JPH0794454B2 - ピラゾロピリジン化合物およびその製造法 - Google Patents
ピラゾロピリジン化合物およびその製造法Info
- Publication number
- JPH0794454B2 JPH0794454B2 JP2012995A JP1299590A JPH0794454B2 JP H0794454 B2 JPH0794454 B2 JP H0794454B2 JP 2012995 A JP2012995 A JP 2012995A JP 1299590 A JP1299590 A JP 1299590A JP H0794454 B2 JPH0794454 B2 JP H0794454B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- oxo
- alkyl group
- carboxy
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 Pyrazolopyridine compound Chemical class 0.000 title claims abstract description 271
- 238000004519 manufacturing process Methods 0.000 title claims description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 141
- 125000001424 substituent group Chemical group 0.000 claims abstract description 76
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 70
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 187
- 125000000217 alkyl group Chemical group 0.000 claims description 89
- 125000004043 oxo group Chemical group O=* 0.000 claims description 67
- 238000006243 chemical reaction Methods 0.000 claims description 65
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 52
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 36
- 125000003277 amino group Chemical group 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000004434 sulfur atom Chemical group 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- HFOAXDYGZAQNTI-UHFFFAOYSA-N 2-phenylpyrazolo[1,5-a]pyridine Chemical compound N=1N2C=CC=CC2=CC=1C1=CC=CC=C1 HFOAXDYGZAQNTI-UHFFFAOYSA-N 0.000 claims description 12
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 7
- 125000005053 dihydropyrimidinyl group Chemical group N1(CN=CC=C1)* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 7
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 238000003379 elimination reaction Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical group OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 19
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000003937 drug carrier Substances 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 139
- 239000000203 mixture Substances 0.000 description 100
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 98
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- 239000002904 solvent Substances 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
- 238000000921 elemental analysis Methods 0.000 description 54
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 239000000243 solution Substances 0.000 description 44
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 27
- 235000019341 magnesium sulphate Nutrition 0.000 description 27
- 239000000284 extract Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 239000002253 acid Substances 0.000 description 23
- 238000001816 cooling Methods 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000002244 precipitate Substances 0.000 description 21
- 229920006395 saturated elastomer Polymers 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 150000002391 heterocyclic compounds Chemical class 0.000 description 15
- 125000004430 oxygen atom Chemical group O* 0.000 description 15
- 239000013078 crystal Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 239000012046 mixed solvent Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 229940124597 therapeutic agent Drugs 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 5
- 230000002411 adverse Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 210000002700 urine Anatomy 0.000 description 5
- MBCUSHSOCQIFLW-UHFFFAOYSA-N 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 MBCUSHSOCQIFLW-UHFFFAOYSA-N 0.000 description 4
- MQIUPPGRSIDEQN-UHFFFAOYSA-N 3-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]propanoic acid Chemical compound C1=CC(=O)N(CCC(=O)O)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 MQIUPPGRSIDEQN-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 230000001882 diuretic effect Effects 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 3
- LAGKMXIFTIXARS-UHFFFAOYSA-N 1-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)ethanone Chemical compound N=1N2C=CC=CC2=C(C(=O)C)C=1C1=CC=CC=C1 LAGKMXIFTIXARS-UHFFFAOYSA-N 0.000 description 3
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 3
- FJRPOHLDJUJARI-UHFFFAOYSA-N 2,3-dihydro-1,2-oxazole Chemical compound C1NOC=C1 FJRPOHLDJUJARI-UHFFFAOYSA-N 0.000 description 3
- QKCNCSMRONBCSQ-UHFFFAOYSA-N 3-(6-chloropyridazin-3-yl)-2-phenylpyrazolo[1,5-a]pyridine Chemical compound N1=NC(Cl)=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 QKCNCSMRONBCSQ-UHFFFAOYSA-N 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 208000034972 Sudden Infant Death Diseases 0.000 description 3
- 206010042440 Sudden infant death syndrome Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- FLCDCROVTYWBMA-UHFFFAOYSA-N 1,1,1-trichloro-3-[4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-yl]propan-2-ol Chemical compound ClC(Cl)(Cl)C(O)CC1=NN=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 FLCDCROVTYWBMA-UHFFFAOYSA-N 0.000 description 2
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 description 2
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 description 2
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- DICFSKMBVGAYFU-UHFFFAOYSA-N 1-(2-carboxyethyl)-2-oxo-5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N(CCC(=O)O)C=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 DICFSKMBVGAYFU-UHFFFAOYSA-N 0.000 description 2
- QWGAIXYNWZNFLT-UHFFFAOYSA-N 1-morpholin-4-yl-2-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)ethanethione Chemical compound C1COCCN1C(=S)CC(=C1C=CC=CN1N=1)C=1C1=CC=CC=C1 QWGAIXYNWZNFLT-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- JXBKZAYVMSNKHA-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-olate Chemical compound OC=1N=NNN=1 JXBKZAYVMSNKHA-UHFFFAOYSA-N 0.000 description 2
- OYJGEOAXBALSMM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole Chemical compound C1NC=CS1 OYJGEOAXBALSMM-UHFFFAOYSA-N 0.000 description 2
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 2
- HMAFIKJTAGWBDM-UHFFFAOYSA-N 2-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acetic acid Chemical compound N=1N2C=CC=CC2=C(CC(=O)O)C=1C1=CC=CC=C1 HMAFIKJTAGWBDM-UHFFFAOYSA-N 0.000 description 2
- VNQQZEBHJCXEQZ-UHFFFAOYSA-N 2-(3-oxo-3-piperidin-1-ylpropyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1CCCCN1C(=O)CCN(C(C=C1)=O)N=C1C(=C1C=CC=CN1N=1)C=1C1=CC=CC=C1 VNQQZEBHJCXEQZ-UHFFFAOYSA-N 0.000 description 2
- BFOAUFWXLXVANZ-UHFFFAOYSA-N 2-hydroxyimino-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)propanoic acid Chemical compound N=1N2C=CC=CC2=C(CC(=NO)C(O)=O)C=1C1=CC=CC=C1 BFOAUFWXLXVANZ-UHFFFAOYSA-N 0.000 description 2
- SPCBRIXWACUPTL-UHFFFAOYSA-N 2-oxo-5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 SPCBRIXWACUPTL-UHFFFAOYSA-N 0.000 description 2
- NLXXIPRNPLMDFQ-UHFFFAOYSA-N 2-oxo-5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1h-pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(=O)O)=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=C1 NLXXIPRNPLMDFQ-UHFFFAOYSA-N 0.000 description 2
- GSGVFADOGIAWSM-UHFFFAOYSA-N 2-phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde Chemical compound N=1N2C=CC=CC2=C(C=O)C=1C1=CC=CC=C1 GSGVFADOGIAWSM-UHFFFAOYSA-N 0.000 description 2
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 2
- BOXRDDIXJOUZLV-UHFFFAOYSA-N 2h-imidazo[4,5-d]thiadiazole Chemical compound N1SC2=NC=NC2=N1 BOXRDDIXJOUZLV-UHFFFAOYSA-N 0.000 description 2
- NWWJFMCCTZLKNT-UHFFFAOYSA-N 3,4-dihydro-2h-thiazine Chemical compound C1CC=CSN1 NWWJFMCCTZLKNT-UHFFFAOYSA-N 0.000 description 2
- QSBQHEHNHCBCAA-UHFFFAOYSA-N 3,4-dihydrooxathiine Chemical compound C1CC=COS1 QSBQHEHNHCBCAA-UHFFFAOYSA-N 0.000 description 2
- XZWKPQSQWMRXJF-UHFFFAOYSA-N 3-(2-chloropyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine Chemical compound C1=NC(Cl)=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=C1 XZWKPQSQWMRXJF-UHFFFAOYSA-N 0.000 description 2
- XIVGKOASJIFWOH-UHFFFAOYSA-N 3-(2-methoxypyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine Chemical compound C1=NC(OC)=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=C1 XIVGKOASJIFWOH-UHFFFAOYSA-N 0.000 description 2
- IPTDTGXHPKQNKW-UHFFFAOYSA-N 3-(3-chloropyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine Chemical compound ClC1=NN=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 IPTDTGXHPKQNKW-UHFFFAOYSA-N 0.000 description 2
- DMZHQGHHFSIOOA-UHFFFAOYSA-N 3-(3-methoxypyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine Chemical compound COC1=NN=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 DMZHQGHHFSIOOA-UHFFFAOYSA-N 0.000 description 2
- COOSAAMCVZZIQF-UHFFFAOYSA-N 3-(3-methylpyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine Chemical compound CC1=NN=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 COOSAAMCVZZIQF-UHFFFAOYSA-N 0.000 description 2
- SNEMHMBGPRVAQC-UHFFFAOYSA-N 3-(3-methylpyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine;hydrochloride Chemical compound Cl.CC1=NN=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 SNEMHMBGPRVAQC-UHFFFAOYSA-N 0.000 description 2
- DSXJSPCLALZSIT-UHFFFAOYSA-N 3-(6-methoxypyridazin-3-yl)-2-phenylpyrazolo[1,5-a]pyridine Chemical compound N1=NC(OC)=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 DSXJSPCLALZSIT-UHFFFAOYSA-N 0.000 description 2
- UOKZZRHJDSCLRY-UHFFFAOYSA-N 3-(dimethylamino)-2-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)prop-2-enal Chemical compound N=1N2C=CC=CC2=C(C(C=O)=CN(C)C)C=1C1=CC=CC=C1 UOKZZRHJDSCLRY-UHFFFAOYSA-N 0.000 description 2
- GUTSSMVBFZVXGH-UHFFFAOYSA-N 3-[2-oxo-4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridin-1-yl]propanoic acid Chemical compound O=C1N(CCC(=O)O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=C1 GUTSSMVBFZVXGH-UHFFFAOYSA-N 0.000 description 2
- ZLWOYOBGKUICCK-UHFFFAOYSA-N 3-[3-cyano-2-oxo-5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridin-1-yl]propanoic acid Chemical compound C1=C(C#N)C(=O)N(CCC(=O)O)C=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 ZLWOYOBGKUICCK-UHFFFAOYSA-N 0.000 description 2
- IKYKDBQGOHTBEK-UHFFFAOYSA-N 3-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]propanamide Chemical compound C1=CC(=O)N(CCC(=O)N)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 IKYKDBQGOHTBEK-UHFFFAOYSA-N 0.000 description 2
- OHXXSPIIJZDOJE-UHFFFAOYSA-N 3-[6-oxo-5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]propanoic acid Chemical compound O=C1N(CCC(=O)O)N=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 OHXXSPIIJZDOJE-UHFFFAOYSA-N 0.000 description 2
- XDINTYDAGAWMTN-UHFFFAOYSA-N 4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1h-pyridin-2-one Chemical compound C1=CNC(=O)C=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 XDINTYDAGAWMTN-UHFFFAOYSA-N 0.000 description 2
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
- BMAICRAJVMSJKC-UHFFFAOYSA-N 5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 BMAICRAJVMSJKC-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- 208000000575 Arteriosclerosis Obliterans Diseases 0.000 description 2
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N Benzoxazolone Natural products C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- SNUGEUAGRWNSTN-UHFFFAOYSA-N C1=C(O)N(CCC(=O)OC)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 Chemical compound C1=C(O)N(CCC(=O)OC)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 SNUGEUAGRWNSTN-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 208000005189 Embolism Diseases 0.000 description 2
- 201000005569 Gout Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 201000001431 Hyperuricemia Diseases 0.000 description 2
- 206010062016 Immunosuppression Diseases 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 208000001647 Renal Insufficiency Diseases 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000924 antiasthmatic agent Substances 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 description 2
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- OEDCKJPCJUJEAL-UHFFFAOYSA-N ethyl 3-chloro-4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-4h-pyridazine-1-carboxylate Chemical compound ClC1=NN(C(=O)OCC)C=CC1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 OEDCKJPCJUJEAL-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 201000006370 kidney failure Diseases 0.000 description 2
- 150000007517 lewis acids Chemical class 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
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GHYPZJWPCGHTAO-UHFFFAOYSA-N methyl 3-[3-cyano-2-oxo-5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridin-1-yl]propanoate Chemical compound C1=C(C#N)C(=O)N(CCC(=O)OC)C=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 GHYPZJWPCGHTAO-UHFFFAOYSA-N 0.000 description 2
- QZVRGMUCGNYDHR-UHFFFAOYSA-N methyl 3-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-4,5-dihydropyridazin-1-yl]propanoate Chemical compound C1CC(=O)N(CCC(=O)OC)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 QZVRGMUCGNYDHR-UHFFFAOYSA-N 0.000 description 2
- QIUVPVMRWUKEKF-UHFFFAOYSA-N methyl 3-[6-oxo-4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2,3-dihydropyridin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)CCC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=C1 QIUVPVMRWUKEKF-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 2
- YBKGERLDRMINOV-UHFFFAOYSA-N oxathiine Chemical compound O1SC=CC=C1 YBKGERLDRMINOV-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 201000005060 thrombophlebitis Diseases 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 201000010875 transient cerebral ischemia Diseases 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
- ZUISYJAGSGZBRY-MDZDMXLPSA-N (e)-3-[4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-yl]prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=NN=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 ZUISYJAGSGZBRY-MDZDMXLPSA-N 0.000 description 1
- OQWFBKFNMDTEDY-MDZDMXLPSA-N (e)-4-oxo-4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)but-2-enoic acid Chemical compound N=1N2C=CC=CC2=C(C(=O)/C=C/C(=O)O)C=1C1=CC=CC=C1 OQWFBKFNMDTEDY-MDZDMXLPSA-N 0.000 description 1
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 description 1
- BXTWRMNZAGYXQQ-UHFFFAOYSA-N 1,2,4-oxadiazol-3-one Chemical compound O=C1N=CON1 BXTWRMNZAGYXQQ-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- OGVWWGVZVJUPHF-UHFFFAOYSA-N 1,2,4-thiadiazol-3-one Chemical compound O=C1N=CSN1 OGVWWGVZVJUPHF-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 1
- SUIZZAKVFWEMTF-UHFFFAOYSA-N 1,2,5-oxadiazol-3-one Chemical compound OC=1C=NON=1 SUIZZAKVFWEMTF-UHFFFAOYSA-N 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DPHVWRMZSWGLLA-UHFFFAOYSA-N 1,2-benzodithiine Chemical compound C1=CC=C2C=CSSC2=C1 DPHVWRMZSWGLLA-UHFFFAOYSA-N 0.000 description 1
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 description 1
- QCGLUKVIKCEVAE-UHFFFAOYSA-N 1,2-oxazolidin-4-one Chemical compound O=C1CNOC1 QCGLUKVIKCEVAE-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- BRQBVEHLEITSPT-UHFFFAOYSA-N 1,3,4-thiadiazolidine Chemical compound C1NNCS1 BRQBVEHLEITSPT-UHFFFAOYSA-N 0.000 description 1
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 description 1
- UIXCHNWBNLBBAZ-UHFFFAOYSA-N 1,3-thiazinan-4-one Chemical compound O=C1CCSCN1 UIXCHNWBNLBBAZ-UHFFFAOYSA-N 0.000 description 1
- GJGROPRLXDXIAN-UHFFFAOYSA-N 1,3-thiazol-4-one Chemical compound O=C1CSC=N1 GJGROPRLXDXIAN-UHFFFAOYSA-N 0.000 description 1
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 description 1
- BGMLUCPALPKNOV-UHFFFAOYSA-N 1,4,5,6-tetrahydropyridazine Chemical compound C1CNN=CC1 BGMLUCPALPKNOV-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YWTTYOZCJQBTEU-UHFFFAOYSA-N 1,4-benzodithiin-3-one Chemical compound C1=CC=C2SC(=O)CSC2=C1 YWTTYOZCJQBTEU-UHFFFAOYSA-N 0.000 description 1
- HZVGMPJZVYBYEK-UHFFFAOYSA-N 1,4-dihydropyridazine Chemical compound C1C=CNN=C1 HZVGMPJZVYBYEK-UHFFFAOYSA-N 0.000 description 1
- WNWOTMKHOLCHRJ-UHFFFAOYSA-N 1,4-dihydrotriazol-5-one Chemical compound O=C1CN=NN1 WNWOTMKHOLCHRJ-UHFFFAOYSA-N 0.000 description 1
- ASOPVKWTZUHEJN-UHFFFAOYSA-N 1,4-oxathian-3-one Chemical compound O=C1COCCS1 ASOPVKWTZUHEJN-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- ZEFGUWRQFNTGGX-UHFFFAOYSA-N 1,6-dihydropyridazine Chemical compound C1NN=CC=C1 ZEFGUWRQFNTGGX-UHFFFAOYSA-N 0.000 description 1
- ZWFHYDOMCZSUJR-UHFFFAOYSA-N 1-[4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridin-3-yl]ethanone Chemical compound CC(=O)C1=CN=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 ZWFHYDOMCZSUJR-UHFFFAOYSA-N 0.000 description 1
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 description 1
- DWKUKQRKVCMOLP-UHFFFAOYSA-N 1-piperideine Chemical compound C1CCN=CC1 DWKUKQRKVCMOLP-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- PNWWHSHNMHTJFW-UHFFFAOYSA-N 2,3-dihydro-1,2,5-thiadiazole Chemical compound C1NSN=C1 PNWWHSHNMHTJFW-UHFFFAOYSA-N 0.000 description 1
- PLYNVXKJUKCUOF-UHFFFAOYSA-N 2,3-dihydro-1h-pyridin-4-one Chemical compound O=C1CCNC=C1 PLYNVXKJUKCUOF-UHFFFAOYSA-N 0.000 description 1
- JCMBRAYXMYWJBY-UHFFFAOYSA-N 2-(2-ethoxyethyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCOCC)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 JCMBRAYXMYWJBY-UHFFFAOYSA-N 0.000 description 1
- RWLXWSVSPDSYGJ-UHFFFAOYSA-N 2-(2-hydroxyethyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCO)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 RWLXWSVSPDSYGJ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- HHNKQDIAOTVKBJ-UHFFFAOYSA-N 2-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acetonitrile Chemical compound N=1N2C=CC=CC2=C(CC#N)C=1C1=CC=CC=C1 HHNKQDIAOTVKBJ-UHFFFAOYSA-N 0.000 description 1
- ZEUSQYFZEFCUEQ-UHFFFAOYSA-N 2-(3-hydroxypropyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCCO)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 ZEUSQYFZEFCUEQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JIBAMDFTLCCWHN-UHFFFAOYSA-N 2-bromo-1-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)ethanone Chemical compound N=1N2C=CC=CC2=C(C(=O)CBr)C=1C1=CC=CC=C1 JIBAMDFTLCCWHN-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WBLKNEZNJUATQB-UHFFFAOYSA-N 2-methyl-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(C)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 WBLKNEZNJUATQB-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
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ZXCYZORKIPKVDY-UHFFFAOYSA-N 2-phenyl-3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyridine Chemical compound C1=NNC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 ZXCYZORKIPKVDY-UHFFFAOYSA-N 0.000 description 1
- WVVOPVKUHZHEDY-UHFFFAOYSA-N 2-phenyl-3-pyridazin-4-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC=CC=C1C1=NN(C=CC=C2)C2=C1C1=CC=NN=C1 WVVOPVKUHZHEDY-UHFFFAOYSA-N 0.000 description 1
- YCGONMMRAXRRDD-UHFFFAOYSA-N 2-phenyl-3-pyridin-4-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC=CC=C1C1=NN(C=CC=C2)C2=C1C1=CC=NC=C1 YCGONMMRAXRRDD-UHFFFAOYSA-N 0.000 description 1
- KYAKUSIGBARXES-UHFFFAOYSA-N 2-phenyl-3-pyrimidin-4-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC=CC=C1C1=NN(C=CC=C2)C2=C1C1=CC=NC=N1 KYAKUSIGBARXES-UHFFFAOYSA-N 0.000 description 1
- XHJFYSOTBLRNNZ-UHFFFAOYSA-N 2-phenyl-3-pyrimidin-5-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC=CC=C1C1=NN(C=CC=C2)C2=C1C1=CN=CN=C1 XHJFYSOTBLRNNZ-UHFFFAOYSA-N 0.000 description 1
- IMJBHWDMQIYCEI-UHFFFAOYSA-N 2-pyridin-1-ium-1-ylacetamide;chloride Chemical compound [Cl-].NC(=O)C[N+]1=CC=CC=C1 IMJBHWDMQIYCEI-UHFFFAOYSA-N 0.000 description 1
- UYWWLYCGNNCLKE-UHFFFAOYSA-N 2-pyridin-4-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=CC=NC=C1 UYWWLYCGNNCLKE-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- QDNNISJAQRZZQV-UHFFFAOYSA-N 2h-indolizin-3-one Chemical compound C1=CC=CN2C(=O)CC=C21 QDNNISJAQRZZQV-UHFFFAOYSA-N 0.000 description 1
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 description 1
- RDOAUPPSCNSYPM-UHFFFAOYSA-N 3,4-dihydropyridine Chemical compound C1CC=NC=C1 RDOAUPPSCNSYPM-UHFFFAOYSA-N 0.000 description 1
- DNNVRTZJRKIUFK-UHFFFAOYSA-N 3,4-dihydroquinoline Chemical compound C1=CC=C2N=CCCC2=C1 DNNVRTZJRKIUFK-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- GWEZCWNOQMSZNL-UHFFFAOYSA-N 3-(1-methylpyrazol-4-yl)-2-phenylpyrazolo[1,5-a]pyridine Chemical compound C1=NN(C)C=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 GWEZCWNOQMSZNL-UHFFFAOYSA-N 0.000 description 1
- RPVCHWPFZYRZTR-UHFFFAOYSA-N 3-(2-chloropyrimidin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine Chemical compound ClC1=NC=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 RPVCHWPFZYRZTR-UHFFFAOYSA-N 0.000 description 1
- WLTLYYUFJDEXGS-UHFFFAOYSA-N 3-(2-methoxypyrimidin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine Chemical compound COC1=NC=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 WLTLYYUFJDEXGS-UHFFFAOYSA-N 0.000 description 1
- VFBBQSWYRXPSPN-UHFFFAOYSA-N 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-sulfanylidenepropanoic acid Chemical compound N=1N2C=CC=CC2=C(CC(=S)C(=O)O)C=1C1=CC=CC=C1 VFBBQSWYRXPSPN-UHFFFAOYSA-N 0.000 description 1
- LJTKCQMPSRFHRP-UHFFFAOYSA-N 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 LJTKCQMPSRFHRP-UHFFFAOYSA-N 0.000 description 1
- FUYGKMCYVHSZHX-UHFFFAOYSA-N 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)prop-2-enal Chemical compound N=1N2C=CC=CC2=C(C=CC=O)C=1C1=CC=CC=C1 FUYGKMCYVHSZHX-UHFFFAOYSA-N 0.000 description 1
- IKEPFXODOUBXLD-UHFFFAOYSA-N 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)prop-2-ynoic acid Chemical compound N=1N2C=CC=CC2=C(C#CC(=O)O)C=1C1=CC=CC=C1 IKEPFXODOUBXLD-UHFFFAOYSA-N 0.000 description 1
- AZYGRFHDIALJQW-UHFFFAOYSA-N 3-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-4,5-dihydropyridazin-1-yl]propanoic acid Chemical compound C1CC(=O)N(CCC(=O)O)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 AZYGRFHDIALJQW-UHFFFAOYSA-N 0.000 description 1
- WJCZMNCEAUPPRZ-UHFFFAOYSA-N 3-[6-oxo-4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2,3-dihydropyridin-1-yl]propanoic acid Chemical compound O=C1N(CCC(=O)O)CCC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=C1 WJCZMNCEAUPPRZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical compound ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- MXDRPNGTQDRKQM-UHFFFAOYSA-N 3-methylpyridazine Chemical compound CC1=CC=CN=N1 MXDRPNGTQDRKQM-UHFFFAOYSA-N 0.000 description 1
- OVZHELCFKSFINS-UHFFFAOYSA-N 3h-1,3,4-thiadiazol-2-one Chemical compound O=C1NN=CS1 OVZHELCFKSFINS-UHFFFAOYSA-N 0.000 description 1
- ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 description 1
- BWULKIJKFXWPNX-UHFFFAOYSA-N 4,6-dihydro-1h-pyridazin-5-one Chemical compound O=C1CNN=CC1 BWULKIJKFXWPNX-UHFFFAOYSA-N 0.000 description 1
- XCJMJKKNVLJARI-UHFFFAOYSA-N 4,6-dihydro-1h-quinolin-5-one Chemical compound C1C=CNC2=C1C(=O)CC=C2 XCJMJKKNVLJARI-UHFFFAOYSA-N 0.000 description 1
- UCXMHNGRXVIVBI-UHFFFAOYSA-N 4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 UCXMHNGRXVIVBI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FKJPZJACCBMNKZ-UHFFFAOYSA-N 4-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]butanoic acid Chemical compound C1=CC(=O)N(CCCC(=O)O)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 FKJPZJACCBMNKZ-UHFFFAOYSA-N 0.000 description 1
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
- FXPASNUDLCLDPV-UHFFFAOYSA-N 4-oxo-4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)butanoic acid Chemical compound N=1N2C=CC=CC2=C(C(=O)CCC(=O)O)C=1C1=CC=CC=C1 FXPASNUDLCLDPV-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- PSBNJJIHAFQBRP-UHFFFAOYSA-N 4h-1,2,3-benzoxadiazol-5-one Chemical compound C1=CC(=O)CC2=C1ON=N2 PSBNJJIHAFQBRP-UHFFFAOYSA-N 0.000 description 1
- GRRBXRZINPHFGD-UHFFFAOYSA-N 4h-quinolin-3-one Chemical compound C1=CC=C2N=CC(=O)CC2=C1 GRRBXRZINPHFGD-UHFFFAOYSA-N 0.000 description 1
- NCCBLJPUWXBQNO-UHFFFAOYSA-N 5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1,2-dihydropyrazol-3-one Chemical compound N1C(O)=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 NCCBLJPUWXBQNO-UHFFFAOYSA-N 0.000 description 1
- NBXJVMHXOPVEPU-UHFFFAOYSA-N 5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=C1 NBXJVMHXOPVEPU-UHFFFAOYSA-N 0.000 description 1
- VYBDKDIRDBWXLN-UHFFFAOYSA-N 5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1h-pyrimidin-2-one Chemical compound N1C(=O)N=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=C1 VYBDKDIRDBWXLN-UHFFFAOYSA-N 0.000 description 1
- YYDULQPFPSZZGM-UHFFFAOYSA-N 5-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]pentanoic acid Chemical compound C1=CC(=O)N(CCCCC(=O)O)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 YYDULQPFPSZZGM-UHFFFAOYSA-N 0.000 description 1
- HMPUHXCGUHDVBI-UHFFFAOYSA-N 5-methyl-1,3,4-thiadiazol-2-amine Chemical compound CC1=NN=C(N)S1 HMPUHXCGUHDVBI-UHFFFAOYSA-N 0.000 description 1
- PXAOVKHVCWUUAJ-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1h-pyrimidin-2-one Chemical compound C1=CNC(=O)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 PXAOVKHVCWUUAJ-UHFFFAOYSA-N 0.000 description 1
- ATTQDJZYFIDUQX-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-propylpyridazin-3-one Chemical compound C1=CC(=O)N(CCC)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 ATTQDJZYFIDUQX-UHFFFAOYSA-N 0.000 description 1
- BENHIPXGILNAKH-UHFFFAOYSA-N 7h-1,2,3-benzothiadiazol-6-one Chemical compound C1=CC(=O)CC2=C1N=NS2 BENHIPXGILNAKH-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000028185 Angioedema Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 206010003178 Arterial thrombosis Diseases 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- ZKATXCJXOVXYDS-UHFFFAOYSA-N C1=C(O)N(CCC(=O)O)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 Chemical compound C1=C(O)N(CCC(=O)O)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 ZKATXCJXOVXYDS-UHFFFAOYSA-N 0.000 description 1
- TYXTXSRKBPOPOB-UHFFFAOYSA-N C1=CC=C(C=C1)C2=NN3C=CC=CC3=C2CCC(=O)O Chemical compound C1=CC=C(C=C1)C2=NN3C=CC=CC3=C2CCC(=O)O TYXTXSRKBPOPOB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000009447 Cardiac Edema Diseases 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010063412 Gestational oedema Diseases 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 206010019860 Hereditary angioedema Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 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 1
- 229940122199 Insulin secretagogue Drugs 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
- 208000025047 Non-histaminic angioedema Diseases 0.000 description 1
- FVGWXWZAADZZTB-UHFFFAOYSA-N O=C1C=CC=C2SC(C=CC=C3)=C3OC12 Chemical compound O=C1C=CC=C2SC(C=CC=C3)=C3OC12 FVGWXWZAADZZTB-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000002862 amidating effect Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 239000000883 anti-obesity agent Substances 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 229940125710 antiobesity agent Drugs 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 208000008784 apnea Diseases 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- DXZDEAJXVCLRLE-UHFFFAOYSA-N azepin-2-one Chemical compound O=C1C=CC=CC=N1 DXZDEAJXVCLRLE-UHFFFAOYSA-N 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 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
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 230000003177 cardiotonic effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- LYZCWDIVOAXKQP-UHFFFAOYSA-N diazinan-3-one Chemical compound O=C1CCCNN1 LYZCWDIVOAXKQP-UHFFFAOYSA-N 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- PYWUMVAFYODONJ-UHFFFAOYSA-N ethyl 2,3-dibromo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)propanoate Chemical compound N=1N2C=CC=CC2=C(C(Br)C(Br)C(=O)OCC)C=1C1=CC=CC=C1 PYWUMVAFYODONJ-UHFFFAOYSA-N 0.000 description 1
- AGZXFHRQPOCVTQ-UHFFFAOYSA-N ethyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-3h-pyridazine-2-carboxylate Chemical compound CCOC(=O)N1N=CC=CC1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 AGZXFHRQPOCVTQ-UHFFFAOYSA-N 0.000 description 1
- DXIJZWSZQSUCHY-UHFFFAOYSA-N ethyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)prop-2-enoate Chemical compound N=1N2C=CC=CC2=C(C=CC(=O)OCC)C=1C1=CC=CC=C1 DXIJZWSZQSUCHY-UHFFFAOYSA-N 0.000 description 1
- PMQPKSGXTXSZBT-UHFFFAOYSA-N ethyl 3-acetyl-4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-4h-pyridine-1-carboxylate Chemical compound CC(=O)C1=CN(C(=O)OCC)C=CC1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 PMQPKSGXTXSZBT-UHFFFAOYSA-N 0.000 description 1
- DCRXOQBBGWJBEW-UHFFFAOYSA-N ethyl 3-cyano-4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-4h-pyridine-1-carboxylate Chemical compound N#CC1=CN(C(=O)OCC)C=CC1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 DCRXOQBBGWJBEW-UHFFFAOYSA-N 0.000 description 1
- OFJMJGGAYZESPT-UHFFFAOYSA-N ethyl 4-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]butanoate Chemical compound C1=CC(=O)N(CCCC(=O)OCC)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 OFJMJGGAYZESPT-UHFFFAOYSA-N 0.000 description 1
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
- BYRQNMWKAABBSD-UHFFFAOYSA-N ethyl 5-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]pentanoate Chemical compound C1=CC(=O)N(CCCCC(=O)OCC)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 BYRQNMWKAABBSD-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- LYINKTVZUSKQEQ-UHFFFAOYSA-N furan-3-one Chemical compound O=C1COC=C1 LYINKTVZUSKQEQ-UHFFFAOYSA-N 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000001965 increasing effect Effects 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000015122 lemonade Nutrition 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 1
- KXPDXPNVLQGDEH-UHFFFAOYSA-N methyl 2-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]acetate Chemical compound C1=CC(=O)N(CC(=O)OC)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 KXPDXPNVLQGDEH-UHFFFAOYSA-N 0.000 description 1
- XVALKKNCQGFCBV-UHFFFAOYSA-N methyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)prop-2-ynoate Chemical compound N=1N2C=CC=CC2=C(C#CC(=O)OC)C=1C1=CC=CC=C1 XVALKKNCQGFCBV-UHFFFAOYSA-N 0.000 description 1
- NPTPWTCDNSNTNW-UHFFFAOYSA-N methyl 3-[2-oxo-4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=C1 NPTPWTCDNSNTNW-UHFFFAOYSA-N 0.000 description 1
- NMVUYNPMGMCYFW-UHFFFAOYSA-N methyl 3-[2-oxo-5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyrimidin-1-yl]propanoate Chemical compound C1=NC(=O)N(CCC(=O)OC)C=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 NMVUYNPMGMCYFW-UHFFFAOYSA-N 0.000 description 1
- JGRZHRFMEOZXRA-UHFFFAOYSA-N methyl 3-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]propanoate Chemical compound C1=CC(=O)N(CCC(=O)OC)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 JGRZHRFMEOZXRA-UHFFFAOYSA-N 0.000 description 1
- XVRPWIPZPDCHNB-UHFFFAOYSA-N methyl 3-[6-oxo-5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)N=CC=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 XVRPWIPZPDCHNB-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- VOVMMMQEDMGRSI-UHFFFAOYSA-N n-pentylhexan-1-amine Chemical compound CCCCCCNCCCCC VOVMMMQEDMGRSI-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- VACPZDQXUAOTFR-UHFFFAOYSA-N n-tert-butylbutan-1-amine Chemical compound CCCCNC(C)(C)C VACPZDQXUAOTFR-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 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
- 229940081066 picolinic acid Drugs 0.000 description 1
- RDNZDMDLRIQQAX-UHFFFAOYSA-N piperidine-2,4-dione Chemical compound O=C1CCNC(=O)C1 RDNZDMDLRIQQAX-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000000106 platelet aggregation inhibitor 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
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000003368 psychostimulant agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 description 1
- MYKHANQTTIRZJK-UHFFFAOYSA-N pyridazine-3,4-dione Chemical compound O=C1C=CN=NC1=O MYKHANQTTIRZJK-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008327 renal blood flow Effects 0.000 description 1
- 206010038464 renal hypertension Diseases 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HSBAPCKJUUSMLH-UHFFFAOYSA-N thiadiazol-4-one Chemical compound O=C1CSN=N1 HSBAPCKJUUSMLH-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- ATAMXDLUUTYFKT-UHFFFAOYSA-N thian-3-one Chemical compound O=C1CCCSC1 ATAMXDLUUTYFKT-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- VOBWLFNYOWWARN-UHFFFAOYSA-N thiophen-3-one Chemical compound O=C1CSC=C1 VOBWLFNYOWWARN-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8901423.7 | 1989-01-23 | ||
| GB898901423A GB8901423D0 (en) | 1989-01-23 | 1989-01-23 | Pyrazolopyridine compound and processes for preparation thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7064422A Division JPH0881465A (ja) | 1989-01-23 | 1995-03-23 | ピラゾロピリジン化合物の用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02243689A JPH02243689A (ja) | 1990-09-27 |
| JPH0794454B2 true JPH0794454B2 (ja) | 1995-10-11 |
Family
ID=10650453
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012995A Expired - Fee Related JPH0794454B2 (ja) | 1989-01-23 | 1990-01-22 | ピラゾロピリジン化合物およびその製造法 |
| JP7064422A Pending JPH0881465A (ja) | 1989-01-23 | 1995-03-23 | ピラゾロピリジン化合物の用途 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7064422A Pending JPH0881465A (ja) | 1989-01-23 | 1995-03-23 | ピラゾロピリジン化合物の用途 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4985444A (enExample) |
| EP (1) | EP0379979B1 (enExample) |
| JP (2) | JPH0794454B2 (enExample) |
| KR (1) | KR0159502B1 (enExample) |
| CN (1) | CN1031570C (enExample) |
| AT (1) | ATE150462T1 (enExample) |
| AU (1) | AU628913B2 (enExample) |
| CA (1) | CA2008263C (enExample) |
| DE (1) | DE69030206T2 (enExample) |
| DK (1) | DK0379979T3 (enExample) |
| ES (1) | ES2098229T3 (enExample) |
| FI (1) | FI96205C (enExample) |
| GB (1) | GB8901423D0 (enExample) |
| GR (1) | GR3023219T3 (enExample) |
| HU (2) | HUT53368A (enExample) |
| IE (1) | IE900161L (enExample) |
| IL (1) | IL93050A (enExample) |
| NO (1) | NO176356C (enExample) |
| PH (1) | PH30968A (enExample) |
| PT (1) | PT92935B (enExample) |
| RU (1) | RU2007403C1 (enExample) |
| UA (1) | UA43821C2 (enExample) |
| ZA (1) | ZA90200B (enExample) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5155114A (en) * | 1989-01-23 | 1992-10-13 | Fujisawa Pharmaceutical Company, Ltd. | Method of treatment using pyrazolopyridine compound |
| US5338743A (en) * | 1988-06-06 | 1994-08-16 | Fujisawa Pharmaceutical Co., Ltd. | New use of the adenosine antagonist |
| GB9015764D0 (en) * | 1990-07-18 | 1990-09-05 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
| GB9107513D0 (en) * | 1991-04-10 | 1991-05-29 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
| WO1993025205A1 (en) * | 1992-06-10 | 1993-12-23 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compounds for the treatment of anemia |
| WO1995007282A1 (en) * | 1993-09-06 | 1995-03-16 | Kyowa Hakko Kogyo Co., Ltd. | Depression remedy |
| EP0737193A1 (en) * | 1993-12-29 | 1996-10-16 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine adenosine antagonists |
| US5646156A (en) * | 1994-04-25 | 1997-07-08 | Merck & Co., Inc. | Inhibition of eosinophil activation through A3 adenosine receptor antagonism |
| RU2172742C2 (ru) * | 1995-12-28 | 2001-08-27 | Пфайзер Инк. | Стимуляторы секреции гормона роста |
| WO1997040047A1 (en) * | 1996-04-25 | 1997-10-30 | Fujisawa Pharmaceutical Co., Ltd. | Preventives and remedies for ischemic intestinal lesion and ileus |
| AUPO111096A0 (en) * | 1996-07-18 | 1996-08-08 | Fujisawa Pharmaceutical Co., Ltd. | New compound |
| CN1083841C (zh) * | 1996-10-04 | 2002-05-01 | 杏林制药株式会社 | 吡唑并吡啶基哒嗪酮衍生物及其制备方法 |
| EP0972525A4 (en) * | 1997-03-18 | 2000-11-29 | Fujisawa Pharmaceutical Co | PREVENTIVE AND HEALING AGENTS AGAINST HYPERPHOSPHATEMIA |
| ATE281458T1 (de) * | 1997-09-05 | 2004-11-15 | Glaxo Group Ltd | Pharmazeutische zusammensetzung, enthaltend 2,3- diaryl-pyrazolo(1,5-b)pyridazin derivate |
| EP1084710B1 (en) * | 1998-06-01 | 2006-10-18 | Astellas Pharma Inc. | Adenosine a1 antagonists for male sterility |
| WO1999067239A1 (en) * | 1998-06-22 | 1999-12-29 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compounds and medicinal uses thereof |
| AUPP672198A0 (en) * | 1998-10-23 | 1998-11-19 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
| US7223772B1 (en) | 1998-11-03 | 2007-05-29 | Smithkline Beecham Corporation | Pyrazolopyridine derivatives as selective cox-2 inhibitors |
| US6541634B2 (en) | 1999-02-26 | 2003-04-01 | Pfizer Inc. | Process for preparing growth hormone secretagogues |
| EP1157025B1 (en) | 1999-02-27 | 2004-03-10 | Glaxo Group Limited | Pyrazolopyridines |
| US20040152659A1 (en) * | 1999-05-12 | 2004-08-05 | Fujisawa Pharmaceutical Co. Ltd. | Method for the treatment of parkinson's disease comprising administering an A1A2a receptor dual antagonist |
| AUPQ441499A0 (en) * | 1999-12-02 | 2000-01-06 | Fujisawa Pharmaceutical Co., Ltd. | Novel compound |
| GB9930358D0 (en) | 1999-12-22 | 2000-02-09 | Glaxo Group Ltd | Process for the preparation of chemical compounds |
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| AUPQ969800A0 (en) * | 2000-08-28 | 2000-09-21 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
| AU2002239348A1 (en) * | 2000-12-15 | 2002-06-24 | Glaxo Group Limited | Pyrazolopyridine derivatives |
| ATE301653T1 (de) * | 2000-12-15 | 2005-08-15 | Glaxo Group Ltd | Pyrazolopyridine |
| ATE416175T1 (de) * | 2001-02-20 | 2008-12-15 | Astrazeneca Ab | 2-arylaminopyrimidine zur behandlung von mit gsk3 in zusammenhang stehenden erkrankungen |
| DE60201074T2 (de) * | 2001-03-08 | 2005-09-15 | Smithkline Beecham Corp. | Pyrazolopyridinderivate |
| JP2004525150A (ja) * | 2001-03-30 | 2004-08-19 | スミスクライン ビーチャム コーポレーション | 治療用化合物としてのピラゾロピリジン類の使用 |
| WO2002078700A1 (en) * | 2001-03-30 | 2002-10-10 | Smithkline Beecham Corporation | Pyralopyridines, process for their preparation and use as therapteutic compounds |
| ATE332301T1 (de) * | 2001-04-10 | 2006-07-15 | Smithkline Beecham Corp | Antivirale pyrazolopyridin verbindungen |
| CA2443802C (en) * | 2001-04-27 | 2010-04-13 | Eisai Co., Ltd. | Pyrazolo[1,5-a]pyridines and medicines containing the same |
| EP1385847B1 (en) * | 2001-04-27 | 2005-06-01 | SmithKline Beecham Corporation | Pyrazolo[1,5-a]pyridine derivatives |
| US6756498B2 (en) | 2001-04-27 | 2004-06-29 | Smithkline Beecham Corporation | Process for the preparation of chemical compounds |
| AUPR548601A0 (en) * | 2001-06-06 | 2001-06-28 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyrazinecompound and pharmaceutical use thereof |
| PL366827A1 (en) * | 2001-06-21 | 2005-02-07 | Smithkline Beecham Corporation | Imidazo[1,2-a]pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
| DE60220525T2 (de) * | 2001-09-07 | 2008-02-07 | Smithkline Beecham Corp. | Pyrazolo-pyridine für die behandlung von herpes-ansteckungen |
| ATE326466T1 (de) * | 2001-10-05 | 2006-06-15 | Smithkline Beecham Corp | Imidazopyridinderivate zur verwendung bei der behandlung von herpes-vireninfektion |
| AUPR916301A0 (en) * | 2001-11-29 | 2001-12-20 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
| ES2292839T3 (es) * | 2001-12-11 | 2008-03-16 | Smithkline Beecham Corporation | Derivados de pirazolo-piridina como agentes contra el herpes. |
| US20040021778A1 (en) * | 2002-08-05 | 2004-02-05 | Oldani Jerome L. | Security system with remote access and control |
| GB0218876D0 (en) * | 2002-08-13 | 2002-09-25 | Merck Sharp & Dohme | Therapeutic agents |
| JP2006504728A (ja) * | 2002-10-03 | 2006-02-09 | スミスクライン ビーチャム コーポレーション | ピラソロピリジン誘導体系治療用化合物 |
| BRPI0712381A2 (pt) * | 2006-06-06 | 2012-07-10 | Avigen Inc | compostos de pirazolo[1,5-a]piridina substituìda e seus métodos de uso |
| KR100809368B1 (ko) * | 2006-08-09 | 2008-03-05 | 한국과학기술원 | 성대파를 이용한 음색 변환 시스템 |
| RU2394034C2 (ru) * | 2007-04-26 | 2010-07-10 | Учреждение Российской академии медицинских наук Научно-исследовательский институт фармакологии имени В.В. Закусова РАМН | ПРОИЗВОДНЫЕ 4,6-ДИМЕТИЛ-2,3-ДИГИДРО-1Н-ПИРАЗОЛО[4,3-c]ПИРИДИН-3-ОНОВ И ЭФИРЫ 2,6-ДИМЕТИЛ-4-ФЕНИЛ-ГИДРАЗИНОНИКОТИНОВЫХ КИСЛОТ В КАЧЕСТВЕ ПРОМЕЖУТОЧНЫХ ПРОДУКТОВ ДЛЯ ИХ СИНТЕЗА, ОБЛАДАЮЩИЕ АНТИДЕПРЕССАНТНОЙ И АНКСИОЛИТИЧЕСКОЙ АКТИВНОСТЬЮ |
| ES2396126T3 (es) | 2008-04-15 | 2013-02-19 | Eisai R&D Management Co., Ltd. | Compuesto de 3-fenilpirazol[5,1-b]tiazol |
| TW201102387A (en) * | 2009-06-08 | 2011-01-16 | Medicinova Inc | Substituted pyrazolo[1,5-a]pyridine compounds having multi-target activity |
| JPWO2011043387A1 (ja) * | 2009-10-08 | 2013-03-04 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピラゾロオキサゾール化合物 |
| AR078521A1 (es) * | 2009-10-08 | 2011-11-16 | Eisai R&D Man Co Ltd | Compuesto pirazolotiazol |
| AU2010331175B2 (en) * | 2009-12-18 | 2014-08-28 | Mitsubishi Tanabe Pharma Corporation | Novel antiplatelet agent |
| WO2013163241A1 (en) | 2012-04-26 | 2013-10-31 | Bristol-Myers Squibb Company | Imidazothiadiazole and imidazopyridazine derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| TWI572605B (zh) | 2012-04-26 | 2017-03-01 | 必治妥美雅史谷比公司 | 血小板聚集之抑制劑 |
| CN104540835B (zh) | 2012-04-26 | 2017-08-08 | 百时美施贵宝公司 | 用于治疗血小板聚集的作为蛋白酶激活受体4(par4)抑制剂的咪唑并噻二唑衍生物 |
| US9572528B1 (en) | 2012-08-06 | 2017-02-21 | Los Angeles Biomedical Research Insitute at Harbor-UCLA Medical Center | Monitor for SIDS research and prevention |
| WO2014192294A1 (en) * | 2013-05-28 | 2014-12-04 | Raqualia Pharma Inc. | Polymorph forms |
| US9617279B1 (en) | 2014-06-24 | 2017-04-11 | Bristol-Myers Squibb Company | Imidazooxadiazole compounds |
| US9598419B1 (en) | 2014-06-24 | 2017-03-21 | Universite De Montreal | Imidazotriazine and imidazodiazine compounds |
| US9873695B2 (en) * | 2014-08-05 | 2018-01-23 | Raqualia Pharma Inc. | Serine derivatives as ghrelin receptor agonists |
| EP3941475A4 (en) * | 2019-03-20 | 2023-01-25 | Goldfinch Bio, Inc. | PYRIDAZINONES AND METHODS OF USE THEREOF |
| WO2022071777A1 (ko) * | 2020-09-29 | 2022-04-07 | 연세대학교 산학협력단 | 호흡기 질환의 예방 또는 치료용 조성물 및 예방 또는 치료 방법 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5154583A (en) * | 1974-11-01 | 1976-05-13 | Kyorin Seiyaku Kk | Shinkipirazoro * 1 55a * pirijinjudotaino seizoho |
| AU556031B2 (en) * | 1982-06-16 | 1986-10-16 | May And Baker Ltd. | 3-(n,n-dimethylcarbamoyl)pyrazolo(1,5-alpha)-pyridine |
| FR2601368B1 (fr) * | 1986-07-08 | 1989-04-07 | Synthelabo | Derives de nitrofuranne, leur preparation et leur application en therapeutique. |
| JPS63135381A (ja) * | 1986-11-26 | 1988-06-07 | Kyorin Pharmaceut Co Ltd | 多剤耐性癌細胞に対する感受性増強剤及びその製造方法 |
| DE3710937A1 (de) * | 1987-04-01 | 1988-10-13 | Boehringer Mannheim Gmbh | Chromogene verbindungen, ihre herstellung und verwendung als enzymsubstrate |
| US4925849A (en) * | 1987-06-15 | 1990-05-15 | Fujisawa Pharmaceutical Company, Ltd. | Pharmaceutically useful pyrazolopyridines |
-
1989
- 1989-01-23 GB GB898901423A patent/GB8901423D0/en active Pending
-
1990
- 1990-01-09 PH PH39909A patent/PH30968A/en unknown
- 1990-01-11 ZA ZA90200A patent/ZA90200B/xx unknown
- 1990-01-14 IL IL9305090A patent/IL93050A/en not_active IP Right Cessation
- 1990-01-15 IE IE900161A patent/IE900161L/xx not_active Application Discontinuation
- 1990-01-18 US US07/466,929 patent/US4985444A/en not_active Expired - Lifetime
- 1990-01-19 DK DK90101042.1T patent/DK0379979T3/da active
- 1990-01-19 EP EP90101042A patent/EP0379979B1/en not_active Expired - Lifetime
- 1990-01-19 AT AT90101042T patent/ATE150462T1/de not_active IP Right Cessation
- 1990-01-19 DE DE69030206T patent/DE69030206T2/de not_active Expired - Fee Related
- 1990-01-19 ES ES90101042T patent/ES2098229T3/es not_active Expired - Lifetime
- 1990-01-19 FI FI900307A patent/FI96205C/fi not_active IP Right Cessation
- 1990-01-22 CA CA002008263A patent/CA2008263C/en not_active Expired - Fee Related
- 1990-01-22 KR KR1019900000690A patent/KR0159502B1/ko not_active Expired - Fee Related
- 1990-01-22 HU HU90228A patent/HUT53368A/hu unknown
- 1990-01-22 RU SU904742944A patent/RU2007403C1/ru not_active IP Right Cessation
- 1990-01-22 NO NO900306A patent/NO176356C/no not_active IP Right Cessation
- 1990-01-22 JP JP2012995A patent/JPH0794454B2/ja not_active Expired - Fee Related
- 1990-01-23 CN CN90100900A patent/CN1031570C/zh not_active Expired - Fee Related
- 1990-01-23 PT PT92935A patent/PT92935B/pt not_active IP Right Cessation
- 1990-01-23 AU AU48696/90A patent/AU628913B2/en not_active Ceased
-
1993
- 1993-06-18 UA UA93002311A patent/UA43821C2/uk unknown
-
1995
- 1995-03-23 JP JP7064422A patent/JPH0881465A/ja active Pending
- 1995-06-22 HU HU95P/P00351P patent/HU211684A9/hu unknown
-
1997
- 1997-04-22 GR GR970400879T patent/GR3023219T3/el unknown
Non-Patent Citations (4)
| Title |
|---|
| ＡｎｔｉｖｉｖａｌＲｅｓ．，２〔６〕，（１９８２），ＰＰ．３１９−３３０ |
| Ｊ．Ｃｈｅｍ．Ｓｏｃ．ＰｅｒｋｉｎＴｒａｎｓ．１，１９７４，ＰＰ．１６８４−１６８６ |
| Ｊ．Ｍｅｄ．Ｃｈｅｍ．，２７〔５〕，（１９８４），ＰＰ．６８０−６８４ |
| Ｊ．Ｍｅｄ．Ｃｈｅｍ．，２７〔８〕，（１９８４），ＰＰ．１０４４−１０４７ |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0794454B2 (ja) | ピラゾロピリジン化合物およびその製造法 | |
| US5155114A (en) | Method of treatment using pyrazolopyridine compound | |
| US6335336B1 (en) | 3(5)-Heteroaryl substituted pyrazoles as p38 kinase inhibitors | |
| US5932576A (en) | 3(5)-heteroaryl substituted pyrazoles as p38 kinase inhibitors | |
| EP0370381B1 (en) | 2(1H)-quinolinone compounds, processes for the preparation thereof and pharmaceutical composition comprising the same | |
| US20090012103A1 (en) | Substituted heterocyclic compounds | |
| US20070043001A1 (en) | Inhibitors of akt activity | |
| JP2008524339A (ja) | Ａｋｔ活性のインヒビター | |
| WO2002018382A1 (en) | Pyrazolopyridine compound and pharmaceutical use thereof | |
| TW201132642A (en) | Diaza-spiro[5.5]undecanes | |
| NZ543287A (en) | Benzoxazinyl-amidocyclopentyl-heterocyclic modulators of chemokine receptors | |
| JP2004512323A (ja) | Ｃｃｒ５ケモカイン受容体活性のピロリジンモジュレーター | |
| US20040067955A1 (en) | Pyridazinone compound and pharmaceutical use thereof | |
| TWI642668B (zh) | 新穎３，４－二氫－２ｈ－異喹啉－１－酮及２，３－二氫異吲哚－１－酮化合物 | |
| JPH11501926A (ja) | ６−アリールピラゾロ［３，４−ｄ］ピリミジン−４−オン、並びにその組成物及び使用法 | |
| JP2001517666A (ja) | チアゾール誘導体 | |
| WO2004016605A1 (en) | 2-aminopyrimidine derivatives as adenosine a1 and a2a receptor antagonists | |
| WO2016107848A1 (en) | New benzimidazole derivatives as antihistamine agents | |
| EP0553682A1 (en) | Imidazo 4,5-b pyridine derivatives as Angiotensin II antagonists | |
| KR100309215B1 (ko) | 항정신병제로서의피리딘이미닐-1,2-벤즈이속사졸및-벤즈이소티아졸 | |
| JP5113751B2 (ja) | ｐ３８キナーゼ阻害剤として有用な二環性複素環化合物 | |
| JP2883995B2 (ja) | ピペリジン誘導体及びその製造中間体 | |
| JP2994702B2 (ja) | 縮合トリアゾール誘導体 | |
| WO1999024424A1 (en) | Pyrazole compounds and medicinal use thereof | |
| OA16796A (en) | Fused Benzoxazepinones as Ion channel modulators. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |