IL42779A - 17alpha-acyloxy-3-oxo-androst-4-ene 17beta-carboxylic acid esters - Google Patents
17alpha-acyloxy-3-oxo-androst-4-ene 17beta-carboxylic acid estersInfo
- Publication number
- IL42779A IL42779A IL42779A IL4277973A IL42779A IL 42779 A IL42779 A IL 42779A IL 42779 A IL42779 A IL 42779A IL 4277973 A IL4277973 A IL 4277973A IL 42779 A IL42779 A IL 42779A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- compounds
- group
- formula
- hydroxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 32
- -1 chloro- Chemical class 0.000 claims description 31
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 13
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 claims description 11
- 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 claims description 10
- 229910052731 fluorine Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
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- 125000000217 alkyl group Chemical group 0.000 claims description 9
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- 239000006071 cream Substances 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
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- 229910021608 Silver(I) fluoride Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
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- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 241000792859 Enema Species 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 229940117975 chromium trioxide Drugs 0.000 claims description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 4
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007920 enema Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 238000007911 parenteral administration Methods 0.000 claims description 4
- 239000000829 suppository Substances 0.000 claims description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
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- 239000000443 aerosol Substances 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
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- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- JWEQRJSCTFBRSI-PCLIKHOPSA-N rboxylate Chemical compound COC(=O)C1C(N2C3=O)C4=CC=CC=C4OC1(C)N=C2S\C3=C\C(C=1)=CC=C(OC)C=1COC1=CC=CC=C1C JWEQRJSCTFBRSI-PCLIKHOPSA-N 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 229940107816 ammonium iodide Drugs 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
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- 229940079360 enema for constipation Drugs 0.000 claims description 2
- 239000007943 implant Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 claims 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 84
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 35
- 150000003431 steroids Chemical class 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
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- 239000000047 product Substances 0.000 description 21
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000013078 crystal Substances 0.000 description 16
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- 239000007787 solid Substances 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000006260 foam Substances 0.000 description 10
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229940057995 liquid paraffin Drugs 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 8
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- 238000004587 chromatography analysis Methods 0.000 description 8
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- 238000003797 solvolysis reaction Methods 0.000 description 2
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 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 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
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- QPKRMWAGAODSHL-UHFFFAOYSA-N CC(=O)C.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl Chemical compound CC(=O)C.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl QPKRMWAGAODSHL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
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- 101100490139 Mus musculus Acer3 gene Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229930193140 Neomycin Natural products 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000001780 adrenocortical effect Effects 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical class [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 208000020670 canker sore Diseases 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
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- 239000004359 castor oil Substances 0.000 description 1
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- 239000003729 cation exchange resin Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- RCTFHBWTYQOVGJ-UHFFFAOYSA-N chloroform;dichloromethane Chemical compound ClCCl.ClC(Cl)Cl RCTFHBWTYQOVGJ-UHFFFAOYSA-N 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
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- 239000000499 gel Substances 0.000 description 1
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
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- 150000002334 glycols Chemical class 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- OILCOWNNRFOYBT-UHFFFAOYSA-N hydroxymethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCO OILCOWNNRFOYBT-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 229940096978 oral tablet Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 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 1
- 238000010992 reflux Methods 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- 230000008719 thickening Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3383472A GB1438940A (en) | 1972-07-19 | 1972-07-19 | 17beta-haloalkoxycarbonyl-17alpha-oxysteroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL42779A true IL42779A (en) | 1977-04-29 |
Family
ID=10358062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42779A IL42779A (en) | 1972-07-19 | 1973-07-18 | 17alpha-acyloxy-3-oxo-androst-4-ene 17beta-carboxylic acid esters |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3856828A (xx) |
| JP (1) | JPS5750800B2 (xx) |
| AU (1) | AU473714B2 (xx) |
| BE (1) | BE802481R (xx) |
| CA (1) | CA1034565A (xx) |
| CH (1) | CH619968A5 (xx) |
| DE (1) | DE2336633A1 (xx) |
| DK (1) | DK133158C (xx) |
| ES (1) | ES417012A2 (xx) |
| FR (1) | FR2192840B2 (xx) |
| GB (1) | GB1438940A (xx) |
| IE (1) | IE37925B1 (xx) |
| IL (1) | IL42779A (xx) |
| LU (1) | LU68039A1 (xx) |
| NL (1) | NL7309992A (xx) |
| PH (1) | PH14795A (xx) |
| SE (1) | SE396079B (xx) |
| ZA (1) | ZA734896B (xx) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3943124A (en) * | 1970-12-17 | 1976-03-09 | Gordon Hanley Phillipps | Chemical compounds |
| US3989686A (en) * | 1972-06-15 | 1976-11-02 | Glaxo Laboratories Limited | Anaesthetic steroids of the androstane series and process for preparing same |
| GB1514476A (en) * | 1974-08-30 | 1978-06-14 | Glaxo Lab Ltd | Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates |
| US4093721A (en) * | 1974-08-30 | 1978-06-06 | Glaxo Laboratories Limited | Pharmaceutical compositions of 6α,9α-difluoro-androst-4-ene-17β-carboxylates and derivatives thereof |
| DK118776A (da) * | 1975-03-21 | 1976-09-22 | Schering Ag | Pregnansyrederivater |
| CH628355A5 (de) * | 1976-02-24 | 1982-02-26 | Ciba Geigy Ag | Verfahren zur herstellung neuer androstadien-17beta-carbonsaeuren und ihrer ester und salze. |
| IT1114534B (it) * | 1978-02-08 | 1986-01-27 | Glaxo Group Ltd | Steroide anti-infiammatorio della serie dell'androstano composizioni che lo contengono e procedimento per produrlo |
| US4187301A (en) * | 1978-04-05 | 1980-02-05 | Syntex (U.S.A.) Inc. | 17 Beta-thiocarboxylic acid esters of 6 alpha, 6 beta-difluoro-3-oxoandrost-4-enes |
| US4188385A (en) * | 1978-04-05 | 1980-02-12 | Syntex (U.S.A.) Inc. | Thioetianic acid derivatives |
| US4252729A (en) * | 1978-05-12 | 1981-02-24 | Hoffmann-La Roche Inc. | Steroids and process for their manufacture |
| AU544517B2 (en) * | 1980-02-15 | 1985-06-06 | Glaxo Group Limited | Androstane carbothioates |
| SE449106B (sv) * | 1980-07-10 | 1987-04-06 | Otsuka Pharma Co Ltd | Steroid med anti-inflammatorisk verkan samt komposition innehallande denna |
| US4996335A (en) * | 1980-07-10 | 1991-02-26 | Nicholas S. Bodor | Soft steroids having anti-inflammatory activity |
| US4710495A (en) * | 1980-07-10 | 1987-12-01 | Otsuka Pharmaceutical Co., Ltd. | Soft steroids having anti-inflammatory activity |
| PT73772B (en) * | 1980-10-06 | 1983-10-14 | Glaxo Group Ltd | Topically administrable pharmaceutical compositions containing anti-inflammatory steroids |
| 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 |
| IL78144A0 (en) * | 1985-04-04 | 1986-07-31 | Draco Ab | Novel androstane-17beta-carboxylic acid esters |
| SE8501693D0 (sv) * | 1985-04-04 | 1985-04-04 | Draco Ab | Novel 16,17-acetalsubstituted androstane-17beta-carboxylic acid esters |
| US4686214A (en) * | 1985-10-30 | 1987-08-11 | Alcon Laboratories, Inc. | Anti-inflammatory compounds for ophthalmic use |
| WO1989003390A1 (en) * | 1987-10-13 | 1989-04-20 | Bodor Nicholas S | Soft steroids having anti-inflammatory activity |
| US5981517A (en) * | 1996-05-09 | 1999-11-09 | Soft Drugs, Inc. | Androstene derivatives |
| GB0015876D0 (en) * | 2000-06-28 | 2000-08-23 | Novartis Ag | Organic compounds |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| DK1305329T4 (da) * | 2000-08-05 | 2015-06-15 | Glaxo Group Ltd | 6alpha, 9alpha-difluor-17alpha-(2-furanylcarboxyl)oxy-11beta-hydroxy-16alpha-methyl-3-oxo-androst-1,4-dien-17-carbothiosyre-S-fluormethylester som et antiinflammatorisk middel |
| US6777400B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6787532B2 (en) | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
| GB0019172D0 (en) * | 2000-08-05 | 2000-09-27 | Glaxo Group Ltd | Novel compounds |
| US6759398B2 (en) * | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| US6858596B2 (en) * | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| UA77656C2 (en) | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
| PL366937A1 (en) * | 2001-04-30 | 2005-02-07 | Glaxo Group Limited | Anti-inflammatory 17.beta.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.alpha |
| GB0125259D0 (en) * | 2001-10-20 | 2001-12-12 | Glaxo Group Ltd | Novel compounds |
| AU2003202044A1 (en) * | 2002-01-15 | 2003-09-09 | Glaxo Group Limited | 17.alpha-cycloalkyl/cycloylkenyl esters of alkyl-or haloalkyl-androst-4-en-3-on-11.beta.,17.alpha.-diol 17.beta.-carboxylates as anti-inflammatory agents |
| WO2003062259A2 (en) * | 2002-01-21 | 2003-07-31 | Glaxo Group Limited | Non-aromatic 17.alpha.-esters of androstane-17.beta.-carboxylate esters as anti-inflammatory agents |
| GB0202216D0 (en) * | 2002-01-31 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| US20050175545A1 (en) * | 2002-02-04 | 2005-08-11 | Keith Biggadike | Formulation for inhalation comprising a glucocorticoid and a beta 2-adrenoreceptor agonist |
| GB0202635D0 (en) * | 2002-02-05 | 2002-03-20 | Glaxo Wellcome Mfg Pte Ltd | Formulation containing novel anti-inflammatory androstane derivative |
| GB2389530B (en) | 2002-06-14 | 2007-01-10 | Cipla Ltd | Pharmaceutical compositions |
| GB0225287D0 (en) * | 2002-10-30 | 2002-12-11 | Glaxo Group Ltd | Novel compounds |
| DE602004008083T2 (de) * | 2003-06-19 | 2008-04-24 | Nicholas S. Gainsville Bodor | Verstärkung der aktivität und/oder wirkdauer von ausgewählten entzündungshemmenden steroiden |
| GB0316290D0 (en) * | 2003-07-11 | 2003-08-13 | Glaxo Group Ltd | Novel compounds |
| WO2006072599A2 (en) * | 2005-01-10 | 2006-07-13 | Glaxo Group Limited | Androstane 17-alpha carbonate derivatives for use in the treatment of allergic and inflammatory conditions |
| US20090124588A1 (en) * | 2005-01-10 | 2009-05-14 | Glaxo Group Limited | Androstane 17-Alpha-Carbonate for Use in the Treatment of Inflammatory and Allergic Conditions |
| GB0507165D0 (en) * | 2005-04-08 | 2005-05-18 | Glaxo Group Ltd | Novel crystalline pharmaceutical product |
| US20070245924A1 (en) * | 2006-04-20 | 2007-10-25 | Hofmann Michael A | Reduced abrasion of titanium dioxide pigments produced from the chloride process |
| GB0615108D0 (en) * | 2006-07-28 | 2006-09-06 | Glaxo Group Ltd | Novel formulations |
| HUE034570T2 (en) | 2010-10-27 | 2018-02-28 | Hovione Int Ltd | Electrophilic reagents for mono-gene methylation, their preparation and use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636010A (en) * | 1968-12-23 | 1972-01-18 | Ciba Geigy Corp | Esters of steroid-17-carboxylic acids |
| GB1384372A (en) * | 1971-01-20 | 1975-02-19 | Glaxo Lab Ltd | Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids |
-
1972
- 1972-07-19 GB GB3383472A patent/GB1438940A/en not_active Expired
-
1973
- 1973-07-16 US US00379471A patent/US3856828A/en not_active Expired - Lifetime
- 1973-07-17 ES ES417012A patent/ES417012A2/es not_active Expired
- 1973-07-18 IE IE1223/73A patent/IE37925B1/xx unknown
- 1973-07-18 NL NL7309992A patent/NL7309992A/xx not_active Application Discontinuation
- 1973-07-18 CH CH1047973A patent/CH619968A5/de not_active IP Right Cessation
- 1973-07-18 SE SE7310070A patent/SE396079B/xx unknown
- 1973-07-18 AU AU58252/73A patent/AU473714B2/en not_active Expired
- 1973-07-18 JP JP48082604A patent/JPS5750800B2/ja not_active Expired
- 1973-07-18 DE DE19732336633 patent/DE2336633A1/de not_active Withdrawn
- 1973-07-18 BE BE133591A patent/BE802481R/xx active
- 1973-07-18 CA CA176,804A patent/CA1034565A/en not_active Expired
- 1973-07-18 FR FR7326267A patent/FR2192840B2/fr not_active Expired
- 1973-07-18 IL IL42779A patent/IL42779A/en unknown
- 1973-07-18 PH PH14839A patent/PH14795A/en unknown
- 1973-07-18 ZA ZA734896A patent/ZA734896B/xx unknown
- 1973-07-18 DK DK397073A patent/DK133158C/da not_active IP Right Cessation
- 1973-07-18 LU LU68039A patent/LU68039A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4980058A (xx) | 1974-08-02 |
| ES417012A2 (es) | 1976-04-16 |
| FR2192840A2 (xx) | 1974-02-15 |
| LU68039A1 (xx) | 1973-09-26 |
| US3856828A (en) | 1974-12-24 |
| AU5825273A (en) | 1975-01-23 |
| DK133158C (da) | 1976-09-06 |
| ZA734896B (en) | 1974-12-24 |
| IE37925L (en) | 1974-01-19 |
| DE2336633A1 (de) | 1974-01-31 |
| GB1438940A (en) | 1976-06-09 |
| AU473714B2 (en) | 1976-07-01 |
| BE802481R (fr) | 1974-01-18 |
| NL7309992A (xx) | 1974-01-22 |
| CA1034565A (en) | 1978-07-11 |
| JPS5750800B2 (xx) | 1982-10-28 |
| DK133158B (da) | 1976-03-29 |
| CH619968A5 (xx) | 1980-10-31 |
| SE396079B (sv) | 1977-09-05 |
| PH14795A (en) | 1981-12-09 |
| FR2192840B2 (xx) | 1976-12-24 |
| IE37925B1 (en) | 1977-11-09 |
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