HU191249B - Process for preparing new pyrazolo /1,5-a/pyridine derivatives - Google Patents
Process for preparing new pyrazolo /1,5-a/pyridine derivatives Download PDFInfo
- Publication number
- HU191249B HU191249B HU84777A HU77784A HU191249B HU 191249 B HU191249 B HU 191249B HU 84777 A HU84777 A HU 84777A HU 77784 A HU77784 A HU 77784A HU 191249 B HU191249 B HU 191249B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- compounds
- hydrogen
- preparation
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003222 pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical class C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000003266 anti-allergic effect Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 abstract description 7
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical class C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000043 antiallergic agent Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- -1 inhalants Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 206010020751 Hypersensitivity Diseases 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 241000700198 Cavia Species 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 230000000172 allergic effect Effects 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 208000010668 atopic eczema Diseases 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 210000003405 ileum Anatomy 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 206010006482 Bronchospasm Diseases 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 230000007885 bronchoconstriction Effects 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DHCWYFYPHUPOFD-UHFFFAOYSA-N 2-methyl-1-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)propan-1-ol Chemical compound C1=CC=CC2=C(C(O)C(C)C)C(C(C)C)=NN21 DHCWYFYPHUPOFD-UHFFFAOYSA-N 0.000 description 2
- YDLUHABALCALTM-UHFFFAOYSA-N 2-propan-2-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=C(C(C)C)C=C21 YDLUHABALCALTM-UHFFFAOYSA-N 0.000 description 2
- PEHWGWDQBPUYCM-UHFFFAOYSA-N 2-propan-2-ylpyrazolo[1,5-a]pyridine-3-carbaldehyde Chemical compound C1=CC=CC2=C(C=O)C(C(C)C)=NN21 PEHWGWDQBPUYCM-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- ZJVFLBOZORBYFE-UHFFFAOYSA-N Ibudilast Chemical compound C1=CC=CC2=C(C(=O)C(C)C)C(C(C)C)=NN21 ZJVFLBOZORBYFE-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010038687 Respiratory distress Diseases 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 229940125715 antihistaminic agent Drugs 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JAVBBFXUGDCHLZ-UHFFFAOYSA-N 1-$l^{1}-oxidanylpropane Chemical group CCC[O] JAVBBFXUGDCHLZ-UHFFFAOYSA-N 0.000 description 1
- IAKXVGXWULHABN-UHFFFAOYSA-N 1-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)propan-1-ol Chemical compound C1=CC=CC2=C(C(O)CC)C(C(C)C)=NN21 IAKXVGXWULHABN-UHFFFAOYSA-N 0.000 description 1
- YTOYRGQFECLFCB-UHFFFAOYSA-N 2,2-dimethyl-1-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)propan-1-ol Chemical compound C1=CC=CC2=C(C(O)C(C)(C)C)C(C(C)C)=NN21 YTOYRGQFECLFCB-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- HQCZGBYFJBEZLG-UHFFFAOYSA-N 2-methyl-3-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)pentan-3-ol Chemical compound C1=CC=CC2=C(C(O)(C(C)C)CC)C(C(C)C)=NN21 HQCZGBYFJBEZLG-UHFFFAOYSA-N 0.000 description 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
- SIUQCSAJRZPJIR-UHFFFAOYSA-N 2-propan-2-yl-3-propylpyrazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=C(CCC)C(C(C)C)=NN21 SIUQCSAJRZPJIR-UHFFFAOYSA-N 0.000 description 1
- KIIBZKPPWFCFDY-UHFFFAOYSA-N 3,6-dibromo-2-propan-2-ylpyrazolo[1,5-a]pyridine Chemical compound C1=C(Br)C=CC2=C(Br)C(C(C)C)=NN21 KIIBZKPPWFCFDY-UHFFFAOYSA-N 0.000 description 1
- PEYYKGXRUBHHIY-UHFFFAOYSA-N 3-(2-methyl-3-propoxypentan-3-yl)-2-propan-2-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=C(C(CC)(C(C)C)OCCC)C(C(C)C)=NN21 PEYYKGXRUBHHIY-UHFFFAOYSA-N 0.000 description 1
- VZAOHFDOVAEAPB-UHFFFAOYSA-N 3-(methoxymethyl)-2-propan-2-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=C(COC)C(C(C)C)=NN21 VZAOHFDOVAEAPB-UHFFFAOYSA-N 0.000 description 1
- SPYMZJBEXDIDJY-UHFFFAOYSA-N 3-bromo-2-propan-2-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=C(Br)C(C(C)C)=NN21 SPYMZJBEXDIDJY-UHFFFAOYSA-N 0.000 description 1
- RJXGLNHXLUKMKW-UHFFFAOYSA-N 3-bromo-6-methoxy-2-propan-2-ylpyrazolo[1,5-a]pyridine Chemical compound C1=C(OC)C=CC2=C(Br)C(C(C)C)=NN21 RJXGLNHXLUKMKW-UHFFFAOYSA-N 0.000 description 1
- GOPABXAQBQDYHB-UHFFFAOYSA-N 6-methoxy-2-propan-2-ylpyrazolo[1,5-a]pyridine Chemical compound C1=C(OC)C=CC2=CC(C(C)C)=NN21 GOPABXAQBQDYHB-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 201000010435 allergic urticaria Diseases 0.000 description 1
- FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 description 1
- 229960003556 aminophylline Drugs 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
- 229960003291 chlorphenamine Drugs 0.000 description 1
- 229940121657 clinical drug Drugs 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 229960000265 cromoglicic acid Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-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
- CKHJHPJFLMFFQY-UHFFFAOYSA-N cyclopentyl-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)methanone Chemical compound CC(C)C1=NN2C=CC=CC2=C1C(=O)C1CCCC1 CKHJHPJFLMFFQY-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 229960000520 diphenhydramine Drugs 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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 |
|---|---|---|---|
| JP58041958A JPS59167590A (ja) | 1983-03-14 | 1983-03-14 | ピラゾロ〔１，５−ａ〕ピリジン誘導体、その製法及びそれを含有する治療剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU191249B true HU191249B (en) | 1987-01-28 |
Family
ID=12622693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU84777A HU191249B (en) | 1983-03-14 | 1984-02-27 | Process for preparing new pyrazolo /1,5-a/pyridine derivatives |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4578392A (en, 2012) |
| EP (1) | EP0118916B1 (en, 2012) |
| JP (1) | JPS59167590A (en, 2012) |
| KR (1) | KR910001135B1 (en, 2012) |
| CA (1) | CA1244434A (en, 2012) |
| DE (1) | DE3465308D1 (en, 2012) |
| DK (1) | DK160277C (en, 2012) |
| ES (3) | ES8603474A1 (en, 2012) |
| HU (1) | HU191249B (en, 2012) |
| NO (1) | NO160442C (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01153634A (ja) * | 1987-12-10 | 1989-06-15 | Kyorin Pharmaceut Co Ltd | 吸入剤 |
| JPH01153633A (ja) * | 1987-12-10 | 1989-06-15 | Kyorin Pharmaceut Co Ltd | 経皮吸収製剤 |
| JPH0225418A (ja) * | 1988-07-14 | 1990-01-26 | Kyorin Pharmaceut Co Ltd | イブジラスト脂肪乳剤およびその製造方法 |
| TW200517114A (en) | 2003-10-15 | 2005-06-01 | Combinatorx Inc | Methods and reagents for the treatment of immunoinflammatory disorders |
| JP2007512337A (ja) | 2003-11-21 | 2007-05-17 | コンビナトアールエックス インコーポレーティッド | 炎症性障害の治療のための方法および試薬 |
| ZA200804550B (en) | 2005-11-09 | 2009-08-26 | Combinatorx Inc | Methods, compositions, and kits for the treatment of medical conditions |
| US7585875B2 (en) * | 2006-06-06 | 2009-09-08 | Avigen, Inc. | Substituted pyrazolo[1,5-a]pyridine compounds and their methods of use |
| WO2010021681A2 (en) * | 2008-08-18 | 2010-02-25 | Combinatorx (Singapore) Pte. Ltd. | Compositions and methods for treatment of viral diseases |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5154583A (en) * | 1974-11-01 | 1976-05-13 | Kyorin Seiyaku Kk | Shinkipirazoro * 1 55a * pirijinjudotaino seizoho |
| US4097483A (en) * | 1974-11-01 | 1978-06-27 | Kyorin Pharmaceutical Co., Ltd. | Pyrazolo 1,5-a!pyridines |
-
1983
- 1983-03-14 JP JP58041958A patent/JPS59167590A/ja active Granted
-
1984
- 1984-02-27 HU HU84777A patent/HU191249B/hu not_active IP Right Cessation
- 1984-02-29 DK DK136784A patent/DK160277C/da not_active IP Right Cessation
- 1984-03-07 US US06/586,928 patent/US4578392A/en not_active Expired - Fee Related
- 1984-03-12 EP EP84102687A patent/EP0118916B1/en not_active Expired
- 1984-03-12 DE DE8484102687T patent/DE3465308D1/de not_active Expired
- 1984-03-13 NO NO840969A patent/NO160442C/no unknown
- 1984-03-13 CA CA000449439A patent/CA1244434A/en not_active Expired
- 1984-03-14 KR KR1019840001287A patent/KR910001135B1/ko not_active Expired
- 1984-03-14 ES ES530574A patent/ES8603474A1/es not_active Expired
-
1985
- 1985-07-01 ES ES544773A patent/ES8701177A1/es not_active Expired
-
1986
- 1986-02-28 ES ES552547A patent/ES8705439A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0118916A2 (en) | 1984-09-19 |
| CA1244434A (en) | 1988-11-08 |
| ES552547A0 (es) | 1987-05-01 |
| EP0118916A3 (en) | 1985-06-05 |
| JPS59167590A (ja) | 1984-09-21 |
| JPH0559117B2 (en, 2012) | 1993-08-30 |
| DK160277C (da) | 1991-07-22 |
| NO840969L (no) | 1984-09-17 |
| NO160442B (no) | 1989-01-09 |
| ES8705439A1 (es) | 1987-05-01 |
| ES544773A0 (es) | 1986-11-16 |
| ES530574A0 (es) | 1985-12-16 |
| DK160277B (da) | 1991-02-18 |
| DK136784D0 (da) | 1984-02-29 |
| NO160442C (no) | 1989-04-19 |
| ES8603474A1 (es) | 1985-12-16 |
| DK136784A (da) | 1984-09-15 |
| KR910001135B1 (ko) | 1991-02-25 |
| ES8701177A1 (es) | 1986-11-16 |
| DE3465308D1 (en) | 1987-09-17 |
| EP0118916B1 (en) | 1987-08-12 |
| KR840008152A (ko) | 1984-12-13 |
| US4578392A (en) | 1986-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |