ZA200506408B - Parazoles and methods of making and using the same - Google Patents
Parazoles and methods of making and using the same Download PDFInfo
- Publication number
- ZA200506408B ZA200506408B ZA200506408A ZA200506408A ZA200506408B ZA 200506408 B ZA200506408 B ZA 200506408B ZA 200506408 A ZA200506408 A ZA 200506408A ZA 200506408 A ZA200506408 A ZA 200506408A ZA 200506408 B ZA200506408 B ZA 200506408B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrazol
- pyridin
- compound
- benzo
- composition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 116
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
- 102000009618 Transforming Growth Factors Human genes 0.000 claims description 40
- 108010009583 Transforming Growth Factors Proteins 0.000 claims description 40
- -1 hydroxy, amino, nitro, oxo, thioxo Chemical group 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 230000002401 inhibitory effect Effects 0.000 claims description 26
- 210000004027 cell Anatomy 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 230000003176 fibrotic effect Effects 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 14
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 claims description 13
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 210000002744 extracellular matrix Anatomy 0.000 claims description 13
- 230000019491 signal transduction Effects 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- 238000009825 accumulation Methods 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 8
- 206010027476 Metastases Diseases 0.000 claims description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 7
- 230000009401 metastasis Effects 0.000 claims description 7
- 230000002018 overexpression Effects 0.000 claims description 7
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- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 6
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 6
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims description 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 230000037390 scarring Effects 0.000 claims description 6
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 206010069351 acute lung injury Diseases 0.000 claims description 4
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 4
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 210000003169 central nervous system Anatomy 0.000 claims description 4
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 4
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- KPUSZZFAYGWAHZ-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octane Chemical compound C1CC2CCC1NC2 KPUSZZFAYGWAHZ-UHFFFAOYSA-N 0.000 claims description 3
- CJQNJRRDTPULTL-UHFFFAOYSA-N 3-azabicyclo[3.2.1]octane Chemical compound C1C2CCC1CNC2 CJQNJRRDTPULTL-UHFFFAOYSA-N 0.000 claims description 3
- 201000009030 Carcinoma Diseases 0.000 claims description 3
- 206010019668 Hepatic fibrosis Diseases 0.000 claims description 3
- 101000635938 Homo sapiens Transforming growth factor beta-1 proprotein Proteins 0.000 claims description 3
- 102100030742 Transforming growth factor beta-1 proprotein Human genes 0.000 claims description 3
- LPCWKMYWISGVSK-UHFFFAOYSA-N bicyclo[3.2.1]octane Chemical compound C1C2CCC1CCC2 LPCWKMYWISGVSK-UHFFFAOYSA-N 0.000 claims description 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 3
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 3
- 230000029663 wound healing Effects 0.000 claims description 3
- CONVAEXWACQJSA-UHFFFAOYSA-N 3-oxabicyclo[2.2.2]octane Chemical compound C1CC2CCC1OC2 CONVAEXWACQJSA-UHFFFAOYSA-N 0.000 claims description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
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- 200000000007 Arterial disease Diseases 0.000 claims description 2
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 2
- 206010004664 Biliary fibrosis Diseases 0.000 claims description 2
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 208000016192 Demyelinating disease Diseases 0.000 claims description 2
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- 208000007659 Fibroadenoma Diseases 0.000 claims description 2
- 208000032612 Glial tumor Diseases 0.000 claims description 2
- 206010018338 Glioma Diseases 0.000 claims description 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 2
- 208000002260 Keloid Diseases 0.000 claims description 2
- 206010023330 Keloid scar Diseases 0.000 claims description 2
- 208000004852 Lung Injury Diseases 0.000 claims description 2
- 208000005777 Lupus Nephritis Diseases 0.000 claims description 2
- 208000034578 Multiple myelomas Diseases 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 206010069363 Traumatic lung injury Diseases 0.000 claims description 2
- 206010046798 Uterine leiomyoma Diseases 0.000 claims description 2
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 210000003445 biliary tract Anatomy 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 230000009787 cardiac fibrosis Effects 0.000 claims description 2
- 230000002490 cerebral effect Effects 0.000 claims description 2
- 210000003679 cervix uteri Anatomy 0.000 claims description 2
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- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 2
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- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 210000003128 head Anatomy 0.000 claims description 2
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- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 2
- 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims description 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 2
- 210000001117 keloid Anatomy 0.000 claims description 2
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- 210000004185 liver Anatomy 0.000 claims description 2
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- 201000001441 melanoma Diseases 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 210000003739 neck Anatomy 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 210000001672 ovary Anatomy 0.000 claims description 2
- 210000000496 pancreas Anatomy 0.000 claims description 2
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 58
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 230000001404 mediated effect Effects 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- PLFVJNCDYWCWML-UHFFFAOYSA-N 1-[6-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]pyridin-2-yl]ethanol Chemical compound CC(O)C1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 PLFVJNCDYWCWML-UHFFFAOYSA-N 0.000 claims 2
- SFZYRCUDHYKJJC-UHFFFAOYSA-N 1-tert-butyl-3-[6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-yl]urea Chemical compound C1=C2C(NC(=O)NC(C)(C)C)=NC=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 SFZYRCUDHYKJJC-UHFFFAOYSA-N 0.000 claims 2
- ISXNRDZPHJMGIT-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 ISXNRDZPHJMGIT-UHFFFAOYSA-N 0.000 claims 2
- WPTMLMRCXDJZNI-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-cyclopropylpyridine Chemical compound C1CC1C1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 WPTMLMRCXDJZNI-UHFFFAOYSA-N 0.000 claims 2
- XPJQTAGLWLONLB-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 XPJQTAGLWLONLB-UHFFFAOYSA-N 0.000 claims 2
- GKMSJYFFCJBASE-UHFFFAOYSA-N 3-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)propanoic acid Chemical compound N=1N(CCC(=O)O)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 GKMSJYFFCJBASE-UHFFFAOYSA-N 0.000 claims 2
- GYSJFFZLKJKITE-UHFFFAOYSA-N 3-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]propanenitrile Chemical compound CC1=CC=CC(C=2C(=CN(CCC#N)N=2)C=2C=C3OCOC3=CC=2)=N1 GYSJFFZLKJKITE-UHFFFAOYSA-N 0.000 claims 2
- HJWAOCQEWUVDQM-UHFFFAOYSA-N 4-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2h-phthalazin-1-one Chemical compound C12=CC=CC=C2C(=O)NN=C1C1=CNN=C1C1=CC=CC=N1 HJWAOCQEWUVDQM-UHFFFAOYSA-N 0.000 claims 2
- RFDFWKWWEIPCNH-UHFFFAOYSA-N 4-[6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-yl]morpholine Chemical compound C1COCCN1C1=NC=NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C12 RFDFWKWWEIPCNH-UHFFFAOYSA-N 0.000 claims 2
- HPUFRDPDKQBLDH-UHFFFAOYSA-N 4-propan-2-yloxy-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazoline Chemical compound C1=C2C(OC(C)C)=NC=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 HPUFRDPDKQBLDH-UHFFFAOYSA-N 0.000 claims 2
- IXIWVJRDBMRDKT-UHFFFAOYSA-N 5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1,3-benzoxazole Chemical compound C=1C=C2OC=NC2=CC=1C1=CNN=C1C1=CC=CC=N1 IXIWVJRDBMRDKT-UHFFFAOYSA-N 0.000 claims 2
- AOCQNXGGMHUVMI-UHFFFAOYSA-N 5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2,1,3-benzothiadiazole Chemical compound C1=CC2=NSN=C2C=C1C1=CNN=C1C1=CC=CC=N1 AOCQNXGGMHUVMI-UHFFFAOYSA-N 0.000 claims 2
- UZPKOKMFDJQROV-UHFFFAOYSA-N 5-[5-(6-methylpyridin-2-yl)-1h-pyrazol-4-yl]-2,1,3-benzothiadiazole Chemical compound CC1=CC=CC(C=2C(=CNN=2)C2=CC3=NSN=C3C=C2)=N1 UZPKOKMFDJQROV-UHFFFAOYSA-N 0.000 claims 2
- RXXDYAWKHHAZHN-UHFFFAOYSA-N 5-methyl-n-[6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-yl]thiophene-2-carboxamide Chemical compound S1C(C)=CC=C1C(=O)NC1=NC=NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C12 RXXDYAWKHHAZHN-UHFFFAOYSA-N 0.000 claims 2
- YXISXWPTVPNZSB-UHFFFAOYSA-N 6-(5-pyridin-2-yl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-b]pyridazine Chemical compound N=1N2N=CN=C2C=CC=1C1=CNN=C1C1=CC=CC=N1 YXISXWPTVPNZSB-UHFFFAOYSA-N 0.000 claims 2
- NCDBZEBGDWSLOO-UHFFFAOYSA-N 6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinolin-4-amine Chemical compound C1=C2C(N)=CC=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 NCDBZEBGDWSLOO-UHFFFAOYSA-N 0.000 claims 2
- HXELQAJSZOVFHS-UHFFFAOYSA-N 6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinoxaline Chemical compound C=1C=C2N=CC=NC2=CC=1C1=CNN=C1C1=CC=CC=N1 HXELQAJSZOVFHS-UHFFFAOYSA-N 0.000 claims 2
- LOIUEFXYTURTON-UHFFFAOYSA-N 6-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-3-fluoro-2-methylpyridine Chemical compound C1=C(F)C(C)=NC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=C1 LOIUEFXYTURTON-UHFFFAOYSA-N 0.000 claims 2
- VXJLYXCHOKEODY-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-1h-pyrazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(C=2C(=CNN=2)C=2C=C3N=CC=NC3=CC=2)=N1 VXJLYXCHOKEODY-UHFFFAOYSA-N 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- ZVTWQRWEZQTOQF-UHFFFAOYSA-N methyl 4-[2-[2-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]ethoxy]ethoxy]bicyclo[2.2.2]octane-1-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12OCCOCCN(N=1)C=C(C=2C=C3OCOC3=CC=2)C=1C1=CC=CC(C)=N1 ZVTWQRWEZQTOQF-UHFFFAOYSA-N 0.000 claims 2
- QMDPZBJUHORZHH-UHFFFAOYSA-N n-methyl-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1C1=CNN=C1C1=CC=CC=N1 QMDPZBJUHORZHH-UHFFFAOYSA-N 0.000 claims 2
- FXPNNBPYKCSUKM-UHFFFAOYSA-N (4-methoxyphenyl)-[6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=NC=NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C12 FXPNNBPYKCSUKM-UHFFFAOYSA-N 0.000 claims 1
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims 1
- BUVRVVBYIQDIDT-UHFFFAOYSA-N 2-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)ethanamine Chemical compound N=1N(CCN)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 BUVRVVBYIQDIDT-UHFFFAOYSA-N 0.000 claims 1
- VQNGFTSKHNQZEI-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-ethenylpyridine Chemical compound C=CC1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 VQNGFTSKHNQZEI-UHFFFAOYSA-N 0.000 claims 1
- BJYFDVHHZLGZSW-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-ethylpyridine Chemical compound CCC1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 BJYFDVHHZLGZSW-UHFFFAOYSA-N 0.000 claims 1
- VZQJKFWHVVOZGS-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-propan-2-ylpyridine Chemical compound CC(C)C1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 VZQJKFWHVVOZGS-UHFFFAOYSA-N 0.000 claims 1
- DDLCKXIXNHICNI-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-propylpyridine Chemical compound CCCC1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 DDLCKXIXNHICNI-UHFFFAOYSA-N 0.000 claims 1
- OUISUIBLHNSWMA-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]acetonitrile Chemical compound CC1=CC=CC(C=2C(=CN(CC#N)N=2)C=2C=C3OCOC3=CC=2)=N1 OUISUIBLHNSWMA-UHFFFAOYSA-N 0.000 claims 1
- GEGAGIPGIGCNRW-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-1h-pyrazol-5-yl]pyridine Chemical compound C=1C=C2OCCOC2=CC=1C1=CNN=C1C1=CC=CC=N1 GEGAGIPGIGCNRW-UHFFFAOYSA-N 0.000 claims 1
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| US20080171755A1 (en) * | 2004-08-31 | 2008-07-17 | Wen-Cherng Lee | Pyrimidinylpyrazoles as Tgf-Beta Inhibitors |
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| TW200639163A (en) | 2005-02-04 | 2006-11-16 | Genentech Inc | RAF inhibitor compounds and methods |
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- 2004-02-11 CL CL200400234A patent/CL2004000234A1/es unknown
- 2004-02-12 EA EA200501274A patent/EA010161B1/ru not_active IP Right Cessation
- 2004-02-12 BR BR0407454-8A patent/BRPI0407454A/pt not_active IP Right Cessation
- 2004-02-12 US US10/545,179 patent/US20060264440A1/en not_active Abandoned
- 2004-02-12 GE GEAP20048973A patent/GEP20084391B/en unknown
- 2004-02-12 CA CA002514382A patent/CA2514382A1/en not_active Abandoned
- 2004-02-12 AU AU2004210855A patent/AU2004210855A1/en not_active Abandoned
- 2004-02-12 NZ NZ542289A patent/NZ542289A/en unknown
- 2004-02-12 EP EP04710613A patent/EP1596656A4/en not_active Withdrawn
- 2004-02-12 KR KR1020057014781A patent/KR20050101547A/ko not_active Application Discontinuation
- 2004-02-12 MX MXPA05008524A patent/MXPA05008524A/es unknown
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- 2004-02-12 WO PCT/US2004/004049 patent/WO2004072033A2/en active Application Filing
- 2004-02-12 JP JP2006503509A patent/JP2006517592A/ja active Pending
- 2004-02-12 RS YUP-2005/0616A patent/RS20050616A/sr unknown
- 2004-02-13 AR ARP040100462A patent/AR043184A1/es unknown
- 2004-12-02 UA UAA200508633A patent/UA82223C2/uk unknown
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| IS7966A (is) | 2005-07-29 |
| KR20050101547A (ko) | 2005-10-24 |
| EA200501274A1 (ru) | 2006-02-24 |
| NO20054200D0 (no) | 2005-09-09 |
| UA82223C2 (uk) | 2008-03-25 |
| MXPA05008524A (es) | 2005-10-20 |
| EP1596656A2 (en) | 2005-11-23 |
| EP1596656A4 (en) | 2006-10-18 |
| EA010161B1 (ru) | 2008-06-30 |
| GEP20084391B (en) | 2008-06-10 |
| NO20054200L (no) | 2005-10-14 |
| CN1770980A (zh) | 2006-05-10 |
| RS20050616A (en) | 2007-09-21 |
| AU2004210855A1 (en) | 2004-08-26 |
| NZ542289A (en) | 2009-03-31 |
| AR043184A1 (es) | 2005-07-20 |
| WO2004072033A3 (en) | 2005-03-17 |
| WO2004072033A2 (en) | 2004-08-26 |
| JP2006517592A (ja) | 2006-07-27 |
| CA2514382A1 (en) | 2004-08-26 |
| BRPI0407454A (pt) | 2006-01-24 |
| CL2004000234A1 (es) | 2005-04-15 |
| US20060264440A1 (en) | 2006-11-23 |
| PL378072A1 (pl) | 2006-02-20 |
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