LT3913B - Novel 16,17-acetal-substituted androstan-17beta-carboxylic acid esters - Google Patents
Novel 16,17-acetal-substituted androstan-17beta-carboxylic acid esters Download PDFInfo
- Publication number
- LT3913B LT3913B LTIP1678A LTIP1678A LT3913B LT 3913 B LT3913 B LT 3913B LT IP1678 A LTIP1678 A LT IP1678A LT IP1678 A LTIP1678 A LT IP1678A LT 3913 B LT3913 B LT 3913B
- Authority
- LT
- Lithuania
- Prior art keywords
- hydrogen
- compounds
- carboxylic acid
- difluoro
- diene
- Prior art date
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- PBXJGQQGODZSQR-CWQDBKDDSA-N (8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-17-carboxylic acid Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(O)=O)[C@@H]4[C@@H]3CCC21 PBXJGQQGODZSQR-CWQDBKDDSA-N 0.000 title claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 239000011737 fluorine Substances 0.000 claims abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- -1 nitro, carboxy Chemical group 0.000 abstract description 36
- 150000001875 compounds Chemical class 0.000 abstract description 29
- 230000000694 effects Effects 0.000 abstract description 14
- 238000000034 method Methods 0.000 abstract description 11
- 239000000460 chlorine Substances 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 238000011282 treatment Methods 0.000 abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 230000004968 inflammatory condition Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 150000003431 steroids Chemical class 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 210000004072 lung Anatomy 0.000 description 20
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- 239000003862 glucocorticoid Substances 0.000 description 18
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- 238000006243 chemical reaction Methods 0.000 description 9
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- UIHJCUHTFKBJQU-UDCWSGSHSA-N (8s,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-17-carboxylic acid Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(O)=O)[C@@H]4[C@@H]3CCC2=C1 UIHJCUHTFKBJQU-UDCWSGSHSA-N 0.000 description 7
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- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 230000027455 binding Effects 0.000 description 6
- 229960004436 budesonide Drugs 0.000 description 6
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 6
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- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 6
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
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- PNYYBUOBTVHFDN-UHFFFAOYSA-N sodium bismuthate Chemical compound [Na+].[O-][Bi](=O)=O PNYYBUOBTVHFDN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
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- 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrrole Compounds (AREA)
- Fats And Perfumes (AREA)
- Threshing Machine Elements (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8501693A SE8501693D0 (sv) | 1985-04-04 | 1985-04-04 | Novel 16,17-acetalsubstituted androstane-17beta-carboxylic acid esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1678A LTIP1678A (en) | 1995-07-25 |
| LT3913B true LT3913B (en) | 1996-04-25 |
Family
ID=20359775
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1678A LT3913B (en) | 1985-04-04 | 1993-12-28 | Novel 16,17-acetal-substituted androstan-17beta-carboxylic acid esters |
| LTIP1677A LT3812B (en) | 1985-04-04 | 1993-12-28 | Process for preparing intermediates of 3-okso-androstan-1,4dien-17beta-carboxylic acid |
| LTIP1676A LT3811B (en) | 1985-04-04 | 1993-12-28 | Novel 16,17-acetal-substituted androstan-17beta-carboxylic acid esters, process for preparing thereof, pharmaceutical preparations |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1677A LT3812B (en) | 1985-04-04 | 1993-12-28 | Process for preparing intermediates of 3-okso-androstan-1,4dien-17beta-carboxylic acid |
| LTIP1676A LT3811B (en) | 1985-04-04 | 1993-12-28 | Novel 16,17-acetal-substituted androstan-17beta-carboxylic acid esters, process for preparing thereof, pharmaceutical preparations |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4950659A (cs) |
| EP (2) | EP0355859B1 (cs) |
| JP (1) | JPH0762028B2 (cs) |
| KR (1) | KR930009444B1 (cs) |
| CN (1) | CN1021444C (cs) |
| AT (2) | ATE83241T1 (cs) |
| AU (1) | AU590545B2 (cs) |
| CA (1) | CA1333597C (cs) |
| CS (1) | CS266581B2 (cs) |
| DD (2) | DD247681A5 (cs) |
| DE (2) | DE3689936T2 (cs) |
| DK (3) | DK165638C (cs) |
| ES (2) | ES8800264A1 (cs) |
| FI (1) | FI85378C (cs) |
| GR (1) | GR860902B (cs) |
| HU (2) | HU196830B (cs) |
| IE (1) | IE61474B1 (cs) |
| IL (1) | IL78143A0 (cs) |
| JO (1) | JO1479B1 (cs) |
| LT (3) | LT3913B (cs) |
| LV (3) | LV10281B (cs) |
| MY (1) | MY102056A (cs) |
| NO (1) | NO165298C (cs) |
| NZ (1) | NZ215586A (cs) |
| PH (2) | PH23547A (cs) |
| PL (2) | PL148272B1 (cs) |
| PT (1) | PT82340B (cs) |
| RU (3) | RU1795972C (cs) |
| SE (1) | SE8501693D0 (cs) |
| UA (2) | UA13319A (cs) |
| ZA (1) | ZA861884B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8501693D0 (sv) | 1985-04-04 | 1985-04-04 | Draco Ab | Novel 16,17-acetalsubstituted androstane-17beta-carboxylic acid esters |
| HU203769B (en) * | 1989-03-09 | 1991-09-30 | Richter Gedeon Vegyeszet | Process for producing new steroide derivatives and pharmaceutical compositions containing them |
| WO1994014834A1 (en) * | 1992-12-24 | 1994-07-07 | Rhone-Poulenc Rorer Limited | New steroids |
| GB9423919D0 (en) * | 1994-11-26 | 1995-01-11 | Rhone Poulenc Rorer Ltd | Chemical process |
| GB0110411D0 (en) * | 2001-04-27 | 2001-06-20 | Astrazeneca Ab | Chemical process |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3828080A (en) * | 1972-01-20 | 1974-08-06 | Glaxo Lab Ltd | Androstane-17beta-carboxylic acids and processes for the preparation thereof |
| SE378109B (cs) * | 1972-05-19 | 1975-08-18 | Bofors Ab | |
| GB1438940A (en) * | 1972-07-19 | 1976-06-09 | Glaxo Lab Ltd | 17beta-haloalkoxycarbonyl-17alpha-oxysteroids |
| GB1517278A (en) * | 1974-08-30 | 1978-07-12 | Glaxo Lab Ltd | Alkyl and haloalkyl androsta-1,4,15-triene and-4,15-diene-17beta-carboxylates |
| CH628355A5 (de) * | 1976-02-24 | 1982-02-26 | Ciba Geigy Ag | Verfahren zur herstellung neuer androstadien-17beta-carbonsaeuren und ihrer ester und salze. |
| US4198336A (en) * | 1978-04-05 | 1980-04-15 | Syntex (U.S.A.) Inc. | Chemical process for preparing androsta-4-ene 17α-carboxylic acids |
| SE449106B (sv) * | 1980-07-10 | 1987-04-06 | Otsuka Pharma Co Ltd | Steroid med anti-inflammatorisk verkan samt komposition innehallande denna |
| ZA814440B (en) * | 1980-07-10 | 1982-10-27 | Otsuka Pharma Co Ltd | Soft steroids having anti-inflammatory activity |
| ZA817929B (en) * | 1980-12-22 | 1982-10-27 | Upjohn Co | 5alpha-and 5beta-androstane-17beta-carboxylates |
| SE8306370D0 (sv) * | 1983-11-18 | 1983-11-18 | Draco Ab | Novel androstane-17beta-carboxylic acid esters, a process and intermediates for their preparation, compositions and method for the treatment of inflammatory conditions |
| 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 |
| JP2687768B2 (ja) * | 1991-07-30 | 1997-12-08 | トヨタ自動車株式会社 | エンジンの制御装置 |
-
1985
- 1985-04-04 SE SE8501693A patent/SE8501693D0/xx unknown
-
1986
- 1986-03-13 ZA ZA861884A patent/ZA861884B/xx unknown
- 1986-03-14 IL IL78143A patent/IL78143A0/xx not_active IP Right Cessation
- 1986-03-19 AU AU54868/86A patent/AU590545B2/en not_active Expired
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1987
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1988
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1991
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1992
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1993
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Non-Patent Citations (1)
| Title |
|---|
| E DAHLBERG ET AL.: "Correlation between chemical structure, receptor binding, and biological activity of some novel, highly active, 16 alpha, 17 alpha-acetal-substituted glucocorticoids", MOL PHARMACOL., 1984, pages 70 - 71 |
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Effective date: 19971228 |