AU762992B2 - Tricyclic pyrazole derivatives - Google Patents

Info

Publication number

AU762992B2

AU762992B2 AU19091/00A AU1909100A AU762992B2 AU 762992 B2 AU762992 B2 AU 762992B2 AU 19091/00 A AU19091/00 A AU 19091/00A AU 1909100 A AU1909100 A AU 1909100A AU 762992 B2 AU762992 B2 AU 762992B2

Authority

AU

Australia

Prior art keywords

phenyl

group

dihydroindeno

alkyl

optionally substituted

Prior art date

1998-11-06

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

Ceased

Links

• Espacenet
• Global Dossier
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• 150000003217 pyrazoles Chemical class 0.000 title description 4
• -1 tri-substituted phenyl Chemical group 0.000 claims description 625
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 447
• 125000000217 alkyl group Chemical group 0.000 claims description 283
• 150000001875 compounds Chemical class 0.000 claims description 228
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 184
• 229910052739 hydrogen Inorganic materials 0.000 claims description 173
• 239000001257 hydrogen Substances 0.000 claims description 160
• 125000003545 alkoxy group Chemical group 0.000 claims description 157
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 155
• 125000005843 halogen group Chemical group 0.000 claims description 144
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 123
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 108
• 150000002431 hydrogen Chemical class 0.000 claims description 107
• 125000003277 amino group Chemical group 0.000 claims description 98
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 81
• 125000004076 pyridyl group Chemical group 0.000 claims description 73
• 229910052757 nitrogen Inorganic materials 0.000 claims description 70
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 66
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 66
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 66
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 63
• 229910052760 oxygen Inorganic materials 0.000 claims description 61
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 57
• 230000000694 effects Effects 0.000 claims description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 55
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 54
• 238000000034 method Methods 0.000 claims description 51
• 150000003839 salts Chemical class 0.000 claims description 51
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 49
• 125000001544 thienyl group Chemical group 0.000 claims description 49
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 48
• 241000689227 Cora <basidiomycete fungus> Species 0.000 claims description 48
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 47
• 125000002541 furyl group Chemical group 0.000 claims description 47
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 45
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 44
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 43
• 229910052799 carbon Inorganic materials 0.000 claims description 42
• 239000000203 mixture Substances 0.000 claims description 41
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 41
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 41
• 125000000623 heterocyclic group Chemical group 0.000 claims description 39
• 125000005842 heteroatom Chemical group 0.000 claims description 38
• 229910052717 sulfur Inorganic materials 0.000 claims description 38
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 201000010099 disease Diseases 0.000 claims description 37
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
• 239000001301 oxygen Substances 0.000 claims description 33
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 32
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
• 102000001253 Protein Kinase Human genes 0.000 claims description 31
• 108060006633 protein kinase Proteins 0.000 claims description 31
• 125000001424 substituent group Chemical group 0.000 claims description 31
• 206010030113 Oedema Diseases 0.000 claims description 30
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 30
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
• 239000004202 carbamide Substances 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 27
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 27
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
• 102000004190 Enzymes Human genes 0.000 claims description 24
• 108090000790 Enzymes Proteins 0.000 claims description 24
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 24
• 230000002792 vascular Effects 0.000 claims description 24
• 108091000080 Phosphotransferase Proteins 0.000 claims description 23
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 23
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
• 230000002401 inhibitory effect Effects 0.000 claims description 23
• 102000020233 phosphotransferase Human genes 0.000 claims description 23
• 108091008598 receptor tyrosine kinases Proteins 0.000 claims description 23
• 206010028980 Neoplasm Diseases 0.000 claims description 22
• 230000033115 angiogenesis Effects 0.000 claims description 22
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 21
• 125000003282 alkyl amino group Chemical group 0.000 claims description 21
• 230000005764 inhibitory process Effects 0.000 claims description 21
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
• 102000027426 receptor tyrosine kinases Human genes 0.000 claims description 21
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• 125000001153 fluoro group Chemical group F* 0.000 claims description 17
• 125000001624 naphthyl group Chemical group 0.000 claims description 17
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 17
• 125000005554 pyridyloxy group Chemical group 0.000 claims description 17
• 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims description 17
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 16
• 125000003368 amide group Chemical group 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 15
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 12
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 238000004519 manufacturing process Methods 0.000 claims description 12
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 11
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
• 102000037979 non-receptor tyrosine kinases Human genes 0.000 claims description 11
• 108091008046 non-receptor tyrosine kinases Proteins 0.000 claims description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 10
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
• 201000011510 cancer Diseases 0.000 claims description 10
• 201000004681 Psoriasis Diseases 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 8
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 8
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 8
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 8
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 8
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 8
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 8
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 8
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
• 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 150000001408 amides Chemical class 0.000 claims description 8
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
• 125000004104 aryloxy group Chemical group 0.000 claims description 8
• JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims description 8
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 8
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 229910052740 iodine Inorganic materials 0.000 claims description 8
• 208000002780 macular degeneration Diseases 0.000 claims description 8
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 8
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 8
• DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 claims description 8
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 8
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
• 150000003852 triazoles Chemical class 0.000 claims description 8
• DGYDIEIMGSEYDK-UHFFFAOYSA-N 1,4-dihydroindeno[1,2-c]pyrazole Chemical compound C12=CC=CC=C2CC2=C1NN=C2 DGYDIEIMGSEYDK-UHFFFAOYSA-N 0.000 claims description 7
• 206010003445 Ascites Diseases 0.000 claims description 7
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 7
• 206010016654 Fibrosis Diseases 0.000 claims description 7
• FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 7
• 101000852966 Rattus norvegicus Interleukin-1 receptor-like 1 Proteins 0.000 claims description 7
• 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
• 150000002923 oximes Chemical class 0.000 claims description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
• 206010048962 Brain oedema Diseases 0.000 claims description 6
• 206010063045 Effusion Diseases 0.000 claims description 6
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 6
• 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 claims description 6
• 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 claims description 6
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 6
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 6
• ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 claims description 6
• 208000006752 brain edema Diseases 0.000 claims description 6
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 5
• 208000010412 Glaucoma Diseases 0.000 claims description 5
• 230000001772 anti-angiogenic effect Effects 0.000 claims description 5
• 230000002490 cerebral effect Effects 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 208000014674 injury Diseases 0.000 claims description 5
• 230000008733 trauma Effects 0.000 claims description 5
• VRWJZGHUCOFGPZ-UHFFFAOYSA-N 2-{[4-(4-pyridin-4-yl-1h-pyrazol-3-yl)phenoxy]methyl}quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1COC(C=C1)=CC=C1C1=NNC=C1C1=CC=NC=C1 VRWJZGHUCOFGPZ-UHFFFAOYSA-N 0.000 claims description 4
• 201000009273 Endometriosis Diseases 0.000 claims description 4
• 206010033266 Ovarian Hyperstimulation Syndrome Diseases 0.000 claims description 4
• 206010037423 Pulmonary oedema Diseases 0.000 claims description 4
• 208000006011 Stroke Diseases 0.000 claims description 4
• 229960001413 acetanilide Drugs 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 230000006020 chronic inflammation Effects 0.000 claims description 4
• 230000004761 fibrosis Effects 0.000 claims description 4
• 210000004072 lung Anatomy 0.000 claims description 4
• LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 4
• 208000005333 pulmonary edema Diseases 0.000 claims description 4
• 229960000581 salicylamide Drugs 0.000 claims description 4
• 150000003536 tetrazoles Chemical class 0.000 claims description 4
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 4
• 230000029663 wound healing Effects 0.000 claims description 4
• DZQLVVLATXPWBK-UHFFFAOYSA-N 3-phenyl-1H-benzofuro[3,2-c]pyrazole Chemical compound C1=CC=CC=C1C1=NNC2=C1OC1=CC=CC=C12 DZQLVVLATXPWBK-UHFFFAOYSA-N 0.000 claims description 3
• 208000003732 Cat-scratch disease Diseases 0.000 claims description 3
• 206010017076 Fracture Diseases 0.000 claims description 3
• 206010018498 Goitre Diseases 0.000 claims description 3
• 208000019693 Lung disease Diseases 0.000 claims description 3
• 208000037062 Polyps Diseases 0.000 claims description 3
• 208000025865 Ulcer Diseases 0.000 claims description 3
• 230000009285 allergic inflammation Effects 0.000 claims description 3
• 230000003501 anti-edematous effect Effects 0.000 claims description 3
• 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 3
• 230000007882 cirrhosis Effects 0.000 claims description 3
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
• 208000031513 cyst Diseases 0.000 claims description 3
• 201000011066 hemangioma Diseases 0.000 claims description 3
• 230000000302 ischemic effect Effects 0.000 claims description 3
• 230000002107 myocardial effect Effects 0.000 claims description 3
• 201000003142 neovascular glaucoma Diseases 0.000 claims description 3
• 201000004595 synovitis Diseases 0.000 claims description 3
• 231100000397 ulcer Toxicity 0.000 claims description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
• AQMKKROATNBRCJ-UHFFFAOYSA-N 2,2,2-trifluoro-n-(3-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-6-yl)acetamide Chemical compound C=1C(NC(=O)C(F)(F)F)=CC=C2C=1CC1=C2NN=C1C1=CC=CC=C1 AQMKKROATNBRCJ-UHFFFAOYSA-N 0.000 claims description 2
• QSWWOFOLIWWUJD-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-n-(3-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-6-yl)propanamide Chemical compound C=1C(NC(=O)C(F)(F)C(F)(F)F)=CC=C2C=1CC1=C2NN=C1C1=CC=CC=C1 QSWWOFOLIWWUJD-UHFFFAOYSA-N 0.000 claims description 2
• JPULUQHTUYCRCO-UHFFFAOYSA-N 2-amino-2-ethyl-n-phenylbutanamide Chemical compound CCC(N)(CC)C(=O)NC1=CC=CC=C1 JPULUQHTUYCRCO-UHFFFAOYSA-N 0.000 claims description 2
• XZUCBHPUPYFPNV-UHFFFAOYSA-N 2-chloro-4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol Chemical compound C1=C(Cl)C(O)=CC=C1C1=NNC2=C1CC1=CC=CC=C21 XZUCBHPUPYFPNV-UHFFFAOYSA-N 0.000 claims description 2
• GVQMFFMYOWZTFS-UHFFFAOYSA-N 2-ethyl-n-(3-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-6-yl)butanamide Chemical compound C=1C(NC(=O)C(CC)CC)=CC=C(C=2NN=3)C=1CC=2C=3C1=CC=CC=C1 GVQMFFMYOWZTFS-UHFFFAOYSA-N 0.000 claims description 2
• PBOJZZXZAYUUEE-UHFFFAOYSA-N 2-fluoro-n-(3-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-6-yl)acetamide Chemical compound C=1C(NC(=O)CF)=CC=C(C=2NN=3)C=1CC=2C=3C1=CC=CC=C1 PBOJZZXZAYUUEE-UHFFFAOYSA-N 0.000 claims description 2
• IHCDQQHNHQCALV-UHFFFAOYSA-N 2-methoxyethylurea Chemical compound COCCNC(N)=O IHCDQQHNHQCALV-UHFFFAOYSA-N 0.000 claims description 2
• SGQJWUFCYNXIRZ-UHFFFAOYSA-N 2-methyl-n-(3-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-6-yl)pentanamide Chemical compound C=1C(NC(=O)C(C)CCC)=CC=C(C=2NN=3)C=1CC=2C=3C1=CC=CC=C1 SGQJWUFCYNXIRZ-UHFFFAOYSA-N 0.000 claims description 2
• BWRNWWSQZROEOA-UHFFFAOYSA-N 2-morpholin-4-ylacetamide Chemical compound NC(=O)CN1CCOCC1 BWRNWWSQZROEOA-UHFFFAOYSA-N 0.000 claims description 2
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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