DE2943776A1 - 17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung - Google Patents
17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellungInfo
- Publication number
- DE2943776A1 DE2943776A1 DE19792943776 DE2943776A DE2943776A1 DE 2943776 A1 DE2943776 A1 DE 2943776A1 DE 19792943776 DE19792943776 DE 19792943776 DE 2943776 A DE2943776 A DE 2943776A DE 2943776 A1 DE2943776 A1 DE 2943776A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- androstan
- propyl
- group
- alkyl
- 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.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- 150000003431 steroids Chemical class 0.000 claims abstract description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- -1 7a-n-propyl-5a-androstan-3ß-ol Chemical compound 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000002280 anti-androgenic effect Effects 0.000 abstract description 12
- 230000000699 topical effect Effects 0.000 abstract description 9
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 208000002874 Acne Vulgaris Diseases 0.000 abstract description 3
- 201000004384 Alopecia Diseases 0.000 abstract description 3
- 206010020112 Hirsutism Diseases 0.000 abstract description 3
- 206010039792 Seborrhoea Diseases 0.000 abstract description 3
- 206010000496 acne Diseases 0.000 abstract description 3
- 231100000360 alopecia Toxicity 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 239000001301 oxygen Substances 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 208000008742 seborrheic dermatitis Diseases 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 210000002374 sebum Anatomy 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 210000000056 organ Anatomy 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 210000004907 gland Anatomy 0.000 description 10
- 239000003098 androgen Substances 0.000 description 8
- 239000000051 antiandrogen Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 210000005069 ears Anatomy 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- UXYRZJKIQKRJCF-TZPFWLJSSA-N mesterolone Chemical compound C1C[C@@H]2[C@@]3(C)[C@@H](C)CC(=O)C[C@@H]3CC[C@H]2[C@@H]2CC[C@H](O)[C@]21C UXYRZJKIQKRJCF-TZPFWLJSSA-N 0.000 description 6
- 229960005272 mesterolone Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 241000699800 Cricetinae Species 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 210000002307 prostate Anatomy 0.000 description 4
- 210000001625 seminal vesicle Anatomy 0.000 description 4
- 229960001712 testosterone propionate Drugs 0.000 description 4
- 201000010653 vesiculitis Diseases 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006567 deketalization reaction Methods 0.000 description 3
- 238000006266 etherification reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229940096529 carboxypolymethylene Drugs 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000004132 lipogenesis Effects 0.000 description 2
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- JVWVEDVHFCYQKJ-HGDYXINXSA-N (1's,5's,8'r,9's,10's,13's,14's)-1',10',13'-trimethylspiro[1,3-dioxolane-2,3'-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthrene]-17'-one Chemical compound C([C@@H]([C@@]1([C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@@H]2CC[C@H]1C1)C)C)C21OCCO2 JVWVEDVHFCYQKJ-HGDYXINXSA-N 0.000 description 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- QPYKYDBKQYZEKG-UHFFFAOYSA-N 2,2-dimethylpropane-1,1-diol Chemical compound CC(C)(C)C(O)O QPYKYDBKQYZEKG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052925 anhydrite Inorganic materials 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- WQZGKKKJIJFFOK-UKLRSMCWSA-N dextrose-2-13c Chemical compound OC[C@H]1OC(O)[13C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-UKLRSMCWSA-N 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000003651 hexanedioyl group Chemical group C(CCCCC(=O)*)(=O)* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- OYICOGPBEIHJEO-UHFFFAOYSA-L magnesium;acetylene;dibromide Chemical compound [Mg+2].[Br-].[Br-].C#C OYICOGPBEIHJEO-UHFFFAOYSA-L 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical class COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003429 steroid acids Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
Classifications
-
- 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
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
-
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
-
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0044—Alkenyl derivatives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
- Compounds Of Unknown Constitution (AREA)
Priority Applications (27)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792943776 DE2943776A1 (de) | 1979-10-26 | 1979-10-26 | 17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
| PT71842A PT71842B (de) | 1979-10-26 | 1980-09-26 | 17 alpha-alkylsteroide diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
| YU02566/80A YU256680A (en) | 1979-10-26 | 1980-10-07 | Process for obtaining 17 alpha-alkylsteroid |
| ES495740A ES8106539A1 (es) | 1979-10-26 | 1980-10-08 | Procedimiento para la preparacion de 17x -alcohilesteroides |
| SU802989151A SU973025A3 (ru) | 1979-10-26 | 1980-10-09 | Способ получени 17 @ -алкилстероидов |
| DK434380A DK163002C (da) | 1979-10-26 | 1980-10-14 | Analogifremgangsmaade til fremstilling af 17alfa-alkylsteroider |
| DE8080106289T DE3061638D1 (en) | 1979-10-26 | 1980-10-16 | 17-alpha-substituted steroids, preparations containing them and process for their production |
| EP80106289A EP0027961B1 (de) | 1979-10-26 | 1980-10-16 | 17-alpha-Substituierte Steroide, diese enthaltende Präparate sowie Verfahren zu ihrer Herstellung |
| AT80106289T ATE2221T1 (de) | 1979-10-26 | 1980-10-16 | 17-alpha-substituierte steroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung. |
| US06/198,383 US4344941A (en) | 1979-10-26 | 1980-10-20 | Antiandrogenic 17α-substituted steroids |
| DD80224695A DD153694A5 (de) | 1979-10-26 | 1980-10-22 | 17 alpha-alkylsteroide,diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
| AU63637/80A AU532515B2 (en) | 1979-10-26 | 1980-10-23 | 17alpha-alkyl, 17beta-ol-steroids |
| IL61332A IL61332A (en) | 1979-10-26 | 1980-10-23 | 1 alpha-methyl-17 alpha-alkyl-5 alpha-androstanes,pharmaceutical preparations containing them and process for their manufacture |
| PL1980227468A PL125169B1 (en) | 1979-10-26 | 1980-10-23 | Process for preparing novel 17-alpha-alkylsteroids |
| HU802577A HU183237B (en) | 1979-10-26 | 1980-10-24 | Process for producing 17-alpha-alkyl-steroides and compositions containing them |
| GR63214A GR71212B (en, 2012) | 1979-10-26 | 1980-10-24 | |
| NO803172A NO154231C (no) | 1979-10-26 | 1980-10-24 | Analogifremgangsmaate ved fremstilling av terapeutisk aktive 17-alfa-alkylsteroider. |
| FI803342A FI69850C (fi) | 1979-10-26 | 1980-10-24 | Foerfarande foer framstaellning av 17alfa-alkylsteroider med antiandrogen verkan |
| IE2202/80A IE52686B1 (en) | 1979-10-26 | 1980-10-24 | 17alpha-substituted steroids,pharmaceutical preparations containing them and process for their manufacture |
| ZA00806565A ZA806565B (en) | 1979-10-26 | 1980-10-24 | 17 -substituted steroids, pharamceutical preparations containing them and process for their manufacture |
| EG651/80A EG14998A (en) | 1979-10-26 | 1980-10-26 | 17a-alkyl steroids,preparations containing them and process for their manufacture |
| JP14949780A JPS5673097A (en) | 1979-10-26 | 1980-10-27 | 17 alphaaalkylsteroid* its manufacture and blend containing it and having antiandrogenic activity |
| CA000363342A CA1160216A (en) | 1979-10-26 | 1980-10-27 | 17.alpha.-SUBSTITUTED STEROIDS, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND PROCESS FOR THEIR MANUFACTURE |
| CS807263A CS228507B2 (en) | 1979-10-26 | 1980-10-27 | Method for the production of 17-alpha-alkylsteroide of an androstane serie |
| US06/380,328 US4456600A (en) | 1979-10-26 | 1982-05-20 | Antiandrogenic 17α-alkyl steroids |
| US06/620,216 US4558041A (en) | 1979-10-26 | 1984-06-13 | Antiandrogenic 17α-substituted steroids |
| US06/918,231 US4892867A (en) | 1979-10-26 | 1986-10-14 | Antiandrogenic 17-alpha-alkyl steroids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792943776 DE2943776A1 (de) | 1979-10-26 | 1979-10-26 | 17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2943776A1 true DE2943776A1 (de) | 1981-05-14 |
Family
ID=6084722
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792943776 Withdrawn DE2943776A1 (de) | 1979-10-26 | 1979-10-26 | 17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
| DE8080106289T Expired DE3061638D1 (en) | 1979-10-26 | 1980-10-16 | 17-alpha-substituted steroids, preparations containing them and process for their production |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8080106289T Expired DE3061638D1 (en) | 1979-10-26 | 1980-10-16 | 17-alpha-substituted steroids, preparations containing them and process for their production |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US4344941A (en, 2012) |
| EP (1) | EP0027961B1 (en, 2012) |
| JP (1) | JPS5673097A (en, 2012) |
| AT (1) | ATE2221T1 (en, 2012) |
| AU (1) | AU532515B2 (en, 2012) |
| CA (1) | CA1160216A (en, 2012) |
| CS (1) | CS228507B2 (en, 2012) |
| DD (1) | DD153694A5 (en, 2012) |
| DE (2) | DE2943776A1 (en, 2012) |
| DK (1) | DK163002C (en, 2012) |
| EG (1) | EG14998A (en, 2012) |
| ES (1) | ES8106539A1 (en, 2012) |
| FI (1) | FI69850C (en, 2012) |
| GR (1) | GR71212B (en, 2012) |
| HU (1) | HU183237B (en, 2012) |
| IE (1) | IE52686B1 (en, 2012) |
| IL (1) | IL61332A (en, 2012) |
| NO (1) | NO154231C (en, 2012) |
| PL (1) | PL125169B1 (en, 2012) |
| PT (1) | PT71842B (en, 2012) |
| SU (1) | SU973025A3 (en, 2012) |
| YU (1) | YU256680A (en, 2012) |
| ZA (1) | ZA806565B (en, 2012) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2943776A1 (de) * | 1979-10-26 | 1981-05-14 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | 17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
| DE3115996A1 (de) * | 1981-04-13 | 1982-11-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 17(alpha)-alkyl-17(beta)-hydroxy-1(alpha)- methyl-4-androsten-3-one-.verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten |
| DE3322285A1 (de) * | 1983-06-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1-alkyl-androsta-1,4-dien-3,17-dione, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate |
| US4885289A (en) * | 1983-12-12 | 1989-12-05 | Breuer Miklos M | Alteration of character of male beard growth |
| US5723502A (en) * | 1985-07-18 | 1998-03-03 | Proctor; Peter H. | Topical spin trap composition and method |
| US5470876A (en) * | 1985-07-18 | 1995-11-28 | Proctor; Peter H. | Topical sod for treating hair loss |
| US5728714A (en) * | 1985-07-18 | 1998-03-17 | Proctor; Peter H. | Method for treating hair loss using tempo |
| US6150405A (en) * | 1985-07-18 | 2000-11-21 | Proctor; Peter H. | Hair loss treatment with ascorbates |
| US5352442A (en) * | 1985-07-18 | 1994-10-04 | Proctor Peter H | Topical tempo |
| US5472687A (en) * | 1985-07-18 | 1995-12-05 | Proctor; Peter H. | Topical pyridine N-oxides |
| US5714510A (en) * | 1985-07-18 | 1998-02-03 | Proctor; Peter H. | Topical proxyl composition and method |
| US5716947A (en) * | 1985-07-18 | 1998-02-10 | Proctor; Peter H. | Topical doxyl composition and method |
| US5714482A (en) * | 1985-07-18 | 1998-02-03 | Proctor; Peter H. | Topical spin labels and method |
| US4898694A (en) * | 1987-11-25 | 1990-02-06 | Schwartz Arthur G | 17-Hydroxy-steroids |
| DE3824247A1 (de) * | 1988-07-13 | 1990-01-18 | Schering Ag | Neue androstan-derivate |
| EP0499779B1 (de) * | 1991-01-24 | 1996-09-11 | Rheinbraun Aktiengesellschaft | Verfahren zum Behandeln von Abfällen |
| US5328686A (en) * | 1991-10-30 | 1994-07-12 | Douglas Shander | Treatment of acne or of pseudofolliculitis barbae |
| ATE218273T1 (de) * | 1991-11-05 | 2002-06-15 | Gillette Co | Veränderung der geschindigkeit und der art des haarwuchses |
| US5364885A (en) * | 1992-11-13 | 1994-11-15 | Ahluwalia Gurpreet S | Reduction of hair growth |
| US5411991A (en) * | 1992-12-22 | 1995-05-02 | Shander; Douglas | Method of reducing hair growth employing sulfhydryl active compounds |
| US6743419B1 (en) | 1992-12-22 | 2004-06-01 | The Gillette Company | Method of reducing hair growth employing sulfhydryl active compounds |
| US5648394A (en) * | 1993-05-27 | 1997-07-15 | Boxall; Brian Alfred | Topical composition for inhibiting hair growth |
| US6414017B2 (en) | 1993-05-28 | 2002-07-02 | The Gillette Company | Inhibition of hair growth |
| US6248751B1 (en) | 1993-05-28 | 2001-06-19 | Gurpreet S. Ahluwalia | Inhibition of hair growth |
| WO1995018821A2 (en) * | 1994-01-06 | 1995-07-13 | Sri International | Novel antiandrogenic agents and related pharmaceutical compositions and methods of use |
| US5474763A (en) * | 1994-03-11 | 1995-12-12 | Shander; Douglas | Reduction of hair growth |
| US5455234A (en) * | 1994-03-16 | 1995-10-03 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
| US5468476A (en) * | 1994-03-16 | 1995-11-21 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
| ES2175084T3 (es) * | 1995-02-28 | 2002-11-16 | Gillette Co | Uso de supresores de angiogenesis para inhibir el crecimiento del pelo. |
| US5674477A (en) * | 1995-02-28 | 1997-10-07 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
| US5728736A (en) * | 1995-11-29 | 1998-03-17 | Shander; Douglas | Reduction of hair growth |
| US5652273A (en) * | 1995-11-30 | 1997-07-29 | Henry; James | Reduction of hair growth |
| ATE473759T1 (de) | 1998-05-22 | 2010-07-15 | Univ Leland Stanford Junior | Bifunktionelle moleküle sowie darauf basierende therapien. |
| US6294188B1 (en) | 1998-07-09 | 2001-09-25 | Aviana Biopharm Inc. | Methods involving changing the constitutive and stimulated secretions of the local reproductive system of women |
| US20070129282A1 (en) * | 1998-11-24 | 2007-06-07 | Ahlem Clarence N | Pharmaceutical treatments and compositions |
| PT1955700E (pt) * | 1999-09-30 | 2011-05-04 | Harbor Biosciences Inc | Tratamento terap?utico de doen?as associadas ao receptor de androg?nios |
| US7285109B2 (en) * | 2003-02-13 | 2007-10-23 | Boston Scientific Scimed, Inc. | Device and method for collapsing an angioplasty balloon |
| DK1889198T3 (da) | 2005-04-28 | 2015-02-09 | Proteus Digital Health Inc | Farma-informatiksystem |
| US9062126B2 (en) | 2005-09-16 | 2015-06-23 | Raptor Pharmaceuticals Inc. | Compositions comprising receptor-associated protein (RAP) variants specific for CR-containing proteins and uses thereof |
| NZ616673A (en) | 2009-02-20 | 2014-08-29 | To Bbb Holding B V | Glutathione-based drug delivery system |
| MX2011011833A (es) | 2009-05-06 | 2012-01-27 | Lab Skin Care Inc | Composiciones de administración dérmica que comprenden complejos de partículas de fosfato de calcio-agente activo y métodos para utilizar las mismas. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1382468A (fr) * | 1964-01-28 | 1964-12-18 | Spofa Vereinigte Pharma Werke | Procédé de préparation des composés de 3-céto-androstane 1-méthyle-substitués, et produits conformes à ceux obtenus par le présent procédé ou procédé similaire |
| US3391168A (en) * | 1965-08-23 | 1968-07-02 | Searle & Co | 1, 17-dimethyl-5-androstane-3beta, 17beta-diol and esters thereof |
| US3705180A (en) * | 1971-09-02 | 1972-12-05 | Paul D Klimstra | 17-oxygenate-2-alpha-methyl-2-methylen-5 alpha-androstan-3-ones and intermediates |
| US4039669A (en) * | 1975-08-01 | 1977-08-02 | Sterling Drug Inc. | Composition for topical application and use thereof |
| DE2943776A1 (de) * | 1979-10-26 | 1981-05-14 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | 17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
-
1979
- 1979-10-26 DE DE19792943776 patent/DE2943776A1/de not_active Withdrawn
-
1980
- 1980-09-26 PT PT71842A patent/PT71842B/pt unknown
- 1980-10-07 YU YU02566/80A patent/YU256680A/xx unknown
- 1980-10-08 ES ES495740A patent/ES8106539A1/es not_active Expired
- 1980-10-09 SU SU802989151A patent/SU973025A3/ru active
- 1980-10-14 DK DK434380A patent/DK163002C/da not_active IP Right Cessation
- 1980-10-16 DE DE8080106289T patent/DE3061638D1/de not_active Expired
- 1980-10-16 AT AT80106289T patent/ATE2221T1/de not_active IP Right Cessation
- 1980-10-16 EP EP80106289A patent/EP0027961B1/de not_active Expired
- 1980-10-20 US US06/198,383 patent/US4344941A/en not_active Expired - Lifetime
- 1980-10-22 DD DD80224695A patent/DD153694A5/de not_active IP Right Cessation
- 1980-10-23 PL PL1980227468A patent/PL125169B1/pl unknown
- 1980-10-23 IL IL61332A patent/IL61332A/xx not_active IP Right Cessation
- 1980-10-23 AU AU63637/80A patent/AU532515B2/en not_active Ceased
- 1980-10-24 HU HU802577A patent/HU183237B/hu not_active IP Right Cessation
- 1980-10-24 GR GR63214A patent/GR71212B/el unknown
- 1980-10-24 ZA ZA00806565A patent/ZA806565B/xx unknown
- 1980-10-24 IE IE2202/80A patent/IE52686B1/en not_active IP Right Cessation
- 1980-10-24 NO NO803172A patent/NO154231C/no unknown
- 1980-10-24 FI FI803342A patent/FI69850C/fi not_active IP Right Cessation
- 1980-10-26 EG EG651/80A patent/EG14998A/xx active
- 1980-10-27 CA CA000363342A patent/CA1160216A/en not_active Expired
- 1980-10-27 JP JP14949780A patent/JPS5673097A/ja active Granted
- 1980-10-27 CS CS807263A patent/CS228507B2/cs unknown
-
1982
- 1982-05-20 US US06/380,328 patent/US4456600A/en not_active Expired - Lifetime
-
1984
- 1984-06-13 US US06/620,216 patent/US4558041A/en not_active Expired - Fee Related
-
1986
- 1986-10-14 US US06/918,231 patent/US4892867A/en not_active Expired - Fee Related
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