IL98629A - 2,4- and 2,5-substituted pyridine-n-oxides processes for their preparation and their use - Google Patents
2,4- and 2,5-substituted pyridine-n-oxides processes for their preparation and their useInfo
- Publication number
- IL98629A IL98629A IL9862991A IL9862991A IL98629A IL 98629 A IL98629 A IL 98629A IL 9862991 A IL9862991 A IL 9862991A IL 9862991 A IL9862991 A IL 9862991A IL 98629 A IL98629 A IL 98629A
- Authority
- IL
- Israel
- Prior art keywords
- radicals
- different
- phenyl
- formula
- unsubstituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 229920001436 collagen Polymers 0.000 claims abstract description 14
- 108010035532 Collagen Proteins 0.000 claims abstract description 13
- 102000008186 Collagen Human genes 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 8
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000011282 treatment Methods 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 6
- 230000004060 metabolic process Effects 0.000 claims abstract description 4
- -1 nitro, nitroxy, amino, carboxyl Chemical group 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 102000004079 Prolyl Hydroxylases Human genes 0.000 claims description 15
- 108010043005 Prolyl Hydroxylases Proteins 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 102000008490 2-Oxoglutarate 5-Dioxygenase Procollagen-Lysine Human genes 0.000 claims description 10
- 108010020504 2-Oxoglutarate 5-Dioxygenase Procollagen-Lysine Proteins 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 150000003222 pyridines Chemical class 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229940125721 immunosuppressive agent Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 230000001506 immunosuppresive effect Effects 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 17
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 7
- 210000004185 liver Anatomy 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- JUCNGMPTCXPMNB-UHFFFAOYSA-N 2-n,4-n-bis(2-methoxyethyl)pyridine-2,4-dicarboxamide Chemical compound COCCNC(=O)C1=CC=NC(C(=O)NCCOC)=C1 JUCNGMPTCXPMNB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 208000019425 cirrhosis of liver Diseases 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- OOXOXZVOZIURRD-UHFFFAOYSA-N pyridine-2,4-dicarboxamide Chemical compound NC(=O)C1=CC=NC(C(N)=O)=C1 OOXOXZVOZIURRD-UHFFFAOYSA-N 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 108010050808 Procollagen Proteins 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 231100000644 Toxic injury Toxicity 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000003510 anti-fibrotic effect Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000003613 bile acid Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000036570 collagen biosynthesis Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229960002591 hydroxyproline Drugs 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- QNFICQBHEOBHMY-UHFFFAOYSA-N 2-N,4-N-bis(3-ethoxypropyl)-2-N-hydroxypyridine-2,4-dicarboxamide Chemical compound CCOCCCNC(=O)C1=CC=NC(C(=O)N(O)CCCOCC)=C1 QNFICQBHEOBHMY-UHFFFAOYSA-N 0.000 description 1
- JZHYCIQNJBUDBD-UHFFFAOYSA-N 2-N-hydroxy-2-N,4-N-bis(2-methoxyethyl)pyridine-2,4-dicarboxamide Chemical compound COCCNC(=O)C1=CC=NC(C(=O)N(O)CCOC)=C1 JZHYCIQNJBUDBD-UHFFFAOYSA-N 0.000 description 1
- LWERFQFSOGYVCH-UHFFFAOYSA-N 2-N-hydroxy-2-N,5-N-bis(3-methoxypropyl)pyridine-2,5-dicarboxamide Chemical compound COCCCNC(=O)C1=CC=C(C(=O)N(O)CCCOC)N=C1 LWERFQFSOGYVCH-UHFFFAOYSA-N 0.000 description 1
- NUKJWCDZSPKZIF-UHFFFAOYSA-N 2-n,4-n-bis(3-ethoxypropyl)pyridine-2,4-dicarboxamide Chemical compound CCOCCCNC(=O)C1=CC=NC(C(=O)NCCCOCC)=C1 NUKJWCDZSPKZIF-UHFFFAOYSA-N 0.000 description 1
- ABKKZPBEHVFPTE-UHFFFAOYSA-N 2-n,4-n-bis(3-propan-2-yloxypropyl)pyridine-2,4-dicarboxamide Chemical compound CC(C)OCCCNC(=O)C1=CC=NC(C(=O)NCCCOC(C)C)=C1 ABKKZPBEHVFPTE-UHFFFAOYSA-N 0.000 description 1
- AWQYRHYRDMLSEB-UHFFFAOYSA-N 2-n,4-n-bis[(3-chlorophenyl)methyl]pyridine-2,4-dicarboxamide Chemical compound ClC1=CC=CC(CNC(=O)C=2C=C(N=CC=2)C(=O)NCC=2C=C(Cl)C=CC=2)=C1 AWQYRHYRDMLSEB-UHFFFAOYSA-N 0.000 description 1
- XVIFRYAVHVXKAH-UHFFFAOYSA-N 2-n,5-n-bis(3-methoxypropyl)pyridine-2,5-dicarboxamide Chemical compound COCCCNC(=O)C1=CC=C(C(=O)NCCCOC)N=C1 XVIFRYAVHVXKAH-UHFFFAOYSA-N 0.000 description 1
- JQBYASSYQUSXBQ-UHFFFAOYSA-N 2-n,5-n-diethylpyridine-2,5-dicarboxamide Chemical compound CCNC(=O)C1=CC=C(C(=O)NCC)N=C1 JQBYASSYQUSXBQ-UHFFFAOYSA-N 0.000 description 1
- LXZKYTKXZYSEOZ-UHFFFAOYSA-N 3-(2-methoxyethyl)pyridine-2,4-dicarboxamide Chemical compound COCCC1=C(C(N)=O)C=CN=C1C(N)=O LXZKYTKXZYSEOZ-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- 102000001187 Collagen Type III Human genes 0.000 description 1
- 108010069502 Collagen Type III Proteins 0.000 description 1
- 102000004266 Collagen Type IV Human genes 0.000 description 1
- 108010042086 Collagen Type IV Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 206010063560 Excessive granulation tissue Diseases 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 208000024781 Immune Complex disease Diseases 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940121383 antituberculosis agent Drugs 0.000 description 1
- 229940076134 benzene Drugs 0.000 description 1
- FZUQJWUFKCWWJD-UHFFFAOYSA-N bis(2-methoxy-2-oxoethyl) 1-oxidopyridin-1-ium-2,4-dicarboxylate Chemical compound COC(=O)COC(=O)C1=CC=[N+]([O-])C(C(=O)OCC(=O)OC)=C1 FZUQJWUFKCWWJD-UHFFFAOYSA-N 0.000 description 1
- LKCIAVLUFJWOEW-UHFFFAOYSA-N bis(2-methoxy-2-oxoethyl) pyridine-2,4-dicarboxylate Chemical compound COC(=O)COC(=O)C1=CC=NC(C(=O)OCC(=O)OC)=C1 LKCIAVLUFJWOEW-UHFFFAOYSA-N 0.000 description 1
- IZGWEXNHUKFUQX-UHFFFAOYSA-N bis(2-methoxyethyl) 1-oxidopyridin-1-ium-2,4-dicarboxylate Chemical compound COCCOC(=O)C1=CC=[N+]([O-])C(C(=O)OCCOC)=C1 IZGWEXNHUKFUQX-UHFFFAOYSA-N 0.000 description 1
- 229960001561 bleomycin Drugs 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000024203 complement activation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 210000001723 extracellular space Anatomy 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000001126 granulation tissue Anatomy 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- MJIVRKPEXXHNJT-UHFFFAOYSA-L lutidinate(2-) Chemical compound [O-]C(=O)C1=CC=NC(C([O-])=O)=C1 MJIVRKPEXXHNJT-UHFFFAOYSA-L 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4020570A DE4020570A1 (de) | 1990-06-28 | 1990-06-28 | 2,4- und 2,5-substituierte pyridin-n-oxide, verfahren zu deren herstellung sowie deren verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL98629A0 IL98629A0 (en) | 1992-07-15 |
| IL98629A true IL98629A (en) | 1996-05-14 |
Family
ID=6409247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9862991A IL98629A (en) | 1990-06-28 | 1991-06-26 | 2,4- and 2,5-substituted pyridine-n-oxides processes for their preparation and their use |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0463592B1 (cs) |
| JP (1) | JPH0832687B2 (cs) |
| KR (1) | KR920000724A (cs) |
| CN (1) | CN1038585C (cs) |
| AT (1) | ATE110059T1 (cs) |
| AU (1) | AU636990B2 (cs) |
| BR (1) | BR9102699A (cs) |
| CA (1) | CA2045868A1 (cs) |
| CZ (1) | CZ283782B6 (cs) |
| DE (2) | DE4020570A1 (cs) |
| DK (1) | DK0463592T3 (cs) |
| EG (1) | EG19851A (cs) |
| ES (1) | ES2061118T3 (cs) |
| FI (1) | FI101070B (cs) |
| HR (1) | HRP940701B1 (cs) |
| HU (1) | HU214627B (cs) |
| IE (1) | IE65300B1 (cs) |
| IL (1) | IL98629A (cs) |
| LT (1) | LT3918B (cs) |
| MA (1) | MA22191A1 (cs) |
| MX (1) | MX26415A (cs) |
| MY (1) | MY107573A (cs) |
| NO (1) | NO178026C (cs) |
| NZ (1) | NZ238701A (cs) |
| PT (1) | PT98108B (cs) |
| YU (1) | YU113391A (cs) |
| ZA (1) | ZA914958B (cs) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU9492A (sh) * | 1991-02-05 | 1995-03-27 | Hoechst Ag. | 2,4- i 2,5-bis-tetrazolilni piridini i postupak za njihovo dobijanje |
| EP0548883A1 (de) * | 1991-12-24 | 1993-06-30 | Hoechst Aktiengesellschaft | Substituierte Pyridin-N-oxide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| TW352384B (en) * | 1992-03-24 | 1999-02-11 | Hoechst Ag | Sulfonamido- or sulfonamidocarbonylpyridine-2-carboxamides, process for their preparation and their use as pharmaceuticals |
| TW222585B (cs) * | 1992-09-11 | 1994-04-21 | Hoechst Ag | |
| DE4233124A1 (de) * | 1992-10-02 | 1994-04-07 | Hoechst Ag | Acylsulfonamido- und Sulfonamidopyridin-2-carbonsäureester sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US6451816B1 (en) | 1997-06-20 | 2002-09-17 | Klinge Pharma Gmbh | Use of pyridyl alkane, pyridyl alkene and/or pyridyl alkine acid amides in the treatment of tumors or for immunosuppression |
| DE19624704A1 (de) * | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | Neue Pyridylalkansäureamide |
| DE19624659A1 (de) | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | Neue Pyridylalken- und Pyridylalkinsäureamide |
| FR2766187B1 (fr) * | 1997-07-17 | 2000-06-02 | Rhone Poulenc Rorer Sa | Derives de pyrazine, leur preparation et les medicaments les contenant |
| DE19756261A1 (de) | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue arylsubstituierte Pyridylalkan-, alken- und alkincarbonsäureamide |
| DE19756235A1 (de) | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue piperidinylsubstituierte Pyridylalkan- alken- und -alkincarbonsäureamide |
| DE19756212A1 (de) | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue, mit einem cyclischen Imid substituierte Pyridylalkan-, alken- und -alkincarbonsäureamide |
| US6903118B1 (en) | 1997-12-17 | 2005-06-07 | Klinge Pharma Gmbh | Piperazinyl-substituted pyridylalkane, alkene and alkine carboxamides |
| EP1031564A1 (en) | 1999-02-26 | 2000-08-30 | Klinge Pharma GmbH | Inhibitors of cellular nicotinamide mononucleotide formation and their use in cancer therapy |
| DOP2002000332A (es) | 2001-02-14 | 2002-08-30 | Warner Lambert Co | Inhibidores de piridina de metaloproteinasas de la matriz |
| BR0207209A (pt) | 2001-02-14 | 2004-01-27 | Warner Lambert Co | Inibidores de metaloproteinase de matriz de pirimidina |
| DOP2002000333A (es) | 2001-02-14 | 2002-09-30 | Warner Lambert Co | Derivados de acido isoftalico como inhibidores de metaloproteinasas de la matriz |
| US6924276B2 (en) | 2001-09-10 | 2005-08-02 | Warner-Lambert Company | Diacid-substituted heteroaryl derivatives as matrix metalloproteinase inhibitors |
| BR0213233A (pt) | 2001-10-12 | 2005-01-04 | Warner Lambert Co | Alcinos inibidores de metaloproteinase de matriz |
| US6933298B2 (en) | 2001-12-08 | 2005-08-23 | Aventis Pharma Deutschland Gmbh | Pyridine-2,4-dicarboxylic acid diamides and pyrimidine-4,6-dicarboxylic acid diamides and the use thereof for selectively inhibiting collagenases |
| DE10160357A1 (de) * | 2001-12-08 | 2003-06-18 | Aventis Pharma Gmbh | Verwendung von Pyridin-2,4-dicarbonsäurediamiden und Pyrimidin-4,6-dicarbonsäurediamiden zur selektiven Inhibierung von Kollagenasen |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5623987B2 (cs) * | 1972-02-04 | 1981-06-03 | ||
| JPS6052702B2 (ja) | 1976-08-27 | 1985-11-20 | 中外製薬株式会社 | ピリジン誘導体およびその製造方法 |
| JPS57109792A (en) * | 1980-12-26 | 1982-07-08 | Banyu Pharmaceut Co Ltd | Penicillin derivative and salt thereof |
| DE3432094A1 (de) | 1984-08-31 | 1986-03-06 | Hoechst Ag, 6230 Frankfurt | Ester der pyridin-2,4- und -2,5- dicarbonsaeure als arzneimittel zur inhibierung der prolin- und lysinhydroxylase |
| JP2512924B2 (ja) * | 1987-01-21 | 1996-07-03 | 萬有製薬株式会社 | 育毛剤 |
| DE3703962A1 (de) | 1987-02-10 | 1988-08-18 | Hoechst Ag | Pyridin-2,4- und 2,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen |
| DE3703959A1 (de) | 1987-02-10 | 1988-08-18 | Hoechst Ag | Pyridin-2,4- und 2,5-dicarbonsaeureamide, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen |
| DE3703963A1 (de) | 1987-02-10 | 1988-08-18 | Hoechst Ag | Pyridin-2,4- und 2,,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben, sowie arzneimittel auf basis dieser verbindungen |
| JP2600786B2 (ja) * | 1988-04-12 | 1997-04-16 | 萬有製薬株式会社 | 育毛剤 |
| DE3826471A1 (de) | 1988-08-04 | 1990-02-22 | Hoechst Ag | Verbessertes verfahren zur herstellung von n,n'-bis(alkoxyalkyl)-pyridin-2,4-dicarbonsaeurediamiden |
| DE3924093A1 (de) | 1989-07-20 | 1991-02-07 | Hoechst Ag | N,n'-bis(alkoxy-alkyl)-pyridin-2,4-dicarbonsaeurediamide, verfahren zu deren herstellung sowie deren verwendung |
| ZA91291B (en) | 1990-01-16 | 1991-09-25 | Hoechst Ag | Di(nitroxyalkyl)amides of pyridine-2,4-and-2,5-dicarboxylic acids,a process for the preparation thereof,and the use thereof |
-
1990
- 1990-06-28 DE DE4020570A patent/DE4020570A1/de not_active Withdrawn
-
1991
- 1991-06-22 DE DE59102547T patent/DE59102547D1/de not_active Expired - Fee Related
- 1991-06-22 AT AT91110343T patent/ATE110059T1/de not_active IP Right Cessation
- 1991-06-22 EP EP91110343A patent/EP0463592B1/de not_active Expired - Lifetime
- 1991-06-22 DK DK91110343.0T patent/DK0463592T3/da active
- 1991-06-22 ES ES91110343T patent/ES2061118T3/es not_active Expired - Lifetime
- 1991-06-26 IL IL9862991A patent/IL98629A/en not_active IP Right Cessation
- 1991-06-26 MY MYPI91001142A patent/MY107573A/en unknown
- 1991-06-26 NZ NZ238701A patent/NZ238701A/en unknown
- 1991-06-26 FI FI913118A patent/FI101070B/fi active IP Right Grant
- 1991-06-26 CZ CS911959A patent/CZ283782B6/cs not_active IP Right Cessation
- 1991-06-26 EG EG39291A patent/EG19851A/xx active
- 1991-06-27 ZA ZA914958A patent/ZA914958B/xx unknown
- 1991-06-27 JP JP3156562A patent/JPH0832687B2/ja not_active Expired - Lifetime
- 1991-06-27 NO NO912541A patent/NO178026C/no not_active IP Right Cessation
- 1991-06-27 IE IE225391A patent/IE65300B1/en unknown
- 1991-06-27 BR BR919102699A patent/BR9102699A/pt not_active Application Discontinuation
- 1991-06-27 MA MA22469A patent/MA22191A1/fr unknown
- 1991-06-27 YU YU113391A patent/YU113391A/sh unknown
- 1991-06-27 CA CA002045868A patent/CA2045868A1/en not_active Abandoned
- 1991-06-27 HU HU912158A patent/HU214627B/hu not_active IP Right Cessation
- 1991-06-27 PT PT98108A patent/PT98108B/pt not_active IP Right Cessation
- 1991-06-27 AU AU79356/91A patent/AU636990B2/en not_active Ceased
- 1991-06-27 MX MX2641591A patent/MX26415A/es unknown
- 1991-06-27 CN CN91104308A patent/CN1038585C/zh not_active Expired - Fee Related
- 1991-06-28 KR KR1019910010858A patent/KR920000724A/ko not_active Withdrawn
-
1993
- 1993-11-12 LT LTIP1464A patent/LT3918B/lt not_active IP Right Cessation
-
1994
- 1994-10-19 HR HRP-1133/91A patent/HRP940701B1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5260323A (en) | 2,4- and 2,5-substituted pyridine-N-oxides, processes for their preparation and their use | |
| IL98629A (en) | 2,4- and 2,5-substituted pyridine-n-oxides processes for their preparation and their use | |
| US5130317A (en) | Pyrimidine-4,6-dicarboxylic acid diamides, processes for the use thereof, and pharmaceuticals based on these compounds | |
| US5037839A (en) | Pyridine-2,4-and -2,5-dicarboxylic acid amides and medicaments based on these compounds | |
| IE67446B1 (en) | Pyridine-2,4- and -2,5-dicarboxylic acid derivatives processes for their preparation the use thereof and medicaments based on these compounds | |
| EP0479177A2 (de) | 4- Oder 5-substituierte Pyridin-2-carbonsäuren, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel | |
| US5240921A (en) | Cyclic pyridine-2,4- and -2,5-dicarboxylic acid diamides, processes for their preparation and their use | |
| US5364873A (en) | Pyridine-2,4- and dicarboxylic acid derivatives, the use thereof and pharmaceutical composition based on these compounds | |
| US5153208A (en) | Pyridine-2,4- and -2,5-dicarboxylic acid amides and their medicinal compositions and methods of use | |
| US5512586A (en) | Medicaments based on pyridine-2,4- and 2,5-dicarboxylic acid amides | |
| AU637848B2 (en) | Pyridine-2,4- and 2,5-dicarboxamides, a process for the preparation thereof, and the use thereof | |
| JPH072777A (ja) | ４−または５−置換ピリジン−２−カルボン酸、その製造方法および医薬としてのその使用 | |
| AU645668B2 (en) | Mixed pyridine-2,4-and-2,5-dicarboxamides, a process for preparing them, the use thereof and pharmaceuticals based on these compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |