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
- 210000004881 tumor cell Anatomy 0.000 claims description 7
- 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
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 206010059245 Angiopathy Diseases 0.000 claims description 2
- 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
- 206010012305 Demyelination Diseases 0.000 claims description 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 2
- 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
- 208000018631 connective tissue disease Diseases 0.000 claims description 2
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 208000010706 fatty liver disease Diseases 0.000 claims description 2
- 206010016629 fibroma Diseases 0.000 claims description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 210000003128 head Anatomy 0.000 claims description 2
- 230000002440 hepatic effect Effects 0.000 claims description 2
- 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
- 208000017169 kidney disease Diseases 0.000 claims description 2
- 201000010260 leiomyoma Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 231100000515 lung injury Toxicity 0.000 claims description 2
- 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
- 208000037803 restenosis Diseases 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 208000010157 sclerosing cholangitis Diseases 0.000 claims description 2
- 208000020431 spinal cord injury Diseases 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 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
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- PKYNGYYFDJWSPD-UHFFFAOYSA-N 3-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)propan-1-amine Chemical compound N=1N(CCCN)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 PKYNGYYFDJWSPD-UHFFFAOYSA-N 0.000 claims 1
- JGJUOHQSJQGVKB-UHFFFAOYSA-N 3-(4-ethylphenyl)-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2,1-benzoxazole Chemical compound C1=CC(CC)=CC=C1C1=C2C=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=CC2=NO1 JGJUOHQSJQGVKB-UHFFFAOYSA-N 0.000 claims 1
- VCIAFTLLDVOKLY-UHFFFAOYSA-N 3-[(4-nitrophenyl)methyl]-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1C(=O)C2=CC(C=3C(=NNC=3)C=3N=CC=CC=3)=CC=C2N=C1 VCIAFTLLDVOKLY-UHFFFAOYSA-N 0.000 claims 1
- KWAPKVNILUFYMY-UHFFFAOYSA-N 3-methyl-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-one Chemical compound C1=C2C(=O)N(C)C=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 KWAPKVNILUFYMY-UHFFFAOYSA-N 0.000 claims 1
- LORWLLUMJKJESN-UHFFFAOYSA-N 4-(4-methoxyphenyl)-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazoline Chemical compound C1=CC(OC)=CC=C1C1=NC=NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C12 LORWLLUMJKJESN-UHFFFAOYSA-N 0.000 claims 1
- XEQUMANZORSJSQ-UHFFFAOYSA-N 4-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2h-isoquinolin-1-one Chemical compound C12=CC=CC=C2C(=O)NC=C1C1=CNN=C1C1=CC=CC=N1 XEQUMANZORSJSQ-UHFFFAOYSA-N 0.000 claims 1
- ZUJOXLNMLFTWFC-UHFFFAOYSA-N 4-[3-pyridin-2-yl-1-[2-(2h-tetrazol-5-yl)ethyl]pyrazol-4-yl]quinoline Chemical compound N1=NNN=C1CCN(N=1)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 ZUJOXLNMLFTWFC-UHFFFAOYSA-N 0.000 claims 1
- YIQGAYJYTUYZAB-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]cyclohexan-1-amine Chemical compound CC1=CC=CC(C=2C(=CN(N=2)C2CCC(N)CC2)C=2C=C3OCOC3=CC=2)=N1 YIQGAYJYTUYZAB-UHFFFAOYSA-N 0.000 claims 1
- RRLJBZBOHXRYQY-UHFFFAOYSA-N 4-methoxy-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazoline Chemical compound C1=C2C(OC)=NC=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 RRLJBZBOHXRYQY-UHFFFAOYSA-N 0.000 claims 1
- QALIECXFYNVXDV-UHFFFAOYSA-N 5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=NNC2=CC=C1C=1C=NNC=1C1=CC=CC=N1 QALIECXFYNVXDV-UHFFFAOYSA-N 0.000 claims 1
- RELRCIMXHZRDPH-UHFFFAOYSA-N 5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1C1=CNN=C1C1=CC=CC=N1 RELRCIMXHZRDPH-UHFFFAOYSA-N 0.000 claims 1
- BJQFRDHFNOSUOI-UHFFFAOYSA-N 5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2,1,3-benzoxadiazole Chemical compound C1=CC2=NON=C2C=C1C1=CNN=C1C1=CC=CC=N1 BJQFRDHFNOSUOI-UHFFFAOYSA-N 0.000 claims 1
- GEGNAAVHSKDFJG-UHFFFAOYSA-N 5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-3-thiophen-3-yl-2,1-benzoxazole Chemical compound S1C=CC(C2=C3C=C(C=CC3=NO2)C=2C(=NNC=2)C=2N=CC=CC=2)=C1 GEGNAAVHSKDFJG-UHFFFAOYSA-N 0.000 claims 1
- PENACLFHOFYJQA-UHFFFAOYSA-N 5-(5-pyridin-2-yl-1h-pyrazol-4-yl)pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=C(C=2N=CC=CC=2)NN=C1 PENACLFHOFYJQA-UHFFFAOYSA-N 0.000 claims 1
- ZSMDWARKZLZBDN-UHFFFAOYSA-N 5-methyl-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC2=NC=NN2C(C)=C1C1=CNN=C1C1=CC=CC=N1 ZSMDWARKZLZBDN-UHFFFAOYSA-N 0.000 claims 1
- SFNKTPUJVDOOMX-UHFFFAOYSA-N 6-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1,3-benzothiazole Chemical compound C1=C2SC=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 SFNKTPUJVDOOMX-UHFFFAOYSA-N 0.000 claims 1
- MDUSFHREFMSKTH-UHFFFAOYSA-N 6-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-quinazolin-4-one Chemical compound C1=C2C(=O)NC=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 MDUSFHREFMSKTH-UHFFFAOYSA-N 0.000 claims 1
- NNVJHCATNYWLHR-UHFFFAOYSA-N 6-(5-pyridin-2-yl-1h-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1N2N=CN=C2C=CC=1C1=CNN=C1C1=CC=CC=N1 NNVJHCATNYWLHR-UHFFFAOYSA-N 0.000 claims 1
- PDNNXJMEHCBLDU-UHFFFAOYSA-N 6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 PDNNXJMEHCBLDU-UHFFFAOYSA-N 0.000 claims 1
- KKKXKQCWDPXMAU-UHFFFAOYSA-N 6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazoline Chemical compound C=1C=C2N=CN=CC2=CC=1C=1C=NNC=1C1=CC=CC=N1 KKKXKQCWDPXMAU-UHFFFAOYSA-N 0.000 claims 1
- KJOVAVDYBDKMTQ-UHFFFAOYSA-N 6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinoline Chemical compound C=1C=C2N=CC=CC2=CC=1C1=CNN=C1C1=CC=CC=N1 KJOVAVDYBDKMTQ-UHFFFAOYSA-N 0.000 claims 1
- OYIXBSCQTFDIDY-UHFFFAOYSA-N 6-[5-(5-fluoro-6-methylpyridin-2-yl)-1h-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=C(F)C(C)=NC(C=2C(=CNN=2)C2=CN3N=CN=C3C=C2)=C1 OYIXBSCQTFDIDY-UHFFFAOYSA-N 0.000 claims 1
- JFQVCSRWSJYYIF-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-1h-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC=CC(C=2C(=CNN=2)C2=CN3N=CN=C3C=C2)=N1 JFQVCSRWSJYYIF-UHFFFAOYSA-N 0.000 claims 1
- PHIYKABHHHBNIA-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-1h-pyrazol-4-yl]quinoline Chemical compound CC1=CC=CC(C=2C(=CNN=2)C=2C=C3C=CC=NC3=CC=2)=N1 PHIYKABHHHBNIA-UHFFFAOYSA-N 0.000 claims 1
- ICXIUJASSXTVBC-UHFFFAOYSA-N 7-(5-pyridin-2-yl-1h-pyrazol-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C(=O)C=CN=C2C=CC=1C1=CNN=C1C1=CC=CC=N1 ICXIUJASSXTVBC-UHFFFAOYSA-N 0.000 claims 1
- 102000007530 Neurofibromin 1 Human genes 0.000 claims 1
- 108010085793 Neurofibromin 1 Proteins 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
- NPPIDUZDOYJWOV-UHFFFAOYSA-N benzyl n-[4-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]cyclohexyl]carbamate Chemical compound CC1=CC=CC(C=2C(=CN(N=2)C2CCC(CC2)NC(=O)OCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 NPPIDUZDOYJWOV-UHFFFAOYSA-N 0.000 claims 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 1
- 239000011159 matrix material Substances 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- VCQMZOLWWYQBIZ-UHFFFAOYSA-N methyl 4-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]bicyclo[2.2.2]octane-1-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12N(N=1)C=C(C=2C=C3OCOC3=CC=2)C=1C1=CC=CC(C)=N1 VCQMZOLWWYQBIZ-UHFFFAOYSA-N 0.000 claims 1
- IIVJQOJFWOXTLG-UHFFFAOYSA-N morpholin-4-yl-[5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazol-3-yl]methanone Chemical compound N=1NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C2C=1C(=O)N1CCOCC1 IIVJQOJFWOXTLG-UHFFFAOYSA-N 0.000 claims 1
- MFKAAQVRMYIPBX-UHFFFAOYSA-N n,n-dimethyl-1h-indazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N(C)C)=NNC2=C1 MFKAAQVRMYIPBX-UHFFFAOYSA-N 0.000 claims 1
- JADDVONWNKKVFF-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NCC(C)(C)C)=NNC2=CC=C1C=1C=NNC=1C1=CC=CC=N1 JADDVONWNKKVFF-UHFFFAOYSA-N 0.000 claims 1
- PCCDINVHZJGVQS-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC=NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C12 PCCDINVHZJGVQS-UHFFFAOYSA-N 0.000 claims 1
- CIJIVQDXYSUZPF-UHFFFAOYSA-N n-[2-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)ethyl]methanesulfonamide Chemical compound N=1N(CCNS(=O)(=O)C)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 CIJIVQDXYSUZPF-UHFFFAOYSA-N 0.000 claims 1
- UFFLRNPZBQSJLA-UHFFFAOYSA-N n-[3-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)propyl]methanesulfonamide Chemical compound N=1N(CCCNS(=O)(=O)C)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 UFFLRNPZBQSJLA-UHFFFAOYSA-N 0.000 claims 1
- HQUAVNGZXPDBGG-UHFFFAOYSA-N n-benzyl-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxamide Chemical compound N=1NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C2C=1C(=O)NCC1=CC=CC=C1 HQUAVNGZXPDBGG-UHFFFAOYSA-N 0.000 claims 1
- ZBEAWGUBZOQONV-UHFFFAOYSA-N n-cyclopentyl-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxamide Chemical compound N=1NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C2C=1C(=O)NC1CCCC1 ZBEAWGUBZOQONV-UHFFFAOYSA-N 0.000 claims 1
- TVGHQAZJZCDHCM-UHFFFAOYSA-N n-hydroxy-3-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)propanamide Chemical compound N=1N(CCC(=O)NO)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 TVGHQAZJZCDHCM-UHFFFAOYSA-N 0.000 claims 1
- VGXNKFNLPSVFAI-UHFFFAOYSA-N n-phenyl-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxamide Chemical compound N=1NC2=CC=C(C3=C(NN=C3)C=3N=CC=CC=3)C=C2C=1C(=O)NC1=CC=CC=C1 VGXNKFNLPSVFAI-UHFFFAOYSA-N 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- AQWOIRBQLOOZGX-UHFFFAOYSA-N triazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=CN=NN21 AQWOIRBQLOOZGX-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 17
- 108010059616 Activins Proteins 0.000 description 12
- 102000005606 Activins Human genes 0.000 description 12
- 239000000488 activin Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UBWXUGDQUBIEIZ-UHFFFAOYSA-N (13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl) 3-phenylpropanoate Chemical compound CC12CCC(C3CCC(=O)C=C3CC3)C3C1CCC2OC(=O)CCC1=CC=CC=C1 UBWXUGDQUBIEIZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010016654 Fibrosis Diseases 0.000 description 3
- 102400000401 Latency-associated peptide Human genes 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 102100025751 Mothers against decapentaplegic homolog 2 Human genes 0.000 description 3
- 101710143123 Mothers against decapentaplegic homolog 2 Proteins 0.000 description 3
- 102100025748 Mothers against decapentaplegic homolog 3 Human genes 0.000 description 3
- 101710143111 Mothers against decapentaplegic homolog 3 Proteins 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 102000001708 Protein Isoforms Human genes 0.000 description 3
- 108010029485 Protein Isoforms Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003102 growth factor Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 108010005853 Anti-Mullerian Hormone Proteins 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102000007350 Bone Morphogenetic Proteins Human genes 0.000 description 2
- 108010007726 Bone Morphogenetic Proteins Proteins 0.000 description 2
- 206010006895 Cachexia Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000000868 anti-mullerian hormone Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229940112869 bone morphogenetic protein Drugs 0.000 description 2
- 230000004761 fibrosis Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000028709 inflammatory response Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 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
- 230000035897 transcription Effects 0.000 description 2
- 238000013518 transcription Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
- 125000004608 5,6,7,8-tetrahydroquinolinyl group Chemical group N1=C(C=CC=2CCCCC12)* 0.000 description 1
- MBBZMMPHUWSWHV-UHFFFAOYSA-N 6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNCC(O)C(O)C(O)C(O)CO MBBZMMPHUWSWHV-UHFFFAOYSA-N 0.000 description 1
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 1
- RYVZYACBVYKUHD-UHFFFAOYSA-N Alk5 Natural products CC#CC#CCCCCC=CC(=O)NCC(C)C RYVZYACBVYKUHD-UHFFFAOYSA-N 0.000 description 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
- 101000635958 Homo sapiens Transforming growth factor beta-2 proprotein Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010062016 Immunosuppression Diseases 0.000 description 1
- 108010004250 Inhibins Proteins 0.000 description 1
- 102000002746 Inhibins Human genes 0.000 description 1
- 101800001155 Latency-associated peptide Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102100025725 Mothers against decapentaplegic homolog 4 Human genes 0.000 description 1
- 101710143112 Mothers against decapentaplegic homolog 4 Proteins 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 101100437153 Rattus norvegicus Acvr2b gene Proteins 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 102000007614 Thrombospondin 1 Human genes 0.000 description 1
- 108010046722 Thrombospondin 1 Proteins 0.000 description 1
- 102100030737 Transforming growth factor beta-2 proprotein Human genes 0.000 description 1
- 102000056172 Transforming growth factor beta-3 Human genes 0.000 description 1
- 108090000097 Transforming growth factor beta-3 Proteins 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000025084 cell cycle arrest Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000006041 cell recruitment Effects 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 230000007783 downstream signaling Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 150000004665 fatty acids Chemical group 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 210000003958 hematopoietic stem cell Anatomy 0.000 description 1
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 239000000893 inhibin Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004324 lymphatic system Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000009681 mesenchymal cell proliferation Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000004897 n-terminal region Anatomy 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 229940012957 plasmin Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 201000002793 renal fibrosis Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 230000007781 signaling event Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000007863 steatosis Effects 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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
- C07D401/14—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 three or more hetero rings
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- 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
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Communicable Diseases (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44677703P | 2003-02-12 | 2003-02-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200506408B true ZA200506408B (en) | 2006-05-31 |
Family
ID=32869552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200506408A ZA200506408B (en) | 2003-02-12 | 2005-08-11 | Parazoles and methods of making and using the same |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20060264440A1 (fr) |
| EP (1) | EP1596656A4 (fr) |
| JP (1) | JP2006517592A (fr) |
| KR (1) | KR20050101547A (fr) |
| CN (1) | CN1770980A (fr) |
| AR (1) | AR043184A1 (fr) |
| AU (1) | AU2004210855A1 (fr) |
| BR (1) | BRPI0407454A (fr) |
| CA (1) | CA2514382A1 (fr) |
| CL (1) | CL2004000234A1 (fr) |
| EA (1) | EA010161B1 (fr) |
| GE (1) | GEP20084391B (fr) |
| IS (1) | IS7966A (fr) |
| MX (1) | MXPA05008524A (fr) |
| NO (1) | NO20054200L (fr) |
| NZ (1) | NZ542289A (fr) |
| PL (1) | PL378072A1 (fr) |
| RS (1) | RS20050616A (fr) |
| UA (1) | UA82223C2 (fr) |
| WO (1) | WO2004072033A2 (fr) |
| ZA (1) | ZA200506408B (fr) |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0313915D0 (en) * | 2003-06-16 | 2003-07-23 | Smithkline Beecham Corp | Compounds |
| AU2005238270A1 (en) * | 2004-04-28 | 2005-11-10 | Arrow Therapeutics Limited | Morpholinylanilinoquinazo- line derivatives for use as antiviral agents |
| WO2006019965A2 (fr) * | 2004-07-16 | 2006-02-23 | Takeda San Diego, Inc. | Inhibiteurs de la dipeptidyl peptidase |
| AU2005280167A1 (en) * | 2004-08-31 | 2006-03-09 | Biogen Idec Ma Inc. | Pyrimidinylpyrazoles as TGF-beta inhibitors |
| US20070275968A1 (en) * | 2004-09-07 | 2007-11-29 | Hitoshi Kurata | Substituted Biphenyl Derivative |
| WO2006044509A2 (fr) * | 2004-10-15 | 2006-04-27 | Biogen Idec Ma Inc. | Procede pour traiter des lesions vasculaires |
| TW200639163A (en) | 2005-02-04 | 2006-11-16 | Genentech Inc | RAF inhibitor compounds and methods |
| KR20080023680A (ko) | 2005-05-10 | 2008-03-14 | 인터뮨, 인크. | 스트레스-활성화 단백질 키나제 시스템을 조절하기 위한피리돈 유도체 |
| GB0520475D0 (en) * | 2005-10-07 | 2005-11-16 | Arrow Therapeutics Ltd | Chemical compounds |
| KR20080083139A (ko) * | 2006-01-11 | 2008-09-16 | 애로우 쎄라퓨틱스 리미티드 | 항-바이러스제로 사용하기 위한트리아졸로아닐리노피리미딘 유도체 |
| CA2645583A1 (fr) | 2006-03-20 | 2007-09-27 | F. Hoffman-La Roche Ag | Procedes d'inhibition des proteines kinase btk et syk |
| CN101062916B (zh) * | 2006-04-29 | 2012-12-26 | 中国人民解放军军事医学科学院毒物药物研究所 | 三取代1h-吡唑化合物、其制备方法、药物组合物及其制药用途 |
| US9259426B2 (en) | 2006-07-20 | 2016-02-16 | Gilead Sciences, Inc. | 4,6-di- and 2,4,6-trisubstituted quinazoline derivatives useful for treating viral infections |
| US8673929B2 (en) * | 2006-07-20 | 2014-03-18 | Gilead Sciences, Inc. | 4,6-di- and 2,4,6-trisubstituted quinazoline derivatives and pharmaceutical compositions useful for treating viral infections |
| US20090258882A1 (en) * | 2006-07-28 | 2009-10-15 | Novartis Ag | 2,4-Substituted Quinazolines as Lipid Kinase Inhibitors |
| MX2009003518A (es) | 2006-10-03 | 2009-08-25 | Genzyme Corp | Uso de antagonistas de tgf-beta para tratar a los infantes en riesgo de desarrollar displasia brocopulmonar. |
| CA2666603C (fr) * | 2006-10-16 | 2013-08-06 | Pfizer Products Inc. | Pyrazolyl thienopyridines therapeutiques et leur utilisation pour le traitement de maladies en fonction du tgf beta |
| JP5507045B2 (ja) | 2006-12-15 | 2014-05-28 | 石原産業株式会社 | アントラニルアミド系化合物の製造方法 |
| WO2009009059A1 (fr) * | 2007-07-09 | 2009-01-15 | Biogen Idec Ma Inc. | Composés spiro en tant qu'antagonistes du tgf-bêta |
| JP4792126B2 (ja) * | 2007-08-01 | 2011-10-12 | ファイザー・インク | ピラゾール化合物およびＲａｆ阻害剤としてのその使用 |
| CL2009000904A1 (es) | 2008-04-21 | 2010-04-30 | Shionogi & Co | Compuestos derivados de ciclohexil sulfonamidas que tienen actividad antagonista en el receptor npy y5, composicion farmaceutica y formulacion farmaceutica que los comprende. |
| EP2296653B1 (fr) | 2008-06-03 | 2016-01-27 | Intermune, Inc. | Composés et procédés de traitement des troubles inflammatoires et fibrotiques |
| RU2615130C2 (ru) | 2009-10-06 | 2017-04-04 | Милленниум Фармасьютикалз, Инк | Гетероциклические соединения, используемые в качестве ингибиторов pdk1 |
| PL2647629T3 (pl) * | 2010-12-01 | 2015-12-31 | Nissan Chemical Ind Ltd | Związki pirazolowe o terapeutycznym działaniu na szpiczaka mnogiego |
| KR101084729B1 (ko) | 2011-06-10 | 2011-11-22 | 재단법인 한국원자력의학원 | 이소옥사졸 유도체를 포함하는 ＴＧＦ-β 활성 저해용 조성물 |
| US20140308275A1 (en) | 2011-07-27 | 2014-10-16 | Inserm (Institut National De La Sante Et De La Recherche Medicale | Methods for diagnosing and treating myhre syndrome |
| AU2011379972B2 (en) | 2011-10-26 | 2016-05-12 | Seattle Children's Research Institute | Cysteamine in the treatment of fibrotic disease |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| WO2013178591A1 (fr) * | 2012-05-31 | 2013-12-05 | F. Hoffmann-La Roche Ag | Dérivés d'aminoquinazoline et de pyridopyrimidine |
| CN104487438B (zh) * | 2012-07-26 | 2016-10-19 | 霍夫曼-拉罗奇有限公司 | 神经发生的苯并异噁唑调节剂 |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| CA2905242C (fr) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Composes indoliques activant l'ampk |
| JP6525437B2 (ja) | 2014-04-02 | 2019-06-05 | インターミューン， インコーポレイテッド | 抗線維性ピリジノン |
| EP3722297A1 (fr) | 2015-03-04 | 2020-10-14 | Gilead Sciences, Inc. | Composés modulateurs de récepteurs de type toll |
| ES2918924T3 (es) | 2015-04-01 | 2022-07-21 | Rigel Pharmaceuticals Inc | Inhibidores de TGF-beta |
| EP3313420B1 (fr) | 2015-06-25 | 2024-03-13 | The Children's Medical Center Corporation | Procédés et compositions se rapportant à l'expansion, l'enrichissement et la conservation de cellules souches hématopoïétiques |
| EP3319968A1 (fr) | 2015-07-06 | 2018-05-16 | Rodin Therapeutics, Inc. | N-aminophényl-amides hétérocycliques en tant qu'inhibiteurs de l'histone désacétylase |
| PT3319959T (pt) | 2015-07-06 | 2021-12-06 | Alkermes Inc | Inibidores hetero-halo de histona desacetilase |
| WO2017161001A1 (fr) | 2016-03-15 | 2017-09-21 | Children's Medical Center Corporation | Procédés et compositions concernant l'expansion de cellules souches hématopoïétiques |
| JP6954932B2 (ja) * | 2016-06-13 | 2021-10-27 | ジェンフリート セラピューティクス（シャンハイ）インコーポレイテッド | ＴＧＦ−βＲＩ阻害剤としてのベンゾトリアゾール由来のα、β−不飽和アミド系化合物 |
| KR102434226B1 (ko) * | 2016-06-30 | 2022-08-19 | 한미약품 주식회사 | Alk5 억제제로서의 신규 피라졸 유도체 및 이의 용도 |
| ES2906581T3 (es) | 2016-09-02 | 2022-04-19 | Gilead Sciences Inc | Compuestos moduladores de los receptores tipo Toll |
| US10640499B2 (en) | 2016-09-02 | 2020-05-05 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| CN108069955B (zh) * | 2016-11-14 | 2021-04-06 | 江苏恒瑞医药股份有限公司 | 3-吡啶基-4-苯并噻唑基吡唑类衍生物、其制备方法及其在医药上的应用 |
| AU2017357333A1 (en) * | 2016-11-14 | 2019-05-02 | Jiangsu Hengrui Medicine Co., Ltd. | 3,4-bipyridyl pyrazole derivative, and preparation method therefor and medical application thereof |
| CA3049443A1 (fr) | 2017-01-11 | 2018-07-19 | Rodin Therapeutics, Inc. | Inhibiteurs bicycliques d'histone desacetylase |
| JP7152471B2 (ja) | 2017-08-07 | 2022-10-12 | ロダン・セラピューティクス，インコーポレーテッド | ヒストン脱アセチル化酵素の二環阻害剤 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| EP3894401A2 (fr) | 2018-12-11 | 2021-10-20 | Theravance Biopharma R&D IP, LLC | Dérivés naphthyridine et quinoléine en tant qu'inhibiteurs de alk5 |
| TWI827760B (zh) | 2018-12-12 | 2024-01-01 | 加拿大商愛彼特生物製藥公司 | 經取代之芳基甲基脲類及雜芳基甲基脲類、其類似物及其使用方法 |
| US20220177978A1 (en) | 2019-04-02 | 2022-06-09 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods of predicting and preventing cancer in patients having premalignant lesions |
| TWI751517B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TWI751516B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| WO2020215094A1 (fr) | 2019-04-18 | 2020-10-22 | The Johns Hopkins University | Dérivés de 2-amino-pyrazolyl-[1,2,4]triazolo[1,5 a] pyridine substitués et leur utilisation |
| TWI879779B (zh) | 2019-06-28 | 2025-04-11 | 美商基利科學股份有限公司 | 類鐸受體調節劑化合物的製備方法 |
| MX2022003769A (es) * | 2019-10-03 | 2022-04-20 | Bristol Myers Squibb Co | Indazol carboxamidas como inhibidores de cinasas. |
| WO2021102468A1 (fr) | 2019-11-22 | 2021-05-27 | Theravance Biopharma R&D Ip, Llc | 1,5-naphtyridines ou quinoléines substituées en tant qu'inhibiteurs d'alk5 |
| MX2022005843A (es) | 2019-11-28 | 2022-07-19 | Agomab Spain S L U | Derivados de bencilamida como inhibidores del receptor i del factor de crecimiento transformante beta/ cinasa similar al receptor de activina 5 (alk5). |
| WO2021120890A1 (fr) | 2019-12-20 | 2021-06-24 | Novartis Ag | Dérivés pyrazolyle utiles en tant qu'agents anticancéreux |
| CN113620956B (zh) * | 2020-05-06 | 2023-06-13 | 赛诺哈勃药业（成都）有限公司 | 转化生长因子受体拮抗剂、其制备方法和应用 |
| CN114230565B (zh) * | 2020-09-09 | 2023-10-27 | 成都奥睿药业有限公司 | 5-取代吲哚3-酰胺衍生物及其制备方法和用途 |
| CN112759592A (zh) * | 2021-02-01 | 2021-05-07 | 无锡鸣鹭医药科技有限公司 | 一种6-碘[1,2,3]三唑并[1,5-a]吡啶的合成方法 |
| AU2022237836B2 (en) * | 2021-03-18 | 2024-07-04 | F. Hoffmann-La Roche Ag | Process for preparing risdiplam |
| WO2024111626A1 (fr) * | 2022-11-25 | 2024-05-30 | カルナバイオサイエンス株式会社 | Nouveau dérivé de thiazole |
Family Cites Families (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940486A (en) * | 1971-05-10 | 1976-02-24 | Ciba-Geigy Corporation | Imidazole derivatives in the treatment of pain |
| US4302464A (en) * | 1980-10-16 | 1981-11-24 | Pfizer Inc. | Imidazolylpyridine therapeutic agents |
| US4686231A (en) * | 1985-12-12 | 1987-08-11 | Smithkline Beckman Corporation | Inhibition of 5-lipoxygenase products |
| US4925857A (en) * | 1989-03-22 | 1990-05-15 | Sterling Drug Inc. | Pyridinyl-1H-pyrazole-1-alkanamides as antiarrhythmic agents |
| JP2753659B2 (ja) * | 1990-09-03 | 1998-05-20 | 株式会社大塚製薬工場 | ピラゾール誘導体 |
| IL104369A0 (en) * | 1992-01-13 | 1993-05-13 | Smithkline Beecham Corp | Novel compounds and compositions |
| US5656644A (en) * | 1994-07-20 | 1997-08-12 | Smithkline Beecham Corporation | Pyridyl imidazoles |
| US5916891A (en) * | 1992-01-13 | 1999-06-29 | Smithkline Beecham Corporation | Pyrimidinyl imidazoles |
| DE4233713A1 (de) * | 1992-10-07 | 1994-04-14 | Bayer Ag | Substituierte 4,5-Dihydro-1-pyrazolcarbonsäureanilide |
| US5593992A (en) * | 1993-07-16 | 1997-01-14 | Smithkline Beecham Corporation | Compounds |
| US5593991A (en) * | 1993-07-16 | 1997-01-14 | Adams; Jerry L. | Imidazole compounds, use and process of making |
| US5670527A (en) * | 1993-07-16 | 1997-09-23 | Smithkline Beecham Corporation | Pyridyl imidazole compounds and compositions |
| US5486534A (en) * | 1994-07-21 | 1996-01-23 | G. D. Searle & Co. | 3,4-substituted pyrazoles for the treatment of inflammation |
| GB9423460D0 (en) * | 1994-11-21 | 1995-01-11 | Merck Sharp & Dohme | Therapeutic agents |
| JP3734180B2 (ja) * | 1994-12-28 | 2006-01-11 | エーザイ株式会社 | 新規ピラゾール誘導体 |
| US5514505A (en) * | 1995-05-15 | 1996-05-07 | Xerox Corporation | Method for obtaining improved image contrast in migration imaging members |
| US5593997A (en) * | 1995-05-23 | 1997-01-14 | Pfizer Inc. | 4-aminopyrazolo(3-,4-D)pyrimidine and 4-aminopyrazolo-(3,4-D)pyridine tyrosine kinase inhibitors |
| IL118544A (en) * | 1995-06-07 | 2001-08-08 | Smithkline Beecham Corp | History of imidazole, the process for their preparation and the pharmaceutical preparations containing them |
| US5739143A (en) * | 1995-06-07 | 1998-04-14 | Smithkline Beecham Corporation | Imidazole compounds and compositions |
| US5854276A (en) * | 1995-06-29 | 1998-12-29 | Fujisawa Pharmaceutical Co., Ltd. | Substance WF16616, process for production thereof, and use thereof |
| US5837719A (en) * | 1995-08-10 | 1998-11-17 | Merck & Co., Inc. | 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use |
| US5792778A (en) * | 1995-08-10 | 1998-08-11 | Merck & Co., Inc. | 2-substituted aryl pyrroles, compositions containing such compounds and methods of use |
| US5717100A (en) * | 1995-10-06 | 1998-02-10 | Merck & Co., Inc. | Substituted imidazoles having anti-cancer and cytokine inhibitory activity |
| ZA9610687B (en) * | 1995-12-22 | 1997-09-29 | Smithkline Beecham Corp | Novel synthesis. |
| ZA97175B (en) * | 1996-01-11 | 1997-11-04 | Smithkline Beecham Corp | Novel substituted imidazole compounds. |
| BR9706973A (pt) * | 1996-01-11 | 1999-04-06 | Smithkline Beecham Corp | Novos compostos de imidazol substituídos |
| US5872136A (en) * | 1996-04-03 | 1999-02-16 | Merck & Co., Inc. | Arylheteroaryl inhibitors of farnesyl-protein transferase |
| US5939557A (en) * | 1996-04-03 | 1999-08-17 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5880140A (en) * | 1996-04-03 | 1999-03-09 | Merck & Co., Inc. | Biheteroaryl inhibitors of farnesyl-protein transferase |
| US5883105A (en) * | 1996-04-03 | 1999-03-16 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5854265A (en) * | 1996-04-03 | 1998-12-29 | Merck & Co., Inc. | Biheteroaryl inhibitors of farnesyl-protein transferase |
| DE69733135T2 (de) * | 1996-06-10 | 2006-03-02 | Merck & Co., Inc. | Substituierte imidazole mit cytokinin-inhibirender wirkung |
| US5854264A (en) * | 1996-07-24 | 1998-12-29 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| BR9713027A (pt) * | 1996-11-12 | 2000-01-25 | Novartis Ag | Derivados de pirazol úteis como herbicidas |
| US5939439A (en) * | 1996-12-30 | 1999-08-17 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| AU7138298A (en) * | 1997-04-24 | 1998-11-13 | Ortho-Mcneil Corporation, Inc. | Substituted imidazoles useful in the treatment of inflammatory diseases |
| EP0983260A2 (fr) * | 1997-05-22 | 2000-03-08 | G.D. Searle & Co. | PYRAZOLES 3(5)-HETEROARYL SUBSTITUEES UTILISEES COMME INHIBITEURS DE KINASE p38 |
| WO2002048115A2 (fr) * | 2000-12-11 | 2002-06-20 | E. I. Du Pont De Nemours And Company | Quinazolinones et pyridinylpyrimidinones pour la regulation de nuisibles invertebres |
| EP1363904A1 (fr) * | 2001-02-02 | 2003-11-26 | Glaxo Group Limited | Pyrazoles utilises comme inhibiteurs du tgf |
| WO2002066462A1 (fr) * | 2001-02-02 | 2002-08-29 | Glaxo Group Limited | Derives pyrazole contre la surexpression du facteur |
| GB0102672D0 (en) * | 2001-02-02 | 2001-03-21 | Glaxo Group Ltd | Compounds |
| DE10113000A1 (de) * | 2001-03-17 | 2002-09-19 | Bayerische Motoren Werke Ag | System aus Verbrennungsmotor und Brennstoffzelle |
| ATE402164T1 (de) * | 2001-04-26 | 2008-08-15 | Eisai R&D Man Co Ltd | Stickstoffhaltige verbindung mit kondensiertem ring und pyrazolylgruppe als substituent und medizinische zusammensetzung davon |
| PT1397364E (pt) * | 2001-05-24 | 2007-10-22 | Lilly Co Eli | Novos derivados de pirrole como agentes farmacêuticos |
| ES2319972T3 (es) * | 2001-10-15 | 2009-05-18 | E.I. Du Pont De Nemours And Company | Iminobenzoxazinas, iminobenzotiazinas e iminoquinazolinas para controlar plagas de invertebrados. |
| AR040726A1 (es) * | 2002-07-31 | 2005-04-20 | Smithkline Beecham Corp | Compuesto de 2- fenilpiridin-4-il-heterociclico, composicion farmaceutica que lo comprende y su uso para la fabricacion de un medicamento |
| GB0217786D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Compounds |
| EA200500377A1 (ru) * | 2002-09-18 | 2005-08-25 | Пфайзер Продактс Инк. | Пиразольные производные как ингибиторы трансформирующего фактора роста (tgf) |
| AU2003268155A1 (en) * | 2002-09-19 | 2004-04-08 | Eli Lilly And Company | Methods of inhibiting tgf beta with substituted pyrazoles |
| GB0313915D0 (en) * | 2003-06-16 | 2003-07-23 | Smithkline Beecham Corp | Compounds |
-
2004
- 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 JP JP2006503509A patent/JP2006517592A/ja active Pending
- 2004-02-12 US US10/545,179 patent/US20060264440A1/en not_active Abandoned
- 2004-02-12 EP EP04710613A patent/EP1596656A4/fr not_active Withdrawn
- 2004-02-12 WO PCT/US2004/004049 patent/WO2004072033A2/fr not_active Ceased
- 2004-02-12 BR BR0407454-8A patent/BRPI0407454A/pt not_active IP Right Cessation
- 2004-02-12 CN CNA200480009623XA patent/CN1770980A/zh active Pending
- 2004-02-12 AU AU2004210855A patent/AU2004210855A1/en not_active Abandoned
- 2004-02-12 RS YUP-2005/0616A patent/RS20050616A/sr unknown
- 2004-02-12 CA CA002514382A patent/CA2514382A1/fr not_active Abandoned
- 2004-02-12 PL PL378072A patent/PL378072A1/pl not_active Application Discontinuation
- 2004-02-12 NZ NZ542289A patent/NZ542289A/en unknown
- 2004-02-12 MX MXPA05008524A patent/MXPA05008524A/es unknown
- 2004-02-12 GE GEAP20048973A patent/GEP20084391B/en unknown
- 2004-02-12 KR KR1020057014781A patent/KR20050101547A/ko not_active Ceased
- 2004-02-13 AR ARP040100462A patent/AR043184A1/es unknown
- 2004-12-02 UA UAA200508633A patent/UA82223C2/uk unknown
-
2005
- 2005-07-29 IS IS7966A patent/IS7966A/is unknown
- 2005-08-11 ZA ZA200506408A patent/ZA200506408B/en unknown
- 2005-09-09 NO NO20054200A patent/NO20054200L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1596656A2 (fr) | 2005-11-23 |
| NO20054200D0 (no) | 2005-09-09 |
| NO20054200L (no) | 2005-10-14 |
| PL378072A1 (pl) | 2006-02-20 |
| AR043184A1 (es) | 2005-07-20 |
| NZ542289A (en) | 2009-03-31 |
| GEP20084391B (en) | 2008-06-10 |
| MXPA05008524A (es) | 2005-10-20 |
| CL2004000234A1 (es) | 2005-04-15 |
| JP2006517592A (ja) | 2006-07-27 |
| UA82223C2 (uk) | 2008-03-25 |
| EP1596656A4 (fr) | 2006-10-18 |
| IS7966A (is) | 2005-07-29 |
| KR20050101547A (ko) | 2005-10-24 |
| BRPI0407454A (pt) | 2006-01-24 |
| CN1770980A (zh) | 2006-05-10 |
| RS20050616A (sr) | 2007-09-21 |
| CA2514382A1 (fr) | 2004-08-26 |
| WO2004072033A2 (fr) | 2004-08-26 |
| EA200501274A1 (ru) | 2006-02-24 |
| WO2004072033A3 (fr) | 2005-03-17 |
| EA010161B1 (ru) | 2008-06-30 |
| AU2004210855A1 (en) | 2004-08-26 |
| US20060264440A1 (en) | 2006-11-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200506408B (en) | Parazoles and methods of making and using the same | |
| CA2841252C (fr) | 2-pyridylimidazoles substitues utilises comme inhibiteurs d'alk5 et/ou d'alk4 | |
| AU2003270318B2 (en) | Imidazolopyridines and methods of making and using the same | |
| ZA200407902B (en) | Tri-substituted hetreroaryls and methods of makingand using the same. | |
| JP5850952B2 (ja) | セリン／スレオニンキナーゼ阻害剤としての新しいアザインドリルフェニルスルホンアミド | |
| AU2011217561B2 (en) | Hetarylaminonaphthyridines | |
| AU2005295734A1 (en) | Methods of treating vascular injuries | |
| JP2006502164A5 (fr) | ||
| ZA200501856B (en) | Pyrazolopyridines and methods of making and using the same | |
| SG182803A1 (en) | Hetaryl-[1,8]naphthyridine derivatives | |
| MX2010013549A (es) | Imidazoles sustituidos con 2-piridilo, como inhibidores de alk4 y/o alk4. | |
| WO2006026306A1 (fr) | Pyrimidinylimidazoles utilises comme inhibiteurs de tgf-beta | |
| AU2005280167A1 (en) | Pyrimidinylpyrazoles as TGF-beta inhibitors |