DD144774A5 - Verfahren zur herstellung von 1h-pyrazolo(3,4-b)pyridin-derivaten und ihren salzen mit saeuren - Google Patents
Verfahren zur herstellung von 1h-pyrazolo(3,4-b)pyridin-derivaten und ihren salzen mit saeuren Download PDFInfo
- Publication number
- DD144774A5 DD144774A5 DD79214181A DD21418179A DD144774A5 DD 144774 A5 DD144774 A5 DD 144774A5 DD 79214181 A DD79214181 A DD 79214181A DD 21418179 A DD21418179 A DD 21418179A DD 144774 A5 DD144774 A5 DD 144774A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- groups
- group
- general formula
- phenyl
- pyrazolo
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 230000008569 process Effects 0.000 title claims abstract description 6
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical class C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 title description 3
- 239000002253 acid Substances 0.000 claims abstract description 10
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- -1 nitro-substituted phenyl groups Chemical group 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- DFIHJRYVCTUJJP-UHFFFAOYSA-N 4-chloro-5-(chloromethyl)-1-ethylpyrazolo[3,4-b]pyridine Chemical compound ClCC1=CN=C2N(CC)N=CC2=C1Cl DFIHJRYVCTUJJP-UHFFFAOYSA-N 0.000 description 3
- 206010017533 Fungal infection Diseases 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DATIEYWEDYPWAM-UHFFFAOYSA-N (1-ethyl-3-methylpyrazolo[3,4-b]pyridin-5-yl)methanol Chemical compound OCC1=CN=C2N(CC)N=C(C)C2=C1 DATIEYWEDYPWAM-UHFFFAOYSA-N 0.000 description 1
- JFVJHNCDIJEVJM-UHFFFAOYSA-N (4-chloro-1-ethyl-3-methylpyrazolo[3,4-b]pyridin-5-yl)methanol Chemical compound OCC1=CN=C2N(CC)N=C(C)C2=C1Cl JFVJHNCDIJEVJM-UHFFFAOYSA-N 0.000 description 1
- HMMMTSXSWRPUOJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-imidazol-1-ylethanol Chemical compound C=1C=C(Cl)C=CC=1C(O)CN1C=CN=C1 HMMMTSXSWRPUOJ-UHFFFAOYSA-N 0.000 description 1
- KSVLMWDFDJYNIT-UHFFFAOYSA-N 1-ethyl-3-methylpyrazolo[3,4-b]pyridine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C2N(CC)N=C(C)C2=C1 KSVLMWDFDJYNIT-UHFFFAOYSA-N 0.000 description 1
- GBGGWCRLSSCPJE-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridin-5-ylmethanol Chemical compound OCC1=CN=C2NN=CC2=C1 GBGGWCRLSSCPJE-UHFFFAOYSA-N 0.000 description 1
- AMSDWLOANMAILF-UHFFFAOYSA-N 2-imidazol-1-ylethanol Chemical class OCCN1C=CN=C1 AMSDWLOANMAILF-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- CTAGQNPKHJEBIF-UHFFFAOYSA-N 4-chloro-1-ethylpyrazolo[3,4-b]pyridine Chemical compound C1=CN=C2N(CC)N=CC2=C1Cl CTAGQNPKHJEBIF-UHFFFAOYSA-N 0.000 description 1
- BGKUDAOVDSQSQP-UHFFFAOYSA-N 4-chloro-5-(chloromethyl)-1-ethyl-3-methylpyrazolo[3,4-b]pyridine Chemical compound ClCC1=CN=C2N(CC)N=C(C)C2=C1Cl BGKUDAOVDSQSQP-UHFFFAOYSA-N 0.000 description 1
- NRLWKOLQCJJLJA-UHFFFAOYSA-N 4-chloro-5-[[1-(2,4-dichlorophenyl)-2-imidazol-1-ylethoxy]methyl]-1-ethyl-3-methylpyrazolo[3,4-b]pyridine hydrochloride Chemical compound Cl.CCn1nc(C)c2c(Cl)c(COC(Cn3ccnc3)c3ccc(Cl)cc3Cl)cnc12 NRLWKOLQCJJLJA-UHFFFAOYSA-N 0.000 description 1
- PQWBCUZPLFEUAY-UHFFFAOYSA-N 4-chloro-5-[[1-(2,4-dichlorophenyl)-2-imidazol-1-ylethoxy]methyl]-1-ethylpyrazolo[3,4-b]pyridine hydrochloride Chemical compound Cl.CCn1ncc2c(Cl)c(COC(Cn3ccnc3)c3ccc(Cl)cc3Cl)cnc12 PQWBCUZPLFEUAY-UHFFFAOYSA-N 0.000 description 1
- QQNYRKDGFHLSRA-UHFFFAOYSA-N 5-(chloromethyl)-1h-pyrazolo[3,4-b]pyridine Chemical class ClCC1=CN=C2NN=CC2=C1 QQNYRKDGFHLSRA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 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
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- XKQJVZKZWRBQGA-UHFFFAOYSA-N ethyl 1-ethyl-3-methylpyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C2N(CC)N=C(C)C2=C1 XKQJVZKZWRBQGA-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 239000012535 impurity 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
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- KEAYESYHFKHZAL-IGMARMGPSA-N sodium-23 atom Chemical compound [23Na] KEAYESYHFKHZAL-IGMARMGPSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/923,418 US4159380A (en) | 1978-07-10 | 1978-07-10 | Imidazolylethoxy derivatives of pyrazolo[3,4-b]pyridine-5-methanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD144774A5 true DD144774A5 (de) | 1980-11-05 |
Family
ID=25448663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79214181A DD144774A5 (de) | 1978-07-10 | 1979-07-06 | Verfahren zur herstellung von 1h-pyrazolo(3,4-b)pyridin-derivaten und ihren salzen mit saeuren |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4159380A (cs) |
| JP (1) | JPS5513298A (cs) |
| AU (1) | AU519835B2 (cs) |
| BE (1) | BE877600A (cs) |
| CS (1) | CS208115B2 (cs) |
| DD (1) | DD144774A5 (cs) |
| DE (1) | DE2927867A1 (cs) |
| DK (1) | DK288079A (cs) |
| ES (1) | ES482280A1 (cs) |
| FR (1) | FR2430946A1 (cs) |
| GB (1) | GB2024815A (cs) |
| GR (1) | GR73111B (cs) |
| IE (1) | IE48442B1 (cs) |
| IT (1) | IT1122056B (cs) |
| LU (1) | LU81477A1 (cs) |
| NL (1) | NL7905242A (cs) |
| NO (1) | NO792275L (cs) |
| NZ (1) | NZ190698A (cs) |
| PH (1) | PH14437A (cs) |
| PL (1) | PL216944A1 (cs) |
| SE (1) | SE7905987L (cs) |
| SU (1) | SU873884A3 (cs) |
| YU (1) | YU163779A (cs) |
| ZA (1) | ZA792908B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1097314B (it) * | 1978-07-26 | 1985-08-31 | Recordati Chem Pharm | Derivati dell'imidazolo ad attivita' anticonvulsivante |
| US4234589A (en) * | 1979-09-24 | 1980-11-18 | E. R. Squibb & Sons, Inc. | Imidazolylethoxymethyl derivatives of 1,3-dioxolo quinolines |
| US4282230A (en) * | 1979-11-15 | 1981-08-04 | E. R. Squibb & Sons, Inc. | Imidazolylethoxy derivatives of quinoline-2- or 4-methanols, antimicrobial compositions containing them and method for treating bacterial or fungal infections with them |
| US4248881A (en) * | 1979-12-20 | 1981-02-03 | E. R. Squibb & Sons, Inc. | Imidazolylethoxymethyl derivatives of pyrazole |
| US4260614A (en) * | 1980-02-08 | 1981-04-07 | E. R. Squibb & Sons, Inc. | 4-(2-(1H-Imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxypyrazolo(3,4-b)pyridines |
| US4260616A (en) * | 1980-02-14 | 1981-04-07 | E. R. Squibb & Sons, Inc. | Antimicrobial imidazolylethoxymethyl derivatives of 1,3-dioxolo quinolines |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU557755A3 (ru) * | 1968-08-19 | 1977-05-05 | Янссен Фармасьютика Н.В. (Фирма) | Способ получени производных имидазола |
| US3658813A (en) * | 1970-01-13 | 1972-04-25 | Janssen Pharmaceutica Nv | 1-(beta-aryl-beta-(r-oxy)-ethyl)-imidazoles |
| US3983128A (en) * | 1973-12-12 | 1976-09-28 | E. R. Squibb & Sons, Inc. | Alcohol derivatives of pyrazolo[3,4-b]pyridines |
| US3928368A (en) * | 1973-12-12 | 1975-12-23 | Squibb & Sons Inc | Alcohol derivatives of pyrazolo{8 3,4-b{9 pyridines |
| US3991201A (en) * | 1974-06-27 | 1976-11-09 | Janssen Pharmaceutica N.V. | 1-(β-Aryl-β-R-ethyl)imidazoles as antimicrobial agents |
-
1978
- 1978-07-10 US US05/923,418 patent/US4159380A/en not_active Expired - Lifetime
-
1979
- 1979-06-11 NZ NZ190698A patent/NZ190698A/xx unknown
- 1979-06-12 ZA ZA792908A patent/ZA792908B/xx unknown
- 1979-06-12 AU AU48001/79A patent/AU519835B2/en not_active Withdrawn - After Issue
- 1979-06-13 GB GB7920516A patent/GB2024815A/en active Pending
- 1979-06-15 GR GR59358A patent/GR73111B/el unknown
- 1979-06-20 FR FR7915802A patent/FR2430946A1/fr not_active Withdrawn
- 1979-06-28 CS CS794480A patent/CS208115B2/cs unknown
- 1979-07-05 NL NL7905242A patent/NL7905242A/nl not_active Application Discontinuation
- 1979-07-05 YU YU01637/79A patent/YU163779A/xx unknown
- 1979-07-06 ES ES482280A patent/ES482280A1/es not_active Expired
- 1979-07-06 IT IT24171/79A patent/IT1122056B/it active
- 1979-07-06 DD DD79214181A patent/DD144774A5/de unknown
- 1979-07-07 PL PL21694479A patent/PL216944A1/xx unknown
- 1979-07-09 DK DK288079A patent/DK288079A/da unknown
- 1979-07-09 SE SE7905987A patent/SE7905987L/xx not_active Application Discontinuation
- 1979-07-09 NO NO792275A patent/NO792275L/no unknown
- 1979-07-09 LU LU81477A patent/LU81477A1/xx unknown
- 1979-07-09 SU SU792782862A patent/SU873884A3/ru active
- 1979-07-10 JP JP8800379A patent/JPS5513298A/ja active Pending
- 1979-07-10 PH PH22764A patent/PH14437A/en unknown
- 1979-07-10 DE DE19792927867 patent/DE2927867A1/de not_active Withdrawn
- 1979-07-10 BE BE0/196221A patent/BE877600A/fr unknown
- 1979-08-08 IE IE1277/79A patent/IE48442B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU519835B2 (en) | 1981-12-24 |
| FR2430946A1 (fr) | 1980-02-08 |
| SU873884A3 (ru) | 1981-10-15 |
| DK288079A (da) | 1980-01-11 |
| PH14437A (en) | 1981-07-16 |
| GB2024815A (en) | 1980-01-16 |
| DE2927867A1 (de) | 1980-01-31 |
| IT7924171A0 (it) | 1979-07-06 |
| IE791277L (en) | 1980-01-10 |
| LU81477A1 (fr) | 1979-10-31 |
| NZ190698A (en) | 1981-10-19 |
| CS208115B2 (en) | 1981-08-31 |
| JPS5513298A (en) | 1980-01-30 |
| YU163779A (en) | 1983-06-30 |
| AU4800179A (en) | 1980-02-07 |
| US4159380A (en) | 1979-06-26 |
| SE7905987L (sv) | 1980-01-11 |
| IT1122056B (it) | 1986-04-23 |
| IE48442B1 (en) | 1985-01-23 |
| ES482280A1 (es) | 1980-04-01 |
| NO792275L (no) | 1980-01-11 |
| BE877600A (fr) | 1980-01-10 |
| GR73111B (cs) | 1984-02-02 |
| NL7905242A (nl) | 1980-01-14 |
| ZA792908B (en) | 1980-06-25 |
| PL216944A1 (cs) | 1980-08-11 |
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