DE2901868A1 - 4-pyridon-3-carbonsaeurederivate und ihre herstellung - Google Patents
4-pyridon-3-carbonsaeurederivate und ihre herstellungInfo
- Publication number
- DE2901868A1 DE2901868A1 DE19792901868 DE2901868A DE2901868A1 DE 2901868 A1 DE2901868 A1 DE 2901868A1 DE 19792901868 DE19792901868 DE 19792901868 DE 2901868 A DE2901868 A DE 2901868A DE 2901868 A1 DE2901868 A1 DE 2901868A1
- Authority
- DE
- Germany
- Prior art keywords
- oxo
- ethyl
- acid
- phenyl
- alkyl
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 styryl radical Chemical class 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 210000003169 central nervous system Anatomy 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 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 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- SSHRVPMSFQLCAG-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine-5-carboxylic acid Chemical class OC(=O)C1=CNCCC1 SSHRVPMSFQLCAG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 230000004936 stimulating effect Effects 0.000 claims description 3
- 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 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 239000008186 active pharmaceutical agent Substances 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 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 claims 1
- UNNHFTDHYGKLQV-UHFFFAOYSA-N 1-(cyclopropylmethyl)-4-oxo-6-phenylpyridine-3-carboxylic acid Chemical compound C=1C=CC=CC=1C1=CC(=O)C(C(=O)O)=CN1CC1CC1 UNNHFTDHYGKLQV-UHFFFAOYSA-N 0.000 claims 1
- OOVFZRBTLXQRIR-UHFFFAOYSA-N 1-butoxy-4-oxo-6-phenylpyridine-3-carboxylic acid Chemical compound CCCCON1C=C(C(O)=O)C(=O)C=C1C1=CC=CC=C1 OOVFZRBTLXQRIR-UHFFFAOYSA-N 0.000 claims 1
- VXAGLICRPDYICY-UHFFFAOYSA-N 1-cyclopentyl-4-oxo-6-phenylpyridine-3-carboxylic acid Chemical compound C=1C=CC=CC=1C1=CC(=O)C(C(=O)O)=CN1C1CCCC1 VXAGLICRPDYICY-UHFFFAOYSA-N 0.000 claims 1
- PESNWCFMIWRFJR-UHFFFAOYSA-N 1-ethyl-4-oxo-6-(4-pyrrolidin-1-ylphenyl)pyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=C(N2CCCC2)C=C1 PESNWCFMIWRFJR-UHFFFAOYSA-N 0.000 claims 1
- GCKGTSAEHKXUID-UHFFFAOYSA-N 1-ethyl-4-oxo-6-pyridin-4-ylpyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=NC=C1 GCKGTSAEHKXUID-UHFFFAOYSA-N 0.000 claims 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 claims 1
- JDSWFARLTUKWFY-UHFFFAOYSA-N 1-ethyl-6-[4-(4-methylpiperazin-1-yl)phenyl]-4-oxopyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=C(N2CCN(C)CC2)C=C1 JDSWFARLTUKWFY-UHFFFAOYSA-N 0.000 claims 1
- AUEIUORFSCQQBI-UHFFFAOYSA-N 1-methoxy-4-oxo-6-phenylpyridine-3-carboxylic acid Chemical compound CON1C=C(C(O)=O)C(=O)C=C1C1=CC=CC=C1 AUEIUORFSCQQBI-UHFFFAOYSA-N 0.000 claims 1
- MZPFGDVMLARUJT-UHFFFAOYSA-N 1-octyl-4-oxo-6-phenylpyridine-3-carboxylic acid Chemical compound CCCCCCCCN1C=C(C(O)=O)C(=O)C=C1C1=CC=CC=C1 MZPFGDVMLARUJT-UHFFFAOYSA-N 0.000 claims 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 claims 1
- HBXCFZJFGXBNPH-UHFFFAOYSA-N 6-(1,3-benzodioxol-5-yl)-1-ethyl-4-oxopyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=C(OCO2)C2=C1 HBXCFZJFGXBNPH-UHFFFAOYSA-N 0.000 claims 1
- MRVSXTHSWQKNJH-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-1-ethyl-4-oxopyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=C(Cl)C=CC=C1Cl MRVSXTHSWQKNJH-UHFFFAOYSA-N 0.000 claims 1
- FSQCLECWIGVZHF-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-1-ethyl-4-oxopyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=C(OC)C(OC)=C1 FSQCLECWIGVZHF-UHFFFAOYSA-N 0.000 claims 1
- OPBFTKVHXAGPPK-UHFFFAOYSA-N 6-[4-(dimethylamino)phenyl]-1-methoxy-4-oxopyridine-3-carboxylic acid Chemical compound CON1C=C(C(O)=O)C(=O)C=C1C1=CC=C(N(C)C)C=C1 OPBFTKVHXAGPPK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 239000002269 analeptic agent Substances 0.000 claims 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical class CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 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 10
- 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
- 239000000203 mixture Substances 0.000 description 7
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 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
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 238000001035 drying Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 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
- 239000002244 precipitate Substances 0.000 description 3
- 239000003826 tablet Substances 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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-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
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 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
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-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
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 150000002814 niacins Chemical class 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
- 238000010992 reflux Methods 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
- 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- OPSXYAFWJPPHQK-UHFFFAOYSA-N 1,2,3,6-tetrahydropyridine-3-carboxylic acid Chemical class OC(=O)C1CNCC=C1 OPSXYAFWJPPHQK-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 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
- HQQRCPMZRSOBLO-UHFFFAOYSA-N 1-ethyl-4-oxo-2-pyridin-3-yl-2,3-dihydropyridine-5-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)CC1C1=CC=CN=C1 HQQRCPMZRSOBLO-UHFFFAOYSA-N 0.000 description 1
- DQIZKUMHBKFRKB-UHFFFAOYSA-N 1-ethyl-4-oxo-6-phenylpyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=CC=C1 DQIZKUMHBKFRKB-UHFFFAOYSA-N 0.000 description 1
- HFLHLTVNZJBRRY-UHFFFAOYSA-N 1-ethyl-4-oxo-6-pyridin-3-ylpyridine-3-carboxylic acid Chemical class 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
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
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- 125000002252 acyl group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
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- 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine 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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- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 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
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 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
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- 239000000463 material Substances 0.000 description 1
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- CPYUVWPVQVORNT-UHFFFAOYSA-N methyl 1-ethyl-4-oxo-2-(3,4,5-trimethoxyphenyl)-2,3-dihydropyridine-5-carboxylate Chemical compound CCN1C=C(C(=O)OC)C(=O)CC1C1=CC(OC)=C(OC)C(OC)=C1 CPYUVWPVQVORNT-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
- XRERRIIXULJOAL-UHFFFAOYSA-N methyl 2-(ethylaminomethylidene)-3-oxo-5-pyridin-3-ylpent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=CN=C1 XRERRIIXULJOAL-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
- 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
- IYPDNXHYXYSYNV-UHFFFAOYSA-N methyl 5-(1,3-benzodioxol-5-yl)-2-[(cyclopropylamino)methylidene]-3-oxopent-4-enoate Chemical compound C=1C=C2OCOC2=CC=1C=CC(=O)C(C(=O)OC)=CNC1CC1 IYPDNXHYXYSYNV-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
- IQTBPDHJGYTSDR-UHFFFAOYSA-N methyl 5-(3,4-dimethoxyphenyl)-2-(ethylaminomethylidene)-3-oxopent-4-enoate Chemical compound CCNC=C(C(=O)OC)C(=O)C=CC1=CC=C(OC)C(OC)=C1 IQTBPDHJGYTSDR-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
- 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 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
- UIRKEFHMCBPTFL-UHFFFAOYSA-N methyl 6-(4-chlorophenyl)-1-ethyl-4-oxopyridine-3-carboxylate Chemical compound CCN1C=C(C(=O)OC)C(=O)C=C1C1=CC=C(Cl)C=C1 UIRKEFHMCBPTFL-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- 230000007935 neutral effect Effects 0.000 description 1
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- WCVVIGQKJZLJDB-UHFFFAOYSA-N o-butylhydroxylamine Chemical compound CCCCON WCVVIGQKJZLJDB-UHFFFAOYSA-N 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
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- 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
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 1
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- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 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
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
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- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
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- 150000003852 triazoles Chemical class 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
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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 (2)
| 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 |
| CH1173478 | 1978-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2901868A1 true DE2901868A1 (de) | 1979-07-19 |
Family
ID=25684790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792901868 Withdrawn DE2901868A1 (de) | 1978-01-18 | 1979-01-18 | 4-pyridon-3-carbonsaeurederivate und ihre herstellung |
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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4698352A (en) * | 1982-10-29 | 1987-10-06 | Toyama Chemical Co., Ltd. | 4-oxo-1,4-dihydronicotinic acid derivatives, salts thereof, and antibacterial agents containing the same |
| 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 |
Families Citing this family (10)
| 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 |
| 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 |
| 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
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4698352A (en) * | 1982-10-29 | 1987-10-06 | Toyama Chemical Co., Ltd. | 4-oxo-1,4-dihydronicotinic acid derivatives, salts thereof, and antibacterial agents containing the same |
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 |
| CA1110234A (en) | 1981-10-06 |
| IL56421A (en) | 1982-08-31 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |