GB1221061A - Quaternary ammonium derivatives, their use as anthelmintics and methods for their preparation - Google Patents
Quaternary ammonium derivatives, their use as anthelmintics and methods for their preparationInfo
- Publication number
- GB1221061A GB1221061A GB32943/67A GB3294367A GB1221061A GB 1221061 A GB1221061 A GB 1221061A GB 32943/67 A GB32943/67 A GB 32943/67A GB 3294367 A GB3294367 A GB 3294367A GB 1221061 A GB1221061 A GB 1221061A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bromide
- group
- ion
- formula
- prepared
- 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
- 230000000507 anthelmentic effect Effects 0.000 title abstract 2
- 125000001453 quaternary ammonium group Chemical group 0.000 title abstract 2
- 229940124339 anthelmintic agent Drugs 0.000 title 1
- 239000000921 anthelmintic agent Substances 0.000 title 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 abstract 11
- 150000001875 compounds Chemical class 0.000 abstract 11
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 9
- -1 hydroxyiminomethyl Chemical group 0.000 abstract 9
- 229910052757 nitrogen Inorganic materials 0.000 abstract 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 7
- 229940006460 bromide ion Drugs 0.000 abstract 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 7
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 7
- 229940005989 chlorate ion Drugs 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 3
- 150000001450 anions Chemical class 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 229940006461 iodide ion Drugs 0.000 abstract 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 abstract 3
- 150000003839 salts Chemical group 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 229910052740 iodine Inorganic materials 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 229940075930 picrate Drugs 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract 2
- DTLTUUJDCNTTSN-UHFFFAOYSA-N 1,4-dioxane;molecular bromine Chemical compound BrBr.C1COCCO1 DTLTUUJDCNTTSN-UHFFFAOYSA-N 0.000 abstract 1
- SUCLFBXGJZQZEH-UHFFFAOYSA-N 1-(1,3-thiazol-4-yl)ethanone Chemical compound CC(=O)C1=CSC=N1 SUCLFBXGJZQZEH-UHFFFAOYSA-N 0.000 abstract 1
- ZMCYPAFFQYZPHY-UHFFFAOYSA-M 1-(2-chloro-2-phenylethyl)-2-methylpyrazol-2-ium bromide Chemical compound [Br-].ClC(CN1[N+](=CC=C1)C)C1=CC=CC=C1 ZMCYPAFFQYZPHY-UHFFFAOYSA-M 0.000 abstract 1
- ABNDDOBSIHWESM-UHFFFAOYSA-N 1-methyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1 ABNDDOBSIHWESM-UHFFFAOYSA-N 0.000 abstract 1
- PXSUMUYPXZEXDT-UHFFFAOYSA-M 1-phenyl-2-pyridin-1-ium-1-ylethanone;bromide Chemical compound [Br-].C=1C=CC=CC=1C(=O)C[N+]1=CC=CC=C1 PXSUMUYPXZEXDT-UHFFFAOYSA-M 0.000 abstract 1
- GQVZQTLLHXMMBD-UHFFFAOYSA-N 2-bromo-1-(1,3-thiazol-4-yl)ethanone;hydrobromide Chemical compound Br.BrCC(=O)C1=CSC=N1 GQVZQTLLHXMMBD-UHFFFAOYSA-N 0.000 abstract 1
- UIALGUXSAGHRLD-UHFFFAOYSA-N 2-bromo-1-(furan-2-yl)ethanone Chemical compound BrCC(=O)C1=CC=CO1 UIALGUXSAGHRLD-UHFFFAOYSA-N 0.000 abstract 1
- DAHHEUQBMDBSLO-UHFFFAOYSA-N 2-bromo-1-phenylethanol Chemical compound BrCC(O)C1=CC=CC=C1 DAHHEUQBMDBSLO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 1
- ZSTBZBURMWJKSQ-UHFFFAOYSA-N 2-diazonio-1-phenylethenolate Chemical compound N#[N+]C=C([O-])C1=CC=CC=C1 ZSTBZBURMWJKSQ-UHFFFAOYSA-N 0.000 abstract 1
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 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 abstract 1
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 abstract 1
- VCJOMHSIIOWCPQ-UHFFFAOYSA-N 3,5-diphenylpyridine Chemical compound C1=CC=CC=C1C1=CN=CC(C=2C=CC=CC=2)=C1 VCJOMHSIIOWCPQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 abstract 1
- ITQTTZVARXURQS-UHFFFAOYSA-O 3-methylpyridin-1-ium Chemical compound CC1=CC=C[NH+]=C1 ITQTTZVARXURQS-UHFFFAOYSA-O 0.000 abstract 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 abstract 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 abstract 1
- YOYWEJPJUSZFRN-UHFFFAOYSA-O N-(1-methyl-3H-pyridin-1-ium-4-ylidene)hydroxylamine Chemical compound ON=C1CC=[N+](C=C1)C YOYWEJPJUSZFRN-UHFFFAOYSA-O 0.000 abstract 1
- OFYLBLSSPQTTHT-UHFFFAOYSA-N N-(pyridin-4-ylmethylidene)hydroxylamine Chemical compound ON=CC1=CC=NC=C1 OFYLBLSSPQTTHT-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- OBLGXXGLFQWPTD-UHFFFAOYSA-M [Br-].OC(CN1[N+](=CC=C1)C)C1=CC=CC=C1 Chemical compound [Br-].OC(CN1[N+](=CC=C1)C)C1=CC=CC=C1 OBLGXXGLFQWPTD-UHFFFAOYSA-M 0.000 abstract 1
- GXRZFMMWAPKJMP-UHFFFAOYSA-M [Br-].OC(C[N+]1=CC=CC=C1)C1=C(C=CC=C1)F Chemical compound [Br-].OC(C[N+]1=CC=CC=C1)C1=C(C=CC=C1)F GXRZFMMWAPKJMP-UHFFFAOYSA-M 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 abstract 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical group 0.000 abstract 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 abstract 1
- 229910001502 inorganic halide Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 abstract 1
- BIJAWQUBRNHZGE-UHFFFAOYSA-N n-pyridin-4-ylacetamide Chemical compound CC(=O)NC1=CC=NC=C1 BIJAWQUBRNHZGE-UHFFFAOYSA-N 0.000 abstract 1
- 229940005654 nitrite ion Drugs 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- JUDUFOKGIZUSFP-UHFFFAOYSA-M silver;4-methylbenzenesulfonate Chemical compound [Ag+].CC1=CC=C(S([O-])(=O)=O)C=C1 JUDUFOKGIZUSFP-UHFFFAOYSA-M 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 abstract 1
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
- C07D213/24—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
-
- 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
- C07D213/20—Quaternary compounds thereof
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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
- C07D213/60—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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB32943/67A GB1221061A (en) | 1967-01-18 | 1967-01-18 | Quaternary ammonium derivatives, their use as anthelmintics and methods for their preparation |
| OA53157A OA03402A (fr) | 1967-01-18 | 1968-01-10 | Procédé de préparation de nouvelles compositions anthelminthiques. |
| BE709527D BE709527A (enrdf_load_stackoverflow) | 1967-01-18 | 1968-01-17 | |
| FR136429A FR7280M (enrdf_load_stackoverflow) | 1967-01-18 | 1968-01-17 | |
| FR1586628D FR1586628A (enrdf_load_stackoverflow) | 1967-01-18 | 1968-01-17 | |
| DE19681667893 DE1667893A1 (de) | 1967-01-18 | 1968-01-18 | Neue Anthelminthica |
| ES349460A ES349460A1 (es) | 1967-01-18 | 1968-01-18 | Procedimiento para la preparacion de composiciones antihel-minticas. |
| NL6800807A NL6800807A (enrdf_load_stackoverflow) | 1967-01-18 | 1968-01-18 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB276567 | 1967-01-18 | ||
| GB32943/67A GB1221061A (en) | 1967-01-18 | 1967-01-18 | Quaternary ammonium derivatives, their use as anthelmintics and methods for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1221061A true GB1221061A (en) | 1971-02-03 |
Family
ID=26237716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32943/67A Expired GB1221061A (en) | 1967-01-18 | 1967-01-18 | Quaternary ammonium derivatives, their use as anthelmintics and methods for their preparation |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE709527A (enrdf_load_stackoverflow) |
| DE (1) | DE1667893A1 (enrdf_load_stackoverflow) |
| ES (1) | ES349460A1 (enrdf_load_stackoverflow) |
| FR (2) | FR7280M (enrdf_load_stackoverflow) |
| GB (1) | GB1221061A (enrdf_load_stackoverflow) |
| NL (1) | NL6800807A (enrdf_load_stackoverflow) |
| OA (1) | OA03402A (enrdf_load_stackoverflow) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2144080A1 (de) * | 1970-09-03 | 1972-03-09 | John Wyeth & Brother Ltd., Taplow, Maidenhead, Berkshire (Grossbritannien) | Heterocyclische Verbindungen, Verfahren zu ihrer Herstellung und ihrer Verwendung |
| EP0020077A1 (en) * | 1979-05-21 | 1980-12-10 | Cilag-Chemie A.G. | Quaternary pyrazole derivatives, process for their preparation and their use as fungicides and bactericides |
| US10786485B1 (en) | 2019-03-11 | 2020-09-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10842798B1 (en) | 2019-11-06 | 2020-11-24 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10927096B2 (en) | 2019-03-11 | 2021-02-23 | Nocion Therapeutics, Inc. | Ester substituted ion channel blockers and methods for use |
| US10933055B1 (en) * | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10934263B2 (en) | 2019-03-11 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10968179B2 (en) | 2019-03-11 | 2021-04-06 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| WO2021191882A1 (en) * | 2020-03-27 | 2021-09-30 | Universidade Do Minho | Antimalarial agent, methods and uses thereof |
| US11332446B2 (en) | 2020-03-11 | 2022-05-17 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12162851B2 (en) | 2020-03-11 | 2024-12-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
-
1967
- 1967-01-18 GB GB32943/67A patent/GB1221061A/en not_active Expired
-
1968
- 1968-01-10 OA OA53157A patent/OA03402A/xx unknown
- 1968-01-17 BE BE709527D patent/BE709527A/xx unknown
- 1968-01-17 FR FR136429A patent/FR7280M/fr not_active Expired
- 1968-01-17 FR FR1586628D patent/FR1586628A/fr not_active Expired
- 1968-01-18 NL NL6800807A patent/NL6800807A/xx unknown
- 1968-01-18 ES ES349460A patent/ES349460A1/es not_active Expired
- 1968-01-18 DE DE19681667893 patent/DE1667893A1/de active Pending
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2144080A1 (de) * | 1970-09-03 | 1972-03-09 | John Wyeth & Brother Ltd., Taplow, Maidenhead, Berkshire (Grossbritannien) | Heterocyclische Verbindungen, Verfahren zu ihrer Herstellung und ihrer Verwendung |
| DE2144080C2 (de) * | 1970-09-03 | 1983-12-08 | John Wyeth & Brother Ltd., Taplow, Maidenhead, Berkshire | 4-Acylaminopiperidinderivate, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen, welche diese Verbindungen enthalten |
| EP0020077A1 (en) * | 1979-05-21 | 1980-12-10 | Cilag-Chemie A.G. | Quaternary pyrazole derivatives, process for their preparation and their use as fungicides and bactericides |
| US10927096B2 (en) | 2019-03-11 | 2021-02-23 | Nocion Therapeutics, Inc. | Ester substituted ion channel blockers and methods for use |
| US10828287B2 (en) | 2019-03-11 | 2020-11-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10786485B1 (en) | 2019-03-11 | 2020-09-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11512058B2 (en) | 2019-03-11 | 2022-11-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12195428B2 (en) | 2019-03-11 | 2025-01-14 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10934263B2 (en) | 2019-03-11 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10968179B2 (en) | 2019-03-11 | 2021-04-06 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11643404B2 (en) | 2019-03-11 | 2023-05-09 | Nocion Therapeutics, Inc. | Ester substituted ion channel blockers and methods for use |
| US11603355B2 (en) | 2019-03-11 | 2023-03-14 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11377422B2 (en) | 2019-03-11 | 2022-07-05 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10842798B1 (en) | 2019-11-06 | 2020-11-24 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11696912B2 (en) | 2019-11-06 | 2023-07-11 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10933055B1 (en) * | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12303496B2 (en) | 2019-11-06 | 2025-05-20 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11332446B2 (en) | 2020-03-11 | 2022-05-17 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12162851B2 (en) | 2020-03-11 | 2024-12-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| WO2021191882A1 (en) * | 2020-03-27 | 2021-09-30 | Universidade Do Minho | Antimalarial agent, methods and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1586628A (enrdf_load_stackoverflow) | 1970-02-27 |
| DE1667893A1 (de) | 1971-10-21 |
| ES349460A1 (es) | 1970-10-16 |
| FR7280M (enrdf_load_stackoverflow) | 1969-09-22 |
| NL6800807A (enrdf_load_stackoverflow) | 1968-07-19 |
| BE709527A (enrdf_load_stackoverflow) | 1968-07-17 |
| OA03402A (fr) | 1970-12-15 |
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