IL98872A - 6-(2-arylpyrazolo [1, 5-a] pyridin-3-YL 2,3-dihydropyridazin-3-one derivatives processes for the preparation thereof and pharmaceutical compositions containing them - Google Patents

6-(2-arylpyrazolo [1, 5-a] pyridin-3-YL 2,3-dihydropyridazin-3-one derivatives processes for the preparation thereof and pharmaceutical compositions containing them

Info

Publication number: IL98872A
Authority: IL; Israel
Prior art keywords: alkyl; compound; salt; alkylamino; formula
Prior art date: 1990-07-18

Application number

IL9887291A

Other languages

English (en)

Other versions

IL98872A0 (en

Inventor

Youichi Shiokawa

Atsushi Akahane

Hirohito Katayama

Takafumi Mitsunaga

Original Assignee

Fujisawa Pharmaceutical Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-07-18

Filing date

1991-07-17

Publication date

1996-12-05

1991-07-17 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

1992-07-15 Publication of IL98872A0 publication Critical patent/IL98872A0/xx

1996-12-05 Publication of IL98872A publication Critical patent/IL98872A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
238000000034 method Methods 0.000 title abstract description 30
230000008569 process Effects 0.000 title abstract description 25
238000002360 preparation method Methods 0.000 title abstract description 24
BOUGPDHDAYIVND-UHFFFAOYSA-N 2-pyridin-3-ylpyridazin-3-one Chemical class O=C1C=CC=NN1C1=CC=CN=C1 BOUGPDHDAYIVND-UHFFFAOYSA-N 0.000 title description 2
-1 pyrazolopyridine compound Chemical class 0.000 claims abstract description 282
125000000217 alkyl group Chemical group 0.000 claims abstract description 157
150000003839 salts Chemical class 0.000 claims abstract description 114
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 64
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 49
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 38
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 38
125000001424 substituent group Chemical group 0.000 claims abstract description 32
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 24
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
239000004480 active ingredient Substances 0.000 claims abstract description 5
239000003937 drug carrier Substances 0.000 claims abstract description 4
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 121
125000003831 tetrazolyl group Chemical group 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 9
125000002757 morpholinyl group Chemical group 0.000 claims description 8
125000005936 piperidyl group Chemical group 0.000 claims description 8
206010030113 Oedema Diseases 0.000 claims description 7
238000003379 elimination reaction Methods 0.000 claims description 6
231100000417 nephrotoxicity Toxicity 0.000 claims description 6
125000000160 oxazolidinyl group Chemical group 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
208000001647 Renal Insufficiency Diseases 0.000 claims description 5
201000006370 kidney failure Diseases 0.000 claims description 5
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
206010033645 Pancreatitis Diseases 0.000 claims description 4
125000005972 dihydrochromenyl group Chemical group 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
206010002383 Angina Pectoris Diseases 0.000 claims description 3
208000000575 Arteriosclerosis Obliterans Diseases 0.000 claims description 3
239000004593 Epoxy Substances 0.000 claims description 3
201000005569 Gout Diseases 0.000 claims description 3
206010019280 Heart failures Diseases 0.000 claims description 3
206010020772 Hypertension Diseases 0.000 claims description 3
201000001431 Hyperuricemia Diseases 0.000 claims description 3
206010061216 Infarction Diseases 0.000 claims description 3
208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 3
208000007536 Thrombosis Diseases 0.000 claims description 3
208000032109 Transient ischaemic attack Diseases 0.000 claims description 3
206010008118 cerebral infarction Diseases 0.000 claims description 3
208000026106 cerebrovascular disease Diseases 0.000 claims description 3
238000007333 cyanation reaction Methods 0.000 claims description 3
238000005755 formation reaction Methods 0.000 claims description 3
230000007574 infarction Effects 0.000 claims description 3
201000005060 thrombophlebitis Diseases 0.000 claims description 3
201000010875 transient cerebral ischemia Diseases 0.000 claims description 3
208000020401 Depressive disease Diseases 0.000 claims description 2
206010029164 Nephrotic syndrome Diseases 0.000 claims description 2
208000008589 Obesity Diseases 0.000 claims description 2
208000025865 Ulcer Diseases 0.000 claims description 2
208000006673 asthma Diseases 0.000 claims description 2
238000006297 dehydration reaction Methods 0.000 claims description 2
206010012601 diabetes mellitus Diseases 0.000 claims description 2
208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 2
208000024714 major depressive disease Diseases 0.000 claims description 2
201000003995 melancholia Diseases 0.000 claims description 2
201000008383 nephritis Diseases 0.000 claims description 2
208000009928 nephrosis Diseases 0.000 claims description 2
231100001027 nephrosis Toxicity 0.000 claims description 2
235000020824 obesity Nutrition 0.000 claims description 2
239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 2
231100000397 ulcer Toxicity 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
PSDPQRITXCPIJU-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-(2-piperidin-1-ylethyl)pyridazin-3-one Chemical compound O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCN1CCCCC1 PSDPQRITXCPIJU-UHFFFAOYSA-N 0.000 claims 1
206010062016 Immunosuppression Diseases 0.000 claims 1
206010061876 Obstruction Diseases 0.000 claims 1
230000001506 immunosuppresive effect Effects 0.000 claims 1
125000004104 aryloxy group Chemical group 0.000 abstract description 13
125000003118 aryl group Chemical group 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
238000006243 chemical reaction Methods 0.000 description 57
239000000203 mixture Substances 0.000 description 50
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
101150041968 CDC13 gene Proteins 0.000 description 42
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
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 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
239000011575 calcium Substances 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
239000000243 solution Substances 0.000 description 21
239000002904 solvent Substances 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
239000002253 acid Substances 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
229940079593 drug Drugs 0.000 description 18
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
125000004433 nitrogen atom Chemical group N* 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
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 12
239000007864 aqueous solution Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
125000002911 monocyclic heterocycle group Chemical group 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000011780 sodium chloride Substances 0.000 description 11
238000004440 column chromatography Methods 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
125000004430 oxygen atom Chemical group O* 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
230000009471 action Effects 0.000 description 7
239000003480 eluent Substances 0.000 description 7
239000000284 extract Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000002126 C01EB10 - Adenosine Substances 0.000 description 6
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
229960005305 adenosine Drugs 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
125000005236 alkanoylamino group Chemical group 0.000 description 6
239000000538 analytical sample Substances 0.000 description 6
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
230000002411 adverse Effects 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
125000004043 oxo group Chemical group O=* 0.000 description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
125000004423 acyloxy group Chemical group 0.000 description 4
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 4
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910052697 platinum Inorganic materials 0.000 description 4
238000000746 purification Methods 0.000 description 4
230000009467 reduction Effects 0.000 description 4
238000010998 test method Methods 0.000 description 4
210000002700 urine Anatomy 0.000 description 4
238000010792 warming Methods 0.000 description 4
238000005303 weighing Methods 0.000 description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 3
PANHWSAHZYVEIV-UHFFFAOYSA-N 2-[2-[(2-hydroxy-3-naphthalen-1-yloxypropyl)amino]ethyl]-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C=1C=CC2=CC=CC=C2C=1OCC(O)CNCCN(C(C=C1)=O)N=C1C(=C1C=CC=CN1N=1)C=1C1=CC=CC=C1 PANHWSAHZYVEIV-UHFFFAOYSA-N 0.000 description 3
WEMSWDZYORDDGX-UHFFFAOYSA-N 2-[2-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCN(C(C=C1)=O)N=C1C(=C1C=CC=CN1N=1)C=1C1=CC=CC=C1 WEMSWDZYORDDGX-UHFFFAOYSA-N 0.000 description 3
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
125000004442 acylamino group Chemical group 0.000 description 3
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 3
125000004391 aryl sulfonyl group Chemical group 0.000 description 3
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
230000001882 diuretic effect Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000010828 elution Methods 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000007918 intramuscular administration Methods 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
230000008327 renal blood flow Effects 0.000 description 3
239000000523 sample Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
KJYGNRVNNRBBRM-UHFFFAOYSA-N 2-(2-aminoethyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCN)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 KJYGNRVNNRBBRM-UHFFFAOYSA-N 0.000 description 2
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 2
UJEQVJCMGDIOJH-UHFFFAOYSA-N 2-(2-morpholin-4-ylethyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one;hydrochloride Chemical compound Cl.O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCN1CCOCC1 UJEQVJCMGDIOJH-UHFFFAOYSA-N 0.000 description 2
HZWFFIYCXGUWSJ-UHFFFAOYSA-N 2-(5-bromopentyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCCCCBr)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 HZWFFIYCXGUWSJ-UHFFFAOYSA-N 0.000 description 2
IBTQITCWKCLLSR-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one;hydrochloride Chemical compound Cl.C1=CC(=O)N(CCN(C)C)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 IBTQITCWKCLLSR-UHFFFAOYSA-N 0.000 description 2
LMFNUFIZISKISG-UHFFFAOYSA-N 2-[2-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]ethylamino]acetic acid Chemical compound C1=CC(=O)N(CCNCC(=O)O)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 LMFNUFIZISKISG-UHFFFAOYSA-N 0.000 description 2
NPZKSOALPIMAAS-UHFFFAOYSA-N 2-[3-(dimethylamino)propyl]-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one;hydrochloride Chemical compound Cl.C1=CC(=O)N(CCCN(C)C)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 NPZKSOALPIMAAS-UHFFFAOYSA-N 0.000 description 2
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
ZICCKDUVBPQRQT-UHFFFAOYSA-N 3-(benzenesulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2C=CC=CC=2)=N1 ZICCKDUVBPQRQT-UHFFFAOYSA-N 0.000 description 2
QBIDZPOGVREMKV-UHFFFAOYSA-N 3-(benzenesulfonyl)-6-(2-phenylethynyl)pyridazine Chemical compound C=1C=C(C#CC=2C=CC=CC=2)N=NC=1S(=O)(=O)C1=CC=CC=C1 QBIDZPOGVREMKV-UHFFFAOYSA-N 0.000 description 2
KTLLKWGXFDYVFU-UHFFFAOYSA-N 3-(benzenesulfonyl)-6-chloropyridazine Chemical compound N1=NC(Cl)=CC=C1S(=O)(=O)C1=CC=CC=C1 KTLLKWGXFDYVFU-UHFFFAOYSA-N 0.000 description 2
XKJKASFWVGAEQV-UHFFFAOYSA-N 3-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]propanenitrile Chemical compound N#CCCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 XKJKASFWVGAEQV-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
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 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
150000001450 anions Chemical class 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
230000000767 anti-ulcer Effects 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
229940077388 benzenesulfonate Drugs 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000003792 electrolyte Substances 0.000 description 2
LSZAMBPIPIZBSI-UHFFFAOYSA-N ethyl 2-[2-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]ethylamino]acetate Chemical compound C1=CC(=O)N(CCNCC(=O)OCC)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 LSZAMBPIPIZBSI-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
230000000297 inotrophic effect Effects 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
230000003907 kidney function Effects 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 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
150000007522 mineralic acids Chemical class 0.000 description 2
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
230000002265 prevention Effects 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
230000002685 pulmonary effect Effects 0.000 description 2
125000002098 pyridazinyl group Chemical group 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
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 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
125000005270 trialkylamine 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
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000002485 urinary effect Effects 0.000 description 2
230000000304 vasodilatating effect Effects 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-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
IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 1
ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 1
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
125000005978 1-naphthyloxy group Chemical group 0.000 description 1
IVLVVPKOTXLEBE-UHFFFAOYSA-N 11-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]undecanenitrile Chemical compound N#CCCCCCCCCCCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 IVLVVPKOTXLEBE-UHFFFAOYSA-N 0.000 description 1
ZCKKVIUQAITWBR-UHFFFAOYSA-N 13-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]tridecanenitrile Chemical compound N#CCCCCCCCCCCCCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 ZCKKVIUQAITWBR-UHFFFAOYSA-N 0.000 description 1
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
AMOYMEBHYUTMKJ-UHFFFAOYSA-N 2-(2-phenylethoxy)ethylbenzene Chemical compound C=1C=CC=CC=1CCOCCC1=CC=CC=C1 AMOYMEBHYUTMKJ-UHFFFAOYSA-N 0.000 description 1
AVUBUYOAHUEHKQ-UHFFFAOYSA-N 2-(4-hydroxybutyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCCCO)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 AVUBUYOAHUEHKQ-UHFFFAOYSA-N 0.000 description 1
OQIXCPMVURANMG-UHFFFAOYSA-N 2-(6-bromohexyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCCCCCBr)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 OQIXCPMVURANMG-UHFFFAOYSA-N 0.000 description 1
AHDMNDHKWDMCQI-UHFFFAOYSA-N 2-(7-bromoheptyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCCCCCCBr)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 AHDMNDHKWDMCQI-UHFFFAOYSA-N 0.000 description 1
VWDFVZXCKVQGLT-UHFFFAOYSA-N 2-(8-bromooctyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCCCCCCCBr)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 VWDFVZXCKVQGLT-UHFFFAOYSA-N 0.000 description 1
IBPQQQLVCSCQCO-UHFFFAOYSA-N 2-(9-bromononyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCCCCCCCCBr)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 IBPQQQLVCSCQCO-UHFFFAOYSA-N 0.000 description 1
SLLFXAQRYSLGTO-UHFFFAOYSA-N 2-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one;dihydrochloride Chemical compound Cl.Cl.C1CN(CCO)CCN1CCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 SLLFXAQRYSLGTO-UHFFFAOYSA-N 0.000 description 1
DUXWHBUCRKLORH-UHFFFAOYSA-N 2-[4-(dimethylamino)butyl]-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one;hydrochloride Chemical compound Cl.C1=CC(=O)N(CCCCN(C)C)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 DUXWHBUCRKLORH-UHFFFAOYSA-N 0.000 description 1
SWIQMMSWUNBSBK-UHFFFAOYSA-N 2-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]acetonitrile Chemical compound N#CCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 SWIQMMSWUNBSBK-UHFFFAOYSA-N 0.000 description 1
BYWHPONVDSUGSD-UHFFFAOYSA-N 2-benzyl-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CC1=CC=CC=C1 BYWHPONVDSUGSD-UHFFFAOYSA-N 0.000 description 1
RGHQKFQZGLKBCF-UHFFFAOYSA-N 2-bromoethyl acetate Chemical compound CC(=O)OCCBr RGHQKFQZGLKBCF-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
PJWIMXNLJDEBAN-UHFFFAOYSA-N 2-ethenyl-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(C=C)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 PJWIMXNLJDEBAN-UHFFFAOYSA-N 0.000 description 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
125000005979 2-naphthyloxy group Chemical group 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 1
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 1
JOGQVWVSTWLLPP-UHFFFAOYSA-N 3-[6-(benzenesulfonyl)pyridazin-3-yl]-2-phenylpyrazolo[1,5-a]pyridine Chemical compound C=1C=C(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)N=NC=1S(=O)(=O)C1=CC=CC=C1 JOGQVWVSTWLLPP-UHFFFAOYSA-N 0.000 description 1
125000006041 3-hexenyl group Chemical group 0.000 description 1
PNGOLQCFBYCCIH-UHFFFAOYSA-N 3-hydroxy-2,2-dimethyl-4-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]-3,4-dihydrochromene-6-carbonitrile Chemical compound OC1C(C)(C)OC2=CC=C(C#N)C=C2C1N(C(C=C1)=O)N=C1C(=C1C=CC=CN1N=1)C=1C1=CC=CC=C1 PNGOLQCFBYCCIH-UHFFFAOYSA-N 0.000 description 1
WLDMPODMCFGWAA-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound C1CCCC2C(=O)NC(=O)C21 WLDMPODMCFGWAA-UHFFFAOYSA-N 0.000 description 1
NBJHDLKSWUDGJG-UHFFFAOYSA-N 4-(2-chloroethyl)morpholin-4-ium;chloride Chemical compound Cl.ClCCN1CCOCC1 NBJHDLKSWUDGJG-UHFFFAOYSA-N 0.000 description 1
HESXSEUFTVRQRX-UHFFFAOYSA-N 4-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]butanenitrile Chemical compound N#CCCCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 HESXSEUFTVRQRX-UHFFFAOYSA-N 0.000 description 1
RRRSFICTRVDLJE-UHFFFAOYSA-N 4-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]butyl acetate Chemical compound C1=CC(=O)N(CCCCOC(=O)C)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 RRRSFICTRVDLJE-UHFFFAOYSA-N 0.000 description 1
PYLDCZJUHYVOAF-UHFFFAOYSA-N 4-chlorobutyl acetate Chemical compound CC(=O)OCCCCCl PYLDCZJUHYVOAF-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
PUTCMHMNFHUZIP-UHFFFAOYSA-N 5-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]pentanenitrile Chemical compound N#CCCCCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 PUTCMHMNFHUZIP-UHFFFAOYSA-N 0.000 description 1
NLWRZIKZMZNEEI-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-(2-piperidin-1-ylethyl)pyridazin-3-one;hydrochloride Chemical compound Cl.O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCN1CCCCC1 NLWRZIKZMZNEEI-UHFFFAOYSA-N 0.000 description 1
GNGROEMMFHFCKH-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-[10-(2h-tetrazol-5-yl)decyl]pyridazin-3-one Chemical compound O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCCCCCCCCCC=1N=NNN=1 GNGROEMMFHFCKH-UHFFFAOYSA-N 0.000 description 1
BMNFTDFJUYYQHH-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-[2-(2h-tetrazol-5-yl)ethyl]pyridazin-3-one Chemical compound O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCC1=NN=NN1 BMNFTDFJUYYQHH-UHFFFAOYSA-N 0.000 description 1
VUUKOYNUOVNRMJ-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-[4-(2h-tetrazol-5-yl)butyl]pyridazin-3-one Chemical compound O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCCCC=1N=NNN=1 VUUKOYNUOVNRMJ-UHFFFAOYSA-N 0.000 description 1
YUUOTQUHLZMWSA-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-[5-(2h-tetrazol-5-yl)pentyl]pyridazin-3-one Chemical compound O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCCCCC1=NN=NN1 YUUOTQUHLZMWSA-UHFFFAOYSA-N 0.000 description 1
JGHMVZQKZFNUAT-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-[7-(2h-tetrazol-5-yl)heptyl]pyridazin-3-one Chemical compound O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCCCCCCC1=NN=NN1 JGHMVZQKZFNUAT-UHFFFAOYSA-N 0.000 description 1
KNRYLVPKGNHRNZ-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-[8-(2h-tetrazol-5-yl)octyl]pyridazin-3-one Chemical compound O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCCCCCCCC1=NN=NN1 KNRYLVPKGNHRNZ-UHFFFAOYSA-N 0.000 description 1
KQYVTJFBCCZCOL-UHFFFAOYSA-N 6-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]hexanenitrile Chemical compound N#CCCCCCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 KQYVTJFBCCZCOL-UHFFFAOYSA-N 0.000 description 1
SDFRQMWRNYOUDC-UHFFFAOYSA-N 7-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]heptanenitrile Chemical compound N#CCCCCCCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 SDFRQMWRNYOUDC-UHFFFAOYSA-N 0.000 description 1
FKTDWUNEJPJSGJ-UHFFFAOYSA-N 8-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]octanenitrile Chemical compound N#CCCCCCCCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 FKTDWUNEJPJSGJ-UHFFFAOYSA-N 0.000 description 1
YGYFMRNEXNBVRR-UHFFFAOYSA-N 9-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]nonanenitrile Chemical compound N#CCCCCCCCCN1C(=O)C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=N1 YGYFMRNEXNBVRR-UHFFFAOYSA-N 0.000 description 1
208000009304 Acute Kidney Injury Diseases 0.000 description 1
206010002091 Anaesthesia Diseases 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
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
208000009447 Cardiac Edema Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
206010008132 Cerebral thrombosis Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910021555 Chromium Chloride Inorganic materials 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
229930105110 Cyclosporin A Natural products 0.000 description 1
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
108010036949 Cyclosporine Proteins 0.000 description 1
108010036941 Cyclosporins Proteins 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
208000007530 Essential hypertension Diseases 0.000 description 1
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
229930182566 Gentamicin Natural products 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
102000004877 Insulin Human genes 0.000 description 1
108090001061 Insulin Proteins 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
206010025538 Malignant ascites Diseases 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
208000025047 Non-histaminic angioedema Diseases 0.000 description 1
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
208000033626 Renal failure acute Diseases 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
208000007107 Stomach Ulcer Diseases 0.000 description 1
QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
WPQZZIPKAKNGSF-UHFFFAOYSA-N acetonitrile;nitrobenzene Chemical compound CC#N.[O-][N+](=O)C1=CC=CC=C1 WPQZZIPKAKNGSF-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
201000011040 acute kidney failure Diseases 0.000 description 1
208000012998 acute renal failure Diseases 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
150000008045 alkali metal halides Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides 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
150000003973 alkyl amines Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000002052 anaphylactic effect Effects 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000001088 anti-asthma Effects 0.000 description 1
230000003579 anti-obesity Effects 0.000 description 1
239000000924 antiasthmatic 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
210000000702 aorta abdominal Anatomy 0.000 description 1
208000008784 apnea Diseases 0.000 description 1
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
125000005239 aroylamino group Chemical group 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 1
125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000001746 atrial effect Effects 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 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
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
230000003435 bronchoconstrictive effect Effects 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
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000496 cardiotonic agent Substances 0.000 description 1
230000003177 cardiotonic effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
229960001265 ciclosporin Drugs 0.000 description 1
230000004087 circulation Effects 0.000 description 1
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
229960004316 cisplatin Drugs 0.000 description 1
230000037411 cognitive enhancing Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
239000006071 cream Substances 0.000 description 1
229940109239 creatinine Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229930182912 cyclosporin Natural products 0.000 description 1
125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000005879 dioxolanyl group Chemical group 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
230000008030 elimination Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
229960002518 gentamicin Drugs 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
235000003642 hunger Nutrition 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 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
239000003112 inhibitor Substances 0.000 description 1
229940125396 insulin Drugs 0.000 description 1
229910000765 intermetallic Inorganic materials 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
230000004130 lipolysis Effects 0.000 description 1
230000003137 locomotive effect Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000004899 motility Effects 0.000 description 1
125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000005475 oxolanyl group Chemical group 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960002275 pentobarbital sodium Drugs 0.000 description 1
125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
239000002304 perfume Substances 0.000 description 1
230000004526 pharmaceutical effect Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 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
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
229940116357 potassium thiocyanate Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
239000003368 psychostimulant agent Substances 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 description 1
NDRLPYIMWROJBG-UHFFFAOYSA-M pyridin-1-ium-1-amine;iodide Chemical compound [I-].N[N+]1=CC=CC=C1 NDRLPYIMWROJBG-UHFFFAOYSA-M 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
210000002254 renal artery Anatomy 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
MYXJYAIKMQJHIB-UHFFFAOYSA-M sodium;benzenesulfinate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)C1=CC=CC=C1 MYXJYAIKMQJHIB-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000002769 thiazolinyl group Chemical group 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- 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
- 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
- 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
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- 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
- A61P9/08—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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Diabetes (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Obesity (AREA)
Biomedical Technology (AREA)
Cardiology (AREA)
Endocrinology (AREA)
Immunology (AREA)
Emergency Medicine (AREA)
Urology & Nephrology (AREA)
Psychiatry (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Vascular Medicine (AREA)
Physical Education & Sports Medicine (AREA)
Reproductive Health (AREA)
Child & Adolescent Psychology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

IL9887291A 1990-07-18 1991-07-17 6-(2-arylpyrazolo [1, 5-a] pyridin-3-YL 2,3-dihydropyridazin-3-one derivatives processes for the preparation thereof and pharmaceutical compositions containing them IL98872A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB909015764A GB9015764D0 (en)	1990-07-18	1990-07-18	Pyrazolopyridine compound and processes for preparation thereof

Publications (2)

Publication Number	Publication Date
IL98872A0 IL98872A0 (en)	1992-07-15
IL98872A true IL98872A (en)	1996-12-05

Family

ID=10679258

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9887291A IL98872A (en)	1990-07-18	1991-07-17	6-(2-arylpyrazolo [1, 5-a] pyridin-3-YL 2,3-dihydropyridazin-3-one derivatives processes for the preparation thereof and pharmaceutical compositions containing them

Country Status (20)

Country	Link
US (1)	US5204346A (de)
EP (1)	EP0467248B1 (de)
JP (1)	JP3123562B2 (de)
KR (1)	KR100219957B1 (de)
CN (1)	CN1042730C (de)
AT (1)	ATE172731T1 (de)
AU (1)	AU651353B2 (de)
CA (1)	CA2047283C (de)
DE (1)	DE69130412T2 (de)
DK (1)	DK0467248T3 (de)
ES (1)	ES2121760T3 (de)
FI (1)	FI96688C (de)
GB (1)	GB9015764D0 (de)
HU (1)	HU218666B (de)
IE (1)	IE912427A1 (de)
IL (1)	IL98872A (de)
NO (1)	NO178697C (de)
PH (1)	PH30486A (de)
PT (1)	PT98358B (de)
ZA (1)	ZA915376B (de)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5338743A (en) *	1988-06-06	1994-08-16	Fujisawa Pharmaceutical Co., Ltd.	New use of the adenosine antagonist
DE69232323T2 (de) *	1991-01-29	2002-08-08	Fujisawa Pharmaceutical Co., Ltd.	Verwendung von Adenosinantagonisten zur Vorbeugung und Behandlung von Pankreatitis und Ulcera
DE4237656A1 (de) *	1992-06-13	1993-12-16	Merck Patent Gmbh	Benzimidazolderivate
CN1046724C (zh) *	1993-12-29	1999-11-24	藤泽药品工业株式会社	吡唑并吡啶化合物、含有它们的药物组合物、及其制法与用途
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
AU733034B2 (en) *	1996-07-18	2001-05-03	Fujisawa Pharmaceutical Co., Ltd.	Pyrazolopyridine compound and pharmaceutical use thereof
ATE229527T1 (de) *	1996-10-04	2002-12-15	Kyorin Seiyaku Kk	Pyrazolopyridylpyrazinon-derivate und ein verfahren zu ihrer herstellung
WO1998041237A1 (en) *	1997-03-18	1998-09-24	Fujisawa Pharmaceutical Co., Ltd.	Preventives and remedies for hyperphosphatemia
DK1032575T3 (da)	1997-09-05	2003-10-20	Glaxo Group Ltd	2,3-diaryl-pyrazol(1,5-b)pyridazinderivater, deres fremstilling og anvendelse som cyclooxygenase 2 (COX-2) inhibitor
US6060481A (en) *	1998-05-28	2000-05-09	The Penn State Research Foundation	Method for improving insulin sensitivity using an adenosine receptor antagonist
ES2273487T3 (es) *	1998-06-01	2007-05-01	Astellas Pharma Inc.	Antagonistas a1 de adenosina contra la esterilidad masculina.
WO1999067239A1 (en) *	1998-06-22	1999-12-29	Fujisawa Pharmaceutical Co., Ltd.	Pyrazolopyridine compounds and medicinal uses thereof
US7223772B1 (en)	1998-11-03	2007-05-29	Smithkline Beecham Corporation	Pyrazolopyridine derivatives as selective cox-2 inhibitors
ATE261444T1 (de)	1999-02-27	2004-03-15	Glaxo Group Ltd	Pyrazolopyridine
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
JP2004515550A (ja) *	2000-12-15	2004-05-27	グラクソグループリミテッド	治療用化合物
ATE301653T1 (de)	2000-12-15	2005-08-15	Glaxo Group Ltd	Pyrazolopyridine
WO2002072581A2 (en) *	2001-03-08	2002-09-19	Smithkline Beecham Corporation	Pyrazolopyriadine derivatives
WO2002078701A1 (en) *	2001-03-30	2002-10-10	Smithkline Beecham Corporation	Use of pyrazolopyridines as therapeutic compounds
WO2002078700A1 (en)	2001-03-30	2002-10-10	Smithkline Beecham Corporation	Pyralopyridines, process for their preparation and use as therapteutic compounds
ES2266487T3 (es)	2001-04-10	2007-03-01	Smithkline Beecham Corporation	Compuestos de pirazolopirina antivirales.
ATE296826T1 (de) *	2001-04-27	2005-06-15	Smithkline Beecham Corp	Pyrazolo(1,5)pyridinderivate
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
ATE337316T1 (de) *	2001-06-21	2006-09-15	Smithkline Beecham Corp	Imidazo 1,2-aöpyridin-derivate zur prophylaxe und behandlung von herpes-infektionen
US20040214834A1 (en) *	2001-09-07	2004-10-28	Kristjan Gudmunsson	Pyrazolo-pyridines for the treatment of herpes infections
EP1432712B1 (de)	2001-10-05	2006-05-17	SmithKline Beecham Corporation	Imidazopyridinderivate zur verwendung bei der behandlung von herpes-vireninfektion
JP2005516916A (ja) *	2001-12-11	2005-06-09	スミスクラインビーチャムコーポレーション	抗ヘルペス薬としてのピラゾロ−ピリジン誘導体
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
UA103319C2 (en)	2008-05-06	2013-10-10	Глаксосмитклайн Ллк	Thiazole- and oxazole-benzene sulfonamide compounds
EP2324028A2 (de) *	2008-08-04	2011-05-25	AstraZeneca AB	Therapeutische mittel 414
IL286481B2 (en) *	2019-03-20	2025-12-01	Goldfinch Bio Inc	Pyridazinones and methods of use thereof

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4024255A (en) *	1973-04-05	1977-05-17	Allen & Hanburys Limited	Tetrazole containing naphthyridine-3-carboxamides
US4304777A (en) *	1979-08-30	1981-12-08	Sterling Drug Inc.	6-(Pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics
JPS5826802A (ja) *	1981-08-10	1983-02-17	Sankyo Co Ltd	農園芸用殺菌剤
US4666902A (en) *	1983-06-20	1987-05-19	Cassella Aktiengesellschaft	Tetrahydropyridazinone derivatives, processes for their preparation and their use
HU195645B (en) *	1985-10-30	1988-06-28	Gyogyszerkutato Intezet	Process for preparing novel 3(2h)-pyridazinone derivatives and pharmaceutical compositions comprising the same
US4925849A (en) *	1987-06-15	1990-05-15	Fujisawa Pharmaceutical Company, Ltd.	Pharmaceutically useful pyrazolopyridines
JPH0710865B2 (ja) *	1987-06-26	1995-02-08	日本バイエルアグロケム株式会社	ニトロ置換ヘテロ環式化合物及び殺虫剤
GB8901423D0 (en) *	1989-01-23	1989-03-15	Fujisawa Pharmaceutical Co	Pyrazolopyridine compound and processes for preparation thereof

1990
- 1990-07-18 GB GB909015764A patent/GB9015764D0/en active Pending
1991
- 1991-07-09 PH PH42760A patent/PH30486A/en unknown
- 1991-07-10 ZA ZA915376A patent/ZA915376B/xx unknown
- 1991-07-11 IE IE242791A patent/IE912427A1/en not_active Application Discontinuation
- 1991-07-13 DE DE69130412T patent/DE69130412T2/de not_active Expired - Fee Related
- 1991-07-13 ES ES91111715T patent/ES2121760T3/es not_active Expired - Lifetime
- 1991-07-13 EP EP91111715A patent/EP0467248B1/de not_active Expired - Lifetime
- 1991-07-13 DK DK91111715T patent/DK0467248T3/da active
- 1991-07-13 AT AT91111715T patent/ATE172731T1/de not_active IP Right Cessation
- 1991-07-15 US US07/729,688 patent/US5204346A/en not_active Expired - Fee Related
- 1991-07-16 JP JP03268125A patent/JP3123562B2/ja not_active Expired - Fee Related
- 1991-07-16 AU AU80468/91A patent/AU651353B2/en not_active Ceased
- 1991-07-17 HU HU397/91A patent/HU218666B/hu not_active IP Right Cessation
- 1991-07-17 CN CN91105592A patent/CN1042730C/zh not_active Expired - Fee Related
- 1991-07-17 PT PT98358A patent/PT98358B/pt not_active IP Right Cessation
- 1991-07-17 IL IL9887291A patent/IL98872A/en not_active IP Right Cessation
- 1991-07-17 CA CA002047283A patent/CA2047283C/en not_active Expired - Fee Related
- 1991-07-17 FI FI913446A patent/FI96688C/fi active
- 1991-07-17 NO NO912805A patent/NO178697C/no unknown
- 1991-07-18 KR KR1019910012195A patent/KR100219957B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ZA915376B (en)	1992-04-29
CN1059143A (zh)	1992-03-04
NO912805L (no)	1992-01-20
CN1042730C (zh)	1999-03-31
AU651353B2 (en)	1994-07-21
PT98358B (pt)	1999-01-29
PT98358A (pt)	1992-05-29
IL98872A0 (en)	1992-07-15
IE912427A1 (en)	1992-01-29
DE69130412T2 (de)	1999-04-22
DK0467248T3 (da)	1999-07-05
EP0467248A2 (de)	1992-01-22
KR100219957B1 (ko)	1999-09-01
DE69130412D1 (de)	1998-12-03
ES2121760T3 (es)	1998-12-16
NO178697C (no)	1996-05-15
EP0467248B1 (de)	1998-10-28
NO178697B (no)	1996-02-05
NO912805D0 (no)	1991-07-17
HU218666B (hu)	2000-10-28
US5204346A (en)	1993-04-20
ATE172731T1 (de)	1998-11-15
KR920002603A (ko)	1992-02-28
JPH04253978A (ja)	1992-09-09
HUT58735A (en)	1992-03-30
FI913446A0 (fi)	1991-07-17
FI96688B (fi)	1996-04-30
CA2047283C (en)	2002-07-02
FI913446L (fi)	1992-01-19
HU912397D0 (en)	1991-12-30
FI96688C (fi)	1996-08-12
PH30486A (en)	1997-05-28
GB9015764D0 (en)	1990-09-05
AU8046891A (en)	1992-01-23
EP0467248A3 (en)	1992-03-11
JP3123562B2 (ja)	2001-01-15
CA2047283A1 (en)	1992-01-19

Legal Events

Date	Code	Title
1997-06-10	FF	Patent granted
1998-01-04	KB	Patent renewed
2001-10-31	KB	Patent renewed
2006-02-21	HC	Change of name of proprietor(s)
2006-04-10	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US5204346A (en)	1993-04-20	Pyrazolopyridine compounds
EP0497258B1 (de)	2002-01-02	Verwendung von Adenosinantagonisten zur Vorbeugung und Behandlung von Pankreatitis und Ulcera
KR100699395B1 (ko)	2007-03-27	나프티리딘 유도체
US20040110763A1 (en)	2004-06-10	Pyrazolopyridine compound and pharmaceutical use thereof
US20110152242A1 (en)	2011-06-23	2,3-Substituted Fused Pyrimidin -4 (3H)-Ones as VR1 Antagonists
EP2273882A1 (de)	2011-01-19	Bioaktive verbindungen zur behandlung von krebs und neurodegenerativen erkrankungen
PT92935B (pt)	1995-12-29	Processo para a preparacao de um composto de pirazolo-piridina e de composicoes farmaceuticas que o contem
TW201927792A (zh)	2019-07-16	作為溴結構域蛋白質抑制劑的化合物和組合物
US5338743A (en)	1994-08-16	New use of the adenosine antagonist
JPH07502743A (ja)	1995-03-23	Ｐａｆ及びアンジオテンシン２の拮抗剤としての複素環スルホンアミド誘導体
EP1244669A1 (de)	2002-10-02	Pyrazolopyrazine und ihre verwendung als adenosin antagonisten
TW202513045A (zh)	2025-04-01	Parg抑制劑
JP6905993B2 (ja)	2021-07-21	置換された二環式ヘテロ環化合物
US5198434A (en)	1993-03-30	Angiotensin ii antagonizing fused pyridinyloxy containing derivatives
EP1042320B1 (de)	2002-02-13	Neue verbindungen, welche antagonisten sind für p2-purinorezeptor 7-transmembran (tm) g-protein gekoppelte rezeptoren
KR20010086593A (ko)	2001-09-13	술폰아미드 화합물 및 그의 의약 용도
JP2010501641A (ja)	2010-01-21	Ｈｓｐ９０阻害剤として有用な１ｈ−ピロロ［２，３−ｂ］ピリジン誘導体
JPH0762017B2 (ja)	1995-07-05	多環式キノリン、ナフチリジンおよびピラジノピリジン誘導体
CA3249905A1 (en)	2023-08-24	Substituted bicyclic heteroaryl compounds useful as TLR9 inhibitors
KR100237505B1 (ko)	2000-02-01	아데노신 길항제의 신규 사용 방법
CN119431384A (zh)	2025-02-14	并内酰胺环类化合物及其用途
HK1190397A1 (zh)	2014-07-04	作为抗肿瘤剂的三环和四环吡唑并[3，4-b]吡啶化合物