SE430508B - 25-halokolest-5-en-3beta,22-dioler och estrar derav - Google Patents
25-halokolest-5-en-3beta,22-dioler och estrar deravInfo
- Publication number
- SE430508B SE430508B SE8005430A SE8005430A SE430508B SE 430508 B SE430508 B SE 430508B SE 8005430 A SE8005430 A SE 8005430A SE 8005430 A SE8005430 A SE 8005430A SE 430508 B SE430508 B SE 430508B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- parts
- water
- diol
- product
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 28
- 230000015572 biosynthetic process Effects 0.000 claims description 6
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- 230000000694 effects Effects 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 claims 1
- 101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 23
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
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- 239000000243 solution Substances 0.000 description 14
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- 235000011152 sodium sulphate Nutrition 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 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 5
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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- 235000021355 Stearic acid Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
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- 239000012071 phase Substances 0.000 description 4
- 239000008159 sesame oil Substances 0.000 description 4
- 235000011803 sesame oil Nutrition 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 235000019483 Peanut oil Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 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 3
- 229930006000 Sucrose Natural products 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
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- 230000005764 inhibitory process Effects 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
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- 239000000463 material Substances 0.000 description 3
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- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 108010010803 Gelatin Chemical class 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- 239000012280 lithium aluminium hydride Substances 0.000 description 2
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- 239000003240 coconut oil Substances 0.000 description 1
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- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
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- 239000007884 disintegrant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
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- ZCLGVXACCAZJOX-UHFFFAOYSA-N ethyl 3-chloropropanoate Chemical compound CCOC(=O)CCCl ZCLGVXACCAZJOX-UHFFFAOYSA-N 0.000 description 1
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- 235000019325 ethyl cellulose Nutrition 0.000 description 1
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- 238000000605 extraction Methods 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
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- 239000005457 ice water Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- XYQKYLPARUIQOX-UHFFFAOYSA-N nonyl 2-hydroxypropanoate Chemical compound CCCCCCCCCOC(=O)C(C)O XYQKYLPARUIQOX-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 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
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940037001 sodium edetate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (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 |
|---|---|---|---|
| US06/061,731 US4230626A (en) | 1979-07-30 | 1979-07-30 | 25-Halocholest-5-ene-3β,22-diols and esters thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8005430L SE8005430L (sv) | 1981-01-31 |
| SE430508B true SE430508B (sv) | 1983-11-21 |
Family
ID=22037752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8005430A SE430508B (sv) | 1979-07-30 | 1980-07-29 | 25-halokolest-5-en-3beta,22-dioler och estrar derav |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4230626A (ja) |
| JP (1) | JPS5622799A (ja) |
| AT (1) | ATA395380A (ja) |
| AU (1) | AU532108B2 (ja) |
| BE (1) | BE884532A (ja) |
| CA (1) | CA1144539A (ja) |
| CH (1) | CH645651A5 (ja) |
| DE (1) | DE3028643A1 (ja) |
| DK (1) | DK146390C (ja) |
| ES (1) | ES8106540A1 (ja) |
| FI (1) | FI802368A (ja) |
| FR (1) | FR2462444A1 (ja) |
| GB (1) | GB2056992B (ja) |
| GR (1) | GR69347B (ja) |
| IE (1) | IE50037B1 (ja) |
| IL (1) | IL60700A0 (ja) |
| IT (1) | IT1128554B (ja) |
| NL (1) | NL8004366A (ja) |
| NO (1) | NO802277L (ja) |
| NZ (1) | NZ194490A (ja) |
| PT (1) | PT71621A (ja) |
| SE (1) | SE430508B (ja) |
| ZA (1) | ZA804617B (ja) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6407086B2 (en) | 1998-05-13 | 2002-06-18 | Novo Nordisk A/S | Meiosis regulating compounds |
| US6486145B2 (en) | 1996-12-20 | 2002-11-26 | Novo Nordisk A/S | Meiosis regulating compounds |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348328A (en) * | 1981-11-09 | 1982-09-07 | G.D. Searle & Co. | 25-Substituted-5α-cholestane-3β,22S-diol |
| US5034548A (en) * | 1987-01-30 | 1991-07-23 | E. I. Du Pont De Nemours And Company | Steroid derivatives useful as hypocholesterolemics |
| US5041432A (en) * | 1987-01-30 | 1991-08-20 | E. I. Du Pont De Nemours And Company | Steroid derivatives useful as hypocholesterolemics |
| US5219879A (en) * | 1990-03-05 | 1993-06-15 | Du Pont Merck Pharmaceutical Company | Heterocyclic steroid compounds |
| US6083497A (en) * | 1997-11-05 | 2000-07-04 | Geltex Pharmaceuticals, Inc. | Method for treating hypercholesterolemia with unsubstituted polydiallylamine polymers |
| CN113956133A (zh) * | 2021-11-08 | 2022-01-21 | 湖南科瑞生物制药股份有限公司 | 25-羟基甾体化合物的合成方法、其侧链的制备方法以及侧链中间体的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069321A (en) * | 1975-10-14 | 1978-01-17 | Merck & Co., Inc. | Blocked cholecalciferol and dihydrotachysterol 3 derivatives |
| DE2837414A1 (de) * | 1977-08-29 | 1979-03-08 | Searle & Co | 25-alkylcholesterin-derivate |
-
1979
- 1979-07-30 US US06/061,731 patent/US4230626A/en not_active Expired - Lifetime
-
1980
- 1980-07-29 IL IL60700A patent/IL60700A0/xx unknown
- 1980-07-29 FR FR8016688A patent/FR2462444A1/fr active Granted
- 1980-07-29 DE DE19803028643 patent/DE3028643A1/de active Granted
- 1980-07-29 NZ NZ194490A patent/NZ194490A/xx unknown
- 1980-07-29 FI FI802368A patent/FI802368A/fi not_active Application Discontinuation
- 1980-07-29 SE SE8005430A patent/SE430508B/sv not_active IP Right Cessation
- 1980-07-29 BE BE0/201573A patent/BE884532A/fr not_active IP Right Cessation
- 1980-07-29 GR GR62565A patent/GR69347B/el unknown
- 1980-07-29 NO NO802277A patent/NO802277L/no unknown
- 1980-07-29 DK DK326980A patent/DK146390C/da active
- 1980-07-29 AU AU60883/80A patent/AU532108B2/en not_active Ceased
- 1980-07-29 ES ES493810A patent/ES8106540A1/es not_active Expired
- 1980-07-29 CA CA000357259A patent/CA1144539A/en not_active Expired
- 1980-07-29 PT PT71621A patent/PT71621A/pt unknown
- 1980-07-29 GB GB8024722A patent/GB2056992B/en not_active Expired
- 1980-07-30 ZA ZA00804617A patent/ZA804617B/xx unknown
- 1980-07-30 IE IE1590/80A patent/IE50037B1/en unknown
- 1980-07-30 AT AT0395380A patent/ATA395380A/de not_active IP Right Cessation
- 1980-07-30 JP JP10495080A patent/JPS5622799A/ja active Granted
- 1980-07-30 NL NL8004366A patent/NL8004366A/xx not_active Application Discontinuation
- 1980-07-30 IT IT49382/80A patent/IT1128554B/it active
- 1980-07-30 CH CH580380A patent/CH645651A5/de not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6486145B2 (en) | 1996-12-20 | 2002-11-26 | Novo Nordisk A/S | Meiosis regulating compounds |
| US6759400B2 (en) | 1996-12-20 | 2004-07-06 | Novo Nordisk A/S | Meiosis regulating compounds |
| US6407086B2 (en) | 1998-05-13 | 2002-06-18 | Novo Nordisk A/S | Meiosis regulating compounds |
| USRE39678E1 (en) * | 1998-05-13 | 2007-06-05 | Novo Nordisk A/S | Meiosis regulating compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2056992A (en) | 1981-03-25 |
| ES493810A0 (es) | 1981-06-16 |
| BE884532A (fr) | 1981-01-29 |
| FR2462444B1 (ja) | 1983-05-20 |
| DK146390B (da) | 1983-09-26 |
| SE8005430L (sv) | 1981-01-31 |
| IL60700A0 (en) | 1980-09-16 |
| ZA804617B (en) | 1982-03-31 |
| IE801590L (en) | 1981-01-30 |
| GR69347B (ja) | 1982-05-18 |
| IE50037B1 (en) | 1986-02-05 |
| FI802368A (fi) | 1981-01-31 |
| ES8106540A1 (es) | 1981-06-16 |
| DK146390C (da) | 1984-03-05 |
| US4230626A (en) | 1980-10-28 |
| DK326980A (da) | 1981-01-31 |
| AU6088380A (en) | 1981-02-05 |
| NZ194490A (en) | 1983-03-15 |
| CH645651A5 (de) | 1984-10-15 |
| FR2462444A1 (fr) | 1981-02-13 |
| AU532108B2 (en) | 1983-09-15 |
| JPS5622799A (en) | 1981-03-03 |
| JPS6360037B2 (ja) | 1988-11-22 |
| IT1128554B (it) | 1986-05-28 |
| NO802277L (no) | 1981-02-02 |
| GB2056992B (en) | 1983-06-22 |
| DE3028643C2 (ja) | 1990-04-12 |
| NL8004366A (nl) | 1981-02-03 |
| CA1144539A (en) | 1983-04-12 |
| PT71621A (en) | 1980-08-01 |
| ATA395380A (de) | 1983-11-15 |
| DE3028643A1 (de) | 1981-02-19 |
| IT8049382A0 (it) | 1980-07-30 |
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