FR2529893A1 - Androstene-17-dithioacetals a action therapeutique - Google Patents
Androstene-17-dithioacetals a action therapeutique Download PDFInfo
- Publication number
- FR2529893A1 FR2529893A1 FR8310759A FR8310759A FR2529893A1 FR 2529893 A1 FR2529893 A1 FR 2529893A1 FR 8310759 A FR8310759 A FR 8310759A FR 8310759 A FR8310759 A FR 8310759A FR 2529893 A1 FR2529893 A1 FR 2529893A1
- Authority
- FR
- France
- Prior art keywords
- fluoro
- hydroxy
- dien
- compound according
- methylthio
- 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.)
- Granted
Links
- 230000001225 therapeutic effect Effects 0.000 title description 2
- -1 HYDROXY GROUP Chemical group 0.000 claims abstract description 36
- 150000003431 steroids Chemical class 0.000 claims abstract description 35
- 150000002367 halogens Chemical group 0.000 claims abstract description 7
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 22
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 11
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- 125000004423 acyloxy group Chemical group 0.000 claims description 4
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
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- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005333 aroyloxy group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
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- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 2
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- 125000004104 aryloxy group Chemical group 0.000 claims description 2
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- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
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- ABHDIZBWYPPTLX-BCYZHJNNSA-N (8r,9s,10r,13r,14s)-13-(hydroxymethyl)-10-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@]1(CO)CCC[C@H]1[C@@H]1CC2)C[C@@H]1[C@]1(C)C2=CC(=O)C=C1 ABHDIZBWYPPTLX-BCYZHJNNSA-N 0.000 claims 1
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- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
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- PNYYBUOBTVHFDN-UHFFFAOYSA-N sodium bismuthate Chemical compound [Na+].[O-][Bi](=O)=O PNYYBUOBTVHFDN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
-
- 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 |
|---|---|---|---|
| US06/396,178 US4447363A (en) | 1982-07-07 | 1982-07-07 | Androstene-17-dithioketals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2529893A1 true FR2529893A1 (fr) | 1984-01-13 |
| FR2529893B1 FR2529893B1 (enExample) | 1985-04-26 |
Family
ID=23566177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8310759A Granted FR2529893A1 (fr) | 1982-07-07 | 1983-06-29 | Androstene-17-dithioacetals a action therapeutique |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4447363A (enExample) |
| JP (1) | JPS5921700A (enExample) |
| CA (1) | CA1213271A (enExample) |
| DE (1) | DE3324403A1 (enExample) |
| FR (1) | FR2529893A1 (enExample) |
| GB (1) | GB2123425B (enExample) |
| IT (1) | IT1165458B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4529547A (en) * | 1984-06-20 | 1985-07-16 | E.R. Squibb & Sons, Inc. | 17-(substituted thio)-17-(substituted dithio)androstenes |
| US4528138A (en) * | 1984-06-20 | 1985-07-09 | E. R. Squibb & Sons, Inc. | 16-Keto-17-substituted thia-17-alkyl(or alkenyl or alkynyl) androstenes |
| JPS6284864A (ja) * | 1985-10-11 | 1987-04-18 | Akio Nakano | ダイカスト機の射出ノズル |
| IE922301A1 (en) * | 1991-07-25 | 1993-01-27 | Squibb & Sons Inc | Selective thioketalization process, process for preparing¹thioenol ethers from thioketals, and process for the¹preparation of thioketals |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091036A (en) * | 1977-05-12 | 1978-05-23 | E. R. Squibb & Sons, Inc. | 17-Alkylthio (and arylthio)-1',2',3',4'-tetrahydroandrosteno [16 α, 17 α-b]naphthalenes and derivatives |
| US4361559A (en) * | 1981-08-20 | 1982-11-30 | E. R. Squibb & Sons, Inc. | Antiinflammatory 17,17-bis (substituted thio) androstenes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4133811A (en) * | 1978-02-17 | 1979-01-09 | E. R. Squibb & Sons, Inc. | 13-Alkylthio (and arylthio)-11,17-epoxy-17-methyl-18-norandrostenes |
| US4265815A (en) * | 1980-03-31 | 1981-05-05 | E. R. Squibb & Sons, Inc. | 17-(Substituted thio)androst-4-ene[16,17,-b]-[1,4]benzodioxin-3-ones |
-
1982
- 1982-07-07 US US06/396,178 patent/US4447363A/en not_active Expired - Fee Related
-
1983
- 1983-06-02 CA CA000429498A patent/CA1213271A/en not_active Expired
- 1983-06-29 FR FR8310759A patent/FR2529893A1/fr active Granted
- 1983-07-06 JP JP58124062A patent/JPS5921700A/ja active Pending
- 1983-07-06 GB GB08318305A patent/GB2123425B/en not_active Expired
- 1983-07-06 DE DE19833324403 patent/DE3324403A1/de not_active Ceased
- 1983-07-07 IT IT21969/83A patent/IT1165458B/it active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091036A (en) * | 1977-05-12 | 1978-05-23 | E. R. Squibb & Sons, Inc. | 17-Alkylthio (and arylthio)-1',2',3',4'-tetrahydroandrosteno [16 α, 17 α-b]naphthalenes and derivatives |
| US4361559A (en) * | 1981-08-20 | 1982-11-30 | E. R. Squibb & Sons, Inc. | Antiinflammatory 17,17-bis (substituted thio) androstenes |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8321969A0 (it) | 1983-07-07 |
| IT1165458B (it) | 1987-04-22 |
| DE3324403A1 (de) | 1984-01-12 |
| US4447363A (en) | 1984-05-08 |
| GB2123425A (en) | 1984-02-01 |
| FR2529893B1 (enExample) | 1985-04-26 |
| GB8318305D0 (en) | 1983-08-10 |
| CA1213271A (en) | 1986-10-28 |
| JPS5921700A (ja) | 1984-02-03 |
| GB2123425B (en) | 1986-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |