CA2473249A1 - New corticosteroids - Google Patents
New corticosteroids Download PDFInfo
- Publication number
- CA2473249A1 CA2473249A1 CA002473249A CA2473249A CA2473249A1 CA 2473249 A1 CA2473249 A1 CA 2473249A1 CA 002473249 A CA002473249 A CA 002473249A CA 2473249 A CA2473249 A CA 2473249A CA 2473249 A1 CA2473249 A1 CA 2473249A1
- Authority
- CA
- Canada
- Prior art keywords
- nitrooxymethyl
- acetate
- compounds according
- prednisolone
- benzoate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003246 corticosteroid Substances 0.000 title claims description 11
- 229960001334 corticosteroids Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- 125000005647 linker group Chemical group 0.000 claims abstract description 30
- 230000003637 steroidlike Effects 0.000 claims abstract description 20
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims abstract description 19
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 57
- 229940022663 acetate Drugs 0.000 claims description 47
- 229960005205 prednisolone Drugs 0.000 claims description 45
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 42
- 150000003431 steroids Chemical class 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 29
- 229960004436 budesonide Drugs 0.000 claims description 23
- 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 claims description 23
- 229960003957 dexamethasone Drugs 0.000 claims description 21
- 239000002243 precursor Substances 0.000 claims description 21
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 20
- -1 Meclonisone Chemical compound 0.000 claims description 18
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 17
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 238000002560 therapeutic procedure Methods 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 9
- 229960003469 flumetasone Drugs 0.000 claims description 9
- WXURHACBFYSXBI-GQKYHHCASA-N flumethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-GQKYHHCASA-N 0.000 claims description 9
- 229960000676 flunisolide Drugs 0.000 claims description 9
- 229960000890 hydrocortisone Drugs 0.000 claims description 9
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims description 9
- 229940011871 estrogen Drugs 0.000 claims description 8
- 239000000262 estrogen Substances 0.000 claims description 8
- 239000003862 glucocorticoid Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 230000007170 pathology Effects 0.000 claims description 7
- 230000000241 respiratory effect Effects 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 230000002456 anti-arthritic effect Effects 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910004679 ONO2 Inorganic materials 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 229960005294 triamcinolone Drugs 0.000 claims description 4
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims description 4
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 3
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 3
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 3
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 3
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 claims description 3
- MKPDWECBUAZOHP-AFYJWTTESA-N Paramethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O MKPDWECBUAZOHP-AFYJWTTESA-N 0.000 claims description 3
- 230000001656 angiogenetic effect Effects 0.000 claims description 3
- 230000000964 angiostatic effect Effects 0.000 claims description 3
- 230000001088 anti-asthma Effects 0.000 claims description 3
- 229940092705 beclomethasone Drugs 0.000 claims description 3
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims description 3
- 229960002537 betamethasone Drugs 0.000 claims description 3
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone 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-DVTGEIKXSA-N 0.000 claims description 3
- 239000003613 bile acid Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229960004544 cortisone Drugs 0.000 claims description 3
- 238000001794 hormone therapy Methods 0.000 claims description 3
- 230000000043 immunodepressive effect Effects 0.000 claims description 3
- 229960004584 methylprednisolone Drugs 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229960002858 paramethasone Drugs 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 229960004618 prednisone Drugs 0.000 claims description 3
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 3
- MYYIMZRZXIQBGI-HVIRSNARSA-N 6alpha-Fluoroprednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3C[C@H](F)C2=C1 MYYIMZRZXIQBGI-HVIRSNARSA-N 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 claims description 2
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 claims description 2
- WYQPLTPSGFELIB-JTQPXKBDSA-N Difluprednate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2CC[C@@](C(=O)COC(C)=O)(OC(=O)CCC)[C@@]2(C)C[C@@H]1O WYQPLTPSGFELIB-JTQPXKBDSA-N 0.000 claims description 2
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims description 2
- WJOHZNCJWYWUJD-IUGZLZTKSA-N Fluocinonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)C)[C@@]2(C)C[C@@H]1O WJOHZNCJWYWUJD-IUGZLZTKSA-N 0.000 claims description 2
- POPFMWWJOGLOIF-XWCQMRHXSA-N Flurandrenolide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O POPFMWWJOGLOIF-XWCQMRHXSA-N 0.000 claims description 2
- YCISZOVUHXIOFY-HKXOFBAYSA-N Halopredone acetate Chemical compound C1([C@H](F)C2)=CC(=O)C(Br)=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2CC[C@](OC(C)=O)(C(=O)COC(=O)C)[C@@]2(C)C[C@@H]1O YCISZOVUHXIOFY-HKXOFBAYSA-N 0.000 claims description 2
- GZENKSODFLBBHQ-ILSZZQPISA-N Medrysone Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@H](C(C)=O)CC[C@H]21 GZENKSODFLBBHQ-ILSZZQPISA-N 0.000 claims description 2
- MTMZZIPTQITGCY-OLGWUGKESA-N Moxestrol Chemical compound OC1=CC=C2[C@H]3[C@@H](OC)C[C@]4(C)[C@@](C#C)(O)CC[C@H]4[C@@H]3CCC2=C1 MTMZZIPTQITGCY-OLGWUGKESA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 208000025747 Rheumatic disease Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 229960001900 algestone Drugs 0.000 claims description 2
- CXDWHYOBSJTRJU-SRWWVFQWSA-N algestone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](O)[C@@](C(=O)C)(O)[C@@]1(C)CC2 CXDWHYOBSJTRJU-SRWWVFQWSA-N 0.000 claims description 2
- 229960003099 amcinonide Drugs 0.000 claims description 2
- ILKJAFIWWBXGDU-MOGDOJJUSA-N amcinonide Chemical compound O([C@@]1([C@H](O2)C[C@@H]3[C@@]1(C[C@H](O)[C@]1(F)[C@@]4(C)C=CC(=O)C=C4CC[C@H]13)C)C(=O)COC(=O)C)C12CCCC1 ILKJAFIWWBXGDU-MOGDOJJUSA-N 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 claims description 2
- 229960001091 chenodeoxycholic acid Drugs 0.000 claims description 2
- 229950006229 chloroprednisone Drugs 0.000 claims description 2
- NPSLCOWKFFNQKK-ZPSUVKRCSA-N chloroprednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3C[C@H](Cl)C2=C1 NPSLCOWKFFNQKK-ZPSUVKRCSA-N 0.000 claims description 2
- 229960003728 ciclesonide Drugs 0.000 claims description 2
- 229960002842 clobetasol Drugs 0.000 claims description 2
- CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate 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)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 claims description 2
- 229960001146 clobetasone Drugs 0.000 claims description 2
- XXIFVOHLGBURIG-OZCCCYNHSA-N clobetasone 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)CCl)(O)[C@@]1(C)CC2=O XXIFVOHLGBURIG-OZCCCYNHSA-N 0.000 claims description 2
- 229960004299 clocortolone Drugs 0.000 claims description 2
- YMTMADLUXIRMGX-RFPWEZLHSA-N clocortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(Cl)[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O YMTMADLUXIRMGX-RFPWEZLHSA-N 0.000 claims description 2
- 229960002219 cloprednol Drugs 0.000 claims description 2
- YTJIBEDMAQUYSZ-FDNPDPBUSA-N cloprednol Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3C=C(Cl)C2=C1 YTJIBEDMAQUYSZ-FDNPDPBUSA-N 0.000 claims description 2
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 claims description 2
- 229960003840 cortivazol Drugs 0.000 claims description 2
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 claims description 2
- 229960001145 deflazacort Drugs 0.000 claims description 2
- FBHSPRKOSMHSIF-GRMWVWQJSA-N deflazacort Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)=N[C@@]3(C(=O)COC(=O)C)[C@@]1(C)C[C@@H]2O FBHSPRKOSMHSIF-GRMWVWQJSA-N 0.000 claims description 2
- 229960003662 desonide Drugs 0.000 claims description 2
- WBGKWQHBNHJJPZ-LECWWXJVSA-N desonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O WBGKWQHBNHJJPZ-LECWWXJVSA-N 0.000 claims description 2
- 229960002593 desoximetasone Drugs 0.000 claims description 2
- VWVSBHGCDBMOOT-IIEHVVJPSA-N desoximetasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@@H]2O VWVSBHGCDBMOOT-IIEHVVJPSA-N 0.000 claims description 2
- 229960004154 diflorasone Drugs 0.000 claims description 2
- WXURHACBFYSXBI-XHIJKXOTSA-N diflorasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-XHIJKXOTSA-N 0.000 claims description 2
- 229960004091 diflucortolone Drugs 0.000 claims description 2
- OGPWIDANBSLJPC-RFPWEZLHSA-N diflucortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O OGPWIDANBSLJPC-RFPWEZLHSA-N 0.000 claims description 2
- 229960004875 difluprednate Drugs 0.000 claims description 2
- 229960005309 estradiol Drugs 0.000 claims description 2
- 229930182833 estradiol Natural products 0.000 claims description 2
- 229960002568 ethinylestradiol Drugs 0.000 claims description 2
- 229950002335 fluazacort Drugs 0.000 claims description 2
- BYZCJOHDXLROEC-RBWIMXSLSA-N fluazacort Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)=N[C@@]3(C(=O)COC(=O)C)[C@@]1(C)C[C@@H]2O BYZCJOHDXLROEC-RBWIMXSLSA-N 0.000 claims description 2
- NJNWEGFJCGYWQT-VSXGLTOVSA-N fluclorolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(Cl)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1Cl NJNWEGFJCGYWQT-VSXGLTOVSA-N 0.000 claims description 2
- 229940094766 flucloronide Drugs 0.000 claims description 2
- 229960004511 fludroxycortide Drugs 0.000 claims description 2
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Landscapes
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- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2002A000148 | 2002-01-29 | ||
| IT2002MI000148A ITMI20020148A1 (it) | 2002-01-29 | 2002-01-29 | Nuovi corticosteroidi |
| PCT/EP2003/000394 WO2003064443A2 (en) | 2002-01-29 | 2003-01-16 | New corticosteroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2473249A1 true CA2473249A1 (en) | 2003-08-07 |
Family
ID=11449016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002473249A Abandoned CA2473249A1 (en) | 2002-01-29 | 2003-01-16 | New corticosteroids |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US20060052594A1 (https=) |
| EP (1) | EP1470150A2 (https=) |
| JP (1) | JP2005516070A (https=) |
| AU (2) | AU2003210161B2 (https=) |
| BR (1) | BR0307027A (https=) |
| CA (1) | CA2473249A1 (https=) |
| IT (1) | ITMI20020148A1 (https=) |
| MX (1) | MXPA04007337A (https=) |
| NO (1) | NO327364B1 (https=) |
| NZ (1) | NZ534147A (https=) |
| PL (1) | PL370457A1 (https=) |
| WO (1) | WO2003064443A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009037584A3 (en) * | 2007-08-10 | 2011-04-28 | Nicox S.A. | Combination of nitroderivatized steroid and bronchodilator for treating respiratory disease |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20070283T3 (en) * | 2003-12-02 | 2007-11-30 | Nicox S.A. | Nitrooxyderivatives of carvedilol and other beta blockers as antihypertensive drugs |
| CN102134269A (zh) * | 2005-09-02 | 2011-07-27 | 尼科克斯公司 | 糖皮质激素硝酰氧基衍生物 |
| US8802726B2 (en) | 2006-02-03 | 2014-08-12 | Nicox S.A. | Use of nitrooxyderivative of drug for the treatment of muscular dystrophies |
| EP2109617A1 (en) * | 2007-02-05 | 2009-10-21 | Nicox S.A. | Nitric oxide releasing steroids |
| EP1964550A1 (en) * | 2007-03-01 | 2008-09-03 | NicOx S.A. | Glucocorticoid-nitrooxyderivative compositions |
| US20090088411A1 (en) * | 2007-08-31 | 2009-04-02 | Topigen Pharmaceuticals Inc. | No-donating corticosteroid with improved pharmacokinetic, anti-inflammatory and vasodilatory properties |
| ES2324007A1 (es) * | 2007-10-25 | 2009-07-28 | Ferrer Internacional, S.A. | Una forma amorfa de un compuesto antiinflamatorio. |
| KR101975843B1 (ko) * | 2008-05-23 | 2019-05-09 | 더 유니버시티 오브 브리티쉬 콜롬비아 | 리포좀 나노입자에 사용하기 위한 변형된 약물 |
| CN101624414B (zh) * | 2008-07-07 | 2013-02-13 | 天津金耀集团有限公司 | 一种抑制血管新生的硝酸酯药物 |
| MX2011001119A (es) | 2008-07-31 | 2011-03-02 | Nicox Sa | Glucocorticoides unidos a esteres de nitrato por medio de un enlazador aromatico en la posicion 21 y su uso en oftalmololgia. |
| JP2011529933A (ja) | 2008-08-05 | 2011-12-15 | ニコックス エス エイ | 網膜および黄斑の疾患の治療のための新規なｎｏ放出性ステロイド |
| CN102040643B (zh) * | 2009-10-16 | 2013-01-09 | 天津金耀集团有限公司 | 环索奈德硝酸酯衍生物 |
| US8716268B2 (en) | 2010-06-07 | 2014-05-06 | Chao Liu | Nitrate esters of corticoid compounds useful as diuretics |
| ES3046537T3 (en) | 2016-11-08 | 2025-12-02 | Regeneron Pharma | Steroids and protein-conjugates thereof |
| KR20200007905A (ko) | 2017-05-18 | 2020-01-22 | 리제너론 파마슈티칼스 인코포레이티드 | 사이클로덱스트린 단백질 약물 접합체 |
| MX2020004691A (es) | 2017-11-07 | 2020-08-20 | Regeneron Pharma | Enlazadores hidrofilicos para conjugados anticuerpo-farmaco. |
| SG11202006510XA (en) | 2018-01-08 | 2020-08-28 | Regeneron Pharma | Steroids and antibody-conjugates thereof |
| CN108484714A (zh) * | 2018-03-13 | 2018-09-04 | 岳阳环宇药业有限公司 | 地夫可特的制备工艺 |
| CN118955710A (zh) | 2018-05-09 | 2024-11-15 | 里珍纳龙药品有限公司 | 抗msr1抗体及其使用方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1037451B (de) * | 1957-04-04 | 1958-08-28 | Schering Ag | Verfahren zur Herstellung der Aminoacetate von gesaettigten und ungesaettigten 21-Hydroxypregnan-verbindungen bzw. deren wasserloeslichen Saeureadditionsprodukten |
| US3183252A (en) * | 1963-09-05 | 1965-05-11 | Syntex Corp | 16-nitratoalkyl-pregnanes |
| US3494941A (en) | 1967-12-04 | 1970-02-10 | American Home Prod | Nitrate esters of 17beta-(hydroxyalkoxy)steroid 3-ols,3-ones and 3-amidinohydrazones |
| HU164115B (https=) | 1971-05-07 | 1973-12-28 | ||
| CY1359A (en) * | 1981-02-02 | 1987-08-07 | Schering Corp | Aromatic heterocyclic esters of steroids, their preparation and pharmaceutical compositions containing them |
| GR1001529B (el) * | 1990-09-07 | 1994-03-31 | Elmuquimica Farm Sl | Μέ?οδος για την λήψη νέων 21-εστέρων της 16-17-ακετάλης της πρ να-1,4-διενο-3,20-διόνης. |
| US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| US5837698A (en) * | 1996-05-02 | 1998-11-17 | G. D. Searle & Co. | Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs |
| IT1285770B1 (it) | 1996-10-04 | 1998-06-18 | Nicox Sa | Composti corticoidei |
| US6248723B1 (en) * | 1997-06-10 | 2001-06-19 | National Jewish Medical And Research Center | Method for treatment of inflammatory disease |
| US6254853B1 (en) * | 1998-05-08 | 2001-07-03 | Vyrex Corporation | Water soluble pro-drugs of propofol |
| IT1311922B1 (it) | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
| IT1320176B1 (it) * | 2000-12-22 | 2003-11-26 | Nicox Sa | Dispersioni solide di principi attivi nitrati. |
| EP1336602A1 (en) * | 2002-02-13 | 2003-08-20 | Giovanni Scaramuzzino | Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases |
-
2002
- 2002-01-29 IT IT2002MI000148A patent/ITMI20020148A1/it unknown
-
2003
- 2003-01-16 WO PCT/EP2003/000394 patent/WO2003064443A2/en not_active Ceased
- 2003-01-16 US US10/501,335 patent/US20060052594A1/en not_active Abandoned
- 2003-01-16 BR BR0307027-1A patent/BR0307027A/pt not_active IP Right Cessation
- 2003-01-16 NZ NZ534147A patent/NZ534147A/en not_active IP Right Cessation
- 2003-01-16 CA CA002473249A patent/CA2473249A1/en not_active Abandoned
- 2003-01-16 AU AU2003210161A patent/AU2003210161B2/en not_active Ceased
- 2003-01-16 EP EP03734674A patent/EP1470150A2/en not_active Ceased
- 2003-01-16 MX MXPA04007337A patent/MXPA04007337A/es unknown
- 2003-01-16 PL PL03370457A patent/PL370457A1/xx unknown
- 2003-01-16 JP JP2003564063A patent/JP2005516070A/ja active Pending
-
2004
- 2004-08-27 NO NO20043595A patent/NO327364B1/no not_active IP Right Cessation
-
2008
- 2008-12-15 AU AU2008258133A patent/AU2008258133A1/en not_active Abandoned
-
2009
- 2009-05-12 US US12/464,562 patent/US20090221543A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009037584A3 (en) * | 2007-08-10 | 2011-04-28 | Nicox S.A. | Combination of nitroderivatized steroid and bronchodilator for treating respiratory disease |
Also Published As
| Publication number | Publication date |
|---|---|
| NO327364B1 (no) | 2009-06-15 |
| EP1470150A2 (en) | 2004-10-27 |
| AU2008258133A1 (en) | 2009-01-08 |
| BR0307027A (pt) | 2004-11-03 |
| WO2003064443A2 (en) | 2003-08-07 |
| NO20043595L (no) | 2004-10-20 |
| MXPA04007337A (es) | 2004-11-26 |
| US20090221543A1 (en) | 2009-09-03 |
| AU2003210161B2 (en) | 2008-12-04 |
| ITMI20020148A0 (it) | 2002-01-29 |
| WO2003064443A3 (en) | 2004-02-26 |
| JP2005516070A (ja) | 2005-06-02 |
| US20060052594A1 (en) | 2006-03-09 |
| NZ534147A (en) | 2006-09-29 |
| ITMI20020148A1 (it) | 2003-07-29 |
| PL370457A1 (en) | 2005-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |