IL95451A - חומצות אומגה פנילאמינו אלקנואיות המותמרות בגרעין הארומטי ע" י 91-נור סטרואיד תהליך להכנתן ותכשירי רוקחותהמכילים אותן - Google Patents
חומצות אומגה פנילאמינו אלקנואיות המותמרות בגרעין הארומטי ע" י 91-נור סטרואיד תהליך להכנתן ותכשירי רוקחותהמכילים אותןInfo
- Publication number
- IL95451A IL95451A IL9545190A IL9545190A IL95451A IL 95451 A IL95451 A IL 95451A IL 9545190 A IL9545190 A IL 9545190A IL 9545190 A IL9545190 A IL 9545190A IL 95451 A IL95451 A IL 95451A
- Authority
- IL
- Israel
- Prior art keywords
- carbon atoms
- radical
- products
- formula
- alkyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 150000003839 salts Chemical class 0.000 title abstract description 13
- 239000002253 acid Substances 0.000 title description 6
- 150000007513 acids Chemical group 0.000 title description 4
- 125000003118 aryl group Chemical group 0.000 title description 4
- -1 amine salt Chemical class 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 150000003254 radicals Chemical class 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229940046836 anti-estrogen Drugs 0.000 claims description 4
- 230000001833 anti-estrogenic effect Effects 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 239000000328 estrogen antagonist Substances 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- 230000000962 progestomimetic effect Effects 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000003098 androgen Substances 0.000 claims description 3
- 230000002280 anti-androgenic effect Effects 0.000 claims description 3
- 230000001028 anti-proliverative effect Effects 0.000 claims description 3
- 239000000051 antiandrogen Substances 0.000 claims description 3
- 229940011871 estrogen Drugs 0.000 claims description 3
- 239000000262 estrogen Substances 0.000 claims description 3
- 125000004436 sodium atom Chemical group 0.000 claims description 3
- 150000003431 steroids Chemical class 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 101150101604 ACVR1B gene Proteins 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 229910003202 NH4 Inorganic materials 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 2
- 238000010306 acid treatment Methods 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 230000036039 immunity Effects 0.000 claims description 2
- 206010022437 insomnia Diseases 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 7
- 229910052705 radium Inorganic materials 0.000 abstract description 3
- 229910052701 rubidium Inorganic materials 0.000 abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract 1
- 238000002483 medication Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 101
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 42
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- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- 239000000377 silicon dioxide Substances 0.000 description 21
- 159000000000 sodium salts Chemical class 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 16
- 238000004809 thin layer chromatography Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 10
- 229940088597 hormone Drugs 0.000 description 10
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- 239000012074 organic phase Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 8
- 239000003862 glucocorticoid Substances 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 238000013019 agitation Methods 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 229960003957 dexamethasone Drugs 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 4
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical class OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
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- 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 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 108010077895 Sarcosine Chemical class 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010047486 Virilism Diseases 0.000 description 1
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- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
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- 238000007792 addition Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 108010080146 androgen receptors Proteins 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Chemical class OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 201000008275 breast carcinoma Diseases 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 229960004203 carnitine Drugs 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Chemical class C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 229940124558 contraceptive agent Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Chemical class SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 229960002433 cysteine Drugs 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- HBFXVTVOSLPOEY-UHFFFAOYSA-N ethoxyethane;2-propan-2-yloxypropane Chemical compound CCOCC.CC(C)OC(C)C HBFXVTVOSLPOEY-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 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
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Chemical class OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000938 luteal effect Effects 0.000 description 1
- 230000029849 luteinization Effects 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000002583 male contraceptive agent Substances 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/42—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of mineralocorticosteroids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8911173A FR2651233B1 (fr) | 1989-08-23 | 1989-08-23 | Nouveaux acides omega-phenylamino alcanouiques substitues sur le noyau aromatique par un radical derive de 19-norsterouides, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL95451A0 IL95451A0 (en) | 1991-06-30 |
| IL95451A true IL95451A (he) | 1995-07-31 |
Family
ID=9384880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9545190A IL95451A (he) | 1989-08-23 | 1990-08-21 | חומצות אומגה פנילאמינו אלקנואיות המותמרות בגרעין הארומטי ע" י 91-נור סטרואיד תהליך להכנתן ותכשירי רוקחותהמכילים אותן |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5166146A (he) |
| EP (1) | EP0414606B1 (he) |
| JP (1) | JP3026997B2 (he) |
| KR (1) | KR910004655A (he) |
| CN (1) | CN1033808C (he) |
| AT (1) | ATE113605T1 (he) |
| AU (1) | AU634569B2 (he) |
| CA (1) | CA2022648A1 (he) |
| DE (1) | DE69013815T2 (he) |
| DK (1) | DK0414606T3 (he) |
| ES (1) | ES2063313T3 (he) |
| FR (1) | FR2651233B1 (he) |
| HU (1) | HU208154B (he) |
| IE (1) | IE65922B1 (he) |
| IL (1) | IL95451A (he) |
| MX (1) | MX22020A (he) |
| PT (1) | PT95066B (he) |
| RU (1) | RU2041236C1 (he) |
| ZA (1) | ZA906341B (he) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5780220A (en) * | 1994-05-19 | 1998-07-14 | Trustees Of The University Of Pennsylvania | Methods and compositions for inhibiting HIV replication |
| US5639598A (en) * | 1994-05-19 | 1997-06-17 | The Trustees Of The University Of Pennsylvania | Method and kit for identification of antiviral agents capable of abrogating HIV Vpr-Rip-1 binding interactions |
| RU2200732C2 (ru) * | 1997-08-12 | 2003-03-20 | Глэксо Вэллкам Инк. | Производные трифенилэтилена, способы лечения и профилактики остеопороза, рака груди и сердечно-сосудистого заболевания |
| US6090798A (en) * | 1997-12-19 | 2000-07-18 | Alcon Laboratories, Inc. | Treatment of GLC1A glaucoma with glucocorticoid antagonists |
| WO2011150209A1 (en) | 2010-05-26 | 2011-12-01 | Corcept Therapeutics, Inc. | Treatment of muscular dystrophy |
| JP6821582B2 (ja) | 2015-03-02 | 2021-01-27 | コーセプト セラピューティクス， インコーポレイテッド | Ａｃｔｈ分泌腫瘍を処置するための糖質コルチコイドレセプターアンタゴニストおよびソマトスタチンアナログの使用 |
| JP6754533B2 (ja) | 2015-03-30 | 2020-09-16 | コーセプト セラピューティクス， インコーポレイテッド | 副腎機能不全を処置するための糖質コルチコイドと組み合わせた糖質コルチコイドレセプターアンタゴニストの使用 |
| MX383318B (es) | 2015-08-13 | 2025-03-13 | Corcept Therapeutics Inc | Metodo para diagnosticar de manera diferencial el sindrome de cushing dependiente de la corticotropina. |
| JP6765443B2 (ja) | 2016-01-19 | 2020-10-07 | コーセプト セラピューティクス， インコーポレイテッド | 異所性クッシング症候群の鑑別診断 |
| US9943505B2 (en) | 2016-09-09 | 2018-04-17 | Corcept Therapeutics, Inc. | Glucocorticoid receptor modulators to treat pancreatic cancer |
| WO2018102369A1 (en) | 2016-11-30 | 2018-06-07 | Arno Therapeutics, Inc. | Methods for onapristone synthesis dehydration and deprotection |
| AU2018244928B2 (en) | 2017-03-31 | 2023-10-19 | Corcept Therapeutics, Inc. | Glucocorticoid receptor modulators to treat cervical cancer |
| WO2018236749A2 (en) | 2017-06-20 | 2018-12-27 | Corcept Therapeutics, Inc. | Methods of treating neuroepithelial tumors using selective glucocorticoid receptor modulators |
| EP4263807A2 (en) | 2020-12-18 | 2023-10-25 | Instil Bio (Uk) Limited | Processing of tumor infiltrating lymphocytes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2566779B2 (fr) * | 1984-06-29 | 1987-03-06 | Roussel Uclaf | Nouveaux derives steroides substitues en 11b, leur procede de preparation et leur application comme medicaments |
| FR2596395B1 (fr) * | 1986-03-26 | 1989-05-26 | Roussel Uclaf | Nouveaux steroides comportant un cycle spirannique en position 17, leur procede de preparation, leur application comme medicaments et les compositions les renfermant |
| DE3619413C2 (de) * | 1986-06-10 | 2000-04-06 | Schering Ag | 9alpha, 10alpha-Methylen-Estrene, deren Herstellung und diese enthaltende pharmazeutische Präparate |
| FR2620707B1 (fr) * | 1987-09-18 | 1989-12-08 | Roussel Uclaf | Nouveaux steroides comportant un cycle spirannique a 3, 4 ou 6 chainons en position 17, leur procede et des intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
-
1989
- 1989-08-23 FR FR8911173A patent/FR2651233B1/fr not_active Expired - Fee Related
-
1990
- 1990-08-03 CA CA002022648A patent/CA2022648A1/fr not_active Abandoned
- 1990-08-10 ZA ZA906341A patent/ZA906341B/xx unknown
- 1990-08-16 US US07/568,597 patent/US5166146A/en not_active Expired - Lifetime
- 1990-08-20 MX MX2202090A patent/MX22020A/es unknown
- 1990-08-20 JP JP02217281A patent/JP3026997B2/ja not_active Expired - Lifetime
- 1990-08-21 IL IL9545190A patent/IL95451A/he not_active IP Right Cessation
- 1990-08-22 KR KR1019900012958A patent/KR910004655A/ko not_active Abandoned
- 1990-08-22 AT AT90402328T patent/ATE113605T1/de not_active IP Right Cessation
- 1990-08-22 DK DK90402328.0T patent/DK0414606T3/da active
- 1990-08-22 AU AU61189/90A patent/AU634569B2/en not_active Ceased
- 1990-08-22 HU HU905275A patent/HU208154B/hu not_active IP Right Cessation
- 1990-08-22 IE IE303190A patent/IE65922B1/en not_active IP Right Cessation
- 1990-08-22 PT PT95066A patent/PT95066B/pt not_active IP Right Cessation
- 1990-08-22 ES ES90402328T patent/ES2063313T3/es not_active Expired - Lifetime
- 1990-08-22 EP EP90402328A patent/EP0414606B1/fr not_active Expired - Lifetime
- 1990-08-22 DE DE69013815T patent/DE69013815T2/de not_active Expired - Lifetime
- 1990-08-23 CN CN90107161A patent/CN1033808C/zh not_active Expired - Fee Related
-
1992
- 1992-05-18 RU SU925011511A patent/RU2041236C1/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0414606B1 (fr) | 1994-11-02 |
| ES2063313T3 (es) | 1995-01-01 |
| RU2041236C1 (ru) | 1995-08-09 |
| JP3026997B2 (ja) | 2000-03-27 |
| EP0414606A3 (en) | 1991-07-24 |
| AU634569B2 (en) | 1993-02-25 |
| JPH0390097A (ja) | 1991-04-16 |
| IE65922B1 (en) | 1995-11-29 |
| KR910004655A (ko) | 1991-03-29 |
| CA2022648A1 (fr) | 1991-02-24 |
| HUT54706A (en) | 1991-03-28 |
| DE69013815D1 (de) | 1994-12-08 |
| FR2651233A1 (fr) | 1991-03-01 |
| CN1051362A (zh) | 1991-05-15 |
| HU208154B (en) | 1993-08-30 |
| ATE113605T1 (de) | 1994-11-15 |
| MX22020A (es) | 1993-11-01 |
| EP0414606A2 (fr) | 1991-02-27 |
| PT95066B (pt) | 1997-05-28 |
| US5166146A (en) | 1992-11-24 |
| FR2651233B1 (fr) | 1991-12-13 |
| PT95066A (pt) | 1991-04-18 |
| ZA906341B (en) | 1991-10-30 |
| DK0414606T3 (da) | 1995-02-27 |
| CN1033808C (zh) | 1997-01-15 |
| IL95451A0 (en) | 1991-06-30 |
| IE903031A1 (en) | 1991-02-27 |
| HU905275D0 (en) | 1991-02-28 |
| DE69013815T2 (de) | 1995-03-16 |
| AU6118990A (en) | 1991-02-28 |
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