DE69712900T2 - Nitratester von corticoid verbindungen und die therapeutische verwendungen davon - Google Patents
Nitratester von corticoid verbindungen und die therapeutische verwendungen davonInfo
- Publication number
- DE69712900T2 DE69712900T2 DE69712900T DE69712900T DE69712900T2 DE 69712900 T2 DE69712900 T2 DE 69712900T2 DE 69712900 T DE69712900 T DE 69712900T DE 69712900 T DE69712900 T DE 69712900T DE 69712900 T2 DE69712900 T2 DE 69712900T2
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- medicaments
- compositions according
- preparation
- carbon atoms
- 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.)
- Expired - Lifetime
Links
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical class 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 title description 5
- 230000001225 therapeutic effect Effects 0.000 title description 4
- 150000002823 nitrates Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000003814 drug Substances 0.000 claims abstract description 12
- 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 55
- 229960000890 hydrocortisone Drugs 0.000 claims description 28
- -1 cortivazole Chemical compound 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 229960003957 dexamethasone Drugs 0.000 claims description 12
- 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 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 150000001408 amides Chemical group 0.000 claims description 6
- 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 5
- 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 5
- 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 5
- 229960004544 cortisone Drugs 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229960005205 prednisolone Drugs 0.000 claims description 5
- 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 5
- 230000000964 angiostatic effect Effects 0.000 claims description 4
- 239000003246 corticosteroid Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229960004618 prednisone Drugs 0.000 claims description 4
- 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 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 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 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
- 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
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 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 3
- 229960001347 fluocinolone acetonide Drugs 0.000 claims description 3
- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide 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)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 claims description 3
- 229960004584 methylprednisolone Drugs 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229960005294 triamcinolone Drugs 0.000 claims description 3
- 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 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
- 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 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
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-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
- TZIZWYVVGLXXFV-FLRHRWPCSA-N Triamcinolone hexacetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)CC(C)(C)C)[C@@]1(C)C[C@@H]2O TZIZWYVVGLXXFV-FLRHRWPCSA-N 0.000 claims description 2
- 229960000552 alclometasone Drugs 0.000 claims description 2
- FJXOGVLKCZQRDN-PHCHRAKRSA-N alclometasone Chemical compound C([C@H]1Cl)C2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O FJXOGVLKCZQRDN-PHCHRAKRSA-N 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
- 230000001088 anti-asthma Effects 0.000 claims description 2
- 239000000924 antiasthmatic agent Substances 0.000 claims description 2
- 229960004436 budesonide Drugs 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229960002842 clobetasol Drugs 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
- 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
- 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
- 229960003469 flumetasone Drugs 0.000 claims description 2
- 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 2
- 229960000676 flunisolide Drugs 0.000 claims description 2
- 229960000785 fluocinonide Drugs 0.000 claims description 2
- 229960003973 fluocortolone Drugs 0.000 claims description 2
- GAKMQHDJQHZUTJ-ULHLPKEOSA-N fluocortolone 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@H](C(=O)CO)[C@@]2(C)C[C@@H]1O GAKMQHDJQHZUTJ-ULHLPKEOSA-N 0.000 claims description 2
- 229960001048 fluorometholone Drugs 0.000 claims description 2
- FAOZLTXFLGPHNG-KNAQIMQKSA-N fluorometholone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FAOZLTXFLGPHNG-KNAQIMQKSA-N 0.000 claims description 2
- 229960003590 fluperolone Drugs 0.000 claims description 2
- 229960002650 fluprednidene acetate Drugs 0.000 claims description 2
- DEFOZIFYUBUHHU-IYQKUMFPSA-N fluprednidene acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC(=C)[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O DEFOZIFYUBUHHU-IYQKUMFPSA-N 0.000 claims description 2
- 229960000618 fluprednisolone Drugs 0.000 claims description 2
- 229960000289 fluticasone propionate Drugs 0.000 claims description 2
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate 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)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims description 2
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- QNXUUBBKHBYRFW-QWAPGEGQSA-N formocortal Chemical compound C1C(C=O)=C2C=C(OCCCl)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)C)[C@@]1(C)C[C@@H]2O QNXUUBBKHBYRFW-QWAPGEGQSA-N 0.000 claims description 2
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- 229950000208 hydrocortamate Drugs 0.000 claims description 2
- FWFVLWGEFDIZMJ-FOMYWIRZSA-N hydrocortamate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)CN(CC)CC)(O)[C@@]1(C)C[C@@H]2O FWFVLWGEFDIZMJ-FOMYWIRZSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000003018 immunosuppressive agent Substances 0.000 claims description 2
- 208000028774 intestinal disease Diseases 0.000 claims description 2
- DMKSVUSAATWOCU-HROMYWEYSA-N loteprednol etabonate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)OCCl)(OC(=O)OCC)[C@@]1(C)C[C@@H]2O DMKSVUSAATWOCU-HROMYWEYSA-N 0.000 claims description 2
- 229960003744 loteprednol etabonate Drugs 0.000 claims description 2
- 229950002555 mazipredone Drugs 0.000 claims description 2
- CZBOZZDZNVIXFC-VRRJBYJJSA-N mazipredone Chemical compound C1CN(C)CCN1CC(=O)[C@]1(O)[C@@]2(C)C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2CC1 CZBOZZDZNVIXFC-VRRJBYJJSA-N 0.000 claims description 2
- 229960001011 medrysone Drugs 0.000 claims description 2
- 229960001810 meprednisone Drugs 0.000 claims description 2
- PIDANAQULIKBQS-RNUIGHNZSA-N meprednisone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)CC2=O PIDANAQULIKBQS-RNUIGHNZSA-N 0.000 claims description 2
- 229960002744 mometasone furoate Drugs 0.000 claims description 2
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 claims description 2
- 229960002858 paramethasone Drugs 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229960002794 prednicarbate Drugs 0.000 claims description 2
- FNPXMHRZILFCKX-KAJVQRHHSA-N prednicarbate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)CC)(OC(=O)OCC)[C@@]1(C)C[C@@H]2O FNPXMHRZILFCKX-KAJVQRHHSA-N 0.000 claims description 2
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- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
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- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- AAXVEMMRQDVLJB-BULBTXNYSA-N fludrocortisone Chemical compound O=C1CC[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 AAXVEMMRQDVLJB-BULBTXNYSA-N 0.000 description 1
- 229960002011 fludrocortisone Drugs 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229960002383 halcinonide Drugs 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- IZZWJPQHPPRVLP-UHFFFAOYSA-N hexane;2-methoxy-2-methylpropane Chemical compound CCCCCC.COC(C)(C)C IZZWJPQHPPRVLP-UHFFFAOYSA-N 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
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- 102000006495 integrins Human genes 0.000 description 1
- 108010044426 integrins Proteins 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
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- 230000003902 lesion Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000011670 long-evans rat Methods 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000009526 moderate injury Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
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- 150000002826 nitrites Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 210000000963 osteoblast Anatomy 0.000 description 1
- 231100000380 osteotoxicity Toxicity 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 210000003455 parietal bone Anatomy 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229950000696 prednival Drugs 0.000 description 1
- BOFKYYWJAOZDPB-FZNHGJLXSA-N prednival Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CO)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O BOFKYYWJAOZDPB-FZNHGJLXSA-N 0.000 description 1
- 150000003126 pregnane derivatives Chemical class 0.000 description 1
- JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane group Chemical group [C@@H]12CC[C@H](CC)[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
- 150000003128 pregnanes Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010972 statistical evaluation Methods 0.000 description 1
- 238000012109 statistical procedure Methods 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 101150018444 sub2 gene Proteins 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003515 testosterones Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Substances ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 230000014616 translation Effects 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
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- 210000001364 upper extremity Anatomy 0.000 description 1
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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
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (12)
1. Verbindungen
der allgemeinen Formel:
B-X&sub1;-NO&sub2;
oder ihre Ester oder Salze, in welchen
B die folgende Struktur hat:
wobei, an der Stelle der Wasserstoffe H in der CH-Gruppe oder zweier
Wasserstoffe H&sub2; in der CH&sub2;-Gruppe, die in der allgemeinen Formel gezeigt sind,
die folgenden Substituenten auftreten können:
an Position 1-2: dort kann eine Doppelbindung auftreten;
an Position 2-3: dort kann der folgende Substituent sein:
an Position 2: Dort kann Cl, Br sein;
an Position 3: dort kann CO, -O-CH&sub2;-CH&sub2;-Cl, OH sein,
an Position 4-5: dort kann eine Doppelbindung sein;
an Position 5-6: dort kann eine Doppelbindung sein;
an Position 6: dort kann Cl, F, CH&sub3;, -CHO sein;
an Position 7: dort kann Cl sein;
an Position 9: dort kann Cl, F sein;
an Position 11: dort kann OH, CO, Cl sein;
an Position 16: dort kann CH&sub3;, OH, =CH&sub2; sein
an Position 17: dort kann OH, CH&sub3;, OCO(O)ua(CH&sub2;)vaCH&sub3;,
oder
sein, wobei ua ein Integer ist, der gleich 0 oder 1 ist, va ein Integer von 0 bis 4 ist;
an Position 16-17: dort können die folgenden Gruppen sein:
R und R' sind gleich oder unterschiedlich voneinander und können Wasserstoff
oder lineare oder verzweigte Alkyle sein, die 1 bis 4 Kohlenstoffatome haben,
vorzugsweise R = R' = CH&sub3;
wenn an Position 9 ein F ist, ist an Position 11 ein OH, an Positionen 1-2 und an
Positionen 4-5 sind zwei Doppelbindungen, an Positionen 3 und 20 zwei CO-
Gruppen, an Positionen 16-17 darf nicht die folgende Gruppe sein:
wobei B ein Corticosteroid-Rest ist;
R" ist -(CO-L)t-(X)tl-
wobei t und tl Integers sind, die beide gleich 1 sind, tl auch 0 ist;
die bivalente Brücke L ausgewählt ist aus:
(CR&sub4;R&sub5;)na(O)nb(CR&sub4;R&sub5;)n'a(CO)n'b(O)n"b(CO)n'''b(CR&sub4;R&sub5;)n"a
wobei na, n'a und n"a gleich oder unterschiedlich zueinander sind und Integers von
0 bis 6, vorzugsweise von 1 bis 3, nb, n'b, n"b und n'''b gleich oder unterschiedlich
zueinander sind und Integers 0 oder 1 sind; R&sub4; und R&sub5; sind gleich oder
unterschiedlich zueinander und sind ausgewählt aus H, linearen oder verzweigten
Alkylen, die 1 bis 5 Kohlenstoffatome haben, vorzugsweise 1 bis 3; X ist gleich X&sub0;,
wobei X&sub0; = O, NH, NR,c, wobei R1c ein lineares oder verzweigtes Alkyl ist, das 1 bis
10 Kohlenstoffatome hat;
X&sub1; ist eine bivalente Verbindungsbrücke ausgewählt aus:
YO
wobei Y linear ist oder, wo möglich, verzweigtes C&sub1;-C&sub2;&sub0;-Alkylen, vorzugsweise
mit 2 bis 5 Kohlenstoffatomen, oder ein optional substituiertes Cycloalkylen mit 5
bis 7 Kohlenstoffatomen;
Y&sub1; ist ausgewählt aus
wobei n&sub3; ein Integer zwischen 0 und 3 ist;
wobei nf in Integer von 1 bis 6 ist, vorzugsweise von 2 bis 4;
wobei Rf' = H, CH&sub3; und nf ein Integer von 1 bis 6 ist, vorzugsweise von 2 bis 4;
wobei die Verbindung zwischen B und X1 ein Ester oder Amid-Typ ist.
2. Verbindungen nach Anspruch 1, in welchen B umfasst die folgenden, wo H&sub2;, H, R,
R', R" definiert sind als die im folgenden aufgelisteten Verbindungen: Budesonid,
Hydrocortison, Alclometason, Algeston, Beclomethason, Betamethason,
Chloroprednison, Clobetasol, Clobetason, Clocortolon, Cloprednol, Cortison,
Corticosteron, Deflazacort, Desonid, Desoximetason, Dexamethason, Diflorason,
Diflucortolon, Difluprednat, Fluazacort, Flucloronid, Flumethason, Flunisolid,
Fluocinolonazetonid, Fluocinonid, Fluocortyn-Butyl, Fluocortolon,
Fluorometholon, Fluperolon-Acetat, Flupredniden-Acetat, Fluprednisolon,
Flurandrenolid, Formocortal, Fhalcinonid, Halobetasol-Propionat, Halometason,
Halopredon-Acetat, Hydrocortamat, Loteprednol-Etabonat, Medryson,
Meprednison, Methylprednisolon, Mometason-Furoat, Paramethason,
Prednicarbat, Prednisolon, Prednisolon-25-Diethylaminoacetat, Prednisolon-
Natriumphosphat, Prednison, Prednival, Prednilyden, Rimexolon, Triamcinolon,
21-Acetoxypregnenolon, Cortivazol, Amcinonid, Fluticason-Propionat,
Mazipredon, Tixocortol, Triamcinolon-Hexacetonid, wobei R" wie in Anspruch 1
definiert ist.
3. Verbindungen oder Zusammensetzungen nach Anspruch 1, die als Medikamente
verwendet werden.
4. Verwendung von Verbindungen und Zusammensetzungen nach Anspruch 2 für die
Zubereitung von Medikamenten wie Corticoide.
5. Verwendung von Verbindungen und Zusammensetzungen nach Anspruch 4 für die
Zubereitung von Medikamenten wie Antiarthritika.
6. Verwendung von Verbindungen und Zusammensetzungen nach Anspruch 4 für die
Zubereitung von Medikamenten wie Immun-suppressiva.
7. Verwendung von Verbindungen und Zusammensetzungen nach Anspruch 4 für die
Zubereitung von Medikamenten wie Angiostatika.
8. Verwendung von Verbindungen und Zusammensetzungen nach Anspruch 4 für die
Zubereitung von Medikamenten wie Antiasthmatika.
9. Verwendung von Verbindungen und Zusammensetzungen nach Anspruch 4 für die
Zubereitung von Medikamenten für Hauterkrankungen.
10. Verwendung von Verbindungen und Zusammensetzungen nach Anspruch 4 für die
Zubereitung von Medikamenten für Augenerkrankungen.
11. Verwendung von Verbindungen und Zusammensetzungen nach Anspruch 4 für die
Zubereitung von Medikamenten für Erkrankungen des Darmes.
12. Pharmazeutische Zusammensetzungen enthaltend als aktive Bestandteile die
Verbindungen aus den Ansprüchen 1 oder 2.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT96MI002048A IT1285770B1 (it) | 1996-10-04 | 1996-10-04 | Composti corticoidei |
| PCT/EP1997/005426 WO1998015568A2 (en) | 1996-10-04 | 1997-10-02 | Nitrate esters of corticoid compounds and pharmaceutical applications thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69712900D1 DE69712900D1 (de) | 2002-07-04 |
| DE69712900T2 true DE69712900T2 (de) | 2002-12-12 |
Family
ID=11374972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69712900T Expired - Lifetime DE69712900T2 (de) | 1996-10-04 | 1997-10-02 | Nitratester von corticoid verbindungen und die therapeutische verwendungen davon |
Country Status (18)
| Country | Link |
|---|---|
| US (8) | US6610676B1 (de) |
| EP (1) | EP0929565B1 (de) |
| JP (1) | JP4388600B2 (de) |
| KR (1) | KR100487898B1 (de) |
| CN (1) | CN1142939C (de) |
| AT (1) | ATE218142T1 (de) |
| AU (1) | AU719250B2 (de) |
| BR (1) | BR9711586A (de) |
| CA (1) | CA2267630C (de) |
| DE (1) | DE69712900T2 (de) |
| DK (1) | DK0929565T3 (de) |
| ES (1) | ES2177952T3 (de) |
| HU (1) | HUP9904149A3 (de) |
| IT (1) | IT1285770B1 (de) |
| PT (1) | PT929565E (de) |
| RU (1) | RU2186781C2 (de) |
| SI (1) | SI0929565T1 (de) |
| WO (1) | WO1998015568A2 (de) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5824669A (en) | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| IT1285770B1 (it) * | 1996-10-04 | 1998-06-18 | Nicox Sa | Composti corticoidei |
| IT1311922B1 (it) * | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
| IT1314184B1 (it) | 1999-08-12 | 2002-12-06 | Nicox Sa | Composizioni farmaceutiche per la terapia di condizioni di stressossidativo |
| IT1320176B1 (it) * | 2000-12-22 | 2003-11-26 | Nicox Sa | Dispersioni solide di principi attivi nitrati. |
| EP1219306A1 (de) | 2000-12-29 | 2002-07-03 | Nicox S.A. | Zyklodextrin und NO-abgebende Arzneimittlen enthaltende Zusammensetzungen |
| US6696592B2 (en) | 2001-05-22 | 2004-02-24 | Nicox-S.A. | Methods of making 21-[4′-(nitrooxyalkyl)benzoate] corticosteroid derivatives and intermediates useful in the synthesis thereof |
| CA2462456C (en) | 2001-10-03 | 2010-05-04 | Merck & Co., Inc. | Androstane 17-beta-carboxamides as androgen receptor modulators |
| ITMI20020148A1 (it) | 2002-01-29 | 2003-07-29 | Nicox Sa | Nuovi corticosteroidi |
| CN100513415C (zh) * | 2005-08-03 | 2009-07-15 | 中国人民解放军军事医学科学院毒物药物研究所 | 胆汁酸衍生物及其医药用途 |
| CN101300265A (zh) * | 2005-09-02 | 2008-11-05 | 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 |
| US7893058B2 (en) * | 2006-05-15 | 2011-02-22 | Janssen Pharmaceutica Nv | Imidazolopyrazine compounds useful for the treatment of degenerative and inflammatory diseases |
| RU2442790C2 (ru) * | 2007-02-05 | 2012-02-20 | Никокс С.А. | Стероиды, высвобождающие оксид азота |
| WO2009037584A2 (en) * | 2007-08-10 | 2009-03-26 | Topigen Pharmaceuticals Inc. | Combination of nitroderivatized steroid and bronchodilator for treating respiratory disease |
| WO2009071990A2 (en) * | 2007-08-31 | 2009-06-11 | Topigen Pharmaceuticals Inc. | No-donating cordicosteroid with improved pharmacokinetic, anti-inflammatory and vasodilatory properties |
| WO2010012567A1 (en) * | 2008-07-31 | 2010-02-04 | Nicox S.A. | Glucocorticoids attached to nitrate esters via an aromatic linker in position 21 and their use in ophthalmology |
| CN102186873A (zh) | 2008-08-05 | 2011-09-14 | 尼科克斯公司 | 用于治疗视网膜和黄斑疾病的新型释放no的甾类化合物 |
| CA2731477A1 (en) * | 2008-08-05 | 2010-02-11 | Nicox S.A. | New no releasing steroids derivatives |
| CA2796963A1 (en) | 2010-04-23 | 2011-10-27 | Piramal Enterprises Limited | Nitric oxide releasing prodrugs of therapeutic agents |
| CN102302501B (zh) | 2010-06-07 | 2012-10-03 | 刘超 | 糖皮质激素硝基衍生物在制备利尿药物制剂中的应用 |
| WO2014111957A1 (en) | 2013-01-21 | 2014-07-24 | Apparao Satyam | Nitric oxide releasing prodrugs of therapeutic agents |
| CN108191938B (zh) * | 2018-01-11 | 2019-07-05 | 湖南新合新生物医药有限公司 | 9,11烯烃甾族化合物的制备方法 |
| CN113069460B (zh) * | 2021-03-24 | 2022-02-08 | 兰州大学 | 哈西奈德及其衍生物用于制备治疗和/或预防脑血管疾病药物中的应用 |
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| US2990401A (en) * | 1958-06-18 | 1961-06-27 | American Cyanamid Co | 11-substituted 16alpha, 17alpha-substituted methylenedioxy steroids |
| GB1054290A (de) | 1963-05-01 | |||
| 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 (de) * | 1971-05-07 | 1973-12-28 | ||
| NZ177056A (en) * | 1974-03-27 | 1978-09-20 | Plurichemie Anstalt | Certain 9 -(chloro or flruoro)-16( or )-methyl-11 ,17 -dihydroxypregna-1,4-diene-3,20-dione 17 -acylates or 11 ,17 -diacylates and certain preparature processes |
| CA1058161A (en) * | 1975-09-08 | 1979-07-10 | Ravi K. Varma | 3,20-DIKETOPREGNENES HAVING AN 11.beta.-ACETAL GROUP AND DERIVATIVES THEREOF |
| IT1256345B (it) | 1992-08-20 | 1995-12-01 | Esteri nitrici di derivati dell'acido 2-(2,6-di-alo-fenilammino) fenilacetico e procedimento per la loro preparazione | |
| IT1256450B (it) | 1992-11-26 | 1995-12-05 | Soldato Piero Del | Esteri nitrici con attivita' farmacologica e procedimento per la loro preparazione |
| US5457207A (en) | 1993-10-05 | 1995-10-10 | Regents Of The University Of Minnesota | Spirovesamicols |
| ATE168986T1 (de) | 1993-10-06 | 1998-08-15 | Nicox Sa | Salzetersaüreester mit entzündungshemmender und/oder schmerzlindernder wirkung und verfahren zu deren herstellung |
| AU702662B2 (en) | 1994-05-10 | 1999-02-25 | Nicox S.A. | Nitro compounds and their compositions having anti-inflammatory, analgesic and anti-thrombotic acitivities |
| 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 |
| US5985862A (en) * | 1996-05-02 | 1999-11-16 | G.D. Searle & Co. | Pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs |
| IT1285770B1 (it) * | 1996-10-04 | 1998-06-18 | Nicox Sa | Composti corticoidei |
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Owner name: NICOX S.A., SOPHIA ANTIPOLIS, VALBONNE, FR |