AU766798B2 - Pharmaceutical compounds - Google Patents
Pharmaceutical compounds Download PDFInfo
- Publication number
- AU766798B2 AU766798B2 AU38201/00A AU3820100A AU766798B2 AU 766798 B2 AU766798 B2 AU 766798B2 AU 38201/00 A AU38201/00 A AU 38201/00A AU 3820100 A AU3820100 A AU 3820100A AU 766798 B2 AU766798 B2 AU 766798B2
- Authority
- AU
- Australia
- Prior art keywords
- acid
- compound
- precursor
- test
- following
- 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.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 169
- 230000036542 oxidative stress Effects 0.000 claims abstract description 15
- 230000003637 steroidlike Effects 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000002243 precursor Substances 0.000 claims description 119
- 239000000243 solution Substances 0.000 claims description 81
- 238000012360 testing method Methods 0.000 claims description 74
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 150000003431 steroids Chemical class 0.000 claims description 44
- 150000003254 radicals Chemical class 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 32
- 239000003814 drug Substances 0.000 claims description 29
- 229940079593 drug Drugs 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 238000002835 absorbance Methods 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 230000005764 inhibitory process Effects 0.000 claims description 22
- -1 isopropyl ester Chemical class 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic 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-UZVSRGJWSA-N 0.000 claims description 13
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims description 12
- 229960004308 acetylcysteine Drugs 0.000 claims description 12
- 229960001661 ursodiol Drugs 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims description 10
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims description 10
- 229940114124 ferulic acid Drugs 0.000 claims description 10
- 235000001785 ferulic acid Nutrition 0.000 claims description 10
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims description 10
- 150000002505 iron Chemical class 0.000 claims description 10
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims description 10
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 claims description 7
- 229960001091 chenodeoxycholic acid Drugs 0.000 claims description 7
- 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 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000309 desoxyribosyl group Chemical class C1(C[C@H](O)[C@H](O1)CO)* 0.000 claims description 7
- 239000012085 test solution Substances 0.000 claims description 7
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 claims description 6
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- JMSVCTWVEWCHDZ-UHFFFAOYSA-N syringic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 claims description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 5
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 5
- 235000018417 cysteine Nutrition 0.000 claims description 5
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 5
- 229960005219 gentisic acid Drugs 0.000 claims description 5
- 150000001261 hydroxy acids Chemical class 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- DZAUWHJDUNRCTF-UHFFFAOYSA-N 3-(3,4-dihydroxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(O)C(O)=C1 DZAUWHJDUNRCTF-UHFFFAOYSA-N 0.000 claims description 4
- 235000001014 amino acid Nutrition 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- HCZHHEIFKROPDY-UHFFFAOYSA-N kynurenic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC(=O)C2=C1 HCZHHEIFKROPDY-UHFFFAOYSA-N 0.000 claims description 4
- 239000008363 phosphate buffer Substances 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims description 4
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 4
- FCKJYANJHNLEEP-XRWYNYHCSA-N (24R)-24,25-dihydroxycalciol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CC[C@@H](O)C(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C FCKJYANJHNLEEP-XRWYNYHCSA-N 0.000 claims description 3
- BZCOSCNPHJNQBP-UPHRSURJSA-N (z)-2,3-dihydroxybut-2-enedioic acid Chemical compound OC(=O)C(\O)=C(\O)C(O)=O BZCOSCNPHJNQBP-UPHRSURJSA-N 0.000 claims description 3
- MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 claims description 3
- 229960002061 ergocalciferol Drugs 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000006187 pill Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 230000035882 stress Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 claims description 3
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 claims description 3
- 235000001892 vitamin D2 Nutrition 0.000 claims description 3
- 239000011653 vitamin D2 Substances 0.000 claims description 3
- FDKWRPBBCBCIGA-REOHCLBHSA-N (2r)-2-azaniumyl-3-$l^{1}-selanylpropanoate Chemical compound [Se]C[C@H](N)C(O)=O FDKWRPBBCBCIGA-REOHCLBHSA-N 0.000 claims description 2
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims description 2
- PVPBBTJXIKFICP-UHFFFAOYSA-N (7-aminophenothiazin-3-ylidene)azanium;chloride Chemical compound [Cl-].C1=CC(=[NH2+])C=C2SC3=CC(N)=CC=C3N=C21 PVPBBTJXIKFICP-UHFFFAOYSA-N 0.000 claims description 2
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims description 2
- FBHLNVZIWOYHIZ-UHFFFAOYSA-N 4-ethoxycyclohexa-1,5-diene-1,4-diol Chemical compound CCOC1(O)CC=C(O)C=C1 FBHLNVZIWOYHIZ-UHFFFAOYSA-N 0.000 claims description 2
- 108010085443 Anserine Proteins 0.000 claims description 2
- 108010087806 Carnosine Proteins 0.000 claims description 2
- FDKWRPBBCBCIGA-UWTATZPHSA-N D-Selenocysteine Natural products [Se]C[C@@H](N)C(O)=O FDKWRPBBCBCIGA-UWTATZPHSA-N 0.000 claims description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- 108010024636 Glutathione Proteins 0.000 claims description 2
- SLRNWACWRVGMKD-UHFFFAOYSA-N L-anserine Natural products CN1C=NC(CC(NC(=O)CCN)C(O)=O)=C1 SLRNWACWRVGMKD-UHFFFAOYSA-N 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
- MNNBCKASUFBXCO-YFKPBYRVSA-N N-acetyl-D-penicillamine Chemical compound CC(=O)N[C@@H](C(O)=O)C(C)(C)S MNNBCKASUFBXCO-YFKPBYRVSA-N 0.000 claims description 2
- CQOVPNPJLQNMDC-UHFFFAOYSA-N N-beta-alanyl-L-histidine Natural products NCCC(=O)NC(C(O)=O)CC1=CN=CN1 CQOVPNPJLQNMDC-UHFFFAOYSA-N 0.000 claims description 2
- 241000210053 Potentilla elegans Species 0.000 claims description 2
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 claims description 2
- RJFAYQIBOAGBLC-UHFFFAOYSA-N Selenomethionine Natural products C[Se]CCC(N)C(O)=O RJFAYQIBOAGBLC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 2
- MYYIAHXIVFADCU-QMMMGPOBSA-N anserine Chemical compound CN1C=NC=C1C[C@H](NC(=O)CC[NH3+])C([O-])=O MYYIAHXIVFADCU-QMMMGPOBSA-N 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
- 235000004883 caffeic acid Nutrition 0.000 claims description 2
- 229940074360 caffeic acid Drugs 0.000 claims description 2
- CQOVPNPJLQNMDC-ZETCQYMHSA-N carnosine Chemical compound [NH3+]CCC(=O)N[C@H](C([O-])=O)CC1=CNC=N1 CQOVPNPJLQNMDC-ZETCQYMHSA-N 0.000 claims description 2
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 229960001484 edetic acid Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229940074391 gallic acid Drugs 0.000 claims description 2
- 235000004515 gallic acid Nutrition 0.000 claims description 2
- 229960003180 glutathione Drugs 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229960001330 hydroxycarbamide Drugs 0.000 claims description 2
- 229960001639 penicillamine Drugs 0.000 claims description 2
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims description 2
- 229950004400 secalciferol Drugs 0.000 claims description 2
- ZKZBPNGNEQAJSX-UHFFFAOYSA-N selenocysteine Natural products [SeH]CC(N)C(O)=O ZKZBPNGNEQAJSX-UHFFFAOYSA-N 0.000 claims description 2
- 235000016491 selenocysteine Nutrition 0.000 claims description 2
- 229940055619 selenocysteine Drugs 0.000 claims description 2
- 229960002718 selenomethionine Drugs 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- YIBXWXOYFGZLRU-UHFFFAOYSA-N syringic aldehyde Natural products CC12CCC(C3(CCC(=O)C(C)(C)C3CC=3)C)C=3C1(C)CCC2C1COC(C)(C)C(O)C(O)C1 YIBXWXOYFGZLRU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- PTNLHDGQWUGONS-OWOJBTEDSA-N trans-p-coumaryl alcohol Chemical compound OC\C=C\C1=CC=C(O)C=C1 PTNLHDGQWUGONS-OWOJBTEDSA-N 0.000 claims description 2
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 claims description 2
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 9
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims 3
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 claims 1
- 101000713585 Homo sapiens Tubulin beta-4A chain Proteins 0.000 claims 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 claims 1
- 102100036788 Tubulin beta-4A chain Human genes 0.000 claims 1
- OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 claims 1
- 230000006870 function Effects 0.000 description 33
- KCWZGJVSDFYRIX-YFKPBYRVSA-N N(gamma)-nitro-L-arginine methyl ester Chemical compound COC(=O)[C@@H](N)CCCN=C(N)N[N+]([O-])=O KCWZGJVSDFYRIX-YFKPBYRVSA-N 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 241001465754 Metazoa Species 0.000 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 description 16
- 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 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 230000003213 activating effect Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- 230000036772 blood pressure Effects 0.000 description 10
- 238000007912 intraperitoneal administration Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 206010048554 Endothelial dysfunction Diseases 0.000 description 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 229960003957 dexamethasone Drugs 0.000 description 8
- 230000008694 endothelial dysfunction Effects 0.000 description 8
- 229940093499 ethyl acetate Drugs 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 229960000890 hydrocortisone Drugs 0.000 description 8
- 229960005205 prednisolone Drugs 0.000 description 8
- 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 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 8
- BMLMGCPTLHPWPY-UHFFFAOYSA-N 2-oxo-1,3-thiazolidine-4-carboxylic acid Chemical compound OC(=O)C1CSC(=O)N1 BMLMGCPTLHPWPY-UHFFFAOYSA-N 0.000 description 7
- 101710134784 Agnoprotein Proteins 0.000 description 7
- 206010067125 Liver injury Diseases 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 231100000234 hepatic damage Toxicity 0.000 description 7
- 230000008818 liver damage Effects 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
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- C—CHEMISTRY; METALLURGY
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- 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
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- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
Landscapes
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| JP2003523958A (ja) | 1999-12-23 | 2003-08-12 | ニトロメド インコーポレーテッド | ニトロソ化およびニトロシル化されたシクロオキシゲナーゼ−２の阻害剤、組成物ならびに使用法 |
| EP1406609B1 (en) | 2000-12-21 | 2006-09-06 | Nitromed, Inc. | Substituted aryl compounds as novel cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| IT1320176B1 (it) * | 2000-12-22 | 2003-11-26 | Nicox Sa | Dispersioni solide di principi attivi nitrati. |
| EP1219306A1 (en) | 2000-12-29 | 2002-07-03 | Nicox S.A. | Compositions comprising cyclodextrins and NO- releasing drugs |
| 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 |
| ITMI20011307A1 (it) * | 2001-06-21 | 2002-12-21 | Nicox Sa | Farmaci per l'epilessia |
| ITMI20020148A1 (it) | 2002-01-29 | 2003-07-29 | Nicox Sa | Nuovi corticosteroidi |
| ITMI20021025A1 (it) * | 2002-05-14 | 2003-11-14 | Nicox Sa | Farmaci per il trattamento acuto di disfunzioni del circolo venoso epatico e portale |
| EP1539134A4 (en) | 2002-06-11 | 2007-04-11 | Nitromed Inc | SELECTIVE INHIBITORS OF CYCLOOXIGENASE-2 NITROSIS AND / OR NITROSYLES, COMPOSITIONS AND METHODS OF USE |
| US7211598B2 (en) | 2002-06-28 | 2007-05-01 | Nitromed, Inc. | Oxime and/or hydrozone containing nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| US7163958B2 (en) | 2002-07-03 | 2007-01-16 | Nitromed Inc. | Nitrosated nonsteroidal antiinflammatory compounds, compositions and methods of use |
| AU2003261281A1 (en) | 2002-07-29 | 2004-02-16 | Nicox S.A. | Cyclooxygenase- 2 selective inhibitors, compositions and methods of use |
| 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 |
| AU2006286838C1 (en) | 2005-09-02 | 2013-05-02 | Ferrer Internacional S.A. | Nitrooxy derivatives of glucocorticoids |
| US8802726B2 (en) | 2006-02-03 | 2014-08-12 | Nicox S.A. | Use of nitrooxyderivative of drug for the treatment of muscular dystrophies |
| US7645748B2 (en) * | 2006-04-03 | 2010-01-12 | Forbes Medi-Tech Inc. | Sterol/stanol phosphorylnitroderivatives and use thereof |
| US7645749B2 (en) * | 2006-04-03 | 2010-01-12 | Forbes Medi-Tech Inc. | Sterol/stanol nitroderivatives and use thereof |
| CN101652380A (zh) * | 2007-02-05 | 2010-02-17 | 尼科克斯公司 | 释放一氧化氮的类固醇 |
| CA2695435A1 (en) * | 2007-08-10 | 2009-03-26 | Nicox S.A. | 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 |
| CA2703723A1 (en) * | 2007-10-19 | 2009-04-23 | Burnham Institute Of Medical Research | Inhibitors of anti-apoptotic proteins |
| US20110130375A1 (en) | 2008-08-05 | 2011-06-02 | Nicox S.A. | New no-releasing steroids for the treatment of retina and macula lutea diseases |
| AU2011243947A1 (en) | 2010-04-23 | 2012-12-06 | Piramal Enterprises Limited | Nitric oxide releasing prodrugs of therapeutic agents |
| CU20110244A7 (es) | 2011-12-27 | 2013-08-29 | Ct De Investigación Y Desarrollo De Medicamentos Cidem | Sistemas espiroesteroidales con efectos neuroactivos y anti-inflamatorios |
| CA2897571C (en) | 2013-01-21 | 2018-12-18 | Apparao Satyam | Nitric oxide releasing prodrugs of therapeutic agents containing at least one carboxylic acid group |
| KR101711513B1 (ko) * | 2015-06-26 | 2017-03-02 | 주식회사 엘지생활건강 | 피부 개선용 조성물 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997041144A1 (en) * | 1996-05-02 | 1997-11-06 | G.D. Searle & Co. | Novel steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs |
| WO1998015568A2 (en) * | 1996-10-04 | 1998-04-16 | Nicox S.A. | Nitrate esters of corticoid compounds and pharmaceutical applications thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| FR2077750B1 (enExample) | 1970-02-11 | 1973-03-16 | Clin Byla Ets | |
| GB1458372A (en) | 1973-03-05 | 1976-12-15 | Leo Ab | Steroid carbamates and allophanates |
| JPS5845724A (ja) | 1981-09-11 | 1983-03-17 | Oriza Yuka Kk | オリザノ−ル乳化液の製造法 |
| FR2600653B1 (fr) | 1986-06-24 | 1988-12-16 | Pasteur Strasbourg Universite | Composes de synthese associative d'acides amines soufres ou non soufres avec des derives du d-4 pregnene 3,20-dione ou avec des derives du d-1,4 pregnadiene 3,20-dione aux proprietes glucocorticoides et anti-inflammatoires, procedes d'obtention, compositions pharmaceutiques les contenant. proprietes pharmacologiques et applications |
| IT1204571B (it) | 1987-05-08 | 1989-03-10 | Chiesi Farma Spa | Esteri di 1,4:3,6-dianidrosorbitolo-2-mononitrato e 5-mononitrato,loro procedimento di preparazione e loro composizioni farmaceutiche |
| EP0688865B1 (en) * | 1987-06-29 | 2002-01-16 | Massachusetts Institute Of Technology | Nucleotide sequence encoding acetoacetyl-CoA reductase and a method for producing polyester biopolymers |
| DE4000397A1 (de) * | 1990-01-09 | 1991-07-11 | Hoechst Ag | Lipidselektive antioxidantien sowie deren herstellung und verwendung |
| JPH04273892A (ja) | 1991-02-27 | 1992-09-30 | Kao Corp | 新規な２１−置換ステロイド化合物 |
| JP3108474B2 (ja) | 1991-08-07 | 2000-11-13 | 日清製粉株式会社 | 活性型ビタミンｄ誘導体 |
| AU656829B2 (en) | 1991-12-26 | 1995-02-16 | Wisconsin Alumni Research Foundation | 26, 27-dimethylene-1 alpha, 25-dihydroxyvitamin D2 and 26,27-dihydroxyvitamin D2 and methods for preparing same |
| EP0562497A1 (en) | 1992-03-27 | 1993-09-29 | Nisshin Flour Milling Co., Ltd. | 1 alpha-hydroxy vitamins D7 and D4' processes for the preparation thereof and pharmaceutical compositions |
| US5194431A (en) | 1992-07-08 | 1993-03-16 | Wisconsin Alumni Research Foundation | 24-cyclopropane vitamin D derivatives |
| US5707984A (en) | 1995-12-08 | 1998-01-13 | G. D. Searle & Co. | Steroid nitrite/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 |
| DE19634793A1 (de) | 1996-08-29 | 1998-03-05 | Sanol Arznei Schwarz Gmbh | S- und O-Nitratoacylverbindungen |
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- 2000-04-11 JP JP2000611546A patent/JP2002542162A/ja active Pending
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997041144A1 (en) * | 1996-05-02 | 1997-11-06 | G.D. Searle & Co. | Novel steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs |
| WO1998015568A2 (en) * | 1996-10-04 | 1998-04-16 | Nicox S.A. | Nitrate esters of corticoid compounds and pharmaceutical applications thereof |
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