CH626362A5 - - Google Patents
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- Publication number
- CH626362A5 CH626362A5 CH1513176A CH1513176A CH626362A5 CH 626362 A5 CH626362 A5 CH 626362A5 CH 1513176 A CH1513176 A CH 1513176A CH 1513176 A CH1513176 A CH 1513176A CH 626362 A5 CH626362 A5 CH 626362A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- pyridine
- imidazo
- radical
- amino
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000005596 alkyl carboxamido group Chemical group 0.000 claims description 2
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- -1 alkanoyl radical Chemical class 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 47
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 24
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 238000007796 conventional method Methods 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- SYWSERLZKPGKDI-UHFFFAOYSA-N methyl n-(2-chloroacetyl)carbamate Chemical compound COC(=O)NC(=O)CCl SYWSERLZKPGKDI-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 9
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
- 150000003930 2-aminopyridines Chemical class 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- ATVRGZFHKLCSLX-UHFFFAOYSA-N 4-phenylsulfanylpyridin-2-amine Chemical compound C1=NC(N)=CC(SC=2C=CC=CC=2)=C1 ATVRGZFHKLCSLX-UHFFFAOYSA-N 0.000 description 3
- ZXHIXCFNYQJPDO-UHFFFAOYSA-N 4-phenylsulfanylpyridine-2-carbohydrazide Chemical compound C1=NC(C(=O)NN)=CC(SC=2C=CC=CC=2)=C1 ZXHIXCFNYQJPDO-UHFFFAOYSA-N 0.000 description 3
- CCZKQXORAMBPSJ-UHFFFAOYSA-N 5-phenylsulfanylpyridin-2-amine Chemical compound C1=NC(N)=CC=C1SC1=CC=CC=C1 CCZKQXORAMBPSJ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- KYKIZOSPUQIILV-UHFFFAOYSA-N CC(=O)NN1C=CC=CC1N Chemical compound CC(=O)NN1C=CC=CC1N KYKIZOSPUQIILV-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 230000000507 anthelmentic effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- AZVVTQGWPFAASW-UHFFFAOYSA-N methyl n-(6-phenylsulfanylimidazo[1,2-a]pyridin-2-yl)carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1SC1=CC=CC=C1 AZVVTQGWPFAASW-UHFFFAOYSA-N 0.000 description 3
- IILMIZOAZZNMIV-UHFFFAOYSA-N methyl n-[6-(benzenesulfinyl)imidazo[1,2-a]pyridin-2-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1S(=O)C1=CC=CC=C1 IILMIZOAZZNMIV-UHFFFAOYSA-N 0.000 description 3
- XEMBQPRURGICON-UHFFFAOYSA-N methyl n-ethylcarbamate Chemical compound [CH2]CNC(=O)OC XEMBQPRURGICON-UHFFFAOYSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- NMPVEAUIHMEAQP-UHFFFAOYSA-N 2-Bromoacetaldehyde Chemical compound BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 description 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 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 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- MOYNSIBKNVTMAO-UHFFFAOYSA-N methyl N-(2-chloroacetyl)-N-ethylcarbamate Chemical compound CCN(C(=O)CCl)C(=O)OC MOYNSIBKNVTMAO-UHFFFAOYSA-N 0.000 description 2
- TVDFZKMJIIWKDO-UHFFFAOYSA-N methyl n-(7-phenylsulfanylimidazo[1,2-a]pyridin-2-yl)carbamate Chemical compound C=1C2=NC(NC(=O)OC)=CN2C=CC=1SC1=CC=CC=C1 TVDFZKMJIIWKDO-UHFFFAOYSA-N 0.000 description 2
- GWHZKFUHVDPMRD-UHFFFAOYSA-N methyl n-[6-(benzenesulfinyl)imidazo[1,2-a]pyridin-2-yl]-n-methylcarbamate Chemical compound C1=CC2=NC(N(C)C(=O)OC)=CN2C=C1S(=O)C1=CC=CC=C1 GWHZKFUHVDPMRD-UHFFFAOYSA-N 0.000 description 2
- CIBLQYOKJPBXQW-UHFFFAOYSA-N methyl n-[6-(benzenesulfonyl)imidazo[1,2-a]pyridin-2-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1S(=O)(=O)C1=CC=CC=C1 CIBLQYOKJPBXQW-UHFFFAOYSA-N 0.000 description 2
- OQWINONDQWUBJI-UHFFFAOYSA-N methyl n-ethyl-n-(6-phenylsulfanylimidazo[1,2-a]pyridin-2-yl)carbamate Chemical compound C1=CC2=NC(N(C(=O)OC)CC)=CN2C=C1SC1=CC=CC=C1 OQWINONDQWUBJI-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 2
- AUURQKAGUCGTLQ-UHFFFAOYSA-N 1-[2-(6-aminopyridin-3-yl)sulfanylphenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1SC1=CC=C(N)N=C1 AUURQKAGUCGTLQ-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical class ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- WYDBFRQNRYIZSL-UHFFFAOYSA-N 3-nitroimidazo[1,2-a]pyridine Chemical compound C1=CC=CN2C([N+](=O)[O-])=CN=C21 WYDBFRQNRYIZSL-UHFFFAOYSA-N 0.000 description 1
- MWNUDZGCZDPQGG-UHFFFAOYSA-N 4-[2-(methoxycarbonylamino)imidazo[1,2-a]pyridin-6-yl]sulfanylbenzoic acid Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1SC1=CC=C(C(O)=O)C=C1 MWNUDZGCZDPQGG-UHFFFAOYSA-N 0.000 description 1
- YCBGNJRJPYQNLG-UHFFFAOYSA-N 5-(4-nitrophenoxy)pyridin-2-amine Chemical compound C1=NC(N)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 YCBGNJRJPYQNLG-UHFFFAOYSA-N 0.000 description 1
- JYIVVGNJAKRKAH-UHFFFAOYSA-N 5-(benzenesulfinyl)pyridin-2-amine Chemical compound C1=NC(N)=CC=C1S(=O)C1=CC=CC=C1 JYIVVGNJAKRKAH-UHFFFAOYSA-N 0.000 description 1
- IWWQIZZQWQZWND-UHFFFAOYSA-N 6-phenylsulfanylimidazo[1,2-a]pyridine Chemical compound C1=CC2=NC=CN2C=C1SC1=CC=CC=C1 IWWQIZZQWQZWND-UHFFFAOYSA-N 0.000 description 1
- IAKSFXUGSZVVJO-UHFFFAOYSA-N 6-phenylsulfanylpyridin-2-amine Chemical compound NC1=CC=CC(SC=2C=CC=CC=2)=N1 IAKSFXUGSZVVJO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000006968 Helminthiasis Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- MXEIFGRJRCYUDJ-UHFFFAOYSA-N ethyl 4-chloropyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC(Cl)=CC=N1 MXEIFGRJRCYUDJ-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- RRIZAXHWQJQZAB-UHFFFAOYSA-N methyl 2-[[6-(benzenesulfinyl)imidazo[1,2-a]pyridin-2-yl]-methoxycarbonylamino]acetate Chemical compound C1=CC2=NC(N(C(=O)OC)CC(=O)OC)=CN2C=C1S(=O)C1=CC=CC=C1 RRIZAXHWQJQZAB-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- QLSHUQAOKVFCJN-UHFFFAOYSA-N methyl n-(6-phenoxyimidazo[1,2-a]pyridin-2-yl)carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1OC1=CC=CC=C1 QLSHUQAOKVFCJN-UHFFFAOYSA-N 0.000 description 1
- FAUQQIHSFKRWJJ-UHFFFAOYSA-N methyl n-(6-phenylsulfanylimidazo[1,2-a]pyridin-2-yl)-n-propylcarbamate Chemical compound C1=CC2=NC(N(C(=O)OC)CCC)=CN2C=C1SC1=CC=CC=C1 FAUQQIHSFKRWJJ-UHFFFAOYSA-N 0.000 description 1
- VALKDZRQDQUGAS-UHFFFAOYSA-N methyl n-(methoxymethyl)-n-(6-phenylsulfanylimidazo[1,2-a]pyridin-2-yl)carbamate Chemical compound C1=CC2=NC(N(C(=O)OC)COC)=CN2C=C1SC1=CC=CC=C1 VALKDZRQDQUGAS-UHFFFAOYSA-N 0.000 description 1
- SYVIZAUYJPLRNM-UHFFFAOYSA-N methyl n-(methylsulfanylmethyl)-n-(6-phenylsulfanylimidazo[1,2-a]pyridin-2-yl)carbamate Chemical compound C1=CC2=NC(N(CSC)C(=O)OC)=CN2C=C1SC1=CC=CC=C1 SYVIZAUYJPLRNM-UHFFFAOYSA-N 0.000 description 1
- LVEBLMXZFCDTTN-UHFFFAOYSA-N methyl n-[6-(2-acetylphenyl)sulfanylimidazo[1,2-a]pyridin-2-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1SC1=CC=CC=C1C(C)=O LVEBLMXZFCDTTN-UHFFFAOYSA-N 0.000 description 1
- IITLOGAXXPIMLG-UHFFFAOYSA-N methyl n-[6-(3-acetamidophenyl)sulfinylimidazo[1,2-a]pyridin-2-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1S(=O)C1=CC=CC(NC(C)=O)=C1 IITLOGAXXPIMLG-UHFFFAOYSA-N 0.000 description 1
- GOXGNVNNRKKFQJ-UHFFFAOYSA-N methyl n-[6-(3-aminophenyl)sulfinylimidazo[1,2-a]pyridin-2-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1S(=O)C1=CC=CC(N)=C1 GOXGNVNNRKKFQJ-UHFFFAOYSA-N 0.000 description 1
- KLVDTTODYNSMCU-UHFFFAOYSA-N methyl n-[6-(3-aminophenyl)sulfonylimidazo[1,2-a]pyridin-2-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1S(=O)(=O)C1=CC=CC(N)=C1 KLVDTTODYNSMCU-UHFFFAOYSA-N 0.000 description 1
- TUSVQOICQFNOHG-UHFFFAOYSA-N methyl n-[6-(3-methoxyphenyl)sulfanylimidazo[1,2-a]pyridin-2-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1SC1=CC=CC(OC)=C1 TUSVQOICQFNOHG-UHFFFAOYSA-N 0.000 description 1
- GPBHWVOLSLUHQV-UHFFFAOYSA-N methyl n-[6-(4-aminophenyl)sulfonylimidazo[1,2-a]pyridin-2-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1S(=O)(=O)C1=CC=C(N)C=C1 GPBHWVOLSLUHQV-UHFFFAOYSA-N 0.000 description 1
- PLKRWHBCQIZNEM-UHFFFAOYSA-N methyl n-[6-(4-methylsulfinylphenyl)sulfanylimidazo[1,2-a]pyridin-2-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1SC1=CC=C(S(C)=O)C=C1 PLKRWHBCQIZNEM-UHFFFAOYSA-N 0.000 description 1
- RQLATXIDVPRBRQ-UHFFFAOYSA-N methyl n-[6-(4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC)=CN2C=C1OC1=CC=C([N+]([O-])=O)C=C1 RQLATXIDVPRBRQ-UHFFFAOYSA-N 0.000 description 1
- DVMCTZFJCDXCCZ-UHFFFAOYSA-N methyl n-[6-(benzenesulfinyl)imidazo[1,2-a]pyridin-2-yl]-n-(2-methoxyethyl)carbamate Chemical compound C1=CC2=NC(N(C(=O)OC)CCOC)=CN2C=C1S(=O)C1=CC=CC=C1 DVMCTZFJCDXCCZ-UHFFFAOYSA-N 0.000 description 1
- PYLWQVBZWKBREI-UHFFFAOYSA-N methyl n-[6-(benzenesulfinyl)imidazo[1,2-a]pyridin-2-yl]-n-(2-methylsulfanylethyl)carbamate Chemical compound C1=CC2=NC(N(CCSC)C(=O)OC)=CN2C=C1S(=O)C1=CC=CC=C1 PYLWQVBZWKBREI-UHFFFAOYSA-N 0.000 description 1
- XQRTYVAAFYANOP-UHFFFAOYSA-N methyl n-[6-(benzenesulfinyl)imidazo[1,2-a]pyridin-2-yl]-n-[(4-chlorophenyl)methyl]carbamate Chemical compound C=1N2C=C(S(=O)C=3C=CC=CC=3)C=CC2=NC=1N(C(=O)OC)CC1=CC=C(Cl)C=C1 XQRTYVAAFYANOP-UHFFFAOYSA-N 0.000 description 1
- HUNRTZQRSSCGBD-UHFFFAOYSA-N methyl n-[6-(benzenesulfinyl)imidazo[1,2-a]pyridin-2-yl]-n-[(4-methoxyphenyl)methyl]carbamate Chemical compound C=1N2C=C(S(=O)C=3C=CC=CC=3)C=CC2=NC=1N(C(=O)OC)CC1=CC=C(OC)C=C1 HUNRTZQRSSCGBD-UHFFFAOYSA-N 0.000 description 1
- QVCUIAMHPIAHTO-UHFFFAOYSA-N methyl n-[6-(benzenesulfinyl)imidazo[1,2-a]pyridin-2-yl]-n-[2-(dimethylamino)ethyl]carbamate Chemical compound C1=CC2=NC(N(CCN(C)C)C(=O)OC)=CN2C=C1S(=O)C1=CC=CC=C1 QVCUIAMHPIAHTO-UHFFFAOYSA-N 0.000 description 1
- VCGCZCUHBXBDBW-UHFFFAOYSA-N methyl n-[6-(benzenesulfinyl)imidazo[1,2-a]pyridin-3-yl]carbamate Chemical compound C=1N2C(NC(=O)OC)=CN=C2C=CC=1S(=O)C1=CC=CC=C1 VCGCZCUHBXBDBW-UHFFFAOYSA-N 0.000 description 1
- COERLBKCQVFBJC-UHFFFAOYSA-N methyl n-[6-(benzenesulfonyl)imidazo[1,2-a]pyridin-2-yl]-n-ethylcarbamate Chemical compound C1=CC2=NC(N(C(=O)OC)CC)=CN2C=C1S(=O)(=O)C1=CC=CC=C1 COERLBKCQVFBJC-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MDKWSWATJYQABQ-UHFFFAOYSA-N n-[4-(6-aminopyridin-3-yl)sulfanylphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1SC1=CC=C(N)N=C1 MDKWSWATJYQABQ-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- 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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—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
- C07D213/60—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
- C07D213/86—Hydrazides; Thio or imino analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63903475A | 1975-12-09 | 1975-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626362A5 true CH626362A5 (pt) | 1981-11-13 |
Family
ID=24562456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1513176A CH626362A5 (pt) | 1975-12-09 | 1976-12-01 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4096264A (pt) |
| JP (1) | JPS5273896A (pt) |
| AR (1) | AR222960A1 (pt) |
| AT (1) | AT361475B (pt) |
| AU (1) | AU505045B2 (pt) |
| BE (1) | BE849123A (pt) |
| CA (1) | CA1084930A (pt) |
| CH (1) | CH626362A5 (pt) |
| DE (1) | DE2655681A1 (pt) |
| DK (1) | DK529276A (pt) |
| ES (1) | ES453947A1 (pt) |
| FI (1) | FI763343A (pt) |
| FR (1) | FR2334357A1 (pt) |
| GB (1) | GB1524589A (pt) |
| GR (1) | GR62009B (pt) |
| IL (1) | IL51024A (pt) |
| NL (1) | NL7613160A (pt) |
| NO (1) | NO764025L (pt) |
| NZ (1) | NZ182756A (pt) |
| OA (1) | OA05506A (pt) |
| PH (1) | PH12259A (pt) |
| PL (1) | PL103751B1 (pt) |
| PT (1) | PT65915B (pt) |
| SE (1) | SE430504B (pt) |
| ZA (1) | ZA767331B (pt) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4105767A (en) * | 1977-03-28 | 1978-08-08 | Merck & Co., Inc. | Imidazo [1,2-a] pyridines substituted with a thienyl, thiazolyl, or thiadiazolyl group |
| US4154835A (en) * | 1977-10-12 | 1979-05-15 | Merck & Co., Inc. | Anthelmintic imidazo [1,2-a] pyridines |
| US4250174A (en) * | 1979-05-02 | 1981-02-10 | Merck & Co., Inc. | 3-Substituted imidazo [1,2-A] pyridines |
| US4221796A (en) * | 1979-09-19 | 1980-09-09 | E. R. Squibb & Sons, Inc. | Substituted imidazolo-pyridines and method |
| ZA81219B (en) * | 1980-01-23 | 1982-01-27 | Schering Corp | Imidazo (1,2-a) pyridines ,process for their preparation and pharmaceutical compositions containing them |
| US4507481A (en) * | 1983-07-29 | 1985-03-26 | Pennwalt Corporation | Pyrrolo[1,2-a]imidazoles and imidazo[1,2-a]pyridines |
| IT1173196B (it) * | 1984-02-02 | 1987-06-18 | Bellon Roger Schoum Rbs Pharma | Composti imidazopiridinici farmacologicamente attivi |
| US5214138A (en) * | 1989-12-20 | 1993-05-25 | Case Western Reserve University | Imidazopyridinium compound and processes for isolating, identifying, and chemically synthesizing same |
| ATE119774T1 (de) * | 1990-07-30 | 1995-04-15 | Takeda Chemical Industries Ltd | Imidazopyridinderivate und ihre verwendung. |
| US6358971B1 (en) | 1998-05-20 | 2002-03-19 | Eli Lilly And Company | Anti-viral compounds |
| EP1077701A4 (en) * | 1998-05-20 | 2002-03-20 | Lilly Co Eli | ANTI-VIRAL COMPOUNDS |
| DE10117184A1 (de) * | 2001-04-05 | 2002-10-17 | Gruenenthal Gmbh | Substituierte Imidazol[1,2-a]-pyridin-3-yl-amid- und -aminverbindungen |
| DE602005015833D1 (de) * | 2004-03-19 | 2009-09-17 | Warner Lambert Co | Imidazopyridin- und imidazopyrimidin-derivate als antibakterielle mittel |
| US7544702B2 (en) * | 2004-08-12 | 2009-06-09 | Amgen Inc. | Bisaryl-sulfonamides |
| CL2008001626A1 (es) * | 2007-06-05 | 2009-06-05 | Takeda Pharmaceuticals Co | Compuestos derivados de heterociclos fusionados, agente farmaceutico que los comprende y su uso en la profilaxis y tratamiento del cancer. |
| US8431608B2 (en) | 2007-08-17 | 2013-04-30 | Icagen Inc. | Heterocycles as potassium channel modulators |
| CA2696631A1 (en) * | 2007-08-17 | 2009-02-26 | Icagen, Inc. | Heterocycles as potassium channel modulators |
| EP2181987B9 (en) * | 2007-08-23 | 2014-09-03 | Takeda Pharmaceutical Company Limited | 2-Carbonylaminobenzothiazoles and their use for the prophylaxis and treatment of cancer |
| EP2184285B1 (en) * | 2007-08-29 | 2015-11-04 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
| JPWO2009128520A1 (ja) | 2008-04-18 | 2011-08-04 | 塩野義製薬株式会社 | Ｐｉ３ｋ阻害活性を有する複素環化合物 |
| WO2009136663A1 (en) * | 2008-05-08 | 2009-11-12 | Takeda Pharmaceutical Company Limited | Fused heterocyclic derivatives and use thereof |
| EP2399921B1 (en) * | 2008-12-01 | 2015-08-12 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
| JO3101B1 (ar) * | 2008-12-02 | 2017-09-20 | Takeda Pharmaceuticals Co | مشتقات بنزوثيازول كعوامل مضادة للسرطان |
| CA2771190C (en) | 2009-08-17 | 2020-01-21 | Memorial Sloan-Kettering Cancer Center | Heat shock protein binding compounds, compositions, and methods for making and using same |
| BR112016026470A8 (pt) | 2014-05-13 | 2021-07-20 | Memorial Sloan Kettering Cancer Center | composto modulador de hsp70, composição farmacêutica que o compreende e uso do referido composto |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3701780A (en) * | 1970-09-18 | 1972-10-31 | Merck & Co Inc | Imidazo(1,2-a)pyridines |
| JPS5124517B1 (pt) * | 1971-03-15 | 1976-07-24 |
-
1976
- 1976-08-26 US US05/718,652 patent/US4096264A/en not_active Expired - Lifetime
- 1976-11-22 FI FI763343A patent/FI763343A/fi not_active Application Discontinuation
- 1976-11-24 DK DK529276A patent/DK529276A/da not_active Application Discontinuation
- 1976-11-24 SE SE7613128A patent/SE430504B/xx unknown
- 1976-11-25 NL NL7613160A patent/NL7613160A/xx not_active Application Discontinuation
- 1976-11-25 NO NO764025A patent/NO764025L/no unknown
- 1976-11-29 NZ NZ182756A patent/NZ182756A/xx unknown
- 1976-11-29 IL IL51024A patent/IL51024A/xx unknown
- 1976-11-30 AU AU20102/76A patent/AU505045B2/en not_active Expired
- 1976-12-01 CH CH1513176A patent/CH626362A5/de not_active IP Right Cessation
- 1976-12-01 AR AR265695A patent/AR222960A1/es active
- 1976-12-02 PT PT65915A patent/PT65915B/pt unknown
- 1976-12-03 ES ES453947A patent/ES453947A1/es not_active Expired
- 1976-12-06 AT AT901876A patent/AT361475B/de not_active IP Right Cessation
- 1976-12-07 GB GB51010/76A patent/GB1524589A/en not_active Expired
- 1976-12-07 GR GR52346A patent/GR62009B/el unknown
- 1976-12-07 BE BE173014A patent/BE849123A/xx not_active IP Right Cessation
- 1976-12-07 PH PH19211A patent/PH12259A/en unknown
- 1976-12-07 FR FR7636779A patent/FR2334357A1/fr active Granted
- 1976-12-07 CA CA267,311A patent/CA1084930A/en not_active Expired
- 1976-12-08 ZA ZA00767331A patent/ZA767331B/xx unknown
- 1976-12-08 DE DE19762655681 patent/DE2655681A1/de not_active Ceased
- 1976-12-08 PL PL1976194238A patent/PL103751B1/pl unknown
- 1976-12-09 OA OA56008A patent/OA05506A/xx unknown
- 1976-12-09 JP JP51147227A patent/JPS5273896A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IL51024A0 (en) | 1977-01-31 |
| JPS6126545B2 (pt) | 1986-06-20 |
| BE849123A (fr) | 1977-06-07 |
| GR62009B (en) | 1979-02-15 |
| AU505045B2 (en) | 1979-11-08 |
| NZ182756A (en) | 1979-11-01 |
| DE2655681A1 (de) | 1977-06-16 |
| US4096264A (en) | 1978-06-20 |
| FR2334357A1 (fr) | 1977-07-08 |
| JPS5273896A (en) | 1977-06-21 |
| IL51024A (en) | 1981-12-31 |
| CA1084930A (en) | 1980-09-02 |
| ZA767331B (en) | 1978-07-26 |
| FI763343A (pt) | 1977-06-10 |
| PT65915A (en) | 1977-01-01 |
| SE7613128L (sv) | 1977-06-10 |
| AR222960A1 (es) | 1981-07-15 |
| AT361475B (de) | 1981-03-10 |
| AU2010276A (en) | 1978-06-08 |
| SE430504B (sv) | 1983-11-21 |
| ATA901876A (de) | 1980-08-15 |
| ES453947A1 (es) | 1978-03-01 |
| PL103751B1 (pl) | 1979-07-31 |
| OA05506A (fr) | 1981-04-30 |
| NL7613160A (nl) | 1977-06-13 |
| GB1524589A (en) | 1978-09-13 |
| NO764025L (pt) | 1977-06-10 |
| PH12259A (en) | 1978-12-12 |
| DK529276A (da) | 1977-06-10 |
| PT65915B (en) | 1978-11-07 |
| FR2334357B1 (pt) | 1982-10-15 |
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Legal Events
| Date | Code | Title | Description |
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| PL | Patent ceased | ||
| PL | Patent ceased |