CA1070307A - Bis-quaternary pyridinium-2-aldoxime salts and a process for their preparation - Google Patents
Bis-quaternary pyridinium-2-aldoxime salts and a process for their preparationInfo
- Publication number
- CA1070307A CA1070307A CA276,042A CA276042A CA1070307A CA 1070307 A CA1070307 A CA 1070307A CA 276042 A CA276042 A CA 276042A CA 1070307 A CA1070307 A CA 1070307A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- carbon atoms
- alkyl
- diiodide
- cyclohexyl
- 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
- MTFJSAGADRTKCI-UHFFFAOYSA-N N-(pyridin-2-ylmethylidene)hydroxylamine Chemical group ON=CC1=CC=CC=N1 MTFJSAGADRTKCI-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 44
- 238000002360 preparation method Methods 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 69
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 45
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 41
- -1 R2 is H Chemical group 0.000 claims abstract description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 23
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 19
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 17
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 22
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 15
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 229960003512 nicotinic acid Drugs 0.000 claims description 8
- 235000001968 nicotinic acid Nutrition 0.000 claims description 8
- 239000011664 nicotinic acid Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- BEZMAXBTMUXQSN-UHFFFAOYSA-N [Cl-].ClCO[N+]1=C(C(=CC=C1)C)C=NO Chemical compound [Cl-].ClCO[N+]1=C(C(=CC=C1)C)C=NO BEZMAXBTMUXQSN-UHFFFAOYSA-N 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 4
- 235000009518 sodium iodide Nutrition 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 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 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- SDAFBHAGZHYODJ-UHFFFAOYSA-N cyclohexyl(pyridin-3-yl)methanone Chemical compound C=1C=CN=CC=1C(=O)C1CCCCC1 SDAFBHAGZHYODJ-UHFFFAOYSA-N 0.000 claims 1
- RYMBAPVTUHZCNF-UHFFFAOYSA-N phenyl(pyridin-3-yl)methanone Chemical compound C=1C=CN=CC=1C(=O)C1=CC=CC=C1 RYMBAPVTUHZCNF-UHFFFAOYSA-N 0.000 claims 1
- 239000000729 antidote Substances 0.000 abstract description 6
- 239000000544 cholinesterase inhibitor Substances 0.000 abstract description 6
- 231100000572 poisoning Toxicity 0.000 abstract description 5
- 230000000607 poisoning effect Effects 0.000 abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 3
- 229940075522 antidotes Drugs 0.000 abstract description 3
- 239000011574 phosphorus Substances 0.000 abstract description 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 3
- GRXKLBBBQUKJJZ-UHFFFAOYSA-N Soman Chemical compound CC(C)(C)C(C)OP(C)(F)=O GRXKLBBBQUKJJZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002575 chemical warfare agent Substances 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 208000005374 Poisoning Diseases 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229940122041 Cholinesterase inhibitor Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- VJRJKHNAQJSREX-UHFFFAOYSA-N hydrate dihydroiodide Chemical compound O.I.I VJRJKHNAQJSREX-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- KVYGGMBOZFWZBQ-UHFFFAOYSA-N benzyl nicotinate Chemical compound C=1C=CN=CC=1C(=O)OCC1=CC=CC=C1 KVYGGMBOZFWZBQ-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- DQULIMIQTCDUAN-UHFFFAOYSA-N butyl pyridine-3-carboxylate Chemical compound CCCCOC(=O)C1=CC=CN=C1 DQULIMIQTCDUAN-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 231100000566 intoxication Toxicity 0.000 description 2
- 230000035987 intoxication Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- XTCRDAUMVZZCDC-UHFFFAOYSA-N (3,4-dichlorophenyl)-pyridin-3-ylmethanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1=CC=CN=C1 XTCRDAUMVZZCDC-UHFFFAOYSA-N 0.000 description 1
- MYNUUPOPJUCZCU-UHFFFAOYSA-N (3,4-dichlorophenyl)-pyridin-4-ylmethanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1=CC=NC=C1 MYNUUPOPJUCZCU-UHFFFAOYSA-N 0.000 description 1
- HAAYSQMAKQEMGW-UHFFFAOYSA-N (3-chloropyridin-2-yl)-phenylmethanone Chemical compound ClC1=CC=CN=C1C(=O)C1=CC=CC=C1 HAAYSQMAKQEMGW-UHFFFAOYSA-N 0.000 description 1
- JVCNCXKAEBIVBO-UHFFFAOYSA-N (4-methoxyphenyl)-pyridin-3-ylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CN=C1 JVCNCXKAEBIVBO-UHFFFAOYSA-N 0.000 description 1
- FGEUIMWNIGSQPB-UHFFFAOYSA-N (4-methoxyphenyl)-pyridin-4-ylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=NC=C1 FGEUIMWNIGSQPB-UHFFFAOYSA-N 0.000 description 1
- ITMBMPNBNKYCEJ-UHFFFAOYSA-N 2,2-dimethyl-1-pyridin-4-ylpropan-1-one Chemical compound CC(C)(C)C(=O)C1=CC=NC=C1 ITMBMPNBNKYCEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- TWDULYDQIGVEKY-UHFFFAOYSA-N 2-methyl-1-pyridin-3-ylpropan-1-one Chemical compound CC(C)C(=O)C1=CC=CN=C1 TWDULYDQIGVEKY-UHFFFAOYSA-N 0.000 description 1
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- XILISKMVHRCEKJ-UHFFFAOYSA-N 2-methylpropyl pyridine-3-carboxylate Chemical compound CC(C)COC(=O)C1=CC=CN=C1 XILISKMVHRCEKJ-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- GVEQCFMNUYFHOE-UHFFFAOYSA-N 2-phenyl-1-pyridin-3-ylethanone Chemical compound C=1C=CN=CC=1C(=O)CC1=CC=CC=C1 GVEQCFMNUYFHOE-UHFFFAOYSA-N 0.000 description 1
- SZKXYKRLZRYFMJ-UHFFFAOYSA-N 2-phenyl-1-pyridin-4-ylethanone Chemical compound C=1C=NC=CC=1C(=O)CC1=CC=CC=C1 SZKXYKRLZRYFMJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- VYGCDRKHWAORDQ-UHFFFAOYSA-N 3,3-dimethylbutan-2-yl pyridine-3-carboxylate Chemical compound CC(C)(C)C(C)OC(=O)C1=CC=CN=C1 VYGCDRKHWAORDQ-UHFFFAOYSA-N 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- RWQQGQLBQBGMTO-UHFFFAOYSA-N 3-(2-methylphenyl)pyridine Chemical compound CC1=CC=CC=C1C1=CC=CN=C1 RWQQGQLBQBGMTO-UHFFFAOYSA-N 0.000 description 1
- LONDBHTYIYKOCM-UHFFFAOYSA-N 3-(3-methylphenyl)pyridine Chemical compound CC1=CC=CC(C=2C=NC=CC=2)=C1 LONDBHTYIYKOCM-UHFFFAOYSA-N 0.000 description 1
- KUZNURGIXXKBEJ-UHFFFAOYSA-N 3-(4-methylphenyl)pyridine Chemical compound C1=CC(C)=CC=C1C1=CC=CN=C1 KUZNURGIXXKBEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WIMXAKQSDVSRIW-UHFFFAOYSA-N 4-(2-methylphenyl)pyridine Chemical compound CC1=CC=CC=C1C1=CC=NC=C1 WIMXAKQSDVSRIW-UHFFFAOYSA-N 0.000 description 1
- IWRUAXOGIJVROI-UHFFFAOYSA-N 4-(3-methylphenyl)pyridine Chemical compound CC1=CC=CC(C=2C=CN=CC=2)=C1 IWRUAXOGIJVROI-UHFFFAOYSA-N 0.000 description 1
- MRAIVJPPOXSJNG-UHFFFAOYSA-N 4-(4-methylphenyl)pyridine Chemical compound C1=CC(C)=CC=C1C1=CC=NC=C1 MRAIVJPPOXSJNG-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 229950004580 benzyl nicotinate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- DMOCRQCRHPKMRK-UHFFFAOYSA-N cyclohexyl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC1CCCCC1 DMOCRQCRHPKMRK-UHFFFAOYSA-N 0.000 description 1
- RTTGIHAIWOHFBI-UHFFFAOYSA-N cyclohexyl(pyridin-4-yl)methanone Chemical compound C=1C=NC=CC=1C(=O)C1CCCCC1 RTTGIHAIWOHFBI-UHFFFAOYSA-N 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- 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 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 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
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UWGJBMHDCRFLHZ-UHFFFAOYSA-N n-(3,3-dimethylbutan-2-yl)pyridine-3-carboxamide Chemical compound CC(C)(C)C(C)NC(=O)C1=CC=CN=C1 UWGJBMHDCRFLHZ-UHFFFAOYSA-N 0.000 description 1
- IYDLXJKXXFJVDU-UHFFFAOYSA-N n-(3,4-dichlorophenyl)pyridine-3-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)C1=CC=CN=C1 IYDLXJKXXFJVDU-UHFFFAOYSA-N 0.000 description 1
- IYJLJJIRPLWNTG-UHFFFAOYSA-N n-benzhydrylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 IYJLJJIRPLWNTG-UHFFFAOYSA-N 0.000 description 1
- JIAOUYONZMRJJD-UHFFFAOYSA-N n-benzylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCC1=CC=CC=C1 JIAOUYONZMRJJD-UHFFFAOYSA-N 0.000 description 1
- VQRIASKDLZXYTO-UHFFFAOYSA-N n-cyclohexylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC1CCCCC1 VQRIASKDLZXYTO-UHFFFAOYSA-N 0.000 description 1
- ZXOAHASJYIUCBG-UHFFFAOYSA-N n-ethylpyridine-3-carboxamide Chemical compound CCNC(=O)C1=CC=CN=C1 ZXOAHASJYIUCBG-UHFFFAOYSA-N 0.000 description 1
- FPTIYMXUGOIUNV-UHFFFAOYSA-N n-methyl-n-phenylpyridine-3-carboxamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC=CN=C1 FPTIYMXUGOIUNV-UHFFFAOYSA-N 0.000 description 1
- NYQXIOZBHWFCBU-UHFFFAOYSA-N n-phenylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC1=CC=CC=C1 NYQXIOZBHWFCBU-UHFFFAOYSA-N 0.000 description 1
- FCTZHFATVFONMW-UHFFFAOYSA-N n-phenylpyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC1=CC=CC=C1 FCTZHFATVFONMW-UHFFFAOYSA-N 0.000 description 1
- CFRIBDQMHYGXLL-UHFFFAOYSA-N n-pyrimidin-2-ylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC1=NC=CC=N1 CFRIBDQMHYGXLL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229960004429 obidoxime Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- ZIFJVJZWVSPZLE-UHFFFAOYSA-N oxo-[[1-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCN1C=CC(=C[NH+]=O)C=C1 ZIFJVJZWVSPZLE-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical group CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- QEJPOSAIULNDLU-UHFFFAOYSA-N phenyl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC1=CC=CC=C1 QEJPOSAIULNDLU-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- GCSHUYKULREZSJ-UHFFFAOYSA-N phenyl(pyridin-2-yl)methanone Chemical compound C=1C=CC=NC=1C(=O)C1=CC=CC=C1 GCSHUYKULREZSJ-UHFFFAOYSA-N 0.000 description 1
- SKFLCXNDKRUHTA-UHFFFAOYSA-N phenyl(pyridin-4-yl)methanone Chemical compound C=1C=NC=CC=1C(=O)C1=CC=CC=C1 SKFLCXNDKRUHTA-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- VSRSQDMWBSKNSF-UHFFFAOYSA-N propan-2-yl pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1 VSRSQDMWBSKNSF-UHFFFAOYSA-N 0.000 description 1
- FBDVYRNKUYCAGB-UHFFFAOYSA-N propan-2-yl pyridine-4-carboxylate Chemical compound CC(C)OC(=O)C1=CC=NC=C1 FBDVYRNKUYCAGB-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- CLAOCVVWIKGTOP-UHFFFAOYSA-N propyl pyridine-3-carboxylate Chemical compound CCCOC(=O)C1=CC=CN=C1 CLAOCVVWIKGTOP-UHFFFAOYSA-N 0.000 description 1
- TZAAGDYITBGHOB-UHFFFAOYSA-N propyl pyridine-4-carboxylate Chemical compound CCCOC(=O)C1=CC=NC=C1 TZAAGDYITBGHOB-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762616481 DE2616481A1 (de) | 1976-04-14 | 1976-04-14 | Bis-quartaere pyridinium-2-aldoxim- salze und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1070307A true CA1070307A (en) | 1980-01-22 |
Family
ID=5975404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA276,042A Expired CA1070307A (en) | 1976-04-14 | 1977-04-13 | Bis-quaternary pyridinium-2-aldoxime salts and a process for their preparation |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4128651A (enExample) |
| JP (1) | JPS52128381A (enExample) |
| AT (1) | AT361923B (enExample) |
| BE (1) | BE853570A (enExample) |
| CA (1) | CA1070307A (enExample) |
| CH (1) | CH627745A5 (enExample) |
| DE (1) | DE2616481A1 (enExample) |
| DK (1) | DK163177A (enExample) |
| ES (1) | ES457791A1 (enExample) |
| FR (1) | FR2348211A1 (enExample) |
| GB (1) | GB1516626A (enExample) |
| IE (1) | IE44737B1 (enExample) |
| IL (1) | IL51857A (enExample) |
| NL (1) | NL7704030A (enExample) |
| SE (1) | SE7704240L (enExample) |
| ZA (1) | ZA772253B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT365410B (de) * | 1978-08-31 | 1982-01-11 | Ciba Geigy Ag | Mittel zum schutz von kulturpflanzen vor aggressi-ven herbiziden |
| NL7905789A (nl) * | 1979-07-26 | 1981-01-28 | Tno | 1-gesubstitueerde-hydroxyiminomethyl-pyridinium zouten, werkwijze voor het bereiden van deze verbindingen, preparaten tegen organo-fosfaatvergiftingingen, alsmede werkwijze voor het bereiden van dergelijke preparaten. |
| DE3332272A1 (de) * | 1983-09-07 | 1985-03-21 | Bayer Ag, 5090 Leverkusen | Herbizide mittel enthaltend metribuzin in kombination mit pyridincarbonsaeureamiden |
| IL72788A (en) * | 1984-08-28 | 1989-07-31 | Israel State | Bis quaternary oxy-bis methylene(or trimethylene)bis-n-quinuclidines,pyridines and piperidines,their preparation and antidotes against organophosphorus and carbamate poisoning containing them |
| US5130438A (en) * | 1985-11-20 | 1992-07-14 | The United States Of America As Represented By The Secretary Of The Army | Bis-methylene ether pyridinium compound preparation |
| US5760049A (en) * | 1997-02-21 | 1998-06-02 | Synapse Pharmaceuticals International, Inc. | Method for controlling tobacco use and alleviating withdrawal symptoms due to cessation of tobacco use |
| RU2243770C1 (ru) * | 2003-06-24 | 2005-01-10 | Государственное учреждение Институт токсикологии Министерства здравоохранения Российской Федерации | Средство для лечения отравлений фосфорорганическими отравляющими веществами |
| US20060247281A1 (en) * | 2005-02-17 | 2006-11-02 | Aerojet Fine Chemicals Llc, A Delaware Limited Liability Company | Process for halomethyl ethers of hydroxyiminomethyl quaternary pyridinium salts |
| US7414135B2 (en) * | 2005-02-17 | 2008-08-19 | Aerojet Fine Chemicals Llc | Process for halomethyl ethers of hydroxyiminomethyl quaternary pyridinium salts |
| US8946200B2 (en) * | 2006-11-02 | 2015-02-03 | Southwest Research Institute | Pharmaceutically active nanosuspensions |
| US8404850B2 (en) * | 2008-03-13 | 2013-03-26 | Southwest Research Institute | Bis-quaternary pyridinium-aldoxime salts and treatment of exposure to cholinesterase inhibitors |
| US8722706B2 (en) * | 2008-08-15 | 2014-05-13 | Southwest Research Institute | Two phase bioactive formulations of bis-quaternary pyridinium oxime sulfonate salts |
| US8309134B2 (en) * | 2008-10-03 | 2012-11-13 | Southwest Research Institute | Modified calcium phosphate nanoparticle formation |
| US9028873B2 (en) * | 2010-02-08 | 2015-05-12 | Southwest Research Institute | Nanoparticles for drug delivery to the central nervous system |
| US9227937B2 (en) * | 2010-05-12 | 2016-01-05 | Mississippi State University | Phenoxyalkyl pyridinium oxime therapeutics for treatment of organophosphate poisoning |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3773775A (en) * | 1968-08-27 | 1973-11-20 | Merck Patent Gmbh | Bis-quaternary pyridinium salts |
-
1976
- 1976-04-14 DE DE19762616481 patent/DE2616481A1/de not_active Withdrawn
-
1977
- 1977-04-08 FR FR7710729A patent/FR2348211A1/fr active Granted
- 1977-04-11 US US05/786,693 patent/US4128651A/en not_active Expired - Lifetime
- 1977-04-11 IL IL51857A patent/IL51857A/xx unknown
- 1977-04-13 AT AT257077A patent/AT361923B/de not_active IP Right Cessation
- 1977-04-13 IE IE759/77A patent/IE44737B1/en unknown
- 1977-04-13 SE SE7704240A patent/SE7704240L/xx not_active Application Discontinuation
- 1977-04-13 CH CH459277A patent/CH627745A5/de not_active IP Right Cessation
- 1977-04-13 NL NL7704030A patent/NL7704030A/xx not_active Application Discontinuation
- 1977-04-13 GB GB15341/77A patent/GB1516626A/en not_active Expired
- 1977-04-13 ZA ZA00772253A patent/ZA772253B/xx unknown
- 1977-04-13 CA CA276,042A patent/CA1070307A/en not_active Expired
- 1977-04-13 DK DK163177A patent/DK163177A/da not_active IP Right Cessation
- 1977-04-14 ES ES457791A patent/ES457791A1/es not_active Expired
- 1977-04-14 JP JP4342577A patent/JPS52128381A/ja active Pending
- 1977-04-14 BE BE2055827A patent/BE853570A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK163177A (da) | 1977-10-15 |
| FR2348211B1 (enExample) | 1980-04-18 |
| FR2348211A1 (fr) | 1977-11-10 |
| ES457791A1 (es) | 1978-08-01 |
| BE853570A (fr) | 1977-10-14 |
| CH627745A5 (de) | 1982-01-29 |
| ATA257077A (de) | 1980-09-15 |
| DE2616481A1 (de) | 1977-11-03 |
| ZA772253B (en) | 1978-03-29 |
| AT361923B (de) | 1981-04-10 |
| US4128651A (en) | 1978-12-05 |
| JPS52128381A (en) | 1977-10-27 |
| IL51857A0 (en) | 1977-06-30 |
| IL51857A (en) | 1980-05-30 |
| NL7704030A (nl) | 1977-10-18 |
| SE7704240L (sv) | 1977-10-15 |
| IE44737L (en) | 1977-10-14 |
| GB1516626A (en) | 1978-07-05 |
| IE44737B1 (en) | 1982-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |