CA1115272A - 4-amino-3-carboxy or cyano-1,2-dihydro-2-oxo-1,8- naphthyridine derivatives - Google Patents
4-amino-3-carboxy or cyano-1,2-dihydro-2-oxo-1,8- naphthyridine derivativesInfo
- Publication number
- CA1115272A CA1115272A CA349,623A CA349623A CA1115272A CA 1115272 A CA1115272 A CA 1115272A CA 349623 A CA349623 A CA 349623A CA 1115272 A CA1115272 A CA 1115272A
- Authority
- CA
- Canada
- Prior art keywords
- oxo
- dihydro
- naphthyridine
- carboxylic acid
- methyl
- 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
Links
- XHFAUSDQLOACQA-UHFFFAOYSA-N 2-oxo-1,8-naphthyridine-1-carbonitrile Chemical class C1=CN=C2N(C#N)C(=O)C=CC2=C1 XHFAUSDQLOACQA-UHFFFAOYSA-N 0.000 title description 4
- 238000000034 method Methods 0.000 claims description 126
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 101
- 230000008569 process Effects 0.000 claims description 98
- 125000004432 carbon atom Chemical group C* 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 67
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 52
- 238000010992 reflux Methods 0.000 claims description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 40
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 239000000047 product Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 29
- -1 4-phenylpiperazinyl Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000002244 precipitate Substances 0.000 claims description 13
- IPOVOSHRRIJKBR-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride Chemical compound CCC(C(Cl)=O)C(Cl)=O IPOVOSHRRIJKBR-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 12
- MZUYYXCNONXVBK-UHFFFAOYSA-N ethyl 4-chloro-1-ethyl-7-methyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=C(C)N=C2N(CC)C(=O)C(C(=O)OCC)=C(Cl)C2=C1 MZUYYXCNONXVBK-UHFFFAOYSA-N 0.000 claims description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- GPDBAOOTLKONEG-UHFFFAOYSA-N 2-(ethylamino)pyridine-3-carbonitrile Chemical compound CCNC1=NC=CC=C1C#N GPDBAOOTLKONEG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- YYXDQRRDNPRJFL-UHFFFAOYSA-N 2-aminopyridine-3-carbonitrile Chemical compound NC1=NC=CC=C1C#N YYXDQRRDNPRJFL-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 230000009935 nitrosation Effects 0.000 claims description 3
- 238000007034 nitrosation reaction Methods 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
- MWUZXVOXGCWJJU-UHFFFAOYSA-N 2-(2-methylpropylamino)pyridine-3-carbonitrile Chemical compound CC(C)CNC1=NC=CC=C1C#N MWUZXVOXGCWJJU-UHFFFAOYSA-N 0.000 claims description 2
- QSPSGUZTVLHQRU-UHFFFAOYSA-N 2-(ethylamino)-6-methylpyridine-3-carbonitrile Chemical compound CCNC1=NC(C)=CC=C1C#N QSPSGUZTVLHQRU-UHFFFAOYSA-N 0.000 claims description 2
- YNXXIFLTPBDEGP-UHFFFAOYSA-N 2-(propylamino)pyridine-3-carbonitrile Chemical compound CCCNC1=NC=CC=C1C#N YNXXIFLTPBDEGP-UHFFFAOYSA-N 0.000 claims description 2
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 claims description 2
- FDBZDXTUWGEFQA-UHFFFAOYSA-N 4-amino-2-oxo-1h-1,8-naphthyridine-3-carboxylic acid Chemical compound C1=CC=C2C(N)=C(C(O)=O)C(=O)NC2=N1 FDBZDXTUWGEFQA-UHFFFAOYSA-N 0.000 claims description 2
- VYCNLIFBEYERKX-UHFFFAOYSA-N 6-chloro-2-(ethylamino)pyridine-3-carbonitrile Chemical compound CCNC1=NC(Cl)=CC=C1C#N VYCNLIFBEYERKX-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 2
- UJLBIJMOVYDTBF-UHFFFAOYSA-N ethyl 4-chloro-1-ethyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=CN=C2N(CC)C(=O)C(C(=O)OCC)=C(Cl)C2=C1 UJLBIJMOVYDTBF-UHFFFAOYSA-N 0.000 claims description 2
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 46
- 235000013350 formula milk Nutrition 0.000 claims 31
- XYVVIQBCIRDZOX-UHFFFAOYSA-N ethyl 4-amino-1-ethyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=CN=C2N(CC)C(=O)C(C(=O)OCC)=C(N)C2=C1 XYVVIQBCIRDZOX-UHFFFAOYSA-N 0.000 claims 4
- 159000000000 sodium salts Chemical class 0.000 claims 4
- DNKZOLRBQNLTRJ-UHFFFAOYSA-N ethyl 4-amino-2-oxo-1h-1,8-naphthyridine-3-carboxylate Chemical compound C1=CN=C2NC(=O)C(C(=O)OCC)=C(N)C2=C1 DNKZOLRBQNLTRJ-UHFFFAOYSA-N 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000004069 aziridinyl group Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- QXSPIWPYGCEJFI-UHFFFAOYSA-N ethyl 4-chloro-1-methyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=CN=C2N(C)C(=O)C(C(=O)OCC)=C(Cl)C2=C1 QXSPIWPYGCEJFI-UHFFFAOYSA-N 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- XDHCBXCABCBGRZ-UHFFFAOYSA-N 1-ethyl-7-methyl-2-oxo-4-pyrrolidin-1-yl-1,8-naphthyridine-3-carbonitrile Chemical compound N#CC=1C(=O)N(CC)C2=NC(C)=CC=C2C=1N1CCCC1 XDHCBXCABCBGRZ-UHFFFAOYSA-N 0.000 claims 1
- FGPXYQBCOHJROQ-UHFFFAOYSA-N 1-ethyl-7-methyl-4-(4-methylpiperazin-1-yl)-2-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound OC(=O)C=1C(=O)N(CC)C2=NC(C)=CC=C2C=1N1CCN(C)CC1 FGPXYQBCOHJROQ-UHFFFAOYSA-N 0.000 claims 1
- WUHHVDQBQZVSJV-UHFFFAOYSA-N 2,2-dibutylpropanedioic acid Chemical compound CCCCC(C(O)=O)(C(O)=O)CCCC WUHHVDQBQZVSJV-UHFFFAOYSA-N 0.000 claims 1
- UCVVPEUOVNJIJP-UHFFFAOYSA-N 2-(cyclohexylamino)pyridine-3-carbonitrile Chemical compound N#CC1=CC=CN=C1NC1CCCCC1 UCVVPEUOVNJIJP-UHFFFAOYSA-N 0.000 claims 1
- AGZQPTBBDDQFKJ-UHFFFAOYSA-N 2-(methylamino)pyridine-3-carbonitrile Chemical compound CNC1=NC=CC=C1C#N AGZQPTBBDDQFKJ-UHFFFAOYSA-N 0.000 claims 1
- GQIYMUQDNPAILQ-UHFFFAOYSA-N 2-(prop-2-ynylamino)pyridine-3-carbonitrile Chemical compound C#CCNC1=NC=CC=C1C#N GQIYMUQDNPAILQ-UHFFFAOYSA-N 0.000 claims 1
- ASVXBGHDTOWGTD-UHFFFAOYSA-N 4-amino-1-ethyl-2-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1=CC=C2C(N)=C(C(O)=O)C(=O)N(CC)C2=N1 ASVXBGHDTOWGTD-UHFFFAOYSA-N 0.000 claims 1
- JOOHPTIVOSYFDY-UHFFFAOYSA-N 4-amino-1-ethyl-7-methyl-2-oxo-1,8-naphthyridine-3-carbonitrile Chemical compound CC1=CC=C2C(N)=C(C#N)C(=O)N(CC)C2=N1 JOOHPTIVOSYFDY-UHFFFAOYSA-N 0.000 claims 1
- YNBNDDKIQZNEOO-UHFFFAOYSA-N 4-amino-1-ethyl-7-methyl-2-oxo-1,8-naphthyridine-3-carboxamide Chemical compound CC1=CC=C2C(N)=C(C(N)=O)C(=O)N(CC)C2=N1 YNBNDDKIQZNEOO-UHFFFAOYSA-N 0.000 claims 1
- XPWMOEXGDUSODD-UHFFFAOYSA-N 4-chloro-1-ethyl-7-methyl-2-oxo-1,8-naphthyridine-3-carbonitrile Chemical compound CC1=CC=C2C(Cl)=C(C#N)C(=O)N(CC)C2=N1 XPWMOEXGDUSODD-UHFFFAOYSA-N 0.000 claims 1
- GHAGPHLQQNGESH-UHFFFAOYSA-N 4-chloro-1-ethyl-7-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound CC1=CC=C2C(Cl)=C(C(O)=O)C(=O)N(CC)C2=N1 GHAGPHLQQNGESH-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- WQTSYSNDWXHCHT-UHFFFAOYSA-N ethyl 1,7-dimethyl-2-oxo-4-pyrrolidin-1-yl-1,8-naphthyridine-3-carboxylate Chemical compound C12=CC=C(C)N=C2N(C)C(=O)C(C(=O)OCC)=C1N1CCCC1 WQTSYSNDWXHCHT-UHFFFAOYSA-N 0.000 claims 1
- LOQUUZLPADRCNJ-UHFFFAOYSA-N ethyl 1,7-dimethyl-4-(4-methylpiperazin-1-yl)-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C12=CC=C(C)N=C2N(C)C(=O)C(C(=O)OCC)=C1N1CCN(C)CC1 LOQUUZLPADRCNJ-UHFFFAOYSA-N 0.000 claims 1
- BLODFSOSCIESKS-UHFFFAOYSA-N ethyl 1-ethyl-2-oxo-4-[(2,2,2-trifluoroacetyl)amino]-1,8-naphthyridine-3-carboxylate Chemical compound C1=CN=C2N(CC)C(=O)C(C(=O)OCC)=C(NC(=O)C(F)(F)F)C2=C1 BLODFSOSCIESKS-UHFFFAOYSA-N 0.000 claims 1
- KVECBFGKYOPDBI-UHFFFAOYSA-N ethyl 1-ethyl-7-methyl-2-oxo-4-(4-phenylpiperazin-1-yl)-1,8-naphthyridine-3-carboxylate Chemical compound C12=CC=C(C)N=C2N(CC)C(=O)C(C(=O)OCC)=C1N(CC1)CCN1C1=CC=CC=C1 KVECBFGKYOPDBI-UHFFFAOYSA-N 0.000 claims 1
- AUSOXODPOZLOFF-UHFFFAOYSA-N ethyl 1-ethyl-7-methyl-2-oxo-4-piperazin-1-yl-1,8-naphthyridine-3-carboxylate Chemical compound C12=CC=C(C)N=C2N(CC)C(=O)C(C(=O)OCC)=C1N1CCNCC1 AUSOXODPOZLOFF-UHFFFAOYSA-N 0.000 claims 1
- UOAOWMXTYYHQRP-UHFFFAOYSA-N ethyl 1-ethyl-7-methyl-4-(4-methylpiperazin-1-yl)-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C12=CC=C(C)N=C2N(CC)C(=O)C(C(=O)OCC)=C1N1CCN(C)CC1 UOAOWMXTYYHQRP-UHFFFAOYSA-N 0.000 claims 1
- UYHQUGRMQXFQBZ-UHFFFAOYSA-N ethyl 1-ethyl-7-methyl-4-morpholin-4-yl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C12=CC=C(C)N=C2N(CC)C(=O)C(C(=O)OCC)=C1N1CCOCC1 UYHQUGRMQXFQBZ-UHFFFAOYSA-N 0.000 claims 1
- CVSSHCUZZVZYRD-UHFFFAOYSA-N ethyl 1-methyl-2-oxo-4-pyrrolidin-1-yl-1,8-naphthyridine-3-carboxylate Chemical compound C12=CC=CN=C2N(C)C(=O)C(C(=O)OCC)=C1N1CCCC1 CVSSHCUZZVZYRD-UHFFFAOYSA-N 0.000 claims 1
- ZKUQBCMQRFPHKY-UHFFFAOYSA-N ethyl 1-methyl-4-(4-methylpiperazin-1-yl)-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C12=CC=CN=C2N(C)C(=O)C(C(=O)OCC)=C1N1CCN(C)CC1 ZKUQBCMQRFPHKY-UHFFFAOYSA-N 0.000 claims 1
- QOJXDZWGUZSAOO-UHFFFAOYSA-N ethyl 4-(diacetylamino)-1-ethyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=CN=C2N(CC)C(=O)C(C(=O)OCC)=C(N(C(C)=O)C(C)=O)C2=C1 QOJXDZWGUZSAOO-UHFFFAOYSA-N 0.000 claims 1
- ODANRFCNCSFVLW-UHFFFAOYSA-N ethyl 4-[3-(dimethylamino)propylamino]-1-ethyl-7-methyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=C(C)N=C2N(CC)C(=O)C(C(=O)OCC)=C(NCCCN(C)C)C2=C1 ODANRFCNCSFVLW-UHFFFAOYSA-N 0.000 claims 1
- YFHMNANRDWFVPV-UHFFFAOYSA-N ethyl 4-amino-1-(2-methylpropyl)-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=CN=C2N(CC(C)C)C(=O)C(C(=O)OCC)=C(N)C2=C1 YFHMNANRDWFVPV-UHFFFAOYSA-N 0.000 claims 1
- AKNLIEGPEJDGKI-UHFFFAOYSA-N ethyl 4-amino-1-cyclohexyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound O=C1C(C(=O)OCC)=C(N)C2=CC=CN=C2N1C1CCCCC1 AKNLIEGPEJDGKI-UHFFFAOYSA-N 0.000 claims 1
- JMEMTDRUKCWTEA-UHFFFAOYSA-N ethyl 4-amino-1-ethyl-7-methyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=C(C)N=C2N(CC)C(=O)C(C(=O)OCC)=C(N)C2=C1 JMEMTDRUKCWTEA-UHFFFAOYSA-N 0.000 claims 1
- ITKSUIQISTXWAB-UHFFFAOYSA-N ethyl 4-amino-2-oxo-1-prop-2-enyl-1,8-naphthyridine-3-carboxylate Chemical compound C1=CN=C2N(CC=C)C(=O)C(C(=O)OCC)=C(N)C2=C1 ITKSUIQISTXWAB-UHFFFAOYSA-N 0.000 claims 1
- PVIUUGUDHDOIGM-UHFFFAOYSA-N ethyl 4-amino-2-oxo-1-prop-2-ynyl-1,8-naphthyridine-3-carboxylate Chemical compound C1=CN=C2N(CC#C)C(=O)C(C(=O)OCC)=C(N)C2=C1 PVIUUGUDHDOIGM-UHFFFAOYSA-N 0.000 claims 1
- CCIAUWVOIDGJAF-UHFFFAOYSA-N ethyl 4-amino-7-chloro-1-ethyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=C(Cl)N=C2N(CC)C(=O)C(C(=O)OCC)=C(N)C2=C1 CCIAUWVOIDGJAF-UHFFFAOYSA-N 0.000 claims 1
- PICACQIQZHKBFT-UHFFFAOYSA-N ethyl 4-amino-7-ethoxy-1-ethyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=C(OCC)N=C2N(CC)C(=O)C(C(=O)OCC)=C(N)C2=C1 PICACQIQZHKBFT-UHFFFAOYSA-N 0.000 claims 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
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- XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 description 1
- CTIXNGAFHVFMRR-UHFFFAOYSA-N 4-amino-1-ethyl-1,8-naphthyridin-2-one Chemical compound C1=CC=C2C(N)=CC(=O)N(CC)C2=N1 CTIXNGAFHVFMRR-UHFFFAOYSA-N 0.000 description 1
- SIADAGFXEHBPGG-UHFFFAOYSA-N 4-chloro-1,8-naphthyridine Chemical compound C1=CC=C2C(Cl)=CC=NC2=N1 SIADAGFXEHBPGG-UHFFFAOYSA-N 0.000 description 1
- ULITUDBGYSIYPV-UHFFFAOYSA-N 4-chloro-3-(trichloromethyl)-1,8-naphthyridine Chemical class C1=CC=C2C(Cl)=C(C(Cl)(Cl)Cl)C=NC2=N1 ULITUDBGYSIYPV-UHFFFAOYSA-N 0.000 description 1
- OZHPBABLIMMEDR-UHFFFAOYSA-N 4-iodo-1,8-naphthyridine Chemical class C1=CC=C2C(I)=CC=NC2=N1 OZHPBABLIMMEDR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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- 241000269350 Anura Species 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910018954 NaNH2 Inorganic materials 0.000 description 1
- 101100513046 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) eth-1 gene Proteins 0.000 description 1
- USSFUVKEHXDAPM-UHFFFAOYSA-N Nicotinamide N-oxide Chemical compound NC(=O)C1=CC=C[N+]([O-])=C1 USSFUVKEHXDAPM-UHFFFAOYSA-N 0.000 description 1
- 101150003479 Parg gene Proteins 0.000 description 1
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- 208000004880 Polyuria Diseases 0.000 description 1
- 101100409194 Rattus norvegicus Ppargc1b gene Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- 125000001721 carboxyacetyl group Chemical group 0.000 description 1
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- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- NFKGQHYUYGYHIS-UHFFFAOYSA-N dibutyl propanedioate Chemical compound CCCCOC(=O)CC(=O)OCCCC NFKGQHYUYGYHIS-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
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- DDCSIHFTXGZHAT-UHFFFAOYSA-N e-3-carbonitrile Chemical compound C1C(C)CCC(S2)=C1C(C#N)C2N(C(C12)=O)C(=O)C1C1C2C2C=CC1C(C1=O)C2C(=O)N1C(C1C#N)SC2=C1CC(C)CC2 DDCSIHFTXGZHAT-UHFFFAOYSA-N 0.000 description 1
- QKKSOVGCSSPZBN-UHFFFAOYSA-N ethyl 4-hydroxy-1-methyl-2-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1=CN=C2N(C)C(=O)C(C(=O)OCC)=C(O)C2=C1 QKKSOVGCSSPZBN-UHFFFAOYSA-N 0.000 description 1
- BITAUJHCWIPUED-UHFFFAOYSA-N ethyl 7-methyl-2-oxo-1h-1,8-naphthyridine-3-carboxylate Chemical compound C1=C(C)N=C2NC(=O)C(C(=O)OCC)=CC2=C1 BITAUJHCWIPUED-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 description 1
- 101150009274 nhr-1 gene Proteins 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004448 titration 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
- C07D213/04—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3125579A | 1979-04-18 | 1979-04-18 | |
| US31,255 | 1979-04-18 | ||
| US125,600 | 1980-02-28 | ||
| US06/125,600 US4324893A (en) | 1979-04-18 | 1980-02-28 | 4-Amino-3-carboxy or cyano-1,2-dihydro-2-oxo-1,8-naphthyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1115272A true CA1115272A (en) | 1981-12-29 |
Family
ID=26707004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA349,623A Expired CA1115272A (en) | 1979-04-18 | 1980-04-11 | 4-amino-3-carboxy or cyano-1,2-dihydro-2-oxo-1,8- naphthyridine derivatives |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4324893A (cg-RX-API-DMAC7.html) |
| EP (2) | EP0018735B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS56500373A (cg-RX-API-DMAC7.html) |
| KR (1) | KR840000076B1 (cg-RX-API-DMAC7.html) |
| AR (2) | AR225437A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU531348B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1115272A (cg-RX-API-DMAC7.html) |
| DK (1) | DK537780A (cg-RX-API-DMAC7.html) |
| ES (1) | ES490645A0 (cg-RX-API-DMAC7.html) |
| FI (1) | FI801229A7 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2053198B (cg-RX-API-DMAC7.html) |
| GR (1) | GR67253B (cg-RX-API-DMAC7.html) |
| HU (1) | HU183125B (cg-RX-API-DMAC7.html) |
| IE (1) | IE49696B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL59667A (cg-RX-API-DMAC7.html) |
| IN (1) | IN150969B (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ193445A (cg-RX-API-DMAC7.html) |
| PH (1) | PH16524A (cg-RX-API-DMAC7.html) |
| PT (1) | PT71081A (cg-RX-API-DMAC7.html) |
| SU (1) | SU1131469A3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO1980002287A1 (cg-RX-API-DMAC7.html) |
| YU (1) | YU105680A (cg-RX-API-DMAC7.html) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4420615A (en) * | 1981-08-24 | 1983-12-13 | Merck & Co., Inc. | Substituted pyridopyrimidines as gastric secretion inhibitors |
| FR2567520B1 (fr) * | 1984-07-11 | 1987-01-02 | Carpibem | Nouvelles phenyl-naphthyridines, leur procede de preparation, medicaments les contenant, notamment anti-ulceres |
| NZ218773A (en) * | 1986-01-06 | 1990-05-28 | Carpibem | 3-methyl-2-oxo-1-(substituted phenyl)-naphthyridines and pharmaceutical compositions |
| FR2592650B1 (fr) * | 1986-01-06 | 1988-04-29 | Carpibem | Nouvelles phenyl-naphtyridines fonctionnalisees en position-3, leur procede de preparation, medicaments les contenant, notamment anti-ulceres. |
| FR2592651B1 (fr) * | 1986-01-06 | 1988-05-13 | Carpibem | Nouvelles phenyl naphtyridines comportant un substituant methyle en position 3, et les medicaments qui en contiennent. |
| FR2592652B1 (fr) * | 1986-01-06 | 1988-04-29 | Carpibem | Nouvelles phenyl-naphtyridines, leur procede de preparation et les medicaments en contenant. |
| FR2592649B1 (fr) * | 1986-01-06 | 1988-04-29 | Carpibem | Cyano et amido phenyl-naphtyridines, leur procede de preparation, medicaments les contenant, notamment anti-ulceres. |
| NZ218774A (en) * | 1986-01-06 | 1990-06-26 | Carpibem | 3-substituted phenylnaphthyridines and pharmaceutical compositions |
| US4916131A (en) * | 1986-10-15 | 1990-04-10 | Schering Corporation | Naphthyridine derivatives and method for treating allergic reactions |
| EP0267691A3 (en) * | 1986-10-15 | 1989-08-23 | Schering Corporation | Use of 1-substituted naphthyridine and pyridopyrazine derivatives for the preparation of medicaments with immunosuppressor activity. |
| US5037826A (en) * | 1986-10-15 | 1991-08-06 | Schering Corporation | 1-substituted naphthyridine and pyridopyrazine derivatives |
| DK273689A (da) * | 1988-06-06 | 1989-12-07 | Sanofi Sa | 4-amino-3-carboxyquinoliner og -naphthyridiner, fremgangsmaade til deres fremstilling og anvendelse deraf i laegemidler |
| FR2632861B1 (fr) * | 1988-06-15 | 1990-11-09 | Sanofi Sa | Derives d'amino-4 carboxy-3 quinoleines et naphtyridines, leur procede de preparation et leur application comme medicaments |
| FR2632639B1 (fr) * | 1988-06-09 | 1990-10-05 | Sanofi Sa | Derives d'amino-4 carboxy-3 naphtyridines, leur preparation et compositions pharmaceutiques qui les contiennent |
| FR2637890B1 (fr) * | 1988-09-14 | 1991-02-01 | Europ Propulsion | Materiau composite a matrice zircone |
| GB9318931D0 (en) * | 1993-09-14 | 1993-10-27 | Boots Co Plc | Therapeutic agents |
| GB9420168D0 (en) * | 1994-10-06 | 1994-11-23 | Boots Co Plc | Therapeutic agents |
| AR029185A1 (es) | 1999-10-25 | 2003-06-18 | Yamanouchi Pharma Co Ltd | Derivado de naftiridina |
| MY140679A (en) | 2001-05-24 | 2010-01-15 | Avanir Pharmaceuticals | Inhibitors of macrohage migration inhibitory factor and methods for identifying the same |
| KR20020092756A (ko) * | 2001-06-05 | 2002-12-12 | 이종완 | 젓갈과 그 제조 방법 |
| TW200418829A (en) | 2003-02-14 | 2004-10-01 | Avanir Pharmaceutics | Inhibitors of macrophage migration inhibitory factor and methods for identifying the same |
| WO2004091627A2 (en) * | 2003-04-07 | 2004-10-28 | Cylene Pharmaceuticals, Inc. | Heterocyclic substituted 1,4-dihydro-4-oxo-1,8-naphthpyridine analogs |
| MXJL06000006A (es) * | 2003-08-22 | 2006-05-04 | Avanir Pharmaceuticals | Derivados de naftiridina sustituidos como inhibidores del factor inhibidor de la migracion de macrofagos y su uso en el tratamiento de enfermedades en el hombre. |
| JP2008534502A (ja) | 2005-03-24 | 2008-08-28 | アバニール・ファーマシューティカルズ | マクロファージ遊走阻止因子の阻害剤としてのチエノピリジノン誘導体 |
| GB0605689D0 (en) * | 2006-03-21 | 2006-05-03 | Novartis Ag | Organic compounds |
| CN113956252A (zh) | 2017-09-28 | 2022-01-21 | 药捷安康(南京)科技股份有限公司 | Pde9抑制剂及其用途 |
| EA202190137A1 (ru) | 2018-06-27 | 2021-05-17 | Бристол-Маерс Сквибб Компани | Нафтиридиноновые соединения для применения в качестве активаторов t-клеток |
| CN112654621B (zh) | 2018-06-27 | 2024-05-14 | 百时美施贵宝公司 | 可作为t细胞活化剂的经取代萘啶酮化合物 |
| AR119821A1 (es) | 2019-08-28 | 2022-01-12 | Bristol Myers Squibb Co | Compuestos de piridopirimidinonilo sustituidos útiles como activadores de células t |
| AR120823A1 (es) | 2019-12-23 | 2022-03-23 | Bristol Myers Squibb Co | Compuestos bicíclicos sustituidos útiles como activadores de células t |
| KR20220120624A (ko) | 2019-12-23 | 2022-08-30 | 브리스톨-마이어스 스큅 컴퍼니 | T 세포 활성화제로서 유용한 치환된 피페라진 유도체 |
| AU2020415377A1 (en) | 2019-12-23 | 2022-08-18 | Bristol-Myers Squibb Company | Substituted quinazolinyl compounds useful as T cell activators |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA947301A (en) * | 1970-01-28 | 1974-05-14 | Sumitomo Chemical Company | Process for the preparation of compound having antibacterial action |
| CA988522A (en) * | 1972-05-05 | 1976-05-04 | Haydn W.R. Williams | 1,8-naphthyridine compounds |
| US3993656A (en) * | 1974-11-19 | 1976-11-23 | Merck & Co., Inc. | 1,8-Naphthyridine compounds |
| US4103257A (en) * | 1976-05-25 | 1978-07-25 | The United States Of America As Represented By The United States Department Of Energy | Azaquinolone dye lasers |
| US4133885A (en) * | 1977-07-18 | 1979-01-09 | Merck & Co., Inc. | Substituted naphthyridinones |
-
1980
- 1980-02-28 US US06/125,600 patent/US4324893A/en not_active Expired - Lifetime
- 1980-03-19 IL IL59667A patent/IL59667A/xx unknown
- 1980-03-22 GR GR61509A patent/GR67253B/el unknown
- 1980-03-24 WO PCT/US1980/000319 patent/WO1980002287A1/en not_active Ceased
- 1980-03-24 JP JP50102580A patent/JPS56500373A/ja active Pending
- 1980-04-10 PT PT71081A patent/PT71081A/pt unknown
- 1980-04-10 EP EP80301157A patent/EP0018735B1/en not_active Expired
- 1980-04-10 EP EP82200534A patent/EP0060012B1/en not_active Expired
- 1980-04-10 GB GB8011911A patent/GB2053198B/en not_active Expired
- 1980-04-11 CA CA349,623A patent/CA1115272A/en not_active Expired
- 1980-04-14 AR AR280667A patent/AR225437A1/es active
- 1980-04-15 NZ NZ193445A patent/NZ193445A/xx unknown
- 1980-04-15 IE IE761/80A patent/IE49696B1/en unknown
- 1980-04-16 AU AU57519/80A patent/AU531348B2/en not_active Ceased
- 1980-04-17 YU YU01056/80A patent/YU105680A/xx unknown
- 1980-04-17 HU HU80935A patent/HU183125B/hu unknown
- 1980-04-17 FI FI801229A patent/FI801229A7/fi not_active Application Discontinuation
- 1980-04-17 ES ES490645A patent/ES490645A0/es active Granted
- 1980-04-17 KR KR1019800001587A patent/KR840000076B1/ko not_active Expired
- 1980-04-17 PH PH23914A patent/PH16524A/en unknown
- 1980-12-10 IN IN1366/CAL/80A patent/IN150969B/en unknown
- 1980-12-17 DK DK537780A patent/DK537780A/da not_active Application Discontinuation
- 1980-12-17 SU SU803220198A patent/SU1131469A3/ru active
-
1981
- 1981-06-16 AR AR285719A patent/AR227427A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| ES8104286A1 (es) | 1981-04-16 |
| AR227427A1 (es) | 1982-10-29 |
| AU5751980A (en) | 1980-10-23 |
| DK537780A (da) | 1980-12-17 |
| US4324893A (en) | 1982-04-13 |
| EP0018735B1 (en) | 1983-07-27 |
| NZ193445A (en) | 1982-09-07 |
| KR840000076B1 (ko) | 1984-02-08 |
| EP0018735A1 (en) | 1980-11-12 |
| IE800761L (en) | 1980-10-18 |
| HU183125B (en) | 1984-04-28 |
| SU1131469A3 (ru) | 1984-12-23 |
| IL59667A (en) | 1983-11-30 |
| EP0060012B1 (en) | 1984-08-29 |
| EP0060012A1 (en) | 1982-09-15 |
| YU105680A (en) | 1983-09-30 |
| AU531348B2 (en) | 1983-08-18 |
| JPS56500373A (cg-RX-API-DMAC7.html) | 1981-03-26 |
| FI801229A7 (fi) | 1981-01-01 |
| AR225437A1 (es) | 1982-03-31 |
| IE49696B1 (en) | 1985-11-27 |
| WO1980002287A1 (en) | 1980-10-30 |
| ES490645A0 (es) | 1981-04-16 |
| KR830002759A (ko) | 1983-05-30 |
| GR67253B (cg-RX-API-DMAC7.html) | 1981-06-26 |
| PH16524A (en) | 1983-11-10 |
| PT71081A (en) | 1980-05-01 |
| GB2053198B (en) | 1983-04-07 |
| IN150969B (cg-RX-API-DMAC7.html) | 1983-02-05 |
| GB2053198A (en) | 1981-02-04 |
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