HU183125B - Process for producing 4-amino-3-bracket-carboxy or cyano-bracket closed-1,2-dihydro-2-oxo-1,8-naphtridine derivatives - Google Patents
Process for producing 4-amino-3-bracket-carboxy or cyano-bracket closed-1,2-dihydro-2-oxo-1,8-naphtridine derivatives Download PDFInfo
- Publication number
- HU183125B HU183125B HU80935A HU93580A HU183125B HU 183125 B HU183125 B HU 183125B HU 80935 A HU80935 A HU 80935A HU 93580 A HU93580 A HU 93580A HU 183125 B HU183125 B HU 183125B
- Authority
- HU
- Hungary
- Prior art keywords
- dihydro
- oxo
- formula
- carboxylic acid
- naphthyridine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 2
- -1 4-methylpiperazinyl Chemical group 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000007514 bases Chemical class 0.000 claims description 3
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 150000005054 naphthyridines Chemical class 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- ZFRUGZMCGCYBRC-UHFFFAOYSA-N 1h-1,8-naphthyridin-2-one Chemical class C1=CC=NC2=NC(O)=CC=C21 ZFRUGZMCGCYBRC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- PYORACMVSIHJEW-UHFFFAOYSA-N 4-amino-1h-1,8-naphthyridin-2-one Chemical class C1=CC=C2C(N)=CC(=O)NC2=N1 PYORACMVSIHJEW-UHFFFAOYSA-N 0.000 claims 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 9
- 230000002496 gastric effect Effects 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
- 230000001882 diuretic effect Effects 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000002934 diuretic Substances 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 208000008469 Peptic Ulcer Diseases 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 230000001262 anti-secretory effect Effects 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- 238000004458 analytical method Methods 0.000 description 39
- 230000005764 inhibitory process Effects 0.000 description 34
- 239000000047 product Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- IPOVOSHRRIJKBR-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride Chemical compound CCC(C(Cl)=O)C(Cl)=O IPOVOSHRRIJKBR-UHFFFAOYSA-N 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 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 7
- 241000700159 Rattus Species 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 210000004051 gastric juice Anatomy 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 208000007107 Stomach Ulcer Diseases 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000028327 secretion Effects 0.000 description 5
- FPMFWNDLLWUVEH-UHFFFAOYSA-N 1,8-naphthyridin-4-amine Chemical class C1=CC=C2C(N)=CC=NC2=N1 FPMFWNDLLWUVEH-UHFFFAOYSA-N 0.000 description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
- FDBZDXTUWGEFQA-UHFFFAOYSA-N 4-amino-2-oxo-1h-1,8-naphthyridine-3-carboxylic acid Chemical class C1=CC=C2C(N)=C(C(O)=O)C(=O)NC2=N1 FDBZDXTUWGEFQA-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 201000005917 gastric ulcer Diseases 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 3
- GPDBAOOTLKONEG-UHFFFAOYSA-N 2-(ethylamino)pyridine-3-carbonitrile Chemical compound CCNC1=NC=CC=C1C#N GPDBAOOTLKONEG-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YYXDQRRDNPRJFL-UHFFFAOYSA-N 2-aminopyridine-3-carbonitrile Chemical class NC1=NC=CC=C1C#N YYXDQRRDNPRJFL-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- SIADAGFXEHBPGG-UHFFFAOYSA-N 4-chloro-1,8-naphthyridine Chemical compound C1=CC=C2C(Cl)=CC=NC2=N1 SIADAGFXEHBPGG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 238000011863 diuretic therapy Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 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 description 2
- 210000002700 urine Anatomy 0.000 description 2
- CGXLVFZJJOXEDF-UHFFFAOYSA-N 1,8-naphthyridine-3-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CN=C21 CGXLVFZJJOXEDF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- NQUIRWXTTAMWIU-UHFFFAOYSA-N 1h-1,8-naphthyridin-4-one Chemical compound C1=CC=C2C(O)=CC=NC2=N1 NQUIRWXTTAMWIU-UHFFFAOYSA-N 0.000 description 1
- MWUZXVOXGCWJJU-UHFFFAOYSA-N 2-(2-methylpropylamino)pyridine-3-carbonitrile Chemical compound CC(C)CNC1=NC=CC=C1C#N MWUZXVOXGCWJJU-UHFFFAOYSA-N 0.000 description 1
- UCVVPEUOVNJIJP-UHFFFAOYSA-N 2-(cyclohexylamino)pyridine-3-carbonitrile Chemical compound N#CC1=CC=CN=C1NC1CCCCC1 UCVVPEUOVNJIJP-UHFFFAOYSA-N 0.000 description 1
- AGZQPTBBDDQFKJ-UHFFFAOYSA-N 2-(methylamino)pyridine-3-carbonitrile Chemical compound CNC1=NC=CC=C1C#N AGZQPTBBDDQFKJ-UHFFFAOYSA-N 0.000 description 1
- YNXXIFLTPBDEGP-UHFFFAOYSA-N 2-(propylamino)pyridine-3-carbonitrile Chemical compound CCCNC1=NC=CC=C1C#N YNXXIFLTPBDEGP-UHFFFAOYSA-N 0.000 description 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-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
- JEAGUUSDJHCXRT-UHFFFAOYSA-N 4-chloro-1,7-dimethyl-1,8-naphthyridin-2-one Chemical compound ClC1=CC(=O)N(C)C2=NC(C)=CC=C21 JEAGUUSDJHCXRT-UHFFFAOYSA-N 0.000 description 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 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PWGFUTVLNROFAK-UHFFFAOYSA-N C(C)C1=C(C(NC2=NC=CC=C12)=O)C(=O)O Chemical compound C(C)C1=C(C(NC2=NC=CC=C12)=O)C(=O)O PWGFUTVLNROFAK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-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
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- PJDIOEIUQLLZAN-UHFFFAOYSA-L disodium 2,2-dibutylpropanedioate Chemical compound C(CCC)C(C(=O)[O-])(C(=O)[O-])CCCC.[Na+].[Na+] PJDIOEIUQLLZAN-UHFFFAOYSA-L 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 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 description 1
- JFWURCREFDQUTD-UHFFFAOYSA-N ethyl 1,8-naphthyridine-3-carboxylate Chemical compound N1=CC=CC2=CC(C(=O)OCC)=CN=C21 JFWURCREFDQUTD-UHFFFAOYSA-N 0.000 description 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 description 1
- 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 description 1
- 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 description 1
- 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 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
- SHQOVONJQDWWRC-UHFFFAOYSA-N ethyl 4-oxo-1h-1,8-naphthyridine-3-carboxylate Chemical compound N1=CC=CC2=C(O)C(C(=O)OCC)=CN=C21 SHQOVONJQDWWRC-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005252 haloacyl group Chemical group 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- AVPHZMKSAAPGGT-UHFFFAOYSA-N methyl 2-(ethylamino)-6-methylpyridine-3-carboxylate Chemical compound CCNC1=NC(C)=CC=C1C(=O)OC AVPHZMKSAAPGGT-UHFFFAOYSA-N 0.000 description 1
- SHKDOGHJQHIIRD-UHFFFAOYSA-N methyl 2-chloro-6-methylpyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(C)N=C1Cl SHKDOGHJQHIIRD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000002731 stomach secretion inhibitor Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 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
- C07D213/04—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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3125579A | 1979-04-18 | 1979-04-18 | |
| 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 |
|---|---|
| HU183125B true HU183125B (en) | 1984-04-28 |
Family
ID=26707004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80935A HU183125B (en) | 1979-04-18 | 1980-04-17 | Process for producing 4-amino-3-bracket-carboxy or cyano-bracket closed-1,2-dihydro-2-oxo-1,8-naphtridine 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 |
| 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 |
| CA1115272A (en) | 1981-12-29 |
| 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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