CA1110234A - 4-pyridone-3-carboxylic acids and process for the preparation thereof - Google Patents
4-pyridone-3-carboxylic acids and process for the preparation thereofInfo
- Publication number
- CA1110234A CA1110234A CA318,702A CA318702A CA1110234A CA 1110234 A CA1110234 A CA 1110234A CA 318702 A CA318702 A CA 318702A CA 1110234 A CA1110234 A CA 1110234A
- Authority
- CA
- Canada
- Prior art keywords
- group
- ethyl
- methyl
- alkyl
- oxo
- 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
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- -1 C1-6--alkyl Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- SSHRVPMSFQLCAG-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine-5-carboxylic acid Chemical class OC(=O)C1=CNCCC1 SSHRVPMSFQLCAG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 125000005504 styryl group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 6
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 210000003169 central nervous system Anatomy 0.000 abstract description 5
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 230000004936 stimulating effect Effects 0.000 abstract description 2
- 238000002844 melting Methods 0.000 description 71
- 230000008018 melting Effects 0.000 description 71
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 229960000443 hydrochloric acid Drugs 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 3
- 229960000564 nitrofurantoin Drugs 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 2
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- AXCXHFKZHDEKTP-NSCUHMNNSA-N 4-methoxycinnamaldehyde Chemical compound COC1=CC=C(\C=C\C=O)C=C1 AXCXHFKZHDEKTP-NSCUHMNNSA-N 0.000 description 2
- YOEBQJYTBWGBTO-UHFFFAOYSA-N 6-(4-chlorophenyl)-1-ethyl-4-oxopyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=C(Cl)C=C1 YOEBQJYTBWGBTO-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 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
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 229960000632 dexamfetamine Drugs 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229950007554 levmetamfetamine Drugs 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- FUTACNYXCNCZTF-UHFFFAOYSA-N methyl 2-(4-chlorophenyl)-1-ethyl-4-oxo-2,3-dihydropyridine-5-carboxylate Chemical compound CCN1C=C(C(=O)OC)C(=O)CC1C1=CC=C(Cl)C=C1 FUTACNYXCNCZTF-UHFFFAOYSA-N 0.000 description 2
- BIBDTWJVWOSUHD-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-3-oxopent-4-enoate Chemical compound COC(=O)CC(=O)C=CC1=CC=C(Cl)C=C1 BIBDTWJVWOSUHD-UHFFFAOYSA-N 0.000 description 2
- JGIZTNNWWRPFSK-UHFFFAOYSA-N methyl 6-(4-chlorophenyl)-4-methoxyhexa-3,5-dienoate Chemical compound COC(=O)CC=C(OC)C=CC1=CC=C(Cl)C=C1 JGIZTNNWWRPFSK-UHFFFAOYSA-N 0.000 description 2
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
- XXPANQJNYNUNES-UHFFFAOYSA-N nomifensine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC=C1 XXPANQJNYNUNES-UHFFFAOYSA-N 0.000 description 2
- 229960001073 nomifensine Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JUNWTBPUAXJQJT-UHFFFAOYSA-M (2,4-dimethoxy-4-oxobut-2-enyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=CC(=O)OC)OC)C1=CC=CC=C1 JUNWTBPUAXJQJT-UHFFFAOYSA-M 0.000 description 1
- MBELGTLJWJJGLF-UHFFFAOYSA-N 1,4-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CNC=CC1 MBELGTLJWJJGLF-UHFFFAOYSA-N 0.000 description 1
- PLGDKJCBRXCPHA-UHFFFAOYSA-N 1-(1-adamantyl)-4-oxo-6-phenylpyridine-3-carboxylic acid Chemical compound C=1C(=O)C(C(=O)O)=CN(C23CC4CC(CC(C4)C2)C3)C=1C1=CC=CC=C1 PLGDKJCBRXCPHA-UHFFFAOYSA-N 0.000 description 1
- JCVZOYIGRRGTAA-UHFFFAOYSA-N 1-ethyl-4-oxo-6-(3,4,5-trimethoxyphenyl)pyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC(OC)=C(OC)C(OC)=C1 JCVZOYIGRRGTAA-UHFFFAOYSA-N 0.000 description 1
- HFLHLTVNZJBRRY-UHFFFAOYSA-N 1-ethyl-4-oxo-6-pyridin-3-ylpyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=CN=C1 HFLHLTVNZJBRRY-UHFFFAOYSA-N 0.000 description 1
- OTCBYAQSZCSRHL-UHFFFAOYSA-N 1-ethyl-6-(3-nitrophenyl)-4-oxopyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=CC([N+]([O-])=O)=C1 OTCBYAQSZCSRHL-UHFFFAOYSA-N 0.000 description 1
- WZEVMSQCRFQUGF-UHFFFAOYSA-N 1-ethyl-6-(4-hydroxyphenyl)-4-oxopyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=C(O)C=C1 WZEVMSQCRFQUGF-UHFFFAOYSA-N 0.000 description 1
- CVXHXXJSTHFTCT-UHFFFAOYSA-N 1-ethyl-6-(4-methylsulfanylphenyl)-4-oxopyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=C(SC)C=C1 CVXHXXJSTHFTCT-UHFFFAOYSA-N 0.000 description 1
- DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 1
- XPUNETSACYSEEZ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-1-ethyl-4-oxo-2,3-dihydropyridine-5-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)CC1C1=CC=C(OCO2)C2=C1 XPUNETSACYSEEZ-UHFFFAOYSA-N 0.000 description 1
- PENMZOZWYJOAHA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-ethyl-4-oxo-2,3-dihydropyridine-5-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)CC1C1=CC=C(OC)C(OC)=C1 PENMZOZWYJOAHA-UHFFFAOYSA-N 0.000 description 1
- CFDHHEBRLPGIMI-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-ethyl-4-oxo-2,3-dihydropyridine-5-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)CC1C1=CC=C(Cl)C=C1 CFDHHEBRLPGIMI-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 1
- SIXYIEWSUKAOEN-UHFFFAOYSA-N 3-aminobenzaldehyde Chemical compound NC1=CC=CC(C=O)=C1 SIXYIEWSUKAOEN-UHFFFAOYSA-N 0.000 description 1
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
- UECXDZSFDGWNTH-UHFFFAOYSA-N 3-methyl-4-(methylamino)benzaldehyde Chemical compound CNC1=CC=C(C=O)C=C1C UECXDZSFDGWNTH-UHFFFAOYSA-N 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LOONFRKFJPYULD-UHFFFAOYSA-N 4-(dimethylamino)-3-methylbenzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1C LOONFRKFJPYULD-UHFFFAOYSA-N 0.000 description 1
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
- WRBAOBVQOLYQOY-UHFFFAOYSA-N 4-oxo-6-phenyl-1-propylpyridine-3-carboxylic acid Chemical compound CCCN1C=C(C(O)=O)C(=O)C=C1C1=CC=CC=C1 WRBAOBVQOLYQOY-UHFFFAOYSA-N 0.000 description 1
- DATXHLPRESKQJK-UHFFFAOYSA-N 4-pyrrolidin-1-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1N1CCCC1 DATXHLPRESKQJK-UHFFFAOYSA-N 0.000 description 1
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
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- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
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- 229920000159 gelatin Polymers 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
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- DBKLSMPMFQFKIV-UHFFFAOYSA-N methyl 1-ethyl-4-oxo-6-(4-pyrrolidin-1-ylphenyl)pyridine-3-carboxylate Chemical compound CCN1C=C(C(=O)OC)C(=O)C=C1C1=CC=C(N2CCCC2)C=C1 DBKLSMPMFQFKIV-UHFFFAOYSA-N 0.000 description 1
- OZBCMVXVAVQXPC-UHFFFAOYSA-N methyl 2-(3,4-dimethoxyphenyl)-1-ethyl-4-oxo-2,3-dihydropyridine-5-carboxylate Chemical compound CCN1C=C(C(=O)OC)C(=O)CC1C1=CC=C(OC)C(OC)=C1 OZBCMVXVAVQXPC-UHFFFAOYSA-N 0.000 description 1
- XJKBJDDNXKBPRC-UHFFFAOYSA-N methyl 2-(ethylaminomethylidene)-3-oxo-5-(3,4,5-trimethoxyphenyl)pent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1 XJKBJDDNXKBPRC-UHFFFAOYSA-N 0.000 description 1
- QJLFXLFSPWDJKD-UHFFFAOYSA-N methyl 2-(ethylaminomethylidene)-3-oxo-5-(4-pyrrolidin-1-ylphenyl)pent-4-enoate Chemical compound C1=CC(C=CC(=O)C(C(=O)OC)=CNCC)=CC=C1N1CCCC1 QJLFXLFSPWDJKD-UHFFFAOYSA-N 0.000 description 1
- QVFOEHVPDHSCJZ-UHFFFAOYSA-N methyl 2-(ethylaminomethylidene)-3-oxo-5-phenylpent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=CC=C1 QVFOEHVPDHSCJZ-UHFFFAOYSA-N 0.000 description 1
- KSUUVKFYHJNBJH-UHFFFAOYSA-N methyl 2-(ethylaminomethylidene)-5-(4-hydroxyphenyl)-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=C(O)C=C1 KSUUVKFYHJNBJH-UHFFFAOYSA-N 0.000 description 1
- OOCPZSFEIVSKCV-UHFFFAOYSA-N methyl 2-(ethylaminomethylidene)-5-(4-methoxyphenyl)-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=C(OC)C=C1 OOCPZSFEIVSKCV-UHFFFAOYSA-N 0.000 description 1
- IVNOQZKUPJLRGU-UHFFFAOYSA-N methyl 2-(ethylaminomethylidene)-5-(4-methylsulfanylphenyl)-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=C(SC)C=C1 IVNOQZKUPJLRGU-UHFFFAOYSA-N 0.000 description 1
- POYAJQWUGLSYFQ-UHFFFAOYSA-N methyl 2-(ethylaminomethylidene)-5-[3-methyl-4-(methylamino)phenyl]-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=C(NC)C(C)=C1 POYAJQWUGLSYFQ-UHFFFAOYSA-N 0.000 description 1
- BKRLHJCQYAWQCT-UHFFFAOYSA-N methyl 2-[(cyclopropylamino)methylidene]-5-(4-methoxyphenyl)-3-oxopent-4-enoate Chemical compound C=1C=C(OC)C=CC=1C=CC(=O)C(C(=O)OC)=CNC1CC1 BKRLHJCQYAWQCT-UHFFFAOYSA-N 0.000 description 1
- LNDZIQFNSBRIST-UHFFFAOYSA-N methyl 5-(1,3-benzodioxol-5-yl)-2-(ethylaminomethylidene)-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=C2OCOC2=C1 LNDZIQFNSBRIST-UHFFFAOYSA-N 0.000 description 1
- JUEZXBOTTQNYPP-UHFFFAOYSA-N methyl 5-(2,6-dichlorophenyl)-2-(ethylaminomethylidene)-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=C(Cl)C=CC=C1Cl JUEZXBOTTQNYPP-UHFFFAOYSA-N 0.000 description 1
- PBPWQVXKXDAMGU-UHFFFAOYSA-N methyl 5-(3-chlorophenyl)-2-(ethylaminomethylidene)-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=CC(Cl)=C1 PBPWQVXKXDAMGU-UHFFFAOYSA-N 0.000 description 1
- ONDLANNXONXESA-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-2-(dimethylaminomethylidene)-3-oxopent-4-enoate Chemical compound COC(=O)C(=CN(C)C)C(=O)C=CC1=CC=C(Cl)C=C1 ONDLANNXONXESA-UHFFFAOYSA-N 0.000 description 1
- SZVWKIOCBZKYCG-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-2-(ethylaminomethylidene)-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=C(Cl)C=C1 SZVWKIOCBZKYCG-UHFFFAOYSA-N 0.000 description 1
- VKLFKOFZOUAGQR-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-2-(methylaminomethylidene)-3-oxopent-4-enoate Chemical compound CNC=C(C(=O)OC)C(=O)C=CC1=CC=C(Cl)C=C1 VKLFKOFZOUAGQR-UHFFFAOYSA-N 0.000 description 1
- BCWOZNWPPAFBEY-UHFFFAOYSA-N methyl 5-[4-(dimethylamino)-3-methylphenyl]-2-(ethylaminomethylidene)-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=C(N(C)C)C(C)=C1 BCWOZNWPPAFBEY-UHFFFAOYSA-N 0.000 description 1
- MVZKJPNQMHVHEG-UHFFFAOYSA-N methyl 5-[4-(dimethylamino)phenyl]-2-(ethylaminomethylidene)-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=C(N(C)C)C=C1 MVZKJPNQMHVHEG-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- AXCXHFKZHDEKTP-UHFFFAOYSA-N para-methoxycinnamaldehyde Natural products COC1=CC=C(C=CC=O)C=C1 AXCXHFKZHDEKTP-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Psychiatry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Communicable Diseases (AREA)
- Neurosurgery (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH51278A CH639073A5 (en) | 1978-01-18 | 1978-01-18 | 4-Pyridone-3-carboxylic acid derivatives and their preparation |
| CH512/78 | 1978-01-18 | ||
| CH11734/78 | 1978-11-15 | ||
| CH1173478 | 1978-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1110234A true CA1110234A (en) | 1981-10-06 |
Family
ID=25684790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA318,702A Expired CA1110234A (en) | 1978-01-18 | 1978-12-28 | 4-pyridone-3-carboxylic acids and process for the preparation thereof |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US4521535A (OSRAM) |
| EP (1) | EP0003144B1 (OSRAM) |
| JP (1) | JPS54100382A (OSRAM) |
| KR (1) | KR820002111B1 (OSRAM) |
| AR (1) | AR223663A1 (OSRAM) |
| AT (1) | AT369731B (OSRAM) |
| AU (1) | AU521148B2 (OSRAM) |
| CA (1) | CA1110234A (OSRAM) |
| DE (1) | DE2901868A1 (OSRAM) |
| DK (1) | DK20279A (OSRAM) |
| ES (1) | ES476917A1 (OSRAM) |
| FI (1) | FI790103A7 (OSRAM) |
| FR (1) | FR2415103A1 (OSRAM) |
| GB (1) | GB2013190B (OSRAM) |
| GR (1) | GR73088B (OSRAM) |
| HU (1) | HU179487B (OSRAM) |
| IE (1) | IE47784B1 (OSRAM) |
| IL (1) | IL56421A (OSRAM) |
| LU (1) | LU80794A1 (OSRAM) |
| MC (1) | MC1239A1 (OSRAM) |
| NL (1) | NL7900264A (OSRAM) |
| NO (1) | NO152089C (OSRAM) |
| NZ (1) | NZ189379A (OSRAM) |
| PT (1) | PT69093A (OSRAM) |
| SE (1) | SE7900318L (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1125762A (en) * | 1979-07-13 | 1982-06-15 | Alexander E. Wick | Dihydronicotinic acid derivatives and process for the preparation thereof |
| US4964896A (en) * | 1980-05-12 | 1990-10-23 | Monsanto Company | Certain-2,6-diphenyl-1,4-dihydro-4-oxo-nicotinates which are useful for inducing male sterility in cereal grain plants |
| US4936904A (en) * | 1980-05-12 | 1990-06-26 | Carlson Glenn R | Aryl-4-oxonicotinates useful for inducing male sterility in cereal grain plants |
| US4714492A (en) * | 1980-05-12 | 1987-12-22 | Rohm And Haas Company | Certain 2-phenyl-4-oxo-nicotinates and their use for inducing male sterility in a cereal grain plant |
| ZA813029B (en) * | 1980-05-12 | 1982-05-26 | Rohm & Haas | Novel substituted oxonicotinates,their use as plant growth regulators and plant growth regulating compositions containing them |
| NZ201395A (en) * | 1981-07-30 | 1987-02-20 | Bayer Ag | Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines |
| DE3338846A1 (de) * | 1982-10-29 | 1984-05-03 | Toyama Chemical Co. Ltd., Tokyo | Neue 4-oxo-1,4-dihydronicotinsaeurederivate und salze derselben, verfahren zu ihrer herstellung und antibakterielle mittel mit einem gehalt derselben |
| JPS5980665A (ja) * | 1982-10-29 | 1984-05-10 | Toyama Chem Co Ltd | ４−オキソ−１，４−ジヒドロニコチン酸誘導体 |
| GB8502424D0 (en) * | 1985-01-31 | 1985-03-06 | Pharis R P | Promotion of flowering fruit trees |
| GB9317314D0 (en) * | 1993-08-20 | 1993-10-06 | Smithkline Beecham Corp | Compounds |
| EP2149547A1 (en) * | 2008-07-30 | 2010-02-03 | LEK Pharmaceuticals D.D. | Process for the synthesis of ezetimibe and intermediates useful therefor |
| US9988373B2 (en) | 2013-12-26 | 2018-06-05 | Shionogi & Co., Ltd. | Nitrogen-containing six-membered cyclic derivatives and pharmaceutical composition comprising the same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3907808A (en) * | 1971-05-17 | 1975-09-23 | Sterling Drug Inc | 1,4-Dihydro-4-oxo-7-pyridyl-3-quinolinecarboxylic acid derivatives |
| IN142614B (OSRAM) * | 1974-08-28 | 1977-08-06 | Lilly Co Eli | |
| CA1125762A (en) * | 1979-07-13 | 1982-06-15 | Alexander E. Wick | Dihydronicotinic acid derivatives and process for the preparation thereof |
| DE3338846A1 (de) * | 1982-10-29 | 1984-05-03 | Toyama Chemical Co. Ltd., Tokyo | Neue 4-oxo-1,4-dihydronicotinsaeurederivate und salze derselben, verfahren zu ihrer herstellung und antibakterielle mittel mit einem gehalt derselben |
-
1978
- 1978-12-28 CA CA318,702A patent/CA1110234A/en not_active Expired
-
1979
- 1979-01-11 AU AU43296/79A patent/AU521148B2/en not_active Ceased
- 1979-01-12 FI FI790103A patent/FI790103A7/fi unknown
- 1979-01-12 IL IL56421A patent/IL56421A/xx unknown
- 1979-01-12 NL NL7900264A patent/NL7900264A/xx not_active Application Discontinuation
- 1979-01-15 MC MC791356A patent/MC1239A1/xx unknown
- 1979-01-15 SE SE7900318A patent/SE7900318L/xx unknown
- 1979-01-15 NZ NZ189379A patent/NZ189379A/en unknown
- 1979-01-15 HU HU79HO2130A patent/HU179487B/hu unknown
- 1979-01-16 GR GR58105A patent/GR73088B/el unknown
- 1979-01-16 LU LU80794A patent/LU80794A1/de unknown
- 1979-01-16 JP JP233079A patent/JPS54100382A/ja active Pending
- 1979-01-16 FR FR7900974A patent/FR2415103A1/fr active Granted
- 1979-01-17 DK DK20279A patent/DK20279A/da not_active Application Discontinuation
- 1979-01-17 AT AT0035079A patent/AT369731B/de not_active IP Right Cessation
- 1979-01-17 ES ES476917A patent/ES476917A1/es not_active Expired
- 1979-01-17 GB GB7901668A patent/GB2013190B/en not_active Expired
- 1979-01-17 KR KR7900120A patent/KR820002111B1/ko not_active Expired
- 1979-01-17 AR AR275201A patent/AR223663A1/es active
- 1979-01-17 NO NO790165A patent/NO152089C/no unknown
- 1979-01-17 PT PT7969093A patent/PT69093A/pt unknown
- 1979-01-18 EP EP79100149A patent/EP0003144B1/de not_active Expired
- 1979-01-18 DE DE19792901868 patent/DE2901868A1/de not_active Withdrawn
- 1979-01-30 IE IE113/79A patent/IE47784B1/en unknown
-
1982
- 1982-04-19 US US06/369,778 patent/US4521535A/en not_active Expired - Fee Related
-
1984
- 1984-11-02 US US06/667,528 patent/US4549022A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54100382A (en) | 1979-08-08 |
| GB2013190A (en) | 1979-08-08 |
| DK20279A (da) | 1979-07-19 |
| FR2415103B1 (OSRAM) | 1982-11-05 |
| NZ189379A (en) | 1984-07-06 |
| IE47784B1 (en) | 1984-06-13 |
| US4521535A (en) | 1985-06-04 |
| AU4329679A (en) | 1979-07-26 |
| IE790113L (en) | 1979-07-18 |
| FI790103A7 (fi) | 1979-07-19 |
| GR73088B (OSRAM) | 1984-02-01 |
| ES476917A1 (es) | 1979-11-16 |
| KR820002111B1 (ko) | 1982-11-10 |
| AT369731B (de) | 1983-01-25 |
| EP0003144B1 (de) | 1981-08-05 |
| IL56421A (en) | 1982-08-31 |
| DE2901868A1 (de) | 1979-07-19 |
| EP0003144A2 (de) | 1979-07-25 |
| PT69093A (en) | 1979-02-01 |
| GB2013190B (en) | 1982-07-14 |
| NO152089C (no) | 1985-08-14 |
| US4549022A (en) | 1985-10-22 |
| MC1239A1 (fr) | 1979-10-26 |
| SE7900318L (sv) | 1979-07-19 |
| NO790165L (no) | 1979-07-19 |
| ATA35079A (de) | 1982-06-15 |
| HU179487B (en) | 1982-10-28 |
| EP0003144A3 (en) | 1979-08-08 |
| AU521148B2 (en) | 1982-03-18 |
| IL56421A0 (en) | 1979-03-12 |
| LU80794A1 (de) | 1980-02-14 |
| NL7900264A (nl) | 1979-07-20 |
| FR2415103A1 (fr) | 1979-08-17 |
| AR223663A1 (es) | 1981-09-15 |
| NO152089B (no) | 1985-04-22 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |