CA1049014A - Heterocycles - Google Patents
HeterocyclesInfo
- Publication number
- CA1049014A CA1049014A CA74190796A CA190796A CA1049014A CA 1049014 A CA1049014 A CA 1049014A CA 74190796 A CA74190796 A CA 74190796A CA 190796 A CA190796 A CA 190796A CA 1049014 A CA1049014 A CA 1049014A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- formula
- alkyl
- oxide
- alkoxy
- 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
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 24
- -1 morpholino, piperidino Chemical group 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- SJUKJZSTBBSGHF-UHFFFAOYSA-N (2,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1Cl SJUKJZSTBBSGHF-UHFFFAOYSA-N 0.000 claims description 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 7
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- RVIQLJBDSLPBBK-UHFFFAOYSA-N S1C(=CC=C1)[ClH]C(=O)Cl Chemical compound S1C(=CC=C1)[ClH]C(=O)Cl RVIQLJBDSLPBBK-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 12
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 7
- 244000005700 microbiome Species 0.000 abstract description 5
- 239000003674 animal food additive Substances 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000002253 acid Substances 0.000 description 15
- 239000013543 active substance Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 125000005587 carbonate group Chemical group 0.000 description 8
- 241000282849 Ruminantia Species 0.000 description 7
- 241000282887 Suidae Species 0.000 description 7
- 230000000845 anti-microbial effect Effects 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000004753 textile Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 244000144977 poultry Species 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000035622 drinking Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 201000006747 infectious mononucleosis Diseases 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- DSPXASHHKFVPCL-UHFFFAOYSA-N 1-isocyanocyclohexene Chemical compound [C-]#[N+]C1=CCCCC1 DSPXASHHKFVPCL-UHFFFAOYSA-N 0.000 description 2
- MYKLQMNSFPAPLZ-UHFFFAOYSA-N 2,5-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(C)=CC1=O MYKLQMNSFPAPLZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 2
- WHKZBVQIMVUGIH-UHFFFAOYSA-N 3-hydroxyquinoline-2-carboxylic acid Chemical class C1=CC=C2C=C(O)C(C(=O)O)=NC2=C1 WHKZBVQIMVUGIH-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 239000007767 bonding agent Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- GPTXWRGISTZRIO-UHFFFAOYSA-N chlorquinaldol Chemical compound ClC1=CC(Cl)=C(O)C2=NC(C)=CC=C21 GPTXWRGISTZRIO-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 2
- 230000000249 desinfective effect Effects 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 230000003641 microbiacidal effect Effects 0.000 description 2
- 244000000010 microbial pathogen Species 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 2
- QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- FNXKBSAUKFCXIK-UHFFFAOYSA-M sodium;hydrogen carbonate;8-hydroxy-7-iodoquinoline-5-sulfonic acid Chemical class [Na+].OC([O-])=O.C1=CN=C2C(O)=C(I)C=C(S(O)(=O)=O)C2=C1 FNXKBSAUKFCXIK-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- KXADAUSFMXEGLQ-UHFFFAOYSA-N (2-anilino-2-oxoethyl)-dimethyl-[2-(methylamino)-3-oxotetradecyl]azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC(=O)C(NC)C[N+](C)(C)CC(=O)NC1=CC=CC=C1 KXADAUSFMXEGLQ-UHFFFAOYSA-N 0.000 description 1
- MBYQPPXEXWRMQC-UHFFFAOYSA-N (2-chlorophenyl)methanol Chemical compound OCC1=CC=CC=C1Cl MBYQPPXEXWRMQC-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- FVJIUQSKXOYFKG-UHFFFAOYSA-N (3,4-dichlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C(Cl)=C1 FVJIUQSKXOYFKG-UHFFFAOYSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- GDAXJBDYNVDMDF-UHFFFAOYSA-N 1,2,4-benzotriazine Chemical compound N1=NC=NC2=CC=CC=C21 GDAXJBDYNVDMDF-UHFFFAOYSA-N 0.000 description 1
- ZHYMGSPDEVXULU-UHFFFAOYSA-N 1,2-benzodiazepin-3-one Chemical class N1=NC(=O)C=CC2=CC=CC=C21 ZHYMGSPDEVXULU-UHFFFAOYSA-N 0.000 description 1
- AAOYLOCWJSLLJU-UHFFFAOYSA-N 1,2-bis(5-bromo-2-hydroxyphenyl)ethane-1,2-dione Chemical group OC1=CC=C(Br)C=C1C(=O)C(=O)C1=CC(Br)=CC=C1O AAOYLOCWJSLLJU-UHFFFAOYSA-N 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 1
- SCONHBCOAUJLJM-UHFFFAOYSA-N 1,3-bis(4-chlorophenyl)-1-(trifluoromethyl)urea Chemical compound C=1C=C(Cl)C=CC=1N(C(F)(F)F)C(=O)NC1=CC=C(Cl)C=C1 SCONHBCOAUJLJM-UHFFFAOYSA-N 0.000 description 1
- IEFOCSYNOKEZEX-UHFFFAOYSA-N 1-chloro-1,3-bis(4-chlorophenyl)urea Chemical compound C=1C=C(Cl)C=CC=1N(Cl)C(=O)NC1=CC=C(Cl)C=C1 IEFOCSYNOKEZEX-UHFFFAOYSA-N 0.000 description 1
- FSVPMOVGAZNEKV-UHFFFAOYSA-N 1-dodecyl-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.CCCCCCCCCCCCN1CCNC1=N FSVPMOVGAZNEKV-UHFFFAOYSA-N 0.000 description 1
- MRRYRUXHZAABOW-UHFFFAOYSA-N 1-dodecylisoquinoline;hydrochloride Chemical compound [Cl-].C1=CC=C2C(CCCCCCCCCCCC)=[NH+]C=CC2=C1 MRRYRUXHZAABOW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
- C07D253/10—Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Animal Husbandry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Food Science & Technology (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Paints Or Removers (AREA)
- Fodder In General (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH155573A CH576231A5 (en) | 1973-02-02 | 1973-02-02 | 1,2,4,-benztriazine-1,4-di-N-oxide derivs. - used in veterinary medicine against pathogenic micro-organisms or to promote growth |
| CH1273373A CH576459A5 (en) | 1973-09-05 | 1973-09-05 | 1,2,4,-benztriazine-1,4-di-N-oxide derivs. - used in veterinary medicine against pathogenic micro-organisms or to promote growth |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049014A true CA1049014A (en) | 1979-02-20 |
Family
ID=25687988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA74190796A Expired CA1049014A (en) | 1973-02-02 | 1974-01-23 | Heterocycles |
Country Status (12)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2538179C2 (de) * | 1975-08-27 | 1986-05-28 | Bayer Ag, 5090 Leverkusen | 3-Alkoxy-benzo-1,2,4-triazine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
| US4247691A (en) * | 1977-02-22 | 1981-01-27 | Ciba-Geigy Corporation | 1,2,4-Benzotriazine-1,4-di-N-oxides |
| DE2802488A1 (de) * | 1978-01-20 | 1979-07-26 | Bayer Ag | 3-azolyl-benzotriazine und -benzotriazin-1-oxide, verfahren zu ihrer herstellung, sowie ihre verwendung zur bekaempfung von pflanzenkrankheiten |
| NZ194612A (en) * | 1979-08-31 | 1982-12-21 | Ici Australia Ltd | Benzotriazine derivatives intermediates and herbicidal compositions |
| US5175287A (en) * | 1986-09-25 | 1992-12-29 | S R I International | Process for preparing 1,2,4-benzotriazine oxides |
| WO1988002366A1 (en) * | 1986-09-25 | 1988-04-07 | Sri International | 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents |
| US5624925A (en) | 1986-09-25 | 1997-04-29 | Sri International | 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents |
| IE62911B1 (en) * | 1988-03-18 | 1995-03-08 | Stanford Res Inst Int | 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents |
| GR1000941B (el) * | 1989-03-17 | 1993-03-16 | Stanford Res Inst Int | Μεθοδος παρασκευης οξειδιων 1,2,4,βενζοτριαζινης. |
| AU646794B2 (en) | 1989-09-18 | 1994-03-10 | Sri International | 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents |
| DE19651415A1 (de) * | 1996-12-11 | 1998-06-18 | Henkel Ecolab Gmbh & Co Ohg | Verfahren zur Instrumentendesinfektion |
| WO2003055482A1 (en) * | 2001-12-21 | 2003-07-10 | Novo Nordisk A/S | Amide derivatives as gk activators |
| EP1531815B1 (en) | 2002-06-27 | 2014-09-24 | Novo Nordisk A/S | Glucokinase activators |
| US20050282814A1 (en) * | 2002-10-03 | 2005-12-22 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| PT1723128E (pt) | 2004-01-06 | 2013-02-27 | Novo Nordisk As | Heteroaril-ureias e o seu uso como activadores da glicoquinase |
| RU2006139258A (ru) * | 2004-04-08 | 2008-05-20 | Таргеджен, Инк. (US) | Бензотриазиновые ингибиторы киназ |
| AU2005276974B2 (en) * | 2004-08-25 | 2012-08-02 | Targegen, Inc. | Heterocyclic compounds and methods of use |
| US20060292203A1 (en) * | 2005-06-08 | 2006-12-28 | Targegen, Inc. | Methods and compositions for the treatment of ocular disorders |
| US7999114B2 (en) | 2005-07-08 | 2011-08-16 | Novo Nordisk A/S | Dicycloalkylcarbamoyl ureas as glucokinase activators |
| US7884210B2 (en) | 2005-07-14 | 2011-02-08 | Novo Nordisk A/S | Ureido-thiazole glucokinase activators |
| US8604042B2 (en) * | 2005-11-01 | 2013-12-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| US8133900B2 (en) * | 2005-11-01 | 2012-03-13 | Targegen, Inc. | Use of bi-aryl meta-pyrimidine inhibitors of kinases |
| NZ592990A (en) * | 2005-11-01 | 2013-01-25 | Targegen Inc | Bi-aryl meta-pyrimidine inhibitors of kinases |
| WO2008084043A1 (en) | 2007-01-09 | 2008-07-17 | Novo Nordisk A/S | Urea glucokinase activators |
| AU2008204530B2 (en) | 2007-01-11 | 2013-08-01 | Vtv Therapeutics Llc | Urea glucokinase activators |
| WO2012060847A1 (en) | 2010-11-07 | 2012-05-10 | Targegen, Inc. | Compositions and methods for treating myelofibrosis |
| WO2013086467A1 (en) * | 2011-12-07 | 2013-06-13 | Sri International | Benzotriazine oxides as drugs targeting mycobacterium tuberculosis |
| CA3093025A1 (en) | 2018-06-12 | 2019-12-19 | Vtv Therapeutics Llc | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
| CN115894385A (zh) * | 2023-01-09 | 2023-04-04 | 中国科学院长春应用化学研究所 | 替拉扎明衍生物及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3957779A (en) * | 1972-11-15 | 1976-05-18 | Bayer Aktiengesellschaft | Benzo-1,2,4-triazines |
| US3991189A (en) * | 1972-11-15 | 1976-11-09 | Bayer Aktiengesellschaft | Microbiocidal methods and compositions using substituted 1,2,4-triazine-1,4-di-N-oxide derivatives |
| SE7501624L (US08063081-20111122-C00115.png) * | 1974-03-15 | 1975-09-16 | Ciba Geigy Ag |
-
1974
- 1974-01-22 IE IE127/74A patent/IE38778B1/xx unknown
- 1974-01-22 IL IL44058A patent/IL44058A/xx unknown
- 1974-01-23 CA CA74190796A patent/CA1049014A/en not_active Expired
- 1974-01-30 DE DE2404375A patent/DE2404375A1/de not_active Withdrawn
- 1974-01-31 NL NL7401370A patent/NL7401370A/xx not_active Application Discontinuation
- 1974-02-01 GB GB486274A patent/GB1465405A/en not_active Expired
- 1974-02-01 BE BE140468A patent/BE810511A/xx unknown
- 1974-02-01 FR FR7403419A patent/FR2215967B1/fr not_active Expired
- 1974-02-01 JP JP49014043A patent/JPS49124235A/ja active Pending
- 1974-11-28 SU SU742078807A patent/SU589914A3/ru active
-
1975
- 1975-01-01 AR AR258398A patent/AR207145A1/es active
-
1977
- 1977-10-19 US US05/843,473 patent/US4160833A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49124235A (US08063081-20111122-C00115.png) | 1974-11-28 |
| AU6485674A (en) | 1975-07-24 |
| SU589914A3 (ru) | 1978-01-25 |
| AR207145A1 (es) | 1976-09-15 |
| US4160833A (en) | 1979-07-10 |
| GB1465405A (en) | 1977-02-23 |
| FR2215967B1 (US08063081-20111122-C00115.png) | 1977-01-28 |
| FR2215967A1 (US08063081-20111122-C00115.png) | 1974-08-30 |
| DE2404375A1 (de) | 1974-08-08 |
| IE38778B1 (en) | 1978-05-24 |
| NL7401370A (US08063081-20111122-C00115.png) | 1974-08-06 |
| IE38778L (en) | 1974-08-02 |
| IL44058A (en) | 1978-10-31 |
| IL44058A0 (en) | 1974-05-16 |
| BE810511A (fr) | 1974-08-01 |
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