IL95451A - Alcoenic omega phenylamino acids converted in the aromatic nucleus by 91-Nur steroid process for their preparation and pharmaceutical preparations containing them - Google Patents
Alcoenic omega phenylamino acids converted in the aromatic nucleus by 91-Nur steroid process for their preparation and pharmaceutical preparations containing themInfo
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 10
- 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
- 239000005556 hormone Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 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
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 5
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
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- 239000000706 filtrate Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- 238000001953 recrystallisation Methods 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 229920002307 Dextran Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
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- 239000000543 intermediate Substances 0.000 description 2
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- 125000004043 oxo group Chemical group O=* 0.000 description 2
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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
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 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
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 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
- 206010000496 acne Diseases 0.000 description 1
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (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 (en) | 1995-07-31 |
Family
ID=9384880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9545190A IL95451A (en) | 1989-08-23 | 1990-08-21 | Alcoenic omega phenylamino acids converted in the aromatic nucleus by 91-Nur steroid process for their preparation and pharmaceutical preparations containing them |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5166146A (pt) |
| EP (1) | EP0414606B1 (pt) |
| JP (1) | JP3026997B2 (pt) |
| KR (1) | KR910004655A (pt) |
| CN (1) | CN1033808C (pt) |
| AT (1) | ATE113605T1 (pt) |
| AU (1) | AU634569B2 (pt) |
| CA (1) | CA2022648A1 (pt) |
| DE (1) | DE69013815T2 (pt) |
| DK (1) | DK0414606T3 (pt) |
| ES (1) | ES2063313T3 (pt) |
| FR (1) | FR2651233B1 (pt) |
| HU (1) | HU208154B (pt) |
| IE (1) | IE65922B1 (pt) |
| IL (1) | IL95451A (pt) |
| MX (1) | MX22020A (pt) |
| PT (1) | PT95066B (pt) |
| RU (1) | RU2041236C1 (pt) |
| ZA (1) | ZA906341B (pt) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5780220A (en) * | 1994-05-19 | 1998-07-14 | Trustees Of The University Of Pennsylvania | Methods and compositions for inhibiting HIV replication |
| 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 |
| AU2016226451B2 (en) | 2015-03-02 | 2019-12-19 | Corcept Therapeutics, Inc. | Use of glucocorticoid receptor antagonist and somatostatin analogues to treat ACTH-secreting tumors |
| SG11201707525TA (en) | 2015-03-30 | 2017-10-30 | Corcept Therapeutics Inc | Use of glucocorticoid receptor antagonists in combination with glucocorticoids to treat adrenal insufficiency |
| ES2865334T3 (es) | 2015-08-13 | 2021-10-15 | Corcept Therapeutics Inc | Método de diagnóstico diferencial de síndrome de Cushing dependiente de ACTH |
| KR102197526B1 (ko) | 2016-01-19 | 2020-12-31 | 코어셉트 쎄라퓨틱스 인코포레이티드 | 이소성 쿠싱 증후군의 감별 진단 |
| WO2018102369A1 (en) | 2016-11-30 | 2018-06-07 | Arno Therapeutics, Inc. | Methods for onapristone synthesis dehydration and deprotection |
| CA3055076C (en) | 2017-03-31 | 2022-02-22 | Corcept Therapeutics, Inc. | Glucocorticoid receptor modulators to treat cervical cancer |
| JP7670462B2 (ja) | 2017-06-20 | 2025-04-30 | コーセプト セラピューティクス， インコーポレイテッド | 選択的グルココルチコイドレセプターモジュレーターを使用して神経上皮腫瘍を処置する方法 |
| WO2022130015A2 (en) | 2020-12-18 | 2022-06-23 | 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/en not_active IP Right Cessation
- 1990-08-22 DK DK90402328.0T patent/DK0414606T3/da active
- 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 AT AT90402328T patent/ATE113605T1/de not_active IP Right Cessation
- 1990-08-22 PT PT95066A patent/PT95066B/pt not_active IP Right Cessation
- 1990-08-22 DE DE69013815T patent/DE69013815T2/de not_active Expired - Lifetime
- 1990-08-22 AU AU61189/90A patent/AU634569B2/en not_active Ceased
- 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 KR KR1019900012958A patent/KR910004655A/ko not_active Abandoned
- 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 |
|---|---|
| EP0414606A2 (fr) | 1991-02-27 |
| ZA906341B (en) | 1991-10-30 |
| FR2651233B1 (fr) | 1991-12-13 |
| EP0414606B1 (fr) | 1994-11-02 |
| MX22020A (es) | 1993-11-01 |
| HU208154B (en) | 1993-08-30 |
| KR910004655A (ko) | 1991-03-29 |
| PT95066B (pt) | 1997-05-28 |
| IE65922B1 (en) | 1995-11-29 |
| DK0414606T3 (da) | 1995-02-27 |
| CA2022648A1 (fr) | 1991-02-24 |
| CN1051362A (zh) | 1991-05-15 |
| EP0414606A3 (en) | 1991-07-24 |
| FR2651233A1 (fr) | 1991-03-01 |
| US5166146A (en) | 1992-11-24 |
| JP3026997B2 (ja) | 2000-03-27 |
| DE69013815D1 (de) | 1994-12-08 |
| RU2041236C1 (ru) | 1995-08-09 |
| JPH0390097A (ja) | 1991-04-16 |
| ES2063313T3 (es) | 1995-01-01 |
| ATE113605T1 (de) | 1994-11-15 |
| HUT54706A (en) | 1991-03-28 |
| HU905275D0 (en) | 1991-02-28 |
| PT95066A (pt) | 1991-04-18 |
| IL95451A0 (en) | 1991-06-30 |
| AU634569B2 (en) | 1993-02-25 |
| IE903031A1 (en) | 1991-02-27 |
| AU6118990A (en) | 1991-02-28 |
| CN1033808C (zh) | 1997-01-15 |
| DE69013815T2 (de) | 1995-03-16 |
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