NO792275L - Fremgangsmaate for fremstilling av farmakologisk aktive pyrazolo-pyridinderivater - Google Patents

Fremgangsmaate for fremstilling av farmakologisk aktive pyrazolo-pyridinderivater

Info

Publication number: NO792275L
Authority: NO; Norway
Prior art keywords: hydrogen; lower alkyl; phenyl; methyl; ethyl
Prior art date: 1978-07-10

Application number

NO792275A

Other languages

English (en)

Norwegian (no)

Inventor

Hans Hoehn

Original Assignee

Squibb & Sons Inc

Priority date (The priority date 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 date listed.)

1978-07-10

Filing date

1979-07-09

Publication date

1980-01-11

1979-07-09 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1980-01-11 Publication of NO792275L publication Critical patent/NO792275L/no

Links

238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 3
150000005229 pyrazolopyridines Chemical class 0.000 title 1
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 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 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
239000000463 material Substances 0.000 claims 4
125000001309 chloro group Chemical group Cl* 0.000 claims 3
-1 2-(1H-imidazol-1-yl)ethoxy derivatives of pyrazolo[3,4-b]pyridine-5-methanols Chemical class 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
239000000203 mixture Substances 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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
239000003610 charcoal Substances 0.000 description 5
239000012458 free base Substances 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
UKVLTPAGJIYSGN-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-imidazol-1-ylethanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)CN1C=CN=C1 UKVLTPAGJIYSGN-UHFFFAOYSA-N 0.000 description 3
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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
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 3
239000012452 mother liquor Substances 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
FGWSTPDGSLKQHS-UHFFFAOYSA-N (1-ethyl-3-methylpyrazolo[3,4-b]pyridin-5-yl)methanol;hydrochloride Chemical compound Cl.OCC1=CN=C2N(CC)N=C(C)C2=C1 FGWSTPDGSLKQHS-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
125000005037 alkyl phenyl group Chemical group 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000002366 halogen compounds Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
150000007522 mineralic acids Chemical class 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000002002 slurry Substances 0.000 description 2
125000001424 substituent group Chemical group 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
XKGYNDQSOFYSJR-UHFFFAOYSA-N (4-chloro-1-ethylpyrazolo[3,4-b]pyridin-5-yl)methanol Chemical compound OCC1=CN=C2N(CC)N=CC2=C1Cl XKGYNDQSOFYSJR-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
AMSDWLOANMAILF-UHFFFAOYSA-N 2-imidazol-1-ylethanol Chemical class OCCN1C=CN=C1 AMSDWLOANMAILF-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 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
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
RJMRAKOPBMLPRR-UHFFFAOYSA-N 4h-pyrazolo[3,4-b]pyridin-5-ylmethanol Chemical compound C1C(CO)=CN=C2N=NC=C21 RJMRAKOPBMLPRR-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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000700198 Cavia Species 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000224527 Trichomonas vaginalis Species 0.000 description 1
241001045770 Trichophyton mentagrophytes Species 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000005036 alkoxyphenyl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 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
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 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
239000011230 binding agent Substances 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
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
229940001468 citrate Drugs 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
FGEWDVKPONESEB-UHFFFAOYSA-N ethyl 4-chloro-1-ethyl-3-methylpyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C2N(CC)N=C(C)C2=C1Cl FGEWDVKPONESEB-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000007429 general method Methods 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
125000005059 halophenyl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 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
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 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
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 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
229940095064 tartrate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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)

NO792275A 1978-07-10 1979-07-09 Fremgangsmaate for fremstilling av farmakologisk aktive pyrazolo-pyridinderivater NO792275L (no)

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
NO792275L true NO792275L (no)	1980-01-11

Family

ID=25448663

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO792275A NO792275L (no)	1978-07-10	1979-07-09	Fremgangsmaate for fremstilling av farmakologisk aktive pyrazolo-pyridinderivater

Country Status (24)

Country	Link
US (1)	US4159380A (fr)
JP (1)	JPS5513298A (fr)
AU (1)	AU519835B2 (fr)
BE (1)	BE877600A (fr)
CS (1)	CS208115B2 (fr)
DD (1)	DD144774A5 (fr)
DE (1)	DE2927867A1 (fr)
DK (1)	DK288079A (fr)
ES (1)	ES482280A1 (fr)
FR (1)	FR2430946A1 (fr)
GB (1)	GB2024815A (fr)
GR (1)	GR73111B (fr)
IE (1)	IE48442B1 (fr)
IT (1)	IT1122056B (fr)
LU (1)	LU81477A1 (fr)
NL (1)	NL7905242A (fr)
NO (1)	NO792275L (fr)
NZ (1)	NZ190698A (fr)
PH (1)	PH14437A (fr)
PL (1)	PL216944A1 (fr)
SE (1)	SE7905987L (fr)
SU (1)	SU873884A3 (fr)
YU (1)	YU163779A (fr)
ZA (1)	ZA792908B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 YU YU01637/79A patent/YU163779A/xx unknown
- 1979-07-05 NL NL7905242A patent/NL7905242A/nl not_active Application Discontinuation
- 1979-07-06 ES ES482280A patent/ES482280A1/es not_active Expired
- 1979-07-06 DD DD79214181A patent/DD144774A5/de unknown
- 1979-07-06 IT IT24171/79A patent/IT1122056B/it active
- 1979-07-07 PL PL21694479A patent/PL216944A1/xx unknown
- 1979-07-09 SU SU792782862A patent/SU873884A3/ru active
- 1979-07-09 NO NO792275A patent/NO792275L/no unknown
- 1979-07-09 LU LU81477A patent/LU81477A1/fr unknown
- 1979-07-09 DK DK288079A patent/DK288079A/da unknown
- 1979-07-09 SE SE7905987A patent/SE7905987L/xx not_active Application Discontinuation
- 1979-07-10 DE DE19792927867 patent/DE2927867A1/de not_active Withdrawn
- 1979-07-10 BE BE0/196221A patent/BE877600A/fr unknown
- 1979-07-10 PH PH22764A patent/PH14437A/en unknown
- 1979-07-10 JP JP8800379A patent/JPS5513298A/ja active Pending
- 1979-08-08 IE IE1277/79A patent/IE48442B1/en unknown

Also Published As

Publication number	Publication date
ZA792908B (en)	1980-06-25
US4159380A (en)	1979-06-26
DD144774A5 (de)	1980-11-05
DE2927867A1 (de)	1980-01-31
FR2430946A1 (fr)	1980-02-08
CS208115B2 (en)	1981-08-31
JPS5513298A (en)	1980-01-30
GB2024815A (en)	1980-01-16
AU519835B2 (en)	1981-12-24
GR73111B (fr)	1984-02-02
BE877600A (fr)	1980-01-10
DK288079A (da)	1980-01-11
LU81477A1 (fr)	1979-10-31
YU163779A (en)	1983-06-30
NL7905242A (nl)	1980-01-14
AU4800179A (en)	1980-02-07
IE791277L (en)	1980-01-10
SE7905987L (sv)	1980-01-11
PH14437A (en)	1981-07-16
IE48442B1 (en)	1985-01-23
SU873884A3 (ru)	1981-10-15
NZ190698A (en)	1981-10-19
PL216944A1 (fr)	1980-08-11
IT7924171A0 (it)	1979-07-06
IT1122056B (it)	1986-04-23
ES482280A1 (es)	1980-04-01

Publication	Publication Date	Title
EP0684945B1 (fr)	2002-07-24	AMIDES ALKYLE SUBSTITUES PAR PYRAZOLE OU ISOXAZOLE EXERANT UNE ACTIVITE INHIBITRICE DE L'ACYLE-CoA: CHOLESTEROL ACYLTRANSFERASE
US3995039A (en)	1976-11-30	Pyrazolo [1,5-a] [1,3,5] triazines
US4020072A (en)	1977-04-26	5-Aminomethyl-1H-pyrazolo[3,4-b]pyridines
US7256195B2 (en)	2007-08-14	Preparation of risperidone
JPS6089474A (ja)	1985-05-20	モルフイナン誘導体，その製造方法，及び該化合物を含有する抗腫瘍剤
DK162629B (da)	1991-11-25	2-substituerede 1-aralkyl-imidazoler og farmaceutiske midler der indeholder disse, anvendelse heraf til fremstilling af farmaceutiske midler samt fremgangsmaade til fremstilling heraf
SU1195903A3 (ru)	1985-11-30	Способ получени 1-фенил- 2-аминокарбонилиндольных соединений или их солей присоединени кислот
NO792275L (no)	1980-01-11	Fremgangsmaate for fremstilling av farmakologisk aktive pyrazolo-pyridinderivater
NO160000B (no)	1988-11-21	Analogifremgangsmaate for fremstilling av terapeutisk aktive forbindelser.
HU195486B (en)	1988-05-30	Process for preparing new pyridine derivatives
US4282230A (en)	1981-08-04	Imidazolylethoxy derivatives of quinoline-2- or 4-methanols, antimicrobial compositions containing them and method for treating bacterial or fungal infections with them
US4273776A (en)	1981-06-16	Antibacterial and antifungal derivatives of 3-(1H-imidazol-1-yl)-2-propen-1-ones
US4048184A (en)	1977-09-13	6-Phenyl-2H-pyrazolo[3,4-b]pyridines
US4109091A (en)	1978-08-22	Derivatives of 1,4- and 4,10-dihydro-4-oxo-pyrimido[1,2-a]benzimidazole-3-carboxylic acid amides
US3985760A (en)	1976-10-12	Amino derivatives of 6-phenylisoxazolo[5,4-b]pyridines
CZ325196A3 (en)	1997-06-11	Derivatives of hydroximic acid, pharmaceutical compositions containing thereof, process of their preparation and intermediates used in the preparation process
DK158944B (da)	1990-08-06	Analogifremgangsmaade til fremstilling af substituerede methylimidazolforbindelser
US4169205A (en)	1979-09-25	Imidazole derivatives of 6,11-dihydrodibenz[b,e]oxepines and 6,11-dihydrodibenz[b,e]thiepines
US4234589A (en)	1980-11-18	Imidazolylethoxymethyl derivatives of 1,3-dioxolo quinolines
US4202985A (en)	1980-05-13	Imidazolylethoxy derivatives of quinoline-3-methanols
US4038281A (en)	1977-07-26	Certain 2,7-dihydro-4H-pyrazolo[3,4-b]pyridine-5-ketones
US4066644A (en)	1978-01-03	Pyrazolo [1,5-a]pyrido[3,2-e]pyrimidine-7-carboxylic acid heterocyclic derivatives
US3733328A (en)	1973-05-15	Pyrazolo(3,4-b)pyridine-5-carboxamides
NO317993B1 (no)	2005-01-17	Benzoylguanidin-derivater, farmasoytisk preparat, fremgangsmate for fremstilling derav og anvendelse av dem ved fremstilling av medikamenter
US4278798A (en)	1981-07-14	1-Ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxonicotinic acid and esters thereof