IL27472A - Halogenated steroids of the androstane,norandrostane and pregnane series and their manufacture - Google Patents
Halogenated steroids of the androstane,norandrostane and pregnane series and their manufactureInfo
- Publication number
- IL27472A IL27472A IL2747267A IL2747267A IL27472A IL 27472 A IL27472 A IL 27472A IL 2747267 A IL2747267 A IL 2747267A IL 2747267 A IL2747267 A IL 2747267A IL 27472 A IL27472 A IL 27472A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- compounds
- hydrogen
- solution
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 title 1
- 150000002844 norandrostanes Chemical class 0.000 title 1
- 150000003128 pregnanes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 230000003054 hormonal effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 86
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 74
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 38
- 239000012044 organic layer Substances 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 23
- 229910052801 chlorine Inorganic materials 0.000 description 23
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
- 235000017557 sodium bicarbonate Nutrition 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
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- 235000011152 sodium sulphate Nutrition 0.000 description 12
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
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- 239000003814 drug Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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 4
- 241001465754 Metazoa Species 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
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- 235000012054 meals Nutrition 0.000 description 4
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- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000001195 anabolic effect Effects 0.000 description 3
- 230000001548 androgenic effect Effects 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
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- 229940079593 drug Drugs 0.000 description 3
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- 239000000706 filtrate Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
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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 description 3
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
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- 238000005245 sintering Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000003871 white petrolatum Substances 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
-
- 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
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Details Of Garments (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52920066A | 1966-02-23 | 1966-02-23 | |
| US60414366A | 1966-12-23 | 1966-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27472A true IL27472A (en) | 1972-03-28 |
Family
ID=27062956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2747267A IL27472A (en) | 1966-02-23 | 1967-02-22 | Halogenated steroids of the androstane,norandrostane and pregnane series and their manufacture |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS493984B1 (en(2012)) |
| AT (1) | AT280492B (en(2012)) |
| BE (1) | BE694288A (en(2012)) |
| CH (2) | CH499505A (en(2012)) |
| DE (1) | DE1618493A1 (en(2012)) |
| DK (1) | DK118461B (en(2012)) |
| ES (1) | ES337169A1 (en(2012)) |
| FI (1) | FI45319C (en(2012)) |
| FR (2) | FR8004M (en(2012)) |
| GB (3) | GB1131443A (en(2012)) |
| GR (1) | GR36816B (en(2012)) |
| IL (1) | IL27472A (en(2012)) |
| NL (1) | NL6702793A (en(2012)) |
| NO (1) | NO128764B (en(2012)) |
| SE (2) | SE337370B (en(2012)) |
| YU (1) | YU32529B (en(2012)) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH536294A (de) * | 1968-09-13 | 1973-04-30 | Schering Ag | Verfahren zur Herstellung von racemischen und optisch aktiven 4,6-Dichlor-4,6-östradienen |
-
1967
- 1967-02-16 CH CH1777069A patent/CH499505A/de not_active IP Right Cessation
- 1967-02-16 CH CH231667A patent/CH492688A/de not_active IP Right Cessation
- 1967-02-18 DE DE19671618493 patent/DE1618493A1/de active Pending
- 1967-02-20 BE BE694288D patent/BE694288A/xx unknown
- 1967-02-20 FR FR95555A patent/FR8004M/fr not_active Expired
- 1967-02-20 AT AT166067A patent/AT280492B/de not_active IP Right Cessation
- 1967-02-21 FR FR95707A patent/FR1513740A/fr not_active Expired
- 1967-02-22 GB GB839167A patent/GB1131443A/en not_active Expired
- 1967-02-22 GR GR670136816A patent/GR36816B/el unknown
- 1967-02-22 FI FI53567A patent/FI45319C/fi active
- 1967-02-22 IL IL2747267A patent/IL27472A/en unknown
- 1967-02-22 YU YU33067A patent/YU32529B/xx unknown
- 1967-02-22 GB GB1851068A patent/GB1131445A/en not_active Expired
- 1967-02-22 ES ES337169A patent/ES337169A1/es not_active Expired
- 1967-02-22 NO NO16697267A patent/NO128764B/no unknown
- 1967-02-22 GB GB1850968A patent/GB1131444A/en not_active Expired
- 1967-02-23 JP JP1125067A patent/JPS493984B1/ja active Pending
- 1967-02-23 NL NL6702793A patent/NL6702793A/xx unknown
- 1967-02-23 DK DK98467A patent/DK118461B/da unknown
- 1967-02-23 SE SE251267A patent/SE337370B/xx unknown
- 1967-02-23 SE SE1693270A patent/SE354861B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6702793A (en(2012)) | 1967-08-24 |
| DK118461B (da) | 1970-08-24 |
| GB1131443A (en) | 1968-10-23 |
| YU32529B (en) | 1975-02-28 |
| NO128764B (en(2012)) | 1974-01-07 |
| ES337169A1 (es) | 1968-02-16 |
| FR1513740A (fr) | 1968-02-16 |
| FR8004M (en(2012)) | 1970-07-27 |
| CH499505A (de) | 1970-11-30 |
| YU33067A (en) | 1974-08-31 |
| JPS493984B1 (en(2012)) | 1974-01-29 |
| GR36816B (el) | 1969-03-11 |
| AT280492B (de) | 1970-04-10 |
| GB1131444A (en) | 1968-10-23 |
| SE354861B (en(2012)) | 1973-03-26 |
| GB1131445A (en) | 1968-10-23 |
| BE694288A (en(2012)) | 1967-08-21 |
| SE337370B (en(2012)) | 1971-08-09 |
| FI45319C (fi) | 1972-05-10 |
| CH492688A (de) | 1970-06-30 |
| FI45319B (en(2012)) | 1972-01-31 |
| DE1618493A1 (de) | 1970-10-29 |
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