CH629488A5 - Processes for preparing novel picolinic acid derivatives. - Google Patents
Processes for preparing novel picolinic acid derivatives. Download PDFInfo
- Publication number
- CH629488A5 CH629488A5 CH1451376A CH1451376A CH629488A5 CH 629488 A5 CH629488 A5 CH 629488A5 CH 1451376 A CH1451376 A CH 1451376A CH 1451376 A CH1451376 A CH 1451376A CH 629488 A5 CH629488 A5 CH 629488A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen
- group
- diphenylmethyl
- compound
- triphenylmethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- -1 cyanomethyl ester Chemical class 0.000 claims description 47
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000005339 cyanocycloalkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 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
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 48
- 239000000203 mixture Substances 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 40
- 238000002844 melting Methods 0.000 description 40
- 230000008018 melting Effects 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 238000010992 reflux Methods 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- GDHQAOKGZLRWCG-UHFFFAOYSA-N 5-tritylpyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GDHQAOKGZLRWCG-UHFFFAOYSA-N 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 206010000496 acne Diseases 0.000 description 9
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 9
- 229940081066 picolinic acid Drugs 0.000 description 9
- 208000002874 Acne Vulgaris Diseases 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 8
- DNCSGDXANQYATE-UHFFFAOYSA-N 5-benzhydrylpyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 DNCSGDXANQYATE-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
- 150000005748 halopyridines Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 5
- BGHGLEYVPJYVLH-UHFFFAOYSA-N cyanomethyl 5-tritylpyridine-2-carboxylate Chemical compound C1=NC(C(OCC#N)=O)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BGHGLEYVPJYVLH-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000012286 potassium permanganate Substances 0.000 description 5
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- ZWLWOTHDIGRTNE-UHFFFAOYSA-N 4-benzhydrylpyridine Chemical compound C1=CC=CC=C1C(C=1C=CN=CC=1)C1=CC=CC=C1 ZWLWOTHDIGRTNE-UHFFFAOYSA-N 0.000 description 3
- GHHJPDLUCFATCP-UHFFFAOYSA-N 4-benzhydrylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GHHJPDLUCFATCP-UHFFFAOYSA-N 0.000 description 3
- BYRNFBSYDXQMKZ-UHFFFAOYSA-N 5-benzhydryl-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BYRNFBSYDXQMKZ-UHFFFAOYSA-N 0.000 description 3
- ORTYSHBSADEXGI-UHFFFAOYSA-N 5-benzhydryl-2-chloropyridine Chemical compound C1=NC(Cl)=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 ORTYSHBSADEXGI-UHFFFAOYSA-N 0.000 description 3
- HVWXCQMWRVIRIV-UHFFFAOYSA-N 5-tritylpyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HVWXCQMWRVIRIV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
- DVULXUNYKFBGCF-UHFFFAOYSA-N 1-oxido-3-tritylpyridin-1-ium Chemical compound [O-][N+]1=CC=CC(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 DVULXUNYKFBGCF-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- MKOPYNUZVFTIDQ-UHFFFAOYSA-N 2-benzhydryl-5-oxohexanenitrile Chemical compound C1(=CC=CC=C1)C(C(CCC(C)=O)C#N)C1=CC=CC=C1 MKOPYNUZVFTIDQ-UHFFFAOYSA-N 0.000 description 2
- CXUSITMWIQPJOI-UHFFFAOYSA-N 2-bromo-5-tritylpyridine Chemical compound C1=NC(Br)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CXUSITMWIQPJOI-UHFFFAOYSA-N 0.000 description 2
- VUCGNEZRDLRPGU-UHFFFAOYSA-N 2-methyl-5-tritylpiperidine Chemical compound C1NC(C)CCC1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VUCGNEZRDLRPGU-UHFFFAOYSA-N 0.000 description 2
- AUZCPAUVTDTZHC-UHFFFAOYSA-N 2-methyl-5-tritylpyridine Chemical compound C1=NC(C)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AUZCPAUVTDTZHC-UHFFFAOYSA-N 0.000 description 2
- HIJRINSXBOZPGQ-UHFFFAOYSA-N 3,3,3-triphenylpropanenitrile Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(CC#N)C1=CC=CC=C1 HIJRINSXBOZPGQ-UHFFFAOYSA-N 0.000 description 2
- INERKLNEVAZSCI-UHFFFAOYSA-N 3,3-diphenylpropanenitrile Chemical compound C=1C=CC=CC=1C(CC#N)C1=CC=CC=C1 INERKLNEVAZSCI-UHFFFAOYSA-N 0.000 description 2
- JXODPVGLKVQQDK-UHFFFAOYSA-N 3,5-dibenzhydryl-1h-pyridin-2-one Chemical compound O=C1NC=C(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 JXODPVGLKVQQDK-UHFFFAOYSA-N 0.000 description 2
- NTLOSBZGYSEVMD-UHFFFAOYSA-N 3,5-dibenzhydryl-2-chloropyridine Chemical compound ClC1=NC=C(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 NTLOSBZGYSEVMD-UHFFFAOYSA-N 0.000 description 2
- QLCCMSXMDVFCMS-UHFFFAOYSA-N 3,5-dibenzhydrylpyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=C(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 QLCCMSXMDVFCMS-UHFFFAOYSA-N 0.000 description 2
- HGVLJGHVYCBNBB-UHFFFAOYSA-N 3-benzhydrylpyridine Chemical compound C1=CC=CC=C1C(C=1C=NC=CC=1)C1=CC=CC=C1 HGVLJGHVYCBNBB-UHFFFAOYSA-N 0.000 description 2
- UMDMSKDGFOWNDU-UHFFFAOYSA-N 4-(1,1-diphenylpropyl)pyridine Chemical compound C=1C=CC=CC=1C(C=1C=CN=CC=1)(CC)C1=CC=CC=C1 UMDMSKDGFOWNDU-UHFFFAOYSA-N 0.000 description 2
- GARIJXFRAFHFPJ-UHFFFAOYSA-N 4-(1,1-diphenylpropyl)pyridine-2-carboxamide Chemical compound C=1C=CC=CC=1C(C=1C=C(N=CC=1)C(N)=O)(CC)C1=CC=CC=C1 GARIJXFRAFHFPJ-UHFFFAOYSA-N 0.000 description 2
- RKBBOAYUDUDSFG-UHFFFAOYSA-N 4-[bis(4-chlorophenyl)methyl]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1 RKBBOAYUDUDSFG-UHFFFAOYSA-N 0.000 description 2
- RVLOBCQGOVIZGX-UHFFFAOYSA-N 4-benzhydrylpyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 RVLOBCQGOVIZGX-UHFFFAOYSA-N 0.000 description 2
- QNMVWLIZZUEHKT-UHFFFAOYSA-N 5-[(4-chlorophenyl)-phenylmethyl]-1h-pyridin-2-one Chemical compound C1=CC(Cl)=CC=C1C(C1=CNC(=O)C=C1)C1=CC=CC=C1 QNMVWLIZZUEHKT-UHFFFAOYSA-N 0.000 description 2
- FDNKTGXIPUZOHF-UHFFFAOYSA-N 5-[(4-chlorophenyl)-phenylmethyl]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 FDNKTGXIPUZOHF-UHFFFAOYSA-N 0.000 description 2
- KZZVXWGXIWQQEJ-UHFFFAOYSA-N 5-[bis(4-chlorophenyl)methyl]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 KZZVXWGXIWQQEJ-UHFFFAOYSA-N 0.000 description 2
- IHPLNGKLODZSBU-UHFFFAOYSA-N 5-benzhydryl-2-methylpyridine Chemical compound C1=NC(C)=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 IHPLNGKLODZSBU-UHFFFAOYSA-N 0.000 description 2
- KYXUYDBEKPXHHQ-UHFFFAOYSA-N 5-benzhydrylpyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 KYXUYDBEKPXHHQ-UHFFFAOYSA-N 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000186427 Cutibacterium acnes Species 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
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- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
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- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- ROCAROJLTBMPBY-UHFFFAOYSA-N cyanomethyl 5-benzhydrylpyridine-2-carboxylate Chemical compound C1=NC(C(OCC#N)=O)=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 ROCAROJLTBMPBY-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
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- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
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- 125000005908 glyceryl ester group Chemical group 0.000 description 1
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- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- HJFMBSAURBVGKV-UHFFFAOYSA-N methyl 5-tritylpyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HJFMBSAURBVGKV-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- WERXEPLMSJVOGL-UHFFFAOYSA-N n,n-diethyl-5-tritylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(CC)CC)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WERXEPLMSJVOGL-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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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- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
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- 239000000825 pharmaceutical preparation Substances 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000057 systemic toxicity Toxicity 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
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Classifications
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- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/12—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
-
- 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
- C07D213/61—Halogen atoms or nitro radicals
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
-
- 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
- C07D213/81—Amides; Imides
-
- 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
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES453555A ES453555A1 (es) | 1975-11-28 | 1976-11-23 | Un procedimiento para la preparacion de derivados del acido picolinico. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63600975A | 1975-11-28 | 1975-11-28 | |
| US05/636,010 US4044140A (en) | 1975-11-28 | 1975-11-28 | Trityl picolinic acid derivatives and their use as anti-acne agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH629488A5 true CH629488A5 (en) | 1982-04-30 |
Family
ID=27092506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1451376A CH629488A5 (en) | 1975-11-28 | 1976-11-18 | Processes for preparing novel picolinic acid derivatives. |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5268186A (enExample) |
| AR (1) | AR223803A1 (enExample) |
| AU (1) | AU506351B2 (enExample) |
| CH (1) | CH629488A5 (enExample) |
| DE (1) | DE2653138A1 (enExample) |
| DK (1) | DK526976A (enExample) |
| FR (1) | FR2332753A1 (enExample) |
| GB (1) | GB1565056A (enExample) |
| GR (1) | GR61662B (enExample) |
| HU (1) | HU175179B (enExample) |
| NL (1) | NL7613041A (enExample) |
| PT (1) | PT65874B (enExample) |
| SE (1) | SE7613090L (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4555520A (en) * | 1984-08-20 | 1985-11-26 | E. R. Squibb & Sons, Inc. | 2-Pyridylcarboxamides which inhibit arachidonic acid release |
| US5501329A (en) * | 1995-04-05 | 1996-03-26 | Provence; Daniel J. | Telephone handset cover |
| US6579891B1 (en) | 1995-12-29 | 2003-06-17 | Novactyl, Inc. | Agent and method for prevention and treatment of cancer in animals |
| US6407125B1 (en) | 1995-12-29 | 2002-06-18 | Novactyl, Inc. | Pharmacological agent and method of treatment |
| US6743771B2 (en) | 1995-12-29 | 2004-06-01 | Novactyl, Inc. | Methods and compositions for controlling protein assembly or aggregation |
| US6441009B1 (en) | 1998-08-01 | 2002-08-27 | Novactyl, Inc. | Agent and method of preventing and treating heavy metal exposure and toxicity |
| US6403618B1 (en) | 2000-02-15 | 2002-06-11 | Novactyl, Inc. | Agent and method for controlling angiogenesis |
| RU2272028C2 (ru) * | 2004-06-04 | 2006-03-20 | Григорьев Лев Викторович | Способ получения тетрахлорпиколиновой кислоты |
| RU2273635C2 (ru) * | 2004-06-04 | 2006-04-10 | Григорьев Лев Викторович | Способ получения тетрахлорпиколиновой кислоты |
| CA3063094A1 (en) * | 2017-05-10 | 2018-11-15 | Dow Agrosciences Llc | 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides |
| US12310364B2 (en) | 2018-11-06 | 2025-05-27 | Corteva Agriscience Llc | Safened compositions comprising pyridine carboxylate herbicides and cloquintocet |
| UA128373C2 (uk) | 2018-11-06 | 2024-06-26 | Кортева Аґрисайєнс Елелсі | Композиції з антидотом, які містять гербіциди на основі піридинкарбоксилату та ізоксадифен |
| LT3876726T (lt) | 2018-11-06 | 2025-03-10 | Corteva Agriscience Llc | Kompozicijos, apimančios piridino karboksilato herbicidus ir azolo karboksilato herbicidų antidotus |
| EP3876733B1 (en) | 2018-11-07 | 2025-07-02 | Corteva Agriscience LLC | Compositions comprising pyridine carboxylate herbicides with photosystem ii and optional hppd inhibitor herbicides |
| DK3876729T3 (da) | 2018-11-07 | 2025-03-31 | Corteva Agriscience Llc | Sammensætninger, som omfatter et pyridincarboxylatherbicid og protoporphyrinogenoxidase (protox)-hæmmerherbicider |
| BR112021008620A2 (pt) | 2018-11-07 | 2021-08-03 | Corteva Agriscience Llc | composições que compreendem herbicidas de carboxilato de piridina com herbicidas inibidores de acetolactato sintase (als) |
| PL3876730T3 (pl) | 2018-11-07 | 2025-11-03 | Corteva Agriscience Llc | Kompozycje zawierające herbicydy pirydynokarboksylanowe oraz herbicydy będące inhibitorami dioksygenazy 4-hydroksyfenylo- pirogronianowej (hppd) |
-
1976
- 1976-11-18 CH CH1451376A patent/CH629488A5/de not_active IP Right Cessation
- 1976-11-23 AU AU19935/76A patent/AU506351B2/en not_active Expired
- 1976-11-23 FR FR7635249A patent/FR2332753A1/fr active Granted
- 1976-11-23 AR AR265573A patent/AR223803A1/es active
- 1976-11-23 NL NL7613041A patent/NL7613041A/xx not_active Application Discontinuation
- 1976-11-23 GR GR52252A patent/GR61662B/el unknown
- 1976-11-23 SE SE7613090A patent/SE7613090L/xx not_active Application Discontinuation
- 1976-11-23 DE DE19762653138 patent/DE2653138A1/de not_active Withdrawn
- 1976-11-23 PT PT65874A patent/PT65874B/pt unknown
- 1976-11-23 GB GB48809/76A patent/GB1565056A/en not_active Expired
- 1976-11-23 DK DK526976A patent/DK526976A/da unknown
- 1976-11-24 JP JP51141073A patent/JPS5268186A/ja active Pending
- 1976-11-25 HU HU76SCHE583A patent/HU175179B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR223803A1 (es) | 1981-09-30 |
| HU175179B (hu) | 1980-05-28 |
| PT65874A (en) | 1976-12-01 |
| JPS5268186A (en) | 1977-06-06 |
| AU506351B2 (en) | 1979-12-20 |
| DK526976A (da) | 1977-05-29 |
| GR61662B (en) | 1978-12-05 |
| NL7613041A (nl) | 1977-06-01 |
| GB1565056A (en) | 1980-04-16 |
| FR2332753A1 (fr) | 1977-06-24 |
| FR2332753B1 (enExample) | 1978-11-17 |
| PT65874B (en) | 1978-05-17 |
| SE7613090L (sv) | 1977-05-29 |
| AU1993576A (en) | 1978-06-01 |
| DE2653138A1 (de) | 1977-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |