CA1115709A - Derives d'acide picolinique hydroxyle, substitue en 5 - Google Patents
Derives d'acide picolinique hydroxyle, substitue en 5Info
- Publication number
- CA1115709A CA1115709A CA323,912A CA323912A CA1115709A CA 1115709 A CA1115709 A CA 1115709A CA 323912 A CA323912 A CA 323912A CA 1115709 A CA1115709 A CA 1115709A
- Authority
- CA
- Canada
- Prior art keywords
- group
- formula
- same
- represented
- picolinic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 5-substituted-hydroxy picolinic acid Chemical class 0.000 title claims abstract description 85
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 54
- 229940081066 picolinic acid Drugs 0.000 claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 25
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 125000003277 amino group Chemical group 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 10
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 8
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 44
- 230000008569 process Effects 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 28
- DHLUJPLHLZJUBW-UHFFFAOYSA-N 6-methylpyridin-3-ol Chemical compound CC1=CC=C(O)C=N1 DHLUJPLHLZJUBW-UHFFFAOYSA-N 0.000 claims description 26
- PEHSSTUGJUBZBI-UHFFFAOYSA-N indan-5-ol Chemical compound OC1=CC=C2CCCC2=C1 PEHSSTUGJUBZBI-UHFFFAOYSA-N 0.000 claims description 20
- 230000001590 oxidative effect Effects 0.000 claims description 15
- 239000007800 oxidant agent Substances 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- NESFDGDRYVANBC-UHFFFAOYSA-N 6-(hydroxymethyl)pyridin-3-ol Chemical compound OCC1=CC=C(O)C=N1 NESFDGDRYVANBC-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- RXHAQWAUXWKINY-UHFFFAOYSA-N 5-(4-chlorophenoxy)pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1OC1=CC=C(Cl)C=C1 RXHAQWAUXWKINY-UHFFFAOYSA-N 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 8
- 229910052751 metal Chemical class 0.000 claims description 8
- 239000002184 metal Chemical class 0.000 claims description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 8
- NPAUPKKDRMTHSQ-UHFFFAOYSA-N 5-(4-chlorobutoxy)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(OCCCCCl)C=N1 NPAUPKKDRMTHSQ-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000012954 diazonium Substances 0.000 claims description 7
- YQGKMQPCIMTPCB-UHFFFAOYSA-N 5-(3-chloropropoxy)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(OCCCCl)C=N1 YQGKMQPCIMTPCB-UHFFFAOYSA-N 0.000 claims description 6
- CHBNFEFUVKGTPY-UHFFFAOYSA-N 5-(2-chlorophenoxy)pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1OC1=CC=CC=C1Cl CHBNFEFUVKGTPY-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 150000001989 diazonium salts Chemical class 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- QBELEDRHMPMKHP-UHFFFAOYSA-N 1-bromo-2-chlorobenzene Chemical compound ClC1=CC=CC=C1Br QBELEDRHMPMKHP-UHFFFAOYSA-N 0.000 claims description 4
- KTHFMMUXNXWKNS-UHFFFAOYSA-N 5-[2-(trifluoromethyl)phenoxy]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1OC1=CC=CC=C1C(F)(F)F KTHFMMUXNXWKNS-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 235000010288 sodium nitrite Nutrition 0.000 claims description 4
- IQHWLPUHSVSHMK-UHFFFAOYSA-N 2-methyl-5-[4-(trifluoromethyl)phenoxy]pyridine Chemical compound C1=NC(C)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 IQHWLPUHSVSHMK-UHFFFAOYSA-N 0.000 claims description 3
- WHVGGUIIUQHOAL-UHFFFAOYSA-N 5-(2-chlorophenoxy)-2-methylpyridine Chemical compound C1=NC(C)=CC=C1OC1=CC=CC=C1Cl WHVGGUIIUQHOAL-UHFFFAOYSA-N 0.000 claims description 3
- LKLOIBKLYSDLFY-UHFFFAOYSA-N 5-(4-chlorophenoxy)-2-methylpyridine Chemical compound C1=NC(C)=CC=C1OC1=CC=C(Cl)C=C1 LKLOIBKLYSDLFY-UHFFFAOYSA-N 0.000 claims description 3
- OMYLZYZQGXVCJW-UHFFFAOYSA-N 5-(5,5,5-trifluoropentoxy)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(OCCCCC(F)(F)F)C=N1 OMYLZYZQGXVCJW-UHFFFAOYSA-N 0.000 claims description 3
- JXPYTHDXGAGHBU-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenoxy]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 JXPYTHDXGAGHBU-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- YWWIVAPTDUGCDE-UHFFFAOYSA-N [5-(3-chloropropoxy)pyridin-2-yl]methanol Chemical compound OCC1=CC=C(OCCCCl)C=N1 YWWIVAPTDUGCDE-UHFFFAOYSA-N 0.000 claims description 3
- GPNKLWSGOAVQBZ-UHFFFAOYSA-N [5-(4-chlorobutoxy)pyridin-2-yl]methanol Chemical compound OCC1=CC=C(OCCCCCl)C=N1 GPNKLWSGOAVQBZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 150000005171 halobenzenes Chemical class 0.000 claims description 3
- 125000004436 sodium atom Chemical group 0.000 claims description 3
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 claims description 2
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 claims description 2
- XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 claims description 2
- BEQKYEJRVRVZNZ-UHFFFAOYSA-N 5-bromo-1,1,1-trifluoropentane Chemical compound FC(F)(F)CCCCBr BEQKYEJRVRVZNZ-UHFFFAOYSA-N 0.000 claims description 2
- VZNBOUOHGXQJTK-UHFFFAOYSA-N [5-(5,5,5-trifluoropentoxy)pyridin-2-yl]methanol Chemical compound OCC1=CC=C(OCCCCC(F)(F)F)C=N1 VZNBOUOHGXQJTK-UHFFFAOYSA-N 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- XJVQMUUYJXFBDH-UHFFFAOYSA-N 2-methyl-5-[2-(trifluoromethyl)phenoxy]pyridine Chemical compound FC(C1=C(OC=2C=CC(=NC2)C)C=CC=C1)(F)F XJVQMUUYJXFBDH-UHFFFAOYSA-N 0.000 claims 2
- RWXUNIMBRXGNEP-UHFFFAOYSA-N 1-bromo-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Br RWXUNIMBRXGNEP-UHFFFAOYSA-N 0.000 claims 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims 1
- CKVQQDUSKCAIDZ-UHFFFAOYSA-N 5-(4,4,4-trifluorobutoxy)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(OCCCC(F)(F)F)C=N1 CKVQQDUSKCAIDZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 29
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 18
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 10
- 239000002220 antihypertensive agent Substances 0.000 abstract description 10
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 8
- 125000004442 acylamino group Chemical group 0.000 abstract description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 5
- 125000002431 aminoalkoxy group Chemical group 0.000 abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 239000011734 sodium Substances 0.000 abstract description 5
- 239000004411 aluminium Substances 0.000 abstract description 2
- 239000011591 potassium Substances 0.000 abstract description 2
- 229910052700 potassium Inorganic materials 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical group OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 35
- 239000013078 crystal Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 23
- 238000002844 melting Methods 0.000 description 22
- 238000000921 elemental analysis Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 235000011167 hydrochloric acid Nutrition 0.000 description 18
- 229960000443 hydrochloric acid Drugs 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 238000007254 oxidation reaction Methods 0.000 description 15
- 230000003647 oxidation Effects 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- DGMPVYSXXIOGJY-UHFFFAOYSA-N Fusaric acid Chemical compound CCCCC1=CC=C(C(O)=O)N=C1 DGMPVYSXXIOGJY-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 11
- 239000012286 potassium permanganate Substances 0.000 description 11
- 230000035484 reaction time Effects 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 229940093499 ethyl acetate Drugs 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 230000036772 blood pressure Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
- 159000000007 calcium salts Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 235000001968 nicotinic acid Nutrition 0.000 description 5
- 239000011664 nicotinic acid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000010531 catalytic reduction reaction Methods 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 239000012065 filter cake Substances 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XXOUHKWIQVEQIH-UHFFFAOYSA-N 5-butoxypyridine-2-carboxylic acid Chemical compound CCCCOC1=CC=C(C(O)=O)N=C1 XXOUHKWIQVEQIH-UHFFFAOYSA-N 0.000 description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- 239000005751 Copper oxide Substances 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- 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 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910000431 copper oxide Inorganic materials 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- 238000005469 granulation Methods 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- OCYOPQMIQQOESK-UHFFFAOYSA-N 5-[2-(trifluoromethyl)phenoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1OC1=CC=CC=C1C(F)(F)F OCYOPQMIQQOESK-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 150000003462 sulfoxides Chemical class 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- 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
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3296678A JPS54125680A (en) | 1978-03-24 | 1978-03-24 | 5-alkoxypicolinic acid ester, its preparation, and hypotensive agent containing the same |
| JP32966/78 | 1978-03-24 | ||
| JP32967/78 | 1978-03-24 | ||
| JP3296778A JPS54125681A (en) | 1978-03-24 | 1978-03-24 | 5-substituted picolinic acid, its preparation, and hypotensive agent containing the same |
| JP80485/78 | 1978-07-04 | ||
| JP8048578A JPS559002A (en) | 1978-07-04 | 1978-07-04 | 5-substituted picolinic acid derivative, its preparation and hypotensive agent containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1115709A true CA1115709A (fr) | 1982-01-05 |
Family
ID=27287919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA323,912A Expired CA1115709A (fr) | 1978-03-24 | 1979-03-21 | Derives d'acide picolinique hydroxyle, substitue en 5 |
Country Status (9)
| Country | Link |
|---|---|
| CA (1) | CA1115709A (fr) |
| CH (1) | CH637941A5 (fr) |
| DE (1) | DE2911492C2 (fr) |
| ES (1) | ES478918A1 (fr) |
| FR (1) | FR2422639A1 (fr) |
| GB (1) | GB2018753B (fr) |
| IT (1) | IT1115064B (fr) |
| NL (1) | NL178251C (fr) |
| SE (1) | SE446863B (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5344572A (en) * | 1976-09-30 | 1978-04-21 | Meiji Seika Kaisha Ltd | 5-alkoxy-picolic acid, its preparation and hypotensives containing the same |
-
1979
- 1979-03-21 CA CA323,912A patent/CA1115709A/fr not_active Expired
- 1979-03-22 CH CH268779A patent/CH637941A5/fr not_active IP Right Cessation
- 1979-03-22 IT IT48451/79A patent/IT1115064B/it active
- 1979-03-23 FR FR7907345A patent/FR2422639A1/fr active Granted
- 1979-03-23 GB GB7910324A patent/GB2018753B/en not_active Expired
- 1979-03-23 SE SE7902665A patent/SE446863B/sv not_active IP Right Cessation
- 1979-03-23 DE DE2911492A patent/DE2911492C2/de not_active Expired
- 1979-03-23 NL NLAANVRAGE7902306,A patent/NL178251C/xx not_active IP Right Cessation
- 1979-03-23 ES ES478918A patent/ES478918A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2911492A1 (de) | 1979-09-27 |
| FR2422639A1 (fr) | 1979-11-09 |
| SE7902665L (sv) | 1979-09-25 |
| FR2422639B1 (fr) | 1983-05-20 |
| IT1115064B (it) | 1986-02-03 |
| NL178251B (nl) | 1985-09-16 |
| GB2018753B (en) | 1982-08-25 |
| DE2911492C2 (de) | 1983-05-05 |
| ES478918A1 (es) | 1979-12-16 |
| IT7948451A0 (it) | 1979-03-22 |
| NL178251C (nl) | 1986-02-17 |
| CH637941A5 (fr) | 1983-08-31 |
| NL7902306A (nl) | 1979-09-26 |
| GB2018753A (en) | 1979-10-24 |
| SE446863B (sv) | 1986-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |