IL37083A - תערובות אנטי-אנדורגניות המכילות אנילידים ותיואנילידים מותמרים - Google Patents
תערובות אנטי-אנדורגניות המכילות אנילידים ותיואנילידים מותמריםInfo
- Publication number
- IL37083A IL37083A IL37083A IL3708371A IL37083A IL 37083 A IL37083 A IL 37083A IL 37083 A IL37083 A IL 37083A IL 3708371 A IL3708371 A IL 3708371A IL 37083 A IL37083 A IL 37083A
- Authority
- IL
- Israel
- Prior art keywords
- composition according
- active ingredient
- nitro
- composition
- israel
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 80
- 230000002280 anti-androgenic effect Effects 0.000 title claims description 13
- 150000003931 anilides Chemical class 0.000 title description 12
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 40
- 239000004480 active ingredient Substances 0.000 claims description 33
- 241001465754 Metazoa Species 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000004615 ingredient Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- -1 3-chloro- -nitroisobutyranilide Chemical group 0.000 claims description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000000796 flavoring agent Substances 0.000 claims description 9
- 230000003139 buffering effect Effects 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 235000013355 food flavoring agent Nutrition 0.000 claims description 8
- 235000003599 food sweetener Nutrition 0.000 claims description 8
- 239000003755 preservative agent Substances 0.000 claims description 8
- 239000000375 suspending agent Substances 0.000 claims description 8
- 239000003765 sweetening agent Substances 0.000 claims description 8
- 230000008719 thickening Effects 0.000 claims description 8
- 239000004150 EU approved colour Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000004040 coloring Methods 0.000 claims description 7
- 239000003995 emulsifying agent Substances 0.000 claims description 7
- 230000001804 emulsifying effect Effects 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 7
- 230000003019 stabilising effect Effects 0.000 claims description 7
- 238000009736 wetting Methods 0.000 claims description 7
- 239000000080 wetting agent Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000006172 buffering agent Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- 239000002562 thickening agent Substances 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 229920002472 Starch Polymers 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000011630 iodine Chemical group 0.000 claims description 5
- 229910052740 iodine Chemical group 0.000 claims description 5
- 235000019359 magnesium stearate Nutrition 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 235000019698 starch Nutrition 0.000 claims description 5
- 239000008107 starch Substances 0.000 claims description 5
- 239000003826 tablet Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000006052 feed supplement Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical group [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- 239000001828 Gelatine Substances 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WMFDYXPRRHDSQS-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 WMFDYXPRRHDSQS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 230000003204 osmotic effect Effects 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- GFXKETSUNPHWTM-UHFFFAOYSA-N 2-methyl-2-nitro-N-phenylpropanamide Chemical compound [N+](=O)([O-])C(C(=O)NC1=CC=CC=C1)(C)C GFXKETSUNPHWTM-UHFFFAOYSA-N 0.000 claims 1
- GETMKVRSDFVVHL-UHFFFAOYSA-N 2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound CC(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 GETMKVRSDFVVHL-UHFFFAOYSA-N 0.000 claims 1
- WDRCPKDLZOQCFU-UHFFFAOYSA-N 2-methyl-n-phenylpropanamide Chemical compound CC(C)C(=O)NC1=CC=CC=C1 WDRCPKDLZOQCFU-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 239000006193 liquid solution Substances 0.000 claims 1
- 239000006194 liquid suspension Substances 0.000 claims 1
- VVFDYYARGWIPOT-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 VVFDYYARGWIPOT-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229920000609 methyl cellulose Polymers 0.000 description 7
- 239000001923 methylcellulose Substances 0.000 description 7
- 235000010981 methylcellulose Nutrition 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000008215 water for injection Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 235000013372 meat Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 4
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000051 antiandrogen Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 230000001605 fetal effect Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 210000004392 genitalia Anatomy 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 201000004240 prostatic hypertrophy Diseases 0.000 description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 3
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 229940011871 estrogen Drugs 0.000 description 2
- 239000000262 estrogen Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000010196 hermaphroditism Effects 0.000 description 2
- 235000013622 meat product Nutrition 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 230000001473 noxious effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 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
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- UTKUVRNVYFTEHF-UHFFFAOYSA-N 4-nitro-3-(trifluoromethyl)aniline Chemical compound NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 UTKUVRNVYFTEHF-UHFFFAOYSA-N 0.000 description 1
- ASPDJZINBYYZRU-UHFFFAOYSA-N 5-amino-2-chlorobenzotrifluoride Chemical compound NC1=CC=C(Cl)C(C(F)(F)F)=C1 ASPDJZINBYYZRU-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000283725 Bos Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001379910 Ephemera danica Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- 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 1
- 108010061951 Methemoglobin Proteins 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010036049 Polycystic ovaries Diseases 0.000 description 1
- 241000283080 Proboscidea <mammal> Species 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 201000004326 Sulfhemoglobinemia Diseases 0.000 description 1
- 206010042490 Sulphaemoglobinaemia Diseases 0.000 description 1
- KFDLHDGFDLHFRW-UHFFFAOYSA-N [O-][N+](Br)=O Chemical compound [O-][N+](Br)=O KFDLHDGFDLHFRW-UHFFFAOYSA-N 0.000 description 1
- CTBNYRDNMZZICP-UHFFFAOYSA-N [O-][N+](I)=O Chemical group [O-][N+](I)=O CTBNYRDNMZZICP-UHFFFAOYSA-N 0.000 description 1
- 238000002679 ablation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 201000010063 epididymitis Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940106582 estrogenic substances Drugs 0.000 description 1
- JKKFKPJIXZFSSB-CBZIJGRNSA-N estrone 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-N 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000001794 hormone therapy Methods 0.000 description 1
- 230000001969 hypertrophic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002485 inorganic esters Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- FQAKRUVXOVCWMO-UHFFFAOYSA-N n-[4-chloro-3-(trifluoromethyl)phenyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 FQAKRUVXOVCWMO-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL37083A IL37083A (he) | 1971-06-17 | 1971-06-17 | תערובות אנטי-אנדורגניות המכילות אנילידים ותיואנילידים מותמרים |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL37083A IL37083A (he) | 1971-06-17 | 1971-06-17 | תערובות אנטי-אנדורגניות המכילות אנילידים ותיואנילידים מותמרים |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL37083A0 IL37083A0 (en) | 1971-08-25 |
| IL37083A true IL37083A (he) | 1977-02-28 |
Family
ID=11045982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL37083A IL37083A (he) | 1971-06-17 | 1971-06-17 | תערובות אנטי-אנדורגניות המכילות אנילידים ותיואנילידים מותמרים |
Country Status (1)
| Country | Link |
|---|---|
| IL (1) | IL37083A (he) |
-
1971
- 1971-06-17 IL IL37083A patent/IL37083A/he unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL37083A0 (en) | 1971-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3875229A (en) | Substituted carboxanilides | |
| US4139638A (en) | Methods for the treatment of hirsutism | |
| US4161540A (en) | Antiandrogenic agents and methods for the treatment of androgen dependent disease states | |
| US3847988A (en) | Substituted imidates | |
| US4536516A (en) | Alkene derivatives | |
| US3995060A (en) | Antiandrogenic agents and method for the treatment of androgen dependent disease states | |
| GB2106105A (en) | Benzo-heterocycles | |
| NO138374B (no) | Analogifremgangsmaate til fremstilling av terapeutisk virksomme 4-fenoksyfenoksyalkankarboksylsyrederivater | |
| DE3876846T2 (de) | Morpholinderivate und deren verwendung. | |
| JPS62142198A (ja) | 新規中間体 | |
| PT94832B (pt) | Processo para a preparacao de derivados substituidos de aminoalcoxibenzeno e de composicoes farmaceuticas que os contem | |
| US3987182A (en) | Novel benzimidazoles useful as anti-androgens | |
| KR0180225B1 (ko) | 항프로게스테론양 화합물로 이루어지는 배란 자극용 제약조성물 | |
| US4654352A (en) | Method for treating diarrhea with benzothiophene derivatives | |
| JP2001524524A (ja) | エストロンスルファターゼのインヒビターとしてのステロイド3−o−スルファメート誘導体 | |
| US3454643A (en) | 5 - (tertiaryaminoalkylene)-5 hydroxy- and 5-(tertiary aminoalkylidene) - dibenzocycloheptatrienes,and salts thereof | |
| US4144270A (en) | Substituted anilides as anti-androgens | |
| FR2540109A1 (fr) | Imino-2 pyrrolidines, leur procede de preparation et leurs applications en therapeutique | |
| IL37083A (he) | תערובות אנטי-אנדורגניות המכילות אנילידים ותיואנילידים מותמרים | |
| US3965176A (en) | Novel substituted amidines | |
| EP0174064B1 (en) | Compositions and compounds for the treatment of prostatic adenoma | |
| RU2091019C1 (ru) | Контрацептивное средство для животных и способ его получения | |
| JPH01250316A (ja) | 抗脂血剤 | |
| US4567000A (en) | 11-Difluoromethylene steroids | |
| DE1298993B (de) | 3-Oxo-8ª‡-17ª‰-hydroxy-17ª‡-aethinyl-oestr-5(10)-en in seiner racemischen und linksdrehenden Form und Verfahren zur Herstellung dieser Verbindungen |