BG106392A - 2-пиразолин -5-они - Google Patents

2-пиразолин -5-они Download PDF

Info

Publication number: BG106392A
Authority: BG; Bulgaria
Prior art keywords: methylene; pyrazolin; pyrrol; methyl; pyrazinyl
Prior art date: 1999-07-30

Application number

BG106392A

Other languages

Bulgarian (bg)

English (en)

Inventor

Marina MOSET

Jose Maria BERLANGA

Isabel FERNANDES

David Calderwood

Paul Rafferty

Lee Arnold

Original Assignee

Abbott Gmbh & Co. Kg

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.)

1999-07-30

Filing date

2002-02-06

Publication date

2002-12-29

2002-02-06 Application filed by Abbott Gmbh & Co. Kg filed Critical Abbott Gmbh & Co. Kg

2002-12-29 Publication of BG106392A publication Critical patent/BG106392A/bg

Links

ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 title claims description 44
150000001875 compounds Chemical class 0.000 claims abstract description 186
238000000034 method Methods 0.000 claims abstract description 80
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 52
230000000694 effects Effects 0.000 claims abstract description 40
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 39
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 39
150000003839 salts Chemical class 0.000 claims abstract description 35
201000010099 disease Diseases 0.000 claims abstract description 33
230000033115 angiogenesis Effects 0.000 claims abstract description 28
206010028980 Neoplasm Diseases 0.000 claims abstract description 24
201000011510 cancer Diseases 0.000 claims abstract description 16
230000003463 hyperproliferative effect Effects 0.000 claims abstract description 12
230000002491 angiogenic effect Effects 0.000 claims abstract description 11
102000009516 Protein Serine-Threonine Kinases Human genes 0.000 claims abstract description 8
108010009341 Protein Serine-Threonine Kinases Proteins 0.000 claims abstract description 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 1161
-1 morpholino, pyrrolidino, piperidino, imidazol-1-yl Chemical group 0.000 claims description 1153
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 279
125000000217 alkyl group Chemical group 0.000 claims description 143
125000003118 aryl group Chemical group 0.000 claims description 93
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 93
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 90
125000003710 aryl alkyl group Chemical group 0.000 claims description 89
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 76
125000000623 heterocyclic group Chemical group 0.000 claims description 66
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 64
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 60
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 59
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 52
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 52
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 48
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 47
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 47
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 44
125000004953 trihalomethyl group Chemical group 0.000 claims description 44
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 43
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 38
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
125000003545 alkoxy group Chemical group 0.000 claims description 35
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 34
102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 34
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 34
102000001253 Protein Kinase Human genes 0.000 claims description 30
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 30
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 30
108060006633 protein kinase Proteins 0.000 claims description 30
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
125000004122 cyclic group Chemical group 0.000 claims description 28
125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 28
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 27
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 26
230000002401 inhibitory effect Effects 0.000 claims description 25
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 24
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 24
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 24
108091008598 receptor tyrosine kinases Proteins 0.000 claims description 24
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 23
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 22
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 22
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 22
102000027426 receptor tyrosine kinases Human genes 0.000 claims description 22
206010030113 Oedema Diseases 0.000 claims description 21
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 21
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 20
229910052751 metal Inorganic materials 0.000 claims description 20
239000002184 metal Substances 0.000 claims description 20
230000002792 vascular Effects 0.000 claims description 19
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
208000035475 disorder Diseases 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
239000008194 pharmaceutical composition Substances 0.000 claims description 17
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 16
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 16
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 16
125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 15
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 claims description 15
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 15
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 15
229930192474 thiophene Natural products 0.000 claims description 15
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 14
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 14
150000001204 N-oxides Chemical class 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 13
238000011161 development Methods 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
230000005764 inhibitory process Effects 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 11
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 10
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 claims description 10
101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 10
125000003107 substituted aryl group Chemical group 0.000 claims description 10
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 9
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 9
102000037979 non-receptor tyrosine kinases Human genes 0.000 claims description 9
108091008046 non-receptor tyrosine kinases Proteins 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
239000002207 metabolite Substances 0.000 claims description 8
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 claims description 7
KQBVVLOYXDVATK-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-indole Chemical compound C1CCCC2=C1C=CN2 KQBVVLOYXDVATK-UHFFFAOYSA-N 0.000 claims description 7
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 7
101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 claims description 7
102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 claims description 7
201000004681 Psoriasis Diseases 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
108091008794 FGF receptors Proteins 0.000 claims description 6
125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 6
ONMGLYGYVUJBQL-UHFFFAOYSA-N 2-pyrazin-2-yl-4h-pyrazol-3-one Chemical compound O=C1CC=NN1C1=CN=CC=N1 ONMGLYGYVUJBQL-UHFFFAOYSA-N 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 5
206010048962 Brain oedema Diseases 0.000 claims description 5
206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
230000001772 anti-angiogenic effect Effects 0.000 claims description 5
208000006752 brain edema Diseases 0.000 claims description 5
230000001684 chronic effect Effects 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
125000000842 isoxazolyl group Chemical group 0.000 claims description 5
208000002780 macular degeneration Diseases 0.000 claims description 5
125000003373 pyrazinyl group Chemical group 0.000 claims description 5
AODWFUQQTSRJST-UHFFFAOYSA-N 2-thiophen-2-yl-4h-pyrazol-3-one Chemical compound O=C1CC=NN1C1=CC=CS1 AODWFUQQTSRJST-UHFFFAOYSA-N 0.000 claims description 4
IVBFAQHEEUITPW-UHFFFAOYSA-N 4-[(1-methylindol-3-yl)methylidene]-3-pyrazin-2-yl-1h-pyrazol-5-one Chemical compound C12=CC=CC=C2N(C)C=C1C=C1C(=O)NN=C1C1=CN=CC=N1 IVBFAQHEEUITPW-UHFFFAOYSA-N 0.000 claims description 4
MJKXJOYHEMUGCP-UHFFFAOYSA-N 4-[[4-(diethylaminomethyl)-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-3-(furan-2-yl)-1H-pyrazol-5-one Chemical compound CCN(CC)CC1=C(C)NC(C=C2C(=NNC2=O)C=2OC=CC=2)=C1C MJKXJOYHEMUGCP-UHFFFAOYSA-N 0.000 claims description 4
DBHHGWWEFJEXFX-UHFFFAOYSA-N 4-[[4-[2-(diethylamino)ethyl]-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound CCN(CC)CCC1=C(C)NC(C=C2C(=NNC2=O)C=2N=CC=NC=2)=C1C DBHHGWWEFJEXFX-UHFFFAOYSA-N 0.000 claims description 4
206010003445 Ascites Diseases 0.000 claims description 4
JYLOUMRNNLIQLA-UHFFFAOYSA-N C1=CC(N)=CC=C1CCC1=NNC(=O)C1=CC1=CC2=CC=CC=C2N1 Chemical compound C1=CC(N)=CC=C1CCC1=NNC(=O)C1=CC1=CC2=CC=CC=C2N1 JYLOUMRNNLIQLA-UHFFFAOYSA-N 0.000 claims description 4
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208000010412 Glaucoma Diseases 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
208000019693 Lung disease Diseases 0.000 claims description 4
206010033266 Ovarian Hyperstimulation Syndrome Diseases 0.000 claims description 4
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229910052794 bromium Inorganic materials 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
230000002490 cerebral effect Effects 0.000 claims description 4
230000006020 chronic inflammation Effects 0.000 claims description 4
UIKZACZOSJZYDN-UHFFFAOYSA-N ethyl 5-[(5-oxo-3-pyrazin-2-yl-1H-pyrazol-4-ylidene)methyl]-1H-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=CNC(C=C2C(=NNC2=O)C=2N=CC=NC=2)=C1 UIKZACZOSJZYDN-UHFFFAOYSA-N 0.000 claims description 4
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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125000001544 thienyl group Chemical group 0.000 claims description 4
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HDYXZPHXWRGGBI-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-4h-pyrazol-3-one Chemical compound O=C1CC=NN1C1=NC=CN1 HDYXZPHXWRGGBI-UHFFFAOYSA-N 0.000 claims description 3
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 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 claims description 3
125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims description 3
PJRIZUNKTYDZTO-UHFFFAOYSA-N 3-cyclopropyl-4-[[4-[(dimethylamino)methyl]-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-1H-pyrazol-5-one Chemical compound CN(C)CC1=C(C)NC(C=C2C(=NNC2=O)C2CC2)=C1C PJRIZUNKTYDZTO-UHFFFAOYSA-N 0.000 claims description 3
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WVSKVMFICWTXSB-UHFFFAOYSA-N C=1NC2=CC=CC=C2C=1C=C1C(=O)NN=C1C1CCCC1 Chemical compound C=1NC2=CC=CC=C2C=1C=C1C(=O)NN=C1C1CCCC1 WVSKVMFICWTXSB-UHFFFAOYSA-N 0.000 claims description 3
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
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125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
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201000004595 synovitis Diseases 0.000 claims description 3
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JVURXNNRGXPWGP-UHFFFAOYSA-N chembl1988692 Chemical compound CC(C)NC1=NNC(=O)C1=CC1=CC2=CC=CC=C2N1 JVURXNNRGXPWGP-UHFFFAOYSA-N 0.000 claims description 2
RRUJKDOVAZSBLK-UHFFFAOYSA-N chembl1989029 Chemical compound CC(C)OC1=NNC(=O)C1=CC1=CNC2=CC=CC=C12 RRUJKDOVAZSBLK-UHFFFAOYSA-N 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
SPUSHKMRZVUUIW-UHFFFAOYSA-N diethyl 2-[(3-cyclopropyloxy-5-oxo-1H-pyrazol-4-ylidene)methyl]-1H-pyrrole-3,4-dicarboxylate Chemical compound CCOC(=O)C1=CNC(C=C2C(=NNC2=O)OC2CC2)=C1C(=O)OCC SPUSHKMRZVUUIW-UHFFFAOYSA-N 0.000 claims description 2
VHAPVWMWQRDCAO-UHFFFAOYSA-N diethyl 2-[(5-oxo-3-thiophen-2-yl-1H-pyrazol-4-ylidene)methyl]-1H-pyrrole-3,4-dicarboxylate Chemical compound CCOC(=O)C1=CNC(C=C2C(=NNC2=O)C=2SC=CC=2)=C1C(=O)OCC VHAPVWMWQRDCAO-UHFFFAOYSA-N 0.000 claims description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
QHKRIUXFVZUIOH-UHFFFAOYSA-N ethyl 2,4-dimethyl-5-[(5-oxo-3-pyridin-3-yl-1H-pyrazol-4-ylidene)methyl]-1H-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=C2C(=NNC2=O)C=2C=NC=CC=2)=C1C QHKRIUXFVZUIOH-UHFFFAOYSA-N 0.000 claims description 2
WQDSDYBTGBYQTP-UHFFFAOYSA-N ethyl 5-[(3-ethoxy-5-oxo-1H-pyrazol-4-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=C2C(=NNC2=O)OCC)=C1C WQDSDYBTGBYQTP-UHFFFAOYSA-N 0.000 claims description 2
LSIVNWOUJZNLHV-UHFFFAOYSA-N ethyl 5-[(5-oxo-3-pyrazin-2-yl-1H-pyrazol-4-ylidene)methyl]-4-phenyl-1H-pyrrole-3-carboxylate Chemical compound C=1C=CC=CC=1C=1C(C(=O)OCC)=CNC=1C=C1C(=O)NN=C1C1=CN=CC=N1 LSIVNWOUJZNLHV-UHFFFAOYSA-N 0.000 claims description 2
IUYDLKVVLYGBNJ-UHFFFAOYSA-N ethyl 5-[[3-(1-methylcyclopropyl)-5-oxo-1H-pyrazol-4-ylidene]methyl]-1H-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=CNC(C=C2C(=NNC2=O)C2(C)CC2)=C1 IUYDLKVVLYGBNJ-UHFFFAOYSA-N 0.000 claims description 2
JHUUIJSUMNXZLP-UHFFFAOYSA-N ethyl 5-[[3-(3-aminophenyl)-5-oxo-1H-pyrazol-4-ylidene]methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=C2C(=NNC2=O)C=2C=C(N)C=CC=2)=C1C JHUUIJSUMNXZLP-UHFFFAOYSA-N 0.000 claims description 2
YITISLHHIJWMSB-UHFFFAOYSA-N ethyl 5-[[3-[2-(4-aminophenyl)ethyl]-5-oxo-1H-pyrazol-4-ylidene]methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=C2C(=NNC2=O)CCC=2C=CC(N)=CC=2)=C1C YITISLHHIJWMSB-UHFFFAOYSA-N 0.000 claims description 2
SMOCFWFTNCJYDD-UHFFFAOYSA-N ethyl 5-oxo-4-(1H-pyrrol-2-ylmethylidene)-1H-pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NNC(=O)C1=CC1=CC=CN1 SMOCFWFTNCJYDD-UHFFFAOYSA-N 0.000 claims description 2
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
KIHCYMFDTGDLRP-UHFFFAOYSA-N methyl 3-[5-oxo-4-(1H-pyrrol-2-ylmethylidene)-1H-pyrazol-3-yl]propanoate Chemical compound COC(=O)CCC1=NNC(=O)C1=CC1=CC=CN1 KIHCYMFDTGDLRP-UHFFFAOYSA-N 0.000 claims description 2
OSEARZYUYYGZJP-UHFFFAOYSA-N methyl 4-[2-(5-oxo-4H-pyrazol-1-yl)ethyl]benzoate Chemical compound COC(=O)C1=CC=C(C=C1)CCN1N=CCC1=O OSEARZYUYYGZJP-UHFFFAOYSA-N 0.000 claims description 2
AUPHSTKMVDKRFI-UHFFFAOYSA-N methyl 5-chloro-2-[(3-cyclopropyloxy-5-oxo-1H-pyrazol-4-ylidene)methyl]-4-(2-methoxy-2-oxoethyl)-1H-pyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(Cl)NC(C=C2C(=NNC2=O)OC2CC2)=C1C(=O)OC AUPHSTKMVDKRFI-UHFFFAOYSA-N 0.000 claims description 2
CSOWEJBMROKAHO-UHFFFAOYSA-N methyl 5-chloro-2-[[3-(furan-2-yl)-5-oxo-1H-pyrazol-4-ylidene]methyl]-4-(2-methoxy-2-oxoethyl)-1H-pyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(Cl)NC(C=C2C(=NNC2=O)C=2OC=CC=2)=C1C(=O)OC CSOWEJBMROKAHO-UHFFFAOYSA-N 0.000 claims description 2
FDOVQCHHJPNVME-UHFFFAOYSA-N methyl 5-ethoxy-2-[(3-ethoxy-5-oxo-1H-pyrazol-4-ylidene)methyl]-4-(2-methoxy-2-oxoethyl)-1H-pyrrole-3-carboxylate Chemical compound CCOC1=NNC(=O)C1=CC1=C(C(=O)OC)C(CC(=O)OC)=C(OCC)N1 FDOVQCHHJPNVME-UHFFFAOYSA-N 0.000 claims description 2
GGXXJJPHFSTVLD-UHFFFAOYSA-N methyl 5-ethoxy-2-[[3-(furan-2-yl)-5-oxo-1H-pyrazol-4-ylidene]methyl]-4-(2-methoxy-2-oxoethyl)-1H-pyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(OCC)NC(C=C2C(=NNC2=O)C=2OC=CC=2)=C1C(=O)OC GGXXJJPHFSTVLD-UHFFFAOYSA-N 0.000 claims description 2
201000003142 neovascular glaucoma Diseases 0.000 claims description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
230000002685 pulmonary effect Effects 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
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DIBFXUBPJISDRE-UHFFFAOYSA-N 3-cyclopropyl-4-[[4-(diethylaminomethyl)-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-1H-pyrazol-5-one Chemical compound CCN(CC)CC1=C(C)NC(C=C2C(=NNC2=O)C2CC2)=C1C DIBFXUBPJISDRE-UHFFFAOYSA-N 0.000 claims 2
SCNGZXPGGXZEAS-UHFFFAOYSA-N 4-[[4-(diethylaminomethyl)-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-3-thiophen-2-yl-1H-pyrazol-5-one Chemical compound CCN(CC)CC1=C(C)NC(C=C2C(=NNC2=O)C=2SC=CC=2)=C1C SCNGZXPGGXZEAS-UHFFFAOYSA-N 0.000 claims 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims 1
VDMJCIPUYPDXSB-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2,4-dimethyl-5-[[3-(1-methylcyclopropyl)-5-oxo-1H-pyrazol-4-ylidene]methyl]-1H-pyrrole-3-carboxylate Chemical compound CN(C)CCOC(=O)C1=C(C)NC(C=C2C(=NNC2=O)C2(C)CC2)=C1C VDMJCIPUYPDXSB-UHFFFAOYSA-N 0.000 claims 1
PKTYQPLDVQEMPD-UHFFFAOYSA-N 2-(dimethylamino)ethyl 5-[[3-[2-(4-hydroxyphenyl)ethyl]-5-oxo-1H-pyrazol-4-ylidene]methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate Chemical compound CN(C)CCOC(=O)C1=C(C)NC(C=C2C(=NNC2=O)CCC=2C=CC(O)=CC=2)=C1C PKTYQPLDVQEMPD-UHFFFAOYSA-N 0.000 claims 1
JPCBUALTGOZZKY-UHFFFAOYSA-N 2-(furan-2-yl)-4h-pyrazol-3-one Chemical compound O=C1CC=NN1C1=CC=CO1 JPCBUALTGOZZKY-UHFFFAOYSA-N 0.000 claims 1
XQOANROBYQKVQH-UHFFFAOYSA-N 2-[(3-cyclopropyl-5-oxo-1H-pyrazol-4-ylidene)methyl]-1,5,6,7-tetrahydroindol-4-one Chemical compound C=1C(C(CCC2)=O)=C2NC=1C=C1C(=O)NN=C1C1CC1 XQOANROBYQKVQH-UHFFFAOYSA-N 0.000 claims 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
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125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
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IGTZHHUMHINWCL-UHFFFAOYSA-N 3-(2-phenylethyl)-4-[[5-(trifluoromethyl)-1H-pyrrol-2-yl]methylidene]-1H-pyrazol-5-one Chemical compound N1C(C(F)(F)F)=CC=C1C=C1C(CCC=2C=CC=CC=2)=NNC1=O IGTZHHUMHINWCL-UHFFFAOYSA-N 0.000 claims 1
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125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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XEYJATUKTSQQIC-UHFFFAOYSA-N 4-[(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-3-(oxolan-3-yl)-1H-pyrazol-5-one Chemical compound CCC1=C(C)NC(C=C2C(=NNC2=O)C2COCC2)=C1C XEYJATUKTSQQIC-UHFFFAOYSA-N 0.000 claims 1
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WGMXCLXUDOKSRM-UHFFFAOYSA-N 4-[2-[4-[(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-5-oxo-1H-pyrazol-3-yl]ethyl]benzamide Chemical compound CCC1=C(C)NC(C=C2C(=NNC2=O)CCC=2C=CC(=CC=2)C(N)=O)=C1C WGMXCLXUDOKSRM-UHFFFAOYSA-N 0.000 claims 1
LGEQMFCKDWCNTC-UHFFFAOYSA-N 4-[[3,5-dicyclopropyl-4-(3-imidazol-1-yl-3-oxopropyl)-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C1=CN=CN1C(=O)CCC(C=1C2CC2)=C(C2CC2)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 LGEQMFCKDWCNTC-UHFFFAOYSA-N 0.000 claims 1
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OBLLUUNOLMQOJH-UHFFFAOYSA-N 4-[[3,5-dimethyl-4-[2-(pyridin-4-ylmethylamino)ethyl]-1H-pyrrol-2-yl]methylidene]-3-(furan-2-yl)-1H-pyrazol-5-one Chemical compound CC=1C(CCNCC=2C=CN=CC=2)=C(C)NC=1C=C1C(=O)NN=C1C1=CC=CO1 OBLLUUNOLMQOJH-UHFFFAOYSA-N 0.000 claims 1
DXSWHXQFFDDJFX-UHFFFAOYSA-N 4-[[3,5-dimethyl-4-[2-(pyridin-4-ylmethylamino)ethyl]-1H-pyrrol-2-yl]methylidene]-3-pyridazin-3-yl-1H-pyrazol-5-one Chemical compound CC=1C(CCNCC=2C=CN=CC=2)=C(C)NC=1C=C1C(=O)NN=C1C1=CC=CN=N1 DXSWHXQFFDDJFX-UHFFFAOYSA-N 0.000 claims 1
RKGQPSYEOPEYNL-UHFFFAOYSA-N 4-[[3-(1H-imidazole-2-carbonyl)-4-(3-imidazol-1-yl-3-oxopropyl)-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound N=1C=CNC=1C(=O)C=1C(CCC(=O)N2C=NC=C2)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 RKGQPSYEOPEYNL-UHFFFAOYSA-N 0.000 claims 1
XHWOLPQIXYXPNV-UHFFFAOYSA-N 4-[[3-[(cyclopropylamino)methyl]-4-[2-(diethylamino)ethyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C1CC1NCC=1C(CCN(CC)CC)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 XHWOLPQIXYXPNV-UHFFFAOYSA-N 0.000 claims 1
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GXMFJKHYGAMZEQ-UHFFFAOYSA-N 4-[[3-cyclobutyl-4-[2-(diethylamino)ethyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C1CCC1C=1C(CCN(CC)CC)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 GXMFJKHYGAMZEQ-UHFFFAOYSA-N 0.000 claims 1
PMEQZSABOGXCDH-UHFFFAOYSA-N 4-[[3-cyclohexyl-4-(3-imidazol-1-yl-3-oxopropyl)-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C1CCCCC1C=1C(CCC(=O)N2C=NC=C2)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 PMEQZSABOGXCDH-UHFFFAOYSA-N 0.000 claims 1
ORWRRXBYGVUFHH-UHFFFAOYSA-N 4-[[3-cyclopropyl-4-(diethylaminomethyl)-5-methyl-1H-pyrrol-2-yl]methylidene]-3-(1,2,4-triazin-3-yl)-1H-pyrazol-5-one Chemical compound C1CC1C=1C(CN(CC)CC)=C(C)NC=1C=C1C(=O)NN=C1C1=NC=CN=N1 ORWRRXBYGVUFHH-UHFFFAOYSA-N 0.000 claims 1
CYPYIFVJTRAWRM-UHFFFAOYSA-N 4-[[3-cyclopropyl-4-(diethylaminomethyl)-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C1CC1C=1C(CN(CC)CC)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 CYPYIFVJTRAWRM-UHFFFAOYSA-N 0.000 claims 1
HQNZLHCEPZLNNT-UHFFFAOYSA-N 4-[[3-cyclopropyl-4-[3-(2,5-dimethylpyrrolidin-1-yl)propyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyrimidin-2-yl-1H-pyrazol-5-one Chemical compound CC1CCC(C)N1CCCC1=C(C)NC(C=C2C(=NNC2=O)C=2N=CC=CN=2)=C1C1CC1 HQNZLHCEPZLNNT-UHFFFAOYSA-N 0.000 claims 1
HMMQJPNJUVWQMF-UHFFFAOYSA-N 4-[[3-cyclopropyl-4-[3-(2,5-dimethylpyrrolidin-1-yl)propyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyrimidin-4-yl-1H-pyrazol-5-one Chemical compound CC1CCC(C)N1CCCC1=C(C)NC(C=C2C(=NNC2=O)C=2N=CN=CC=2)=C1C1CC1 HMMQJPNJUVWQMF-UHFFFAOYSA-N 0.000 claims 1
LNRSIFUEHKCENZ-UHFFFAOYSA-N 4-[[3-cyclopropyl-4-[3-(diethylamino)propyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyridazin-3-yl-1H-pyrazol-5-one Chemical compound C1CC1C=1C(CCCN(CC)CC)=C(C)NC=1C=C1C(=O)NN=C1C1=CC=CN=N1 LNRSIFUEHKCENZ-UHFFFAOYSA-N 0.000 claims 1
UCYMDOFXGWKNSA-UHFFFAOYSA-N 4-[[3-cyclopropyl-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1H-pyrrol-2-yl]methylidene]-3-pyridazin-3-yl-1H-pyrazol-5-one Chemical compound C1CC1C=1C(CCN2CCCC2)=C(C)NC=1C=C1C(=O)NN=C1C1=CC=CN=N1 UCYMDOFXGWKNSA-UHFFFAOYSA-N 0.000 claims 1
FDTIUPXGHWXHNB-UHFFFAOYSA-N 4-[[3-cyclopropyl-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1H-pyrrol-2-yl]methylidene]-3-pyrimidin-2-yl-1H-pyrazol-5-one Chemical compound C1CC1C=1C(CCN2CCCC2)=C(C)NC=1C=C1C(=O)NN=C1C1=NC=CC=N1 FDTIUPXGHWXHNB-UHFFFAOYSA-N 0.000 claims 1
MDAXFBOIAVCDDQ-UHFFFAOYSA-N 4-[[3-tert-butyl-4-[2-(diethylamino)ethyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound CCN(CC)CCC1=C(C)NC(C=C2C(=NNC2=O)C=2N=CC=NC=2)=C1C(C)(C)C MDAXFBOIAVCDDQ-UHFFFAOYSA-N 0.000 claims 1
QLEBLHSSTQAVPH-UHFFFAOYSA-N 4-[[4-(2-aminoethyl)-3-(4-methoxyphenyl)-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=C2C(=NNC2=O)C=2N=CC=NC=2)NC(C)=C1CCN QLEBLHSSTQAVPH-UHFFFAOYSA-N 0.000 claims 1
YMGWRYQEJWNCIS-UHFFFAOYSA-N 4-[[4-(2-aminoethyl)-5-methyl-3-(trifluoromethyl)-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound NCCC1=C(C)NC(C=C2C(=NNC2=O)C=2N=CC=NC=2)=C1C(F)(F)F YMGWRYQEJWNCIS-UHFFFAOYSA-N 0.000 claims 1
WKQLGOZWOOTHGT-UHFFFAOYSA-N 4-[[4-(2-aminoethyl)-5-methyl-3-phenyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C=1C=CC=CC=1C=1C(CCN)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 WKQLGOZWOOTHGT-UHFFFAOYSA-N 0.000 claims 1
NMRBXWASFMQDCY-UHFFFAOYSA-N 4-[[4-(3-imidazol-1-yl-3-oxopropyl)-5-methyl-3-(1,2-oxazol-3-yl)-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C1=CON=C1C=1C(CCC(=O)N2C=NC=C2)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 NMRBXWASFMQDCY-UHFFFAOYSA-N 0.000 claims 1
KKIMRXJJNJNNQY-UHFFFAOYSA-N 4-[[4-(3-imidazol-1-yl-3-oxopropyl)-5-methyl-3-(trifluoromethyl)-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound FC(F)(F)C=1C(CCC(=O)N2C=NC=C2)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 KKIMRXJJNJNNQY-UHFFFAOYSA-N 0.000 claims 1
SOFHHMJQPNNBAP-UHFFFAOYSA-N 4-[[4-(3-imidazol-1-yl-3-oxopropyl)-5-methyl-3-pyrazin-2-yl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C=1N=CC=NC=1C=1C(CCC(=O)N2C=NC=C2)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 SOFHHMJQPNNBAP-UHFFFAOYSA-N 0.000 claims 1
GIJZINRVQGERHZ-UHFFFAOYSA-N 4-[[4-(aminomethyl)-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-3-cyclopropyl-1H-pyrazol-5-one Chemical compound NCC1=C(C)NC(C=C2C(=NNC2=O)C2CC2)=C1C GIJZINRVQGERHZ-UHFFFAOYSA-N 0.000 claims 1
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JMWCJIBFZQJLMM-UHFFFAOYSA-N 4-[[4-(diethylaminomethyl)-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-3-ethoxy-1H-pyrazol-5-one Chemical compound CCOC1=NNC(=O)C1=CC1=C(C)C(CN(CC)CC)=C(C)N1 JMWCJIBFZQJLMM-UHFFFAOYSA-N 0.000 claims 1
OINYLGGICHSVAY-UHFFFAOYSA-N 4-[[4-(diethylaminomethyl)-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound CCN(CC)CC1=C(C)NC(C=C2C(=NNC2=O)C=2N=CC=NC=2)=C1C OINYLGGICHSVAY-UHFFFAOYSA-N 0.000 claims 1
KDIIDJASNQASHW-UHFFFAOYSA-N 4-[[4-(diethylaminomethyl)-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-3-pyridazin-3-yl-1H-pyrazol-5-one Chemical compound CCN(CC)CC1=C(C)NC(C=C2C(=NNC2=O)C=2N=NC=CC=2)=C1C KDIIDJASNQASHW-UHFFFAOYSA-N 0.000 claims 1
BLNANWHPTHLMHU-UHFFFAOYSA-N 4-[[4-(diethylaminomethyl)-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-3-pyridin-3-yl-1H-pyrazol-5-one Chemical compound CCN(CC)CC1=C(C)NC(C=C2C(=NNC2=O)C=2C=NC=CC=2)=C1C BLNANWHPTHLMHU-UHFFFAOYSA-N 0.000 claims 1
RDJKFMWJUDVYNE-UHFFFAOYSA-N 4-[[4-(diethylaminomethyl)-5-methyl-3-propan-2-yl-1H-pyrrol-2-yl]methylidene]-3-thiophen-2-yl-1H-pyrazol-5-one Chemical compound CCN(CC)CC1=C(C)NC(C=C2C(=NNC2=O)C=2SC=CC=2)=C1C(C)C RDJKFMWJUDVYNE-UHFFFAOYSA-N 0.000 claims 1
CMBWXZWMLSTGQF-UHFFFAOYSA-N 4-[[4-(dimethylamino)-4,5,6,7-tetrahydro-1H-indol-2-yl]methylidene]-3-(1,2-oxazol-5-yl)-1H-pyrazol-5-one Chemical compound C=1C=2C(N(C)C)CCCC=2NC=1C=C1C(=O)NN=C1C1=CC=NO1 CMBWXZWMLSTGQF-UHFFFAOYSA-N 0.000 claims 1
IEJQJPBQWSISPJ-UHFFFAOYSA-N 4-[[4-(dimethylamino)-4,5,6,7-tetrahydro-1H-indol-2-yl]methylidene]-3-(furan-2-yl)-1H-pyrazol-5-one Chemical compound C=1C=2C(N(C)C)CCCC=2NC=1C=C1C(=O)NN=C1C1=CC=CO1 IEJQJPBQWSISPJ-UHFFFAOYSA-N 0.000 claims 1
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FNWGSWCGVXBQJT-UHFFFAOYSA-N 4-[[4-(ethylaminomethyl)-3-(furan-2-yl)-5-methyl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C=1C=COC=1C=1C(CNCC)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 FNWGSWCGVXBQJT-UHFFFAOYSA-N 0.000 claims 1
APKWIHJUHQMYRI-UHFFFAOYSA-N 4-[[4-(ethylaminomethyl)-5-(hydroxymethyl)-3-propan-2-yl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound CCNCC1=C(CO)NC(C=C2C(=NNC2=O)C=2N=CC=NC=2)=C1C(C)C APKWIHJUHQMYRI-UHFFFAOYSA-N 0.000 claims 1
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OFVAJRPFYNFWGK-UHFFFAOYSA-N 4-[[4-[(cyclopropylamino)methyl]-5-methyl-3-pyrazin-2-yl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound C=1N=CC=NC=1C=1C(CNC2CC2)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 OFVAJRPFYNFWGK-UHFFFAOYSA-N 0.000 claims 1
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ITMPVVHUXOFHCJ-UHFFFAOYSA-N 4-[[4-[(dimethylamino)methyl]-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-3-pyrimidin-5-yl-1H-pyrazol-5-one Chemical compound CN(C)CC1=C(C)NC(C=C2C(=NNC2=O)C=2C=NC=NC=2)=C1C ITMPVVHUXOFHCJ-UHFFFAOYSA-N 0.000 claims 1
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NHHSUWKSRJFNAY-UHFFFAOYSA-N 4-[[4-[(dimethylamino)methyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-3-propan-2-yloxy-1H-pyrazol-5-one Chemical compound CC(C)OC1=NNC(=O)C1=CC1=CC(CN(C)C)=C(C)N1 NHHSUWKSRJFNAY-UHFFFAOYSA-N 0.000 claims 1
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VHWIUFJTVXNUGU-UHFFFAOYSA-N 4-[[4-[2-(diethylamino)ethyl]-5-methyl-3-pyrimidin-2-yl-1H-pyrrol-2-yl]methylidene]-3-pyrazin-2-yl-1H-pyrazol-5-one Chemical compound N=1C=CC=NC=1C=1C(CCN(CC)CC)=C(C)NC=1C=C1C(=O)NN=C1C1=CN=CC=N1 VHWIUFJTVXNUGU-UHFFFAOYSA-N 0.000 claims 1
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UIVNBCXRKWOFEI-UHFFFAOYSA-N methyl 5-chloro-4-(2-methoxy-2-oxoethyl)-2-[[3-(1-methylcyclopropyl)-5-oxo-1H-pyrazol-4-ylidene]methyl]-1H-pyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(Cl)NC(C=C2C(=NNC2=O)C2(C)CC2)=C1C(=O)OC UIVNBCXRKWOFEI-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4152—1,2-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Hematology (AREA)
Endocrinology (AREA)
Ophthalmology & Optometry (AREA)
Obesity (AREA)
Oncology (AREA)
Dermatology (AREA)
Immunology (AREA)
Heart & Thoracic Surgery (AREA)
Rheumatology (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Vascular Medicine (AREA)
Physical Education & Sports Medicine (AREA)
Nutrition Science (AREA)
Epidemiology (AREA)
Communicable Diseases (AREA)
Gastroenterology & Hepatology (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Reproductive Health (AREA)
Orthopedic Medicine & Surgery (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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BG106392A 1999-07-30 2002-02-06 2-пиразолин -5-они BG106392A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US14656399P	1999-07-30	1999-07-30
PCT/US2000/020628 WO2001009121A2 (en)	1999-07-30	2000-07-28	2-pyrazolin-5-ones_as tyrosine kinase inhibitors

Publications (1)

Publication Number	Publication Date
BG106392A true BG106392A (bg)	2002-12-29

Family

ID=22517965

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG106392A BG106392A (bg)	1999-07-30	2002-02-06	2-пиразолин -5-они

Country Status (21)

Country	Link
EP (1)	EP1218373A2 (cs)
JP (1)	JP2003506368A (cs)
KR (1)	KR20020091829A (cs)
CN (1)	CN1193026C (cs)
AR (1)	AR032279A1 (cs)
AU (1)	AU6388900A (cs)
BG (1)	BG106392A (cs)
BR (1)	BR0012896A (cs)
CA (1)	CA2380644A1 (cs)
CZ (1)	CZ2002302A3 (cs)
HK (1)	HK1049154A1 (cs)
HU (1)	HUP0400540A3 (cs)
IL (1)	IL147757A0 (cs)
MX (1)	MXPA02001088A (cs)
NO (1)	NO20020487L (cs)
NZ (1)	NZ516850A (cs)
PL (1)	PL354144A1 (cs)
SK (1)	SK1512002A3 (cs)
TR (1)	TR200200928T2 (cs)
WO (1)	WO2001009121A2 (cs)
ZA (1)	ZA200200477B (cs)

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PL2084174T3 (pl)	2006-10-10	2013-12-31	Gilead Pharmasset Llc	Sposób otrzymywania nukleozydów rybofuranozylopirymidynowych
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HUE027598T2 (en)	2009-04-03	2016-10-28	Hoffmann La Roche	Propane-1-sulfonic acid {3- [5- (4-chlorophenyl) -1H-pyrrolo [2,3-B] pyridine-3-carbonyl] -2,4-difluorophenyl} amide compositions and their uses
TWI583692B (zh)	2009-05-20	2017-05-21	基利法瑪席特有限責任公司	核苷磷醯胺
US8618076B2 (en)	2009-05-20	2013-12-31	Gilead Pharmasset Llc	Nucleoside phosphoramidates
ES2633317T3 (es)	2009-11-06	2017-09-20	Plexxikon, Inc.	Compuestos y métodos para la modulación de quinasas, e indicaciones para ello
CL2011000716A1 (es)	2010-03-31	2012-04-20	Gilead Pharmasset Llc	Formas cristalinas 1 6 de (s)-isopropil-2-(((s)-(((2r.3r.4r.5r)-5-(2,4-dioxo-3,4-dihidropirimidin-1(2h)-il)-4-fluoro-3-hidroxi-4-metil tetrahidrofuran-2-il)metoxi)(fenoxi)fosforil)amino)propanoato; composicion y combinacion farmaceutica; y su uso para tratar una infeccion por el virus de la hepatitis c.
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MA34948B1 (fr)	2011-02-07	2014-03-01	Plexxikon Inc	Composes et procedes de modulation de kinase, et leurs indications
TWI558702B (zh)	2011-02-21	2016-11-21	普雷辛肯公司	醫藥活性物質的固態形式
US8889159B2 (en)	2011-11-29	2014-11-18	Gilead Pharmasset Llc	Compositions and methods for treating hepatitis C virus
US9150570B2 (en)	2012-05-31	2015-10-06	Plexxikon Inc.	Synthesis of heterocyclic compounds
WO2014017803A1 (ko)	2012-07-23	2014-01-30	주식회사 유한양행	퓨란-함유 융합 고리 화합물 또는 그의 염 및 이를 포함하는 약학 조성물
SG11201606149YA (en)	2014-02-14	2016-09-29	Inception 2 Inc	Pyrazolone compounds and uses thereof
CN105037269B (zh) *	2015-07-10	2018-01-19	中国人民解放军第二军医大学	取代吡唑酮类分泌型天冬氨酸蛋白酶抑制剂及其制备方法
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2000
- 2000-07-28 PL PL00354144A patent/PL354144A1/xx not_active Application Discontinuation
- 2000-07-28 MX MXPA02001088A patent/MXPA02001088A/es unknown
- 2000-07-28 SK SK151-2002A patent/SK1512002A3/sk unknown
- 2000-07-28 TR TR2002/00928T patent/TR200200928T2/xx unknown
- 2000-07-28 KR KR1020027001343A patent/KR20020091829A/ko not_active Withdrawn
- 2000-07-28 HU HU0400540A patent/HUP0400540A3/hu unknown
- 2000-07-28 NZ NZ516850A patent/NZ516850A/en unknown
- 2000-07-28 HK HK02109301.3A patent/HK1049154A1/zh unknown
- 2000-07-28 EP EP00950852A patent/EP1218373A2/en not_active Withdrawn
- 2000-07-28 BR BR0012896-1A patent/BR0012896A/pt not_active IP Right Cessation
- 2000-07-28 CN CNB008136823A patent/CN1193026C/zh not_active Expired - Fee Related
- 2000-07-28 IL IL14775700A patent/IL147757A0/xx unknown
- 2000-07-28 JP JP2001514324A patent/JP2003506368A/ja not_active Withdrawn
- 2000-07-28 CZ CZ2002302A patent/CZ2002302A3/cs unknown
- 2000-07-28 AU AU63889/00A patent/AU6388900A/en not_active Abandoned
- 2000-07-28 WO PCT/US2000/020628 patent/WO2001009121A2/en not_active Ceased
- 2000-07-28 CA CA002380644A patent/CA2380644A1/en not_active Abandoned
- 2000-07-31 AR ARP000103955A patent/AR032279A1/es unknown
2002
- 2002-01-18 ZA ZA200200477A patent/ZA200200477B/xx unknown
- 2002-01-30 NO NO20020487A patent/NO20020487L/no not_active Application Discontinuation
- 2002-02-06 BG BG106392A patent/BG106392A/bg unknown

Also Published As

Publication number	Publication date
AU6388900A (en)	2001-02-19
ZA200200477B (en)	2003-06-25
JP2003506368A (ja)	2003-02-18
HUP0400540A3 (en)	2004-09-28
WO2001009121A2 (en)	2001-02-08
CZ2002302A3 (cs)	2002-06-12
PL354144A1 (en)	2003-12-29
MXPA02001088A (es)	2003-09-22
WO2001009121A3 (en)	2002-05-02
HUP0400540A2 (hu)	2004-06-28
KR20020091829A (ko)	2002-12-06
CN1193026C (zh)	2005-03-16
BR0012896A (pt)	2002-06-18
EP1218373A2 (en)	2002-07-03
TR200200928T2 (tr)	2002-09-23
CA2380644A1 (en)	2001-02-08
CN1377346A (zh)	2002-10-30
NO20020487L (no)	2002-03-12
NZ516850A (en)	2004-09-24
AR032279A1 (es)	2003-11-05
NO20020487D0 (no)	2002-01-30
HK1049154A1 (zh)	2003-05-02
SK1512002A3 (en)	2002-11-06
IL147757A0 (en)	2002-08-14

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