/IL42155A/en unknown
- 1973-05-09 GB GB2219473A patent/GB1429922A/en not_active Expired
- 1973-05-09 CY CY1013A patent/CY1013A/xx unknown
- 1973-05-09 DE DE2323215A patent/DE2323215C3/de not_active Expired
- 1973-05-11 ES ES414673A patent/ES414673A1/es not_active Expired
- 1973-05-14 FI FI731542A patent/FI50631C/fi active Protection Beyond IP Right Term
- 1973-05-14 US US360051A patent/US3929768A/en not_active Expired - Lifetime
- 1973-05-16 CH CH699973A patent/CH595400A5/xx not_active IP Right Cessation
- 1973-05-16 YU YU1291/73A patent/YU35896B/xx unknown
- 1973-05-17 DD DD170888A patent/DD104295A5/xx unknown
- 1973-05-17 DK DK277273AA patent/DK134783B/da active Protection Beyond IP Right Term
- 1973-05-18 NO NO2059/73A patent/NO139640C/no unknown
- 1973-05-18 FR FR7318125A patent/FR2185405B1/fr not_active Expired
- 1973-05-18 CA CA171,785A patent/CA1002938A/en not_active Expired
- 1973-05-18 HU HUBO1438A patent/HU166680B/hu unknown
- 1973-05-18 BE BE131270A patent/BE799727A/xx active Protection Beyond IP Right Term
- 1973-05-18 PL PL1973162650A patent/PL87765B1/pl unknown
- 1973-05-18 NL NLAANVRAGE7306978,A patent/NL177493C/xx active Protection Beyond IP Right Term
- 1973-05-18 CS CS3590A patent/CS178129B2/cs unknown
- 1973-05-18 SU SU1923451A patent/SU470954A3/ru active
- 1973-05-18 AT AT436573A patent/AT328630B/de not_active IP Right Cessation
- 1973-05-19 JP JP5623373A patent/JPS5521760B2/ja not_active Expired
-
1975
- 1975-11-06 US US05/629,389 patent/US3983233A/en not_active Expired - Lifetime
-
1979
- 1979-06-20 KE KE2970A patent/KE2970A/xx unknown
- 1979-07-19 HK HK491/79A patent/HK49179A/xx unknown
-
1993
- 1993-04-13 NL NL930025C patent/NL930025I1/nl unknown
-
1994
- 1994-08-31 NO NO1994013C patent/NO1994013I1/no unknown
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