IL43847A - 3beta-cycloalkyloxy-16alpha-cyanopregn-5-en-20-ones their preparation and compositions containing them for the reduction of serum lipid levels - Google Patents
3beta-cycloalkyloxy-16alpha-cyanopregn-5-en-20-ones their preparation and compositions containing them for the reduction of serum lipid levelsInfo
- Publication number
- IL43847A IL43847A IL43847A IL4384773A IL43847A IL 43847 A IL43847 A IL 43847A IL 43847 A IL43847 A IL 43847A IL 4384773 A IL4384773 A IL 4384773A IL 43847 A IL43847 A IL 43847A
- Authority
- IL
- Israel
- Prior art keywords
- cyanopregn
- animals
- liver
- day
- levels
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 16
- 210000002966 serum Anatomy 0.000 title description 16
- 150000002632 lipids Chemical class 0.000 title description 12
- 230000009467 reduction Effects 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 9
- -1 cycloalkyl halide Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 description 33
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- 238000012360 testing method Methods 0.000 description 24
- 239000000463 material Substances 0.000 description 19
- 230000002440 hepatic effect Effects 0.000 description 14
- 210000004185 liver Anatomy 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 11
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- 239000008101 lactose Substances 0.000 description 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 206010019708 Hepatic steatosis Diseases 0.000 description 2
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 201000007930 alcohol dependence Diseases 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
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- 239000005556 hormone Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000008818 liver damage Effects 0.000 description 2
- 208000019423 liver disease Diseases 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 231100000240 steatosis hepatitis Toxicity 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
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- 229930195730 Aflatoxin Natural products 0.000 description 1
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- WDJUZGPOPHTGOT-OAXVISGBSA-N Digitoxin Natural products O([C@H]1[C@@H](C)O[C@@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@H](C6=CC(=O)OC6)CC5)CC4)CC3)CC2)C[C@H]1O)[C@H]1O[C@@H](C)[C@H](O[C@H]2O[C@@H](C)[C@@H](O)[C@@H](O)C2)[C@@H](O)C1 WDJUZGPOPHTGOT-OAXVISGBSA-N 0.000 description 1
- 206010014486 Elevated triglycerides Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 231100000678 Mycotoxin Toxicity 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- WDJUZGPOPHTGOT-XUDUSOBPSA-N digitoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O WDJUZGPOPHTGOT-XUDUSOBPSA-N 0.000 description 1
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- 235000013312 flour Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
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- 208000006454 hepatitis Diseases 0.000 description 1
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- 229960000905 indomethacin Drugs 0.000 description 1
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- 239000000312 peanut oil Substances 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
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- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 235000013311 vegetables Nutrition 0.000 description 1
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Classifications
-
- 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
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31599772A | 1972-12-18 | 1972-12-18 | |
| US05/417,972 US3947479A (en) | 1972-12-18 | 1973-11-21 | Reduction of serum lipid levels, and agents and compositions useful therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43847A0 IL43847A0 (en) | 1974-06-30 |
| IL43847A true IL43847A (en) | 1977-05-31 |
Family
ID=26980179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43847A IL43847A (en) | 1972-12-18 | 1973-12-18 | 3beta-cycloalkyloxy-16alpha-cyanopregn-5-en-20-ones their preparation and compositions containing them for the reduction of serum lipid levels |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3947479A (fr) |
| JP (1) | JPS5344463B2 (fr) |
| AR (1) | AR203833A1 (fr) |
| AT (1) | AT330967B (fr) |
| AU (1) | AU477429B2 (fr) |
| CA (1) | CA1016536A (fr) |
| CH (1) | CH591524A5 (fr) |
| DK (1) | DK134236B (fr) |
| ES (1) | ES421570A1 (fr) |
| FI (1) | FI52589C (fr) |
| FR (1) | FR2210411B1 (fr) |
| GB (1) | GB1434378A (fr) |
| IE (1) | IE38967B1 (fr) |
| IL (1) | IL43847A (fr) |
| NL (1) | NL7317048A (fr) |
| NO (1) | NO137599C (fr) |
| SE (1) | SE404192B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4996252A (fr) * | 1973-01-19 | 1974-09-12 | ||
| JPS5624346Y2 (fr) * | 1976-10-01 | 1981-06-08 | ||
| JPS5916060U (ja) * | 1982-07-23 | 1984-01-31 | 株式会社東芝 | シヤドウマスク構体 |
| JPS628431A (ja) * | 1985-07-02 | 1987-01-16 | Mitsubishi Electric Corp | アパーチャマスクの製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3151132A (en) * | 1960-07-02 | 1964-09-29 | Syntex Corp | Polyhalomethyl pregnenes |
-
1973
- 1973-11-21 US US05/417,972 patent/US3947479A/en not_active Expired - Lifetime
- 1973-12-05 CA CA187,387A patent/CA1016536A/en not_active Expired
- 1973-12-11 FI FI733780A patent/FI52589C/fi active
- 1973-12-12 DK DK673873AA patent/DK134236B/da unknown
- 1973-12-12 AU AU63544/73A patent/AU477429B2/en not_active Expired
- 1973-12-12 NL NL7317048A patent/NL7317048A/xx not_active Application Discontinuation
- 1973-12-12 GB GB5764173A patent/GB1434378A/en not_active Expired
- 1973-12-13 CH CH1749073A patent/CH591524A5/xx not_active IP Right Cessation
- 1973-12-17 AR AR251555A patent/AR203833A1/es active
- 1973-12-17 ES ES421570A patent/ES421570A1/es not_active Expired
- 1973-12-17 NO NO4811/73A patent/NO137599C/no unknown
- 1973-12-17 SE SE7317014A patent/SE404192B/xx unknown
- 1973-12-17 FR FR7345104A patent/FR2210411B1/fr not_active Expired
- 1973-12-17 IE IE02280/73A patent/IE38967B1/xx unknown
- 1973-12-17 JP JP14173773A patent/JPS5344463B2/ja not_active Expired
- 1973-12-18 AT AT1061073A patent/AT330967B/de not_active IP Right Cessation
- 1973-12-18 IL IL43847A patent/IL43847A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1016536A (en) | 1977-08-30 |
| DK134236C (fr) | 1977-03-07 |
| ATA1061073A (de) | 1975-10-15 |
| FR2210411B1 (fr) | 1976-09-03 |
| IE38967L (en) | 1974-06-18 |
| ES421570A1 (es) | 1977-01-01 |
| US3947479A (en) | 1976-03-30 |
| DK134236B (da) | 1976-10-04 |
| AU477429B2 (en) | 1975-06-12 |
| DE2362813A1 (de) | 1974-07-11 |
| AR203833A1 (es) | 1975-10-31 |
| JPS5344463B2 (fr) | 1978-11-29 |
| JPS5024426A (fr) | 1975-03-15 |
| AT330967B (de) | 1976-07-26 |
| CH591524A5 (fr) | 1977-09-30 |
| DE2362813B2 (de) | 1976-03-11 |
| IL43847A0 (en) | 1974-06-30 |
| NL7317048A (fr) | 1974-06-20 |
| FR2210411A1 (fr) | 1974-07-12 |
| SE404192B (sv) | 1978-09-25 |
| GB1434378A (en) | 1976-05-05 |
| NO137599C (no) | 1978-03-29 |
| NO137599B (no) | 1977-12-12 |
| IE38967B1 (en) | 1978-07-05 |
| FI52589B (fr) | 1977-06-30 |
| FI52589C (fi) | 1977-10-10 |
| AU6354473A (en) | 1975-06-12 |
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