CA2802641C - Pyrazolo [1, 5a] pyrimidine and thieno [3, 2b] pyrimidine derivatives as irak4 modulators - Google Patents
Pyrazolo [1, 5a] pyrimidine and thieno [3, 2b] pyrimidine derivatives as irak4 modulators Download PDFInfo
- Publication number
- CA2802641C CA2802641C CA2802641A CA2802641A CA2802641C CA 2802641 C CA2802641 C CA 2802641C CA 2802641 A CA2802641 A CA 2802641A CA 2802641 A CA2802641 A CA 2802641A CA 2802641 C CA2802641 C CA 2802641C
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- phenyl
- chloro
- pyrimidine
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 title description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- 238000011282 treatment Methods 0.000 claims abstract description 29
- 230000001404 mediated effect Effects 0.000 claims abstract description 14
- 102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 claims abstract description 13
- 101710199015 Interleukin-1 receptor-associated kinase 1 Proteins 0.000 claims abstract description 12
- -1 hydroxy, amino Chemical group 0.000 claims description 556
- 239000000203 mixture Substances 0.000 claims description 286
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 144
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
- 125000003386 piperidinyl group Chemical group 0.000 claims description 67
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 66
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 50
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 49
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
- 201000010099 disease Diseases 0.000 claims description 37
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 30
- PUWCNAHJTYTHKV-UHFFFAOYSA-N thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound N1=CN=C2C(C(=O)O)=CSC2=C1 PUWCNAHJTYTHKV-UHFFFAOYSA-N 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 125000004193 piperazinyl group Chemical group 0.000 claims description 27
- 125000003725 azepanyl group Chemical group 0.000 claims description 25
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 23
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 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 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000002971 oxazolyl group Chemical group 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 13
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 206010003246 arthritis Diseases 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 230000002757 inflammatory effect Effects 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 208000023504 respiratory system disease Diseases 0.000 claims description 7
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 208000019693 Lung disease Diseases 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 6
- PCHWCLBVSAKTKO-UHFFFAOYSA-N 3-(2-amino-4-chlorophenoxy)propan-1-ol Chemical compound NC1=CC(Cl)=CC=C1OCCCO PCHWCLBVSAKTKO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- FIKOGHBRNAAIAL-UHFFFAOYSA-N 4-(2-amino-4-chlorophenoxy)cyclohexan-1-ol Chemical compound NC1=CC(Cl)=CC=C1OC1CCC(O)CC1 FIKOGHBRNAAIAL-UHFFFAOYSA-N 0.000 claims description 4
- 208000009079 Bronchial Spasm Diseases 0.000 claims description 4
- 208000014181 Bronchial disease Diseases 0.000 claims description 4
- 206010006482 Bronchospasm Diseases 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- 230000001363 autoimmune Effects 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 230000000414 obstructive effect Effects 0.000 claims description 4
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- OKAAFIKHHROVHN-UHFFFAOYSA-N 6-bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(Br)C=NC2=C(C(=O)O)C=NN21 OKAAFIKHHROVHN-UHFFFAOYSA-N 0.000 claims description 2
- INIORSSITPVKJU-UHFFFAOYSA-N [3-(2-amino-4-chlorophenoxy)cyclopentyl]methanol Chemical compound NC1=CC(Cl)=CC=C1OC1CC(CO)CC1 INIORSSITPVKJU-UHFFFAOYSA-N 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- RKBDEYDDNCNVHV-UHFFFAOYSA-N [1-(2-amino-4-chlorophenyl)piperidin-4-yl]methanol Chemical compound NC1=CC(Cl)=CC=C1N1CCC(CO)CC1 RKBDEYDDNCNVHV-UHFFFAOYSA-N 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- UCIHGIGRCAGUSD-UHFFFAOYSA-N 2-[4-(aminomethyl)piperidin-1-yl]-5-chloroaniline Chemical compound C1CC(CN)CCN1C1=CC=C(Cl)C=C1N UCIHGIGRCAGUSD-UHFFFAOYSA-N 0.000 claims 3
- BFOQYOCNAFPILH-UHFFFAOYSA-N 5-chloro-2-piperidin-1-ylaniline Chemical compound NC1=CC(Cl)=CC=C1N1CCCCC1 BFOQYOCNAFPILH-UHFFFAOYSA-N 0.000 claims 2
- QVTMXACHOQRSAX-UHFFFAOYSA-N (3-amino-4-piperidin-1-ylphenyl)methanol Chemical compound NC1=CC(CO)=CC=C1N1CCCCC1 QVTMXACHOQRSAX-UHFFFAOYSA-N 0.000 claims 1
- CZBXTHMRCUGAHE-UHFFFAOYSA-N 1-(2-amino-4-chlorophenyl)piperidin-4-amine Chemical compound NC1CCN(CC1)c1ccc(Cl)cc1N CZBXTHMRCUGAHE-UHFFFAOYSA-N 0.000 claims 1
- LTHFHPRRYKAMNS-UHFFFAOYSA-N 1-(2-amino-4-chlorophenyl)piperidin-4-ol Chemical compound NC1=CC(Cl)=CC=C1N1CCC(O)CC1 LTHFHPRRYKAMNS-UHFFFAOYSA-N 0.000 claims 1
- CPOALQAOZYXUPJ-UHFFFAOYSA-N 1-(2-amino-4-chlorophenyl)piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC=C(Cl)C=C1N CPOALQAOZYXUPJ-UHFFFAOYSA-N 0.000 claims 1
- FZGRDZYPVPZTIW-UHFFFAOYSA-N 1-[1-(2-amino-4-chlorophenyl)pyrrolidin-3-yl]ethanol Chemical compound C1C(C(O)C)CCN1C1=CC=C(Cl)C=C1N FZGRDZYPVPZTIW-UHFFFAOYSA-N 0.000 claims 1
- ZBRZYIHPBZPHJY-UHFFFAOYSA-N 2-(2-amino-4-chlorophenoxy)ethanol Chemical compound NC1=CC(Cl)=CC=C1OCCO ZBRZYIHPBZPHJY-UHFFFAOYSA-N 0.000 claims 1
- FRWWOTCTTUUMFK-UHFFFAOYSA-N 2-[4-(1-aminoethyl)piperidin-1-yl]-5-chloroaniline Chemical compound C1CC(C(N)C)CCN1C1=CC=C(Cl)C=C1N FRWWOTCTTUUMFK-UHFFFAOYSA-N 0.000 claims 1
- VDVPKUCZXPCBJE-UHFFFAOYSA-N 3-(2-amino-4-chlorophenoxy)cyclopentan-1-ol Chemical compound NC1=CC(Cl)=CC=C1OC1CC(O)CC1 VDVPKUCZXPCBJE-UHFFFAOYSA-N 0.000 claims 1
- YXQUGGJCURTCJR-UHFFFAOYSA-N 5-chloro-2-[4-(methylaminomethyl)piperidin-1-yl]aniline Chemical compound CNCC1CCN(CC1)c1ccc(Cl)cc1N YXQUGGJCURTCJR-UHFFFAOYSA-N 0.000 claims 1
- GZAFTZKFOXXEHE-UHFFFAOYSA-N 5-chloro-2-[4-[(dimethylamino)methyl]piperidin-1-yl]aniline Chemical compound C1CC(CN(C)C)CCN1C1=CC=C(Cl)C=C1N GZAFTZKFOXXEHE-UHFFFAOYSA-N 0.000 claims 1
- MWDWRKMVOHRBHW-UHFFFAOYSA-N 5-chloro-2-pyrrolidin-1-ylaniline Chemical compound NC1=CC(Cl)=CC=C1N1CCCC1 MWDWRKMVOHRBHW-UHFFFAOYSA-N 0.000 claims 1
- VYZUBHRSGQAROM-UHFFFAOYSA-N 5-fluoro-2-methoxyaniline Chemical compound COC1=CC=C(F)C=C1N VYZUBHRSGQAROM-UHFFFAOYSA-N 0.000 claims 1
- RPZAHRQFGVSMOO-UHFFFAOYSA-N [4-(2-amino-4-chlorophenyl)phenyl]methanol Chemical compound NC1=CC(Cl)=CC=C1C1=CC=C(CO)C=C1 RPZAHRQFGVSMOO-UHFFFAOYSA-N 0.000 claims 1
- JVOWUKRCRGTNNZ-UHFFFAOYSA-N n-(7-methoxyquinolin-6-yl)-2-(propan-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N1=C(NC(C)C)N=C2C(C(=O)NC3=CC4=CC=CN=C4C=C3OC)=CSC2=C1 JVOWUKRCRGTNNZ-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 306
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 304
- 230000015572 biosynthetic process Effects 0.000 description 276
- 238000003786 synthesis reaction Methods 0.000 description 275
- 239000007787 solid Substances 0.000 description 186
- 230000002829 reductive effect Effects 0.000 description 181
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 148
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 139
- 238000000034 method Methods 0.000 description 123
- 239000011541 reaction mixture Substances 0.000 description 123
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 122
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
- 239000000243 solution Substances 0.000 description 110
- 239000000843 powder Substances 0.000 description 106
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 103
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 88
- 238000002360 preparation method Methods 0.000 description 86
- 238000003818 flash chromatography Methods 0.000 description 69
- 230000008569 process Effects 0.000 description 68
- 239000007864 aqueous solution Substances 0.000 description 67
- HNYVPKNVKSTVJO-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC=NC2=C(C(=O)O)C=NN21 HNYVPKNVKSTVJO-UHFFFAOYSA-N 0.000 description 65
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- 125000000217 alkyl group Chemical group 0.000 description 60
- 239000012267 brine Substances 0.000 description 59
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 59
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 58
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 239000000284 extract Substances 0.000 description 47
- 239000012044 organic layer Substances 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- KCQYKVZIORIDPZ-UHFFFAOYSA-N pyrazolo[1,5-c]pyrimidine-3-carboxylic acid Chemical compound C1=NC=CC2=C(C(=O)O)C=NN21 KCQYKVZIORIDPZ-UHFFFAOYSA-N 0.000 description 39
- 238000007792 addition Methods 0.000 description 38
- 150000001408 amides Chemical class 0.000 description 38
- 239000000706 filtrate Substances 0.000 description 35
- 238000001914 filtration Methods 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
- 239000007858 starting material Substances 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- 125000002947 alkylene group Chemical group 0.000 description 29
- 239000000725 suspension Substances 0.000 description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- 238000000746 purification Methods 0.000 description 25
- 238000010992 reflux Methods 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 239000010410 layer Substances 0.000 description 22
- 235000019441 ethanol Nutrition 0.000 description 21
- 125000001072 heteroaryl group Chemical group 0.000 description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 208000002193 Pain Diseases 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 125000000753 cycloalkyl group Chemical group 0.000 description 17
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000012298 atmosphere Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 12
- 239000012065 filter cake Substances 0.000 description 12
- 239000005457 ice water Substances 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000008194 pharmaceutical composition Substances 0.000 description 10
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 102100023533 Interleukin-1 receptor-associated kinase 4 Human genes 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 108010072621 Interleukin-1 Receptor-Associated Kinases Proteins 0.000 description 8
- 102000006940 Interleukin-1 Receptor-Associated Kinases Human genes 0.000 description 8
- 101710199010 Interleukin-1 receptor-associated kinase 4 Proteins 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 235000019270 ammonium chloride Nutrition 0.000 description 8
- 208000010668 atopic eczema Diseases 0.000 description 8
- 239000002775 capsule Substances 0.000 description 8
- 125000000068 chlorophenyl group Chemical group 0.000 description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 8
- 239000002552 dosage form Substances 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 235000010446 mineral oil Nutrition 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 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 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 102000000551 Syk Kinase Human genes 0.000 description 7
- 108010016672 Syk Kinase Proteins 0.000 description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000006071 cream Substances 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- VGYKDJPYLUPHEA-UHFFFAOYSA-N 6-methoxypyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(OC)C=NC2=C(C(O)=O)C=NN21 VGYKDJPYLUPHEA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 241000699670 Mus sp. Species 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 230000000172 allergic effect Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- 125000001041 indolyl group Chemical group 0.000 description 6
- 208000002551 irritable bowel syndrome Diseases 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- 239000001119 stannous chloride Substances 0.000 description 6
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
- IFNQGJYKKMXQJF-UHFFFAOYSA-N 2-chlorothieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound N1=C(Cl)N=C2C(C(=O)O)=CSC2=C1 IFNQGJYKKMXQJF-UHFFFAOYSA-N 0.000 description 5
- KMRVTZLKQPFHFS-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carboxylic acid Chemical compound NC=1NN=CC=1C(O)=O KMRVTZLKQPFHFS-UHFFFAOYSA-N 0.000 description 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 201000004681 Psoriasis Diseases 0.000 description 5
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 230000001154 acute effect Effects 0.000 description 5
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 5
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 5
- WXJIIQGIBGAQCL-UHFFFAOYSA-N ethyl 3-(2-amino-4-chlorophenoxy)cyclopentane-1-carboxylate Chemical compound C1C(C(=O)OCC)CCC1OC1=CC=C(Cl)C=C1N WXJIIQGIBGAQCL-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 208000014674 injury Diseases 0.000 description 5
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 5
- 239000012286 potassium permanganate Substances 0.000 description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 5
- 229960002218 sodium chlorite Drugs 0.000 description 5
- 235000011150 stannous chloride Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000003107 substituted aryl group Chemical group 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- PAXOFIORPRCXBV-UHFFFAOYSA-N 2-methoxybenzene-1,3-diamine Chemical compound COC1=C(N)C=CC=C1N PAXOFIORPRCXBV-UHFFFAOYSA-N 0.000 description 4
- CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 description 4
- HMHCWMXNFBXJNZ-UHFFFAOYSA-N 3-(3-amino-2-piperidin-1-ylanilino)propan-1-ol Chemical compound NC1=CC=CC(NCCCO)=C1N1CCCCC1 HMHCWMXNFBXJNZ-UHFFFAOYSA-N 0.000 description 4
- LDSIOPGMLLPSSR-UHFFFAOYSA-N 3-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C(Cl)=C1 LDSIOPGMLLPSSR-UHFFFAOYSA-N 0.000 description 4
- JVUHWSGOORVDML-UHFFFAOYSA-N 3-methoxy-4-nitroaniline Chemical compound COC1=CC(N)=CC=C1[N+]([O-])=O JVUHWSGOORVDML-UHFFFAOYSA-N 0.000 description 4
- RIUWTXCSPDSWEL-UHFFFAOYSA-N 4-(2-tert-butylsilyloxypropan-2-yl)-2-methoxyaniline Chemical compound C(C)(C)(C)[SiH2]OC(C1=CC(=C(C=C1)N)OC)(C)C RIUWTXCSPDSWEL-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- WFUNCADYNINKKV-UHFFFAOYSA-N 4-amino-2-chloro-5-methoxy-n-phenylbenzamide Chemical compound C1=C(N)C(OC)=CC(C(=O)NC=2C=CC=CC=2)=C1Cl WFUNCADYNINKKV-UHFFFAOYSA-N 0.000 description 4
- PJKKOUHPNPDYBG-UHFFFAOYSA-N 4-amino-3-methoxy-n,n-dimethylbenzamide Chemical compound COC1=CC(C(=O)N(C)C)=CC=C1N PJKKOUHPNPDYBG-UHFFFAOYSA-N 0.000 description 4
- NWSIFTLPLKCTSX-UHFFFAOYSA-N 4-chloro-2-nitrophenol Chemical compound OC1=CC=C(Cl)C=C1[N+]([O-])=O NWSIFTLPLKCTSX-UHFFFAOYSA-N 0.000 description 4
- YDBZZPGFKSOBNU-UHFFFAOYSA-N 4-ethenyl-1-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(C=C)C=C1[N+]([O-])=O YDBZZPGFKSOBNU-UHFFFAOYSA-N 0.000 description 4
- GXMFLLVURQXDPD-UHFFFAOYSA-N 5-chloro-2-ethylaniline Chemical compound CCC1=CC=C(Cl)C=C1N GXMFLLVURQXDPD-UHFFFAOYSA-N 0.000 description 4
- GKTSEIIVLRUWJJ-UHFFFAOYSA-N 5-ethyl-2-methoxyaniline Chemical compound CCC1=CC=C(OC)C(N)=C1 GKTSEIIVLRUWJJ-UHFFFAOYSA-N 0.000 description 4
- XGDUAVQQMOGVEB-UHFFFAOYSA-N 6-ethoxycarbonylthieno[3,2-b]pyridine-3-carboxylic acid Chemical compound CCOC(=O)C1=CN=C2C(C(O)=O)=CSC2=C1 XGDUAVQQMOGVEB-UHFFFAOYSA-N 0.000 description 4
- ISWMWYCPINAUDZ-UHFFFAOYSA-N 7-methoxy-6-nitroquinoline Chemical compound C1=CC=C2C=C([N+]([O-])=O)C(OC)=CC2=N1 ISWMWYCPINAUDZ-UHFFFAOYSA-N 0.000 description 4
- BVOZCEBWUBXHQW-UHFFFAOYSA-N 7-methoxyquinolin-6-amine Chemical compound C1=CC=C2C=C(N)C(OC)=CC2=N1 BVOZCEBWUBXHQW-UHFFFAOYSA-N 0.000 description 4
- ZDHMVXYJWKLOQS-UHFFFAOYSA-N 7-methylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound CC1=CC=NC2=C(C(O)=O)C=NN12 ZDHMVXYJWKLOQS-UHFFFAOYSA-N 0.000 description 4
- 208000026872 Addison Disease Diseases 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 208000011231 Crohn disease Diseases 0.000 description 4
- 108090000695 Cytokines Proteins 0.000 description 4
- 102000004127 Cytokines Human genes 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- COHDHYZHOPQOFD-UHFFFAOYSA-N arsenic pentoxide Chemical compound O=[As](=O)O[As](=O)=O COHDHYZHOPQOFD-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- YPXGHKWOJXQLQU-UHFFFAOYSA-N ethyl 5-amino-1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1N YPXGHKWOJXQLQU-UHFFFAOYSA-N 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000007937 lozenge Substances 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- DJLFOMMCQBAMAA-UHFFFAOYSA-N methyl 4-amino-3-methoxybenzoate Chemical compound COC(=O)C1=CC=C(N)C(OC)=C1 DJLFOMMCQBAMAA-UHFFFAOYSA-N 0.000 description 4
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 4
- 235000019796 monopotassium phosphate Nutrition 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 201000008482 osteoarthritis Diseases 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000012746 preparative thin layer chromatography Methods 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 238000013268 sustained release Methods 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 3
- FQBXIHVNYNWJCP-UHFFFAOYSA-N 1-pyrrolidin-3-ylethanol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC(O)C1CCNC1 FQBXIHVNYNWJCP-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- XMLWSZYAIGBOFV-UHFFFAOYSA-N 2-(propan-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound CC(C)Nc1ncc2scc(C(O)=O)c2n1 XMLWSZYAIGBOFV-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QFKSNSOVYKDGKD-UHFFFAOYSA-N 2-[(6-amino-7-methoxyquinolin-2-yl)amino]ethanol Chemical compound OCCNC1=CC=C2C=C(N)C(OC)=CC2=N1 QFKSNSOVYKDGKD-UHFFFAOYSA-N 0.000 description 3
- COFFTQCBKCOCLL-UHFFFAOYSA-N 2-[(7-methoxy-6-nitroquinolin-2-yl)amino]ethanol Chemical compound OCCNC1=CC=C2C=C([N+]([O-])=O)C(OC)=CC2=N1 COFFTQCBKCOCLL-UHFFFAOYSA-N 0.000 description 3
- GMFPMSFBSIJEHV-UHFFFAOYSA-N 2-chloro-5-methoxy-4-nitro-n-phenylbenzamide Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(C(=O)NC=2C=CC=CC=2)=C1Cl GMFPMSFBSIJEHV-UHFFFAOYSA-N 0.000 description 3
- AQBLWMRQXJGHSE-UHFFFAOYSA-N 2-chloro-7-methylthieno[3,2-d]pyrimidine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1 AQBLWMRQXJGHSE-UHFFFAOYSA-N 0.000 description 3
- DZVZPFZSAYLSDU-UHFFFAOYSA-N 2-methoxy-1,3-dinitrobenzene Chemical compound COC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O DZVZPFZSAYLSDU-UHFFFAOYSA-N 0.000 description 3
- VFWWGFYZNFLPTE-UHFFFAOYSA-N 2-methoxy-4-phenylaniline Chemical compound C1=C(N)C(OC)=CC(C=2C=CC=CC=2)=C1 VFWWGFYZNFLPTE-UHFFFAOYSA-N 0.000 description 3
- WWDVLLPGIHACLO-UHFFFAOYSA-N 2-o-ethyl 5-o-methyl 1-aminopyrrole-2,5-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OC)N1N WWDVLLPGIHACLO-UHFFFAOYSA-N 0.000 description 3
- QAFPXFLIOZUZAW-UHFFFAOYSA-N 2-o-ethyl 5-o-methyl 1h-pyrrole-2,5-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OC)N1 QAFPXFLIOZUZAW-UHFFFAOYSA-N 0.000 description 3
- RAEFIDKCIFDVLM-UHFFFAOYSA-N 2-piperidin-1-ylbenzene-1,3-diamine Chemical compound NC1=CC=CC(N)=C1N1CCCCC1 RAEFIDKCIFDVLM-UHFFFAOYSA-N 0.000 description 3
- SGLHGIDKAJLZDY-UHFFFAOYSA-N 3-chloro-4-nitro-n-phenylbenzamide Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC=C1C(=O)NC1=CC=CC=C1 SGLHGIDKAJLZDY-UHFFFAOYSA-N 0.000 description 3
- PWURRRRGLCVBMX-UHFFFAOYSA-N 3-methoxy-4-nitrobenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1[N+]([O-])=O PWURRRRGLCVBMX-UHFFFAOYSA-N 0.000 description 3
- KRQVYRBGZFQQJP-UHFFFAOYSA-N 4-(3-aminonaphthalen-2-yl)oxycyclohexan-1-ol Chemical compound NC1=CC2=CC=CC=C2C=C1OC1CCC(O)CC1 KRQVYRBGZFQQJP-UHFFFAOYSA-N 0.000 description 3
- OONNZMCLGSRPOP-UHFFFAOYSA-N 4-chloro-1-ethyl-2-nitrobenzene Chemical compound CCC1=CC=C(Cl)C=C1[N+]([O-])=O OONNZMCLGSRPOP-UHFFFAOYSA-N 0.000 description 3
- IYJDOVYAFDVIDB-UHFFFAOYSA-N 4-chloro-7-methylthieno[3,2-d]pyrimidine Chemical compound N1=CN=C2C(C)=CSC2=C1Cl IYJDOVYAFDVIDB-UHFFFAOYSA-N 0.000 description 3
- OUVUXCBBKYHSLC-UHFFFAOYSA-N 4-ethyl-3-nitroaniline Chemical compound CCC1=CC=C(N)C=C1[N+]([O-])=O OUVUXCBBKYHSLC-UHFFFAOYSA-N 0.000 description 3
- FFSJSUBADRUOBW-UHFFFAOYSA-N 5,7-dichloro-3-methylthieno[3,2-b]pyridine Chemical compound C1=C(Cl)N=C2C(C)=CSC2=C1Cl FFSJSUBADRUOBW-UHFFFAOYSA-N 0.000 description 3
- PINRTDKGFKITJL-UHFFFAOYSA-N 5-chloro-2-(3-methoxypropoxy)aniline Chemical compound COCCCOC1=CC=C(Cl)C=C1N PINRTDKGFKITJL-UHFFFAOYSA-N 0.000 description 3
- VXBJBSZTDJTFBZ-UHFFFAOYSA-N 5-chlorothieno[3,2-b]pyridine-3-carbaldehyde Chemical compound ClC1=CC=C2SC=C(C=O)C2=N1 VXBJBSZTDJTFBZ-UHFFFAOYSA-N 0.000 description 3
- RZMVOIDCAVZMGU-UHFFFAOYSA-N 5-ethenyl-2-methoxyaniline Chemical compound COC1=CC=C(C=C)C=C1N RZMVOIDCAVZMGU-UHFFFAOYSA-N 0.000 description 3
- XXBOTQXVXTXRRN-UHFFFAOYSA-N 6-(hydroxymethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(CO)C=NC2=C(C(O)=O)C=NN21 XXBOTQXVXTXRRN-UHFFFAOYSA-N 0.000 description 3
- TUPFYNVMQMYIMU-UHFFFAOYSA-N 6-(hydroxymethyl)thieno[3,2-b]pyridine-3-carboxylic acid Chemical compound OCc1cnc2c(csc2c1)C(O)=O TUPFYNVMQMYIMU-UHFFFAOYSA-N 0.000 description 3
- RIHILEUGTHDKEZ-UHFFFAOYSA-N 6-chlorothieno[2,3-b]pyridine-3-carboxylic acid Chemical compound ClC1=CC=C2C(C(=O)O)=CSC2=N1 RIHILEUGTHDKEZ-UHFFFAOYSA-N 0.000 description 3
- GHEKVHASRAQCNU-UHFFFAOYSA-N 6-methoxy-1h-indazol-5-amine Chemical compound C1=C(N)C(OC)=CC2=C1C=NN2 GHEKVHASRAQCNU-UHFFFAOYSA-N 0.000 description 3
- QULAONDBWZZTOI-UHFFFAOYSA-N 6-methoxy-5-nitro-1h-indazole Chemical compound C1=C([N+]([O-])=O)C(OC)=CC2=C1C=NN2 QULAONDBWZZTOI-UHFFFAOYSA-N 0.000 description 3
- JCNOXGKQXXFWCM-UHFFFAOYSA-N 6-methylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C)C=NC2=C(C(O)=O)C=NN21 JCNOXGKQXXFWCM-UHFFFAOYSA-N 0.000 description 3
- ZQIZEVMRKLSEGK-UHFFFAOYSA-N 7-bromo-3-methoxynaphthalen-2-amine Chemical compound C1=C(Br)C=C2C=C(N)C(OC)=CC2=C1 ZQIZEVMRKLSEGK-UHFFFAOYSA-N 0.000 description 3
- QUAVESQJWNBXDZ-UHFFFAOYSA-N 7-bromo-3-methoxynaphthalene-2-carboxylic acid Chemical compound C1=C(Br)C=C2C=C(C(O)=O)C(OC)=CC2=C1 QUAVESQJWNBXDZ-UHFFFAOYSA-N 0.000 description 3
- PKJPESBDOWOQAI-UHFFFAOYSA-N 7-chloro-6-nitroquinoline Chemical compound C1=CN=C2C=C(Cl)C([N+](=O)[O-])=CC2=C1 PKJPESBDOWOQAI-UHFFFAOYSA-N 0.000 description 3
- KJTYNZWEAIRZHT-UHFFFAOYSA-N 7-methyl-1h-thieno[3,2-d]pyrimidin-4-one Chemical compound N1C=NC(=O)C2=C1C(C)=CS2 KJTYNZWEAIRZHT-UHFFFAOYSA-N 0.000 description 3
- HCDWIFDKDPYXLO-UHFFFAOYSA-N 7-methylthieno[3,2-d]pyrimidine Chemical compound N1=CN=C2C(C)=CSC2=C1 HCDWIFDKDPYXLO-UHFFFAOYSA-N 0.000 description 3
- 241000220479 Acacia Species 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 3
- SZGNWWMNMYPQAE-UHFFFAOYSA-N C1=C(C(O)=O)C=NC2=C(C(=O)O)C=NN21 Chemical compound C1=C(C(O)=O)C=NC2=C(C(=O)O)C=NN21 SZGNWWMNMYPQAE-UHFFFAOYSA-N 0.000 description 3
- 201000004624 Dermatitis Diseases 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 3
- 201000005569 Gout Diseases 0.000 description 3
- 206010018634 Gouty Arthritis Diseases 0.000 description 3
- 102000000589 Interleukin-1 Human genes 0.000 description 3
- 108010002352 Interleukin-1 Proteins 0.000 description 3
- 102100023530 Interleukin-1 receptor-associated kinase 3 Human genes 0.000 description 3
- 101710199012 Interleukin-1 receptor-associated kinase 3 Proteins 0.000 description 3
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
- 206010027476 Metastases Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 206010029240 Neuritis Diseases 0.000 description 3
- 208000030852 Parasitic disease Diseases 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 208000025747 Rheumatic disease Diseases 0.000 description 3
- 102000002689 Toll-like receptor Human genes 0.000 description 3
- 108020000411 Toll-like receptor Proteins 0.000 description 3
- 208000036142 Viral infection Diseases 0.000 description 3
- 208000026935 allergic disease Diseases 0.000 description 3
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 208000022362 bacterial infectious disease Diseases 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- BTKSAOLUPOBASF-UHFFFAOYSA-N ethyl 3-(4-chloro-2-nitrophenoxy)cyclopentane-1-carboxylate Chemical compound C1C(C(=O)OCC)CCC1OC1=CC=C(Cl)C=C1[N+]([O-])=O BTKSAOLUPOBASF-UHFFFAOYSA-N 0.000 description 3
- QGHJPACIUQNSOD-UHFFFAOYSA-N ethyl 3-methylthieno[3,2-b]pyridine-6-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(C)=CSC2=C1 QGHJPACIUQNSOD-UHFFFAOYSA-N 0.000 description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000004404 heteroalkyl group Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VWAFUFNJBJNZLH-GQCTYLIASA-N methyl (e)-3-(4-methoxy-3-nitrophenyl)prop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=C(OC)C([N+]([O-])=O)=C1 VWAFUFNJBJNZLH-GQCTYLIASA-N 0.000 description 3
- YICRPERKKBDRSP-UHFFFAOYSA-N methyl 3-amino-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C)C=1N YICRPERKKBDRSP-UHFFFAOYSA-N 0.000 description 3
- RDTGKUXAFSMVJE-UHFFFAOYSA-N methyl 7-bromo-3-methoxynaphthalene-2-carboxylate Chemical compound BrC1=CC=C2C=C(OC)C(C(=O)OC)=CC2=C1 RDTGKUXAFSMVJE-UHFFFAOYSA-N 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- 201000006417 multiple sclerosis Diseases 0.000 description 3
- VFIIQVVDBAZISM-UHFFFAOYSA-N n-(4-ethyl-3-nitrophenyl)acetamide Chemical compound CCC1=CC=C(NC(C)=O)C=C1[N+]([O-])=O VFIIQVVDBAZISM-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000008506 pathogenesis Effects 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 230000000770 proinflammatory effect Effects 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000006308 propyl amino group Chemical group 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- PWNFNWLDJMZSIG-UHFFFAOYSA-N (5-acetamido-2-nitrophenyl) acetate Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C(OC(C)=O)=C1 PWNFNWLDJMZSIG-UHFFFAOYSA-N 0.000 description 2
- LQICCOKQYGVLPL-NSCUHMNNSA-N (e)-3-(3-amino-4-methoxyphenyl)prop-2-en-1-ol Chemical compound COC1=CC=C(\C=C\CO)C=C1N LQICCOKQYGVLPL-NSCUHMNNSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 2
- UZYRSBACWZIFIX-UHFFFAOYSA-N 1-(2,6-dinitrophenyl)piperidine Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1N1CCCCC1 UZYRSBACWZIFIX-UHFFFAOYSA-N 0.000 description 2
- YFEZMPRCOONSFD-UHFFFAOYSA-N 1-(4-methoxybutyl)-4-nitrobenzene Chemical compound COCCCCC1=CC=C([N+]([O-])=O)C=C1 YFEZMPRCOONSFD-UHFFFAOYSA-N 0.000 description 2
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- WUXYWALKGQDXFI-UHFFFAOYSA-N 2,4-dichloro-7-methylthieno[3,2-d]pyrimidine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1Cl WUXYWALKGQDXFI-UHFFFAOYSA-N 0.000 description 2
- NJIAIWQGLXKGDK-UHFFFAOYSA-N 2-[2-hydroxyethyl(methyl)amino]thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound OCCN(C=1N=CC2=C(N=1)C(=CS2)C(=O)O)C NJIAIWQGLXKGDK-UHFFFAOYSA-N 0.000 description 2
- FTOMMCKFAUZUQD-UHFFFAOYSA-N 2-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]-5-chloroaniline Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC(C=2C(=CC(Cl)=CC=2)N)=C1 FTOMMCKFAUZUQD-UHFFFAOYSA-N 0.000 description 2
- OQSVMUQKSCCCIS-UHFFFAOYSA-N 2-[4-[tert-butyl(dimethyl)silyl]oxycyclohexyl]oxy-5-chloroaniline Chemical compound C1CC(O[Si](C)(C)C(C)(C)C)CCC1OC1=CC=C(Cl)C=C1N OQSVMUQKSCCCIS-UHFFFAOYSA-N 0.000 description 2
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 2
- OJMMHUJTCVSTMS-UHFFFAOYSA-N 2-chloro-5-methoxy-4-nitrobenzoic acid Chemical compound COC1=CC(C(O)=O)=C(Cl)C=C1[N+]([O-])=O OJMMHUJTCVSTMS-UHFFFAOYSA-N 0.000 description 2
- UBAISGHYQHUEGR-UHFFFAOYSA-N 2-chloro-7-methoxy-6-nitroquinoline Chemical compound ClC1=CC=C2C=C([N+]([O-])=O)C(OC)=CC2=N1 UBAISGHYQHUEGR-UHFFFAOYSA-N 0.000 description 2
- MMAGRHBUXJZMKM-UHFFFAOYSA-N 2-methoxy-1-nitro-4-phenylbenzene Chemical group C1=C([N+]([O-])=O)C(OC)=CC(C=2C=CC=CC=2)=C1 MMAGRHBUXJZMKM-UHFFFAOYSA-N 0.000 description 2
- JOXBQHVNCWEXIQ-UHFFFAOYSA-N 3-[4-[tert-butyl(dimethyl)silyl]oxycyclohexyl]oxynaphthalen-2-amine Chemical compound C1CC(O[Si](C)(C)C(C)(C)C)CCC1OC1=CC2=CC=CC=C2C=C1N JOXBQHVNCWEXIQ-UHFFFAOYSA-N 0.000 description 2
- TZPGGFYKIOBMCN-UHFFFAOYSA-N 3-chloro-4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C(Cl)=C1 TZPGGFYKIOBMCN-UHFFFAOYSA-N 0.000 description 2
- GCIPOLAGPBUILO-UHFFFAOYSA-N 3-methoxy-4-nitro-n-phenylbenzamide Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(C(=O)NC=2C=CC=CC=2)=C1 GCIPOLAGPBUILO-UHFFFAOYSA-N 0.000 description 2
- XGCCUZRKNCUVJK-UHFFFAOYSA-N 4-[tert-butyl(dimethyl)silyl]oxycyclohexan-1-ol Chemical compound CC(C)(C)[Si](C)(C)OC1CCC(O)CC1 XGCCUZRKNCUVJK-UHFFFAOYSA-N 0.000 description 2
- BRJISLAGAJNYRH-UHFFFAOYSA-N 4-chloro-1-(3-methoxypropoxy)-2-nitrobenzene Chemical compound COCCCOC1=CC=C(Cl)C=C1[N+]([O-])=O BRJISLAGAJNYRH-UHFFFAOYSA-N 0.000 description 2
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
- YTCRQCGRYCKYNO-UHFFFAOYSA-N 4-methoxy-3-nitrobenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1[N+]([O-])=O YTCRQCGRYCKYNO-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- ABVIGOXMNGMPCR-UHFFFAOYSA-N 5-chloro-2-[[2-tri(propan-2-yl)silyl-1,3-oxazol-5-yl]methoxy]aniline Chemical compound O1C([Si](C(C)C)(C(C)C)C(C)C)=NC=C1COC1=CC=C(Cl)C=C1N ABVIGOXMNGMPCR-UHFFFAOYSA-N 0.000 description 2
- OGKCLQAJNTXVQO-UHFFFAOYSA-N 5-chloro-2-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=C(Cl)C=C1N OGKCLQAJNTXVQO-UHFFFAOYSA-N 0.000 description 2
- KYCHABLSTDGOLI-UHFFFAOYSA-N 5-chloro-3-methylthieno[3,2-b]pyridine Chemical compound C1=C(Cl)N=C2C(C)=CSC2=C1 KYCHABLSTDGOLI-UHFFFAOYSA-N 0.000 description 2
- CADNVJNUYBVVFU-UHFFFAOYSA-N 5-methylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound N1=C(C)C=CN2N=CC(C(O)=O)=C21 CADNVJNUYBVVFU-UHFFFAOYSA-N 0.000 description 2
- ZHSNJCKEJWLPRA-UHFFFAOYSA-N 6-(2-hydroxyethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(CCO)C=NC2=C(C(O)=O)C=NN21 ZHSNJCKEJWLPRA-UHFFFAOYSA-N 0.000 description 2
- ZYLIVCXNTPXFMJ-UHFFFAOYSA-N 6-carbamoylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(=O)N)C=NC2=C(C(O)=O)C=NN21 ZYLIVCXNTPXFMJ-UHFFFAOYSA-N 0.000 description 2
- GPUJYTJJEYDBLA-UHFFFAOYSA-N 6-chloro-1,6-dinitrocyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1=CC=CCC1(Cl)[N+]([O-])=O GPUJYTJJEYDBLA-UHFFFAOYSA-N 0.000 description 2
- ZPKMHFJUYHHTTM-UHFFFAOYSA-N 6-nitroquinolin-7-ol Chemical compound C1=CC=C2C=C([N+]([O-])=O)C(O)=CC2=N1 ZPKMHFJUYHHTTM-UHFFFAOYSA-N 0.000 description 2
- JEMZGJXHARVCHU-UHFFFAOYSA-N 6-phenylmethoxy-7H-pyrazolo[1,5-c]pyrimidine-3-carboxylic acid Chemical compound C1=CC2=C(C(=O)O)C=NN2CN1OCC1=CC=CC=C1 JEMZGJXHARVCHU-UHFFFAOYSA-N 0.000 description 2
- CQCBSKFVOAJZKC-UHFFFAOYSA-N 7-[4-[tert-butyl(dimethyl)silyl]oxycyclohexyl]oxyquinolin-6-amine Chemical compound C1CC(O[Si](C)(C)C(C)(C)C)CCC1OC1=CC2=NC=CC=C2C=C1N CQCBSKFVOAJZKC-UHFFFAOYSA-N 0.000 description 2
- MOIOLYRRZWMWMG-UHFFFAOYSA-N 7-amino-6-methoxynaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C=C(N)C(OC)=CC2=C1 MOIOLYRRZWMWMG-UHFFFAOYSA-N 0.000 description 2
- ISDFLIYWWIWNNJ-UHFFFAOYSA-N 7-methoxy-6-nitro-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C=C(OC)C([N+]([O-])=O)=C2 ISDFLIYWWIWNNJ-UHFFFAOYSA-N 0.000 description 2
- XFXGDEBYBPGDLF-UHFFFAOYSA-N 7-methyl-1h-thieno[3,2-d]pyrimidine-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C(C)=CS2 XFXGDEBYBPGDLF-UHFFFAOYSA-N 0.000 description 2
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
- 206010002199 Anaphylactic shock Diseases 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 2
- 206010048962 Brain oedema Diseases 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 206010058019 Cancer Pain Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 208000006561 Cluster Headache Diseases 0.000 description 2
- 206010010741 Conjunctivitis Diseases 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 206010012442 Dermatitis contact Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 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
- 206010017533 Fungal infection Diseases 0.000 description 2
- 206010018364 Glomerulonephritis Diseases 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 102000009438 IgE Receptors Human genes 0.000 description 2
- 108010073816 IgE Receptors Proteins 0.000 description 2
- 206010065390 Inflammatory pain Diseases 0.000 description 2
- 101710182491 Interleukin-1 receptor-associated kinase-like 2 Proteins 0.000 description 2
- 102100036433 Interleukin-1 receptor-associated kinase-like 2 Human genes 0.000 description 2
- 208000005615 Interstitial Cystitis Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 201000009906 Meningitis Diseases 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 206010027603 Migraine headaches Diseases 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- 102000010168 Myeloid Differentiation Factor 88 Human genes 0.000 description 2
- 108010077432 Myeloid Differentiation Factor 88 Proteins 0.000 description 2
- 208000028389 Nerve injury Diseases 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 208000005374 Poisoning Diseases 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 206010065347 Premenstrual pain Diseases 0.000 description 2
- 206010037423 Pulmonary oedema Diseases 0.000 description 2
- 206010039085 Rhinitis allergic Diseases 0.000 description 2
- 206010039807 Secondary adrenocortical insufficiency Diseases 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 208000016247 Soft tissue disease Diseases 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 206010052779 Transplant rejections Diseases 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 208000024780 Urticaria Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 102000035181 adaptor proteins Human genes 0.000 description 2
- 108091005764 adaptor proteins Proteins 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 201000010105 allergic rhinitis Diseases 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000002917 arthritic effect Effects 0.000 description 2
- 125000002785 azepinyl group Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 208000006752 brain edema Diseases 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 208000010247 contact dermatitis Diseases 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 201000002491 encephalomyelitis Diseases 0.000 description 2
- 239000002158 endotoxin Substances 0.000 description 2
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 2
- HMKZKDVSPVBXIC-UHFFFAOYSA-N ethyl 3-formylthieno[3,2-b]pyridine-6-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(C=O)=CSC2=C1 HMKZKDVSPVBXIC-UHFFFAOYSA-N 0.000 description 2
- JWYDJDGPIZQXNN-UHFFFAOYSA-N ethyl 4-chloropyrrolo[2,1-f][1,2,4]triazine-7-carboxylate Chemical compound ClC1=NC=NN2C(C(=O)OCC)=CC=C21 JWYDJDGPIZQXNN-UHFFFAOYSA-N 0.000 description 2
- YBTZWVILEHWETK-UHFFFAOYSA-N ethyl 4-oxo-1h-pyrrolo[2,1-f][1,2,4]triazine-7-carboxylate Chemical compound N1=CNC(=O)C=2N1C(C(=O)OCC)=CC=2 YBTZWVILEHWETK-UHFFFAOYSA-N 0.000 description 2
- 208000012997 experimental autoimmune encephalomyelitis Diseases 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 208000006454 hepatitis Diseases 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 210000003630 histaminocyte Anatomy 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000015788 innate immune response Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 208000037906 ischaemic injury Diseases 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 210000001503 joint Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 229920006008 lipopolysaccharide Polymers 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- PVVFEPFLFHDHHK-UHFFFAOYSA-N methyl 3-methoxy-4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C(OC)=C1 PVVFEPFLFHDHHK-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical compound OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 2
- KUAYZLXOOIEGDN-UHFFFAOYSA-N n-(3-chloro-4-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C(Cl)=C1 KUAYZLXOOIEGDN-UHFFFAOYSA-N 0.000 description 2
- VKLYSIQGYYNIHS-UHFFFAOYSA-N n-(5-methoxy-2-methylphenyl)acetamide Chemical compound COC1=CC=C(C)C(NC(C)=O)=C1 VKLYSIQGYYNIHS-UHFFFAOYSA-N 0.000 description 2
- 210000003928 nasal cavity Anatomy 0.000 description 2
- 230000008764 nerve damage Effects 0.000 description 2
- 208000004296 neuralgia Diseases 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 201000006292 polyarteritis nodosa Diseases 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- HRSDPDBQVZHCRC-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3-carboxylic acid Chemical compound C1=CC=CC2=C(C(=O)O)C=NN21 HRSDPDBQVZHCRC-UHFFFAOYSA-N 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- GUMNWRMUBOJYLH-UHFFFAOYSA-N pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid Chemical compound C1=NC=NN2C(C(=O)O)=CC=C21 GUMNWRMUBOJYLH-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 201000000306 sarcoidosis Diseases 0.000 description 2
- 208000023087 secondary adrenal insufficiency Diseases 0.000 description 2
- 230000036303 septic shock Effects 0.000 description 2
- 230000011664 signaling Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- UEHNUNXDGWNBEM-UHFFFAOYSA-N tert-butyl 4-(2-amino-4-chlorophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C(Cl)C=C1N UEHNUNXDGWNBEM-UHFFFAOYSA-N 0.000 description 2
- VYMHWULDUNEJMY-UHFFFAOYSA-N tert-butyl 4-(4-chloro-2-nitrophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C(Cl)C=C1[N+]([O-])=O VYMHWULDUNEJMY-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VHYXAWLOJGIJPC-UHFFFAOYSA-N tert-butyl n-(piperidin-4-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCNCC1 VHYXAWLOJGIJPC-UHFFFAOYSA-N 0.000 description 2
- KYJSIYOKJBQXLX-UHFFFAOYSA-N tert-butyl-[(3-methoxy-4-nitrophenyl)methoxy]-dimethylsilane Chemical compound COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1[N+]([O-])=O KYJSIYOKJBQXLX-UHFFFAOYSA-N 0.000 description 2
- SNLXNNDVIOMUHG-UHFFFAOYSA-N tert-butyl-[4-(4-chloro-2-nitrophenoxy)cyclohexyl]oxy-dimethylsilane Chemical compound C1CC(O[Si](C)(C)C(C)(C)C)CCC1OC1=CC=C(Cl)C=C1[N+]([O-])=O SNLXNNDVIOMUHG-UHFFFAOYSA-N 0.000 description 2
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- DMXABPANVQBYLS-UHFFFAOYSA-N thieno[3,2-b]pyridine-3-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CSC2=C1 DMXABPANVQBYLS-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 208000009935 visceral pain Diseases 0.000 description 2
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
- IWXYLEKOKGKRTN-UHFFFAOYSA-N (2-methoxy-4-nitrophenyl)methanol Chemical compound COC1=CC([N+]([O-])=O)=CC=C1CO IWXYLEKOKGKRTN-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- ONWKGGFEPJUBHK-UHFFFAOYSA-N (3-acetamidophenyl) acetate Chemical compound CC(=O)NC1=CC=CC(OC(C)=O)=C1 ONWKGGFEPJUBHK-UHFFFAOYSA-N 0.000 description 1
- UWPQCXSTSNEMAO-UHFFFAOYSA-N (5-acetamido-2-nitrophenyl) acetate (3-acetamidophenyl) acetate Chemical compound C(C)(=O)NC=1C=C(C=CC1)OC(C)=O.C(C)(=O)NC=1C=CC(=C(C1)OC(C)=O)[N+](=O)[O-] UWPQCXSTSNEMAO-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- XTYLJMKJLMHFJK-UHFFFAOYSA-N 1,1,3,3-tetraethoxy-2-methylpropane Chemical compound CCOC(OCC)C(C)C(OCC)OCC XTYLJMKJLMHFJK-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- FBZVZUSVGKOWHG-UHFFFAOYSA-N 1,1-dimethoxy-n,n-dimethylethanamine Chemical compound COC(C)(OC)N(C)C FBZVZUSVGKOWHG-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- ZPXDNSYFDIHPOJ-UHFFFAOYSA-N 1,5-dichloro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C=C1Cl ZPXDNSYFDIHPOJ-UHFFFAOYSA-N 0.000 description 1
- QNNVZKXADLERMM-UHFFFAOYSA-N 1-(2-amino-4-chlorophenyl)pyrrolidin-3-ol Chemical compound NC1=CC(Cl)=CC=C1N1CC(O)CC1 QNNVZKXADLERMM-UHFFFAOYSA-N 0.000 description 1
- CEVMYGZHEJSOHZ-UHFFFAOYSA-N 1-bromo-3-methoxypropane Chemical compound COCCCBr CEVMYGZHEJSOHZ-UHFFFAOYSA-N 0.000 description 1
- MICMHFIQSAMEJG-UHFFFAOYSA-N 1-bromopyrrolidine-2,5-dione Chemical compound BrN1C(=O)CCC1=O.BrN1C(=O)CCC1=O MICMHFIQSAMEJG-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 1
- NYKGERLHQSWZHA-UHFFFAOYSA-N 1-chloro-4-methoxy-2-methyl-5-nitrobenzene Chemical compound COC1=CC(C)=C(Cl)C=C1[N+]([O-])=O NYKGERLHQSWZHA-UHFFFAOYSA-N 0.000 description 1
- KPDPGZNHKMJEFZ-UHFFFAOYSA-N 1-chloro-5-methyl-2,4-dinitrobenzene Chemical compound CC1=CC(Cl)=C([N+]([O-])=O)C=C1[N+]([O-])=O KPDPGZNHKMJEFZ-UHFFFAOYSA-N 0.000 description 1
- DFPYXQYWILNVAU-UHFFFAOYSA-N 1-hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1.C1=CC=C2N(O)N=NC2=C1 DFPYXQYWILNVAU-UHFFFAOYSA-N 0.000 description 1
- AXTRWLSNGZCQJE-UHFFFAOYSA-N 1-methoxyindazole Chemical compound C1=CC=C2N(OC)N=CC2=C1 AXTRWLSNGZCQJE-UHFFFAOYSA-N 0.000 description 1
- DZCCNHQOMASNEB-UHFFFAOYSA-N 1-methoxynaphthalen-2-amine Chemical compound C1=CC=C2C(OC)=C(N)C=CC2=C1 DZCCNHQOMASNEB-UHFFFAOYSA-N 0.000 description 1
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 1
- OOCLDXHGACDYDO-UHFFFAOYSA-N 1-piperidin-4-ylethanamine Chemical compound CC(N)C1CCNCC1 OOCLDXHGACDYDO-UHFFFAOYSA-N 0.000 description 1
- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- WPJPIMHGGGPFKE-UHFFFAOYSA-N 1h-pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical compound N1=CN=C2C(C(=O)O)=NNC2=C1 WPJPIMHGGGPFKE-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- YEGQIBOZCOBKEJ-UHFFFAOYSA-N 2-(2,3-dihydroxypropylamino)thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound OCC(O)CNC1=NC=C2SC=C(C(O)=O)C2=N1 YEGQIBOZCOBKEJ-UHFFFAOYSA-N 0.000 description 1
- UIEHXCCYHAUOFD-UHFFFAOYSA-N 2-(2-aminoethylamino)-n-(5-chloro-2-methoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1=CSC2=CN=C(NCCN)N=C12 UIEHXCCYHAUOFD-UHFFFAOYSA-N 0.000 description 1
- SNDKVGYZVOPURR-UHFFFAOYSA-N 2-(2-hydroxyethylamino)thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound OCCNc1ncc2scc(C(O)=O)c2n1 SNDKVGYZVOPURR-UHFFFAOYSA-N 0.000 description 1
- BBRWJFSHFRUICK-UHFFFAOYSA-N 2-(2-methylpropylamino)thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound C(C(C)C)NC=1N=CC2=C(N=1)C(=CS2)C(=O)O BBRWJFSHFRUICK-UHFFFAOYSA-N 0.000 description 1
- JKVISNLAQABLDO-UHFFFAOYSA-N 2-(3-amino-2-piperidin-1-ylanilino)ethanol Chemical compound NC1=CC=CC(NCCO)=C1N1CCCCC1 JKVISNLAQABLDO-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- DSWRLBYAWFSSJP-UHFFFAOYSA-N 2-(cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound C1(CC1)NC=1N=CC2=C(N1)C(=CS2)C(=O)O DSWRLBYAWFSSJP-UHFFFAOYSA-N 0.000 description 1
- WUTCYTOQCLAUQG-UHFFFAOYSA-N 2-(dimethylaminomethylidene)propanedial Chemical compound CN(C)C=C(C=O)C=O WUTCYTOQCLAUQG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- SQBFVOKUEBYDNJ-UHFFFAOYSA-N 2-[2-hydroxyethyl(propan-2-yl)amino]thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound OCCN(C=1N=CC2=C(N=1)C(=CS2)C(=O)O)C(C)C SQBFVOKUEBYDNJ-UHFFFAOYSA-N 0.000 description 1
- JZVVWEKLBHGCRX-UHFFFAOYSA-N 2-[3-[tert-butyl(dimethyl)silyl]oxypropoxy]-5-chloroaniline Chemical compound CC(C)(C)[Si](C)(C)OCCCOC1=CC=C(Cl)C=C1N JZVVWEKLBHGCRX-UHFFFAOYSA-N 0.000 description 1
- OLOJHMNWTGXBGI-UHFFFAOYSA-N 2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-5-chloroaniline Chemical compound C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C1=CC=C(Cl)C=C1N OLOJHMNWTGXBGI-UHFFFAOYSA-N 0.000 description 1
- XCLBHYQEDQXRBJ-RXMQYKEDSA-N 2-[[(2R)-1-hydroxypropan-2-yl]amino]thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound OC[C@@H](C)NC=1N=CC2=C(N=1)C(=CS2)C(=O)O XCLBHYQEDQXRBJ-RXMQYKEDSA-N 0.000 description 1
- LVEYPINONYKYBT-UHFFFAOYSA-N 2-[methyl(propan-2-yl)amino]thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound CC(C)N(C)c1ncc2scc(C(O)=O)c2n1 LVEYPINONYKYBT-UHFFFAOYSA-N 0.000 description 1
- SURMYNZXHKLDFO-UHFFFAOYSA-N 2-bromopropanedial Chemical compound O=CC(Br)C=O SURMYNZXHKLDFO-UHFFFAOYSA-N 0.000 description 1
- KGSQRFPDZCBVBS-UHFFFAOYSA-N 2-chloro-4-methyl-1-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C(Cl)=C1 KGSQRFPDZCBVBS-UHFFFAOYSA-N 0.000 description 1
- LVFUVLSBWJJAGC-UHFFFAOYSA-N 2-chlorothieno[3,2-d]pyrimidine-7-carbaldehyde Chemical compound ClC1=NC=C2SC=C(C=O)C2=N1 LVFUVLSBWJJAGC-UHFFFAOYSA-N 0.000 description 1
- IQPMGTJUOSEWIS-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride 3-methyl-4H-thieno[3,2-b]pyridine-5,7-dione Chemical compound C(C)C(C(=O)Cl)C(=O)Cl.CC1=CSC2=C1NC(CC2=O)=O IQPMGTJUOSEWIS-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- HQJBYCPQFNTCNM-UHFFFAOYSA-N 2-methoxy-3,5-dimethylaniline Chemical compound COC1=C(C)C=C(C)C=C1N HQJBYCPQFNTCNM-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical compound NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
- UDIPIOHLDFSMLR-UHFFFAOYSA-N 2-phenylmethoxypropane-1,3-diol Chemical compound OCC(CO)OCC1=CC=CC=C1 UDIPIOHLDFSMLR-UHFFFAOYSA-N 0.000 description 1
- FBQMBIDSILZYSW-UHFFFAOYSA-N 2-tri(propan-2-yl)silyl-1,3-oxazole-5-carbaldehyde Chemical compound CC(C)[Si](C(C)C)(C(C)C)C1=NC=C(C=O)O1 FBQMBIDSILZYSW-UHFFFAOYSA-N 0.000 description 1
- AKTDHHFJFNIILG-UHFFFAOYSA-N 3,3-diethoxypropanoic acid Chemical compound CCOC(CC(O)=O)OCC AKTDHHFJFNIILG-UHFFFAOYSA-N 0.000 description 1
- DADUIQAUVKKGNW-UHFFFAOYSA-N 3-(1-azidoethyl)-1-(4-chloro-2-nitrophenyl)pyrrolidine Chemical compound C1C(C(N=[N+]=[N-])C)CCN1C1=CC=C(Cl)C=C1[N+]([O-])=O DADUIQAUVKKGNW-UHFFFAOYSA-N 0.000 description 1
- MPDHDCBAAYSNIR-UHFFFAOYSA-N 3-(2-amino-4-chlorophenoxy)cyclohexan-1-ol Chemical compound NC1=CC(Cl)=CC=C1OC1CC(O)CCC1 MPDHDCBAAYSNIR-UHFFFAOYSA-N 0.000 description 1
- BTPNXOBYTGNHRK-UHFFFAOYSA-N 3-(3-amino-4-methoxyphenyl)propan-1-ol Chemical compound COC1=CC=C(CCCO)C=C1N BTPNXOBYTGNHRK-UHFFFAOYSA-N 0.000 description 1
- UJKIXSHIVPZDLI-UHFFFAOYSA-N 3-(3-aminonaphthalen-2-yl)oxycyclopentan-1-ol Chemical compound NC1=CC2=CC=CC=C2C=C1OC1CCC(O)C1 UJKIXSHIVPZDLI-UHFFFAOYSA-N 0.000 description 1
- CVTVAXANDBQYHW-UHFFFAOYSA-N 3-(3-aminonaphthalen-2-yl)oxypropan-1-ol Chemical compound C1=CC=C2C=C(OCCCO)C(N)=CC2=C1 CVTVAXANDBQYHW-UHFFFAOYSA-N 0.000 description 1
- SPALOAYIDBENJA-UHFFFAOYSA-N 3-(4-chloro-2-nitrophenoxy)propan-1-ol Chemical compound OCCCOC1=CC=C(Cl)C=C1[N+]([O-])=O SPALOAYIDBENJA-UHFFFAOYSA-N 0.000 description 1
- LDCMZDBMEMCWBB-UHFFFAOYSA-N 3-(4-chloro-2-nitrophenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC(Cl)=CC=2)[N+]([O-])=O)=C1 LDCMZDBMEMCWBB-UHFFFAOYSA-N 0.000 description 1
- RRUXUDNMISMLAO-UHFFFAOYSA-N 3-(dimethylamino)-2-formylprop-2-enenitrile Chemical compound CN(C)C=C(C=O)C#N RRUXUDNMISMLAO-UHFFFAOYSA-N 0.000 description 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
- ZHVPTERSBUMMHK-UHFFFAOYSA-N 3-aminonaphthalen-2-ol Chemical compound C1=CC=C2C=C(O)C(N)=CC2=C1 ZHVPTERSBUMMHK-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 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
- FIGABNZMCORYCP-UHFFFAOYSA-N 3-chloro-6-methoxy-2h-indazol-5-amine Chemical compound C1=C(N)C(OC)=CC2=C1C(Cl)=NN2 FIGABNZMCORYCP-UHFFFAOYSA-N 0.000 description 1
- JZPHAJFIZZEAEK-UHFFFAOYSA-N 3-chloro-6-methoxy-2h-indazole Chemical compound COC1=CC=C2C(Cl)=NNC2=C1 JZPHAJFIZZEAEK-UHFFFAOYSA-N 0.000 description 1
- QZWZUKDSLNQYNM-UHFFFAOYSA-N 3-methoxy-n,n-dimethyl-4-nitrobenzamide Chemical compound COC1=CC(C(=O)N(C)C)=CC=C1[N+]([O-])=O QZWZUKDSLNQYNM-UHFFFAOYSA-N 0.000 description 1
- CFNQDELKWADFQO-UHFFFAOYSA-N 3-methyl-4h-thieno[3,2-b]pyridine-5,7-dione Chemical compound N1C(=O)CC(=O)C2=C1C(C)=CS2 CFNQDELKWADFQO-UHFFFAOYSA-N 0.000 description 1
- RHSSAEZVCVVURO-UHFFFAOYSA-N 3-methylthieno[3,2-b]pyridine Chemical compound C1=CN=C2C(C)=CSC2=C1 RHSSAEZVCVVURO-UHFFFAOYSA-N 0.000 description 1
- OCOBFMZGRJOSOU-UHFFFAOYSA-N 3-o-tert-butyl 1-o-ethyl propanedioate Chemical compound CCOC(=O)CC(=O)OC(C)(C)C OCOBFMZGRJOSOU-UHFFFAOYSA-N 0.000 description 1
- PKQIDSVLSKFZQC-UHFFFAOYSA-N 3-oxobutanal Chemical compound CC(=O)CC=O PKQIDSVLSKFZQC-UHFFFAOYSA-N 0.000 description 1
- PJCCSZUMZMCWSX-UHFFFAOYSA-N 4,4-Dimethoxy-2-butanone Chemical compound COC(OC)CC(C)=O PJCCSZUMZMCWSX-UHFFFAOYSA-N 0.000 description 1
- IUISLYLTUZCHDD-UHFFFAOYSA-N 4-(2-amino-4-chlorophenoxy)piperidine-1-carboxylic acid Chemical compound NC1=C(OC2CCN(CC2)C(=O)O)C=CC(=C1)Cl IUISLYLTUZCHDD-UHFFFAOYSA-N 0.000 description 1
- VYUPIZHTLUCPFI-UHFFFAOYSA-N 4-(2-aminophenoxy)cyclohexan-1-ol Chemical compound NC1=CC=CC=C1OC1CCC(O)CC1 VYUPIZHTLUCPFI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JAJNGGYXSDACJA-UHFFFAOYSA-N 4-(4-chloro-2-nitrophenyl)butan-1-ol Chemical compound OCCCCC1=CC=C(Cl)C=C1[N+]([O-])=O JAJNGGYXSDACJA-UHFFFAOYSA-N 0.000 description 1
- QIRMSRRCGFUJSW-UHFFFAOYSA-N 4-amino-3-methoxy-n-phenylbenzamide Chemical compound C1=C(N)C(OC)=CC(C(=O)NC=2C=CC=CC=2)=C1 QIRMSRRCGFUJSW-UHFFFAOYSA-N 0.000 description 1
- TTYAIPDCSDAUJI-UHFFFAOYSA-N 4-amino-n-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCO[Si](C)(C)C(C)(C)C)=CC=C1N TTYAIPDCSDAUJI-UHFFFAOYSA-N 0.000 description 1
- ABEUJUYEUCCZQF-UHFFFAOYSA-N 4-chloro-2-methoxy-1-nitrobenzene Chemical compound COC1=CC(Cl)=CC=C1[N+]([O-])=O ABEUJUYEUCCZQF-UHFFFAOYSA-N 0.000 description 1
- NSMZCUAVEOTJDS-UHFFFAOYSA-N 4-chloro-2-methyl-1-nitrobenzene Chemical compound CC1=CC(Cl)=CC=C1[N+]([O-])=O NSMZCUAVEOTJDS-UHFFFAOYSA-N 0.000 description 1
- JBMGJOKJUYGIJH-UHFFFAOYSA-N 4-chloro-5-methyl-2-nitrophenol Chemical compound CC1=CC(O)=C([N+]([O-])=O)C=C1Cl JBMGJOKJUYGIJH-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- HDYFZIBCLZCJHO-UHFFFAOYSA-N 5-chloro-2-(2-methylpropoxy)aniline Chemical compound CC(C)COC1=CC=C(Cl)C=C1N HDYFZIBCLZCJHO-UHFFFAOYSA-N 0.000 description 1
- MDARILWSGLRXMZ-SECBINFHSA-N 5-chloro-2-[[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]aniline Chemical compound O1C(C)(C)OC[C@H]1COC1=CC=C(Cl)C=C1N MDARILWSGLRXMZ-SECBINFHSA-N 0.000 description 1
- OEMQDUWQOXASQX-UHFFFAOYSA-N 5-chloro-2-cyclohexylaniline Chemical compound NC1=CC(Cl)=CC=C1C1CCCCC1 OEMQDUWQOXASQX-UHFFFAOYSA-N 0.000 description 1
- OAYFKAANHGOOOY-UHFFFAOYSA-N 5-chloro-2-cyclohexyloxyaniline Chemical compound NC1=CC(Cl)=CC=C1OC1CCCCC1 OAYFKAANHGOOOY-UHFFFAOYSA-N 0.000 description 1
- UEYYCZFZTFTKAY-UHFFFAOYSA-N 5-chloro-6-nitroquinoline Chemical compound N1=CC=CC2=C(Cl)C([N+](=O)[O-])=CC=C21 UEYYCZFZTFTKAY-UHFFFAOYSA-N 0.000 description 1
- RPJXLEZOFUNGNZ-UHFFFAOYSA-N 5-methoxy-2-methylaniline Chemical compound COC1=CC=C(C)C(N)=C1 RPJXLEZOFUNGNZ-UHFFFAOYSA-N 0.000 description 1
- PLNIQZFNLLDSLU-UHFFFAOYSA-N 6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(CCO[Si](C)(C)C(C)(C)C)C=NC2=C(C(O)=O)C=NN21 PLNIQZFNLLDSLU-UHFFFAOYSA-N 0.000 description 1
- YLEILJCLPSXCTJ-UHFFFAOYSA-N 6-bromo-n-[5-chloro-2-(4-hydroxycyclohexyl)oxyphenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1CC(O)CCC1OC1=CC=C(Cl)C=C1NC(=O)C1=C2N=CC(Br)=CN2N=C1 YLEILJCLPSXCTJ-UHFFFAOYSA-N 0.000 description 1
- KSEHCKMSLDOXTR-UHFFFAOYSA-N 6-formyl-7H-pyrazolo[1,5-c]pyrimidine-3-carboxylic acid Chemical compound C1N(C=O)C=CC2=C(C(=O)O)C=NN21 KSEHCKMSLDOXTR-UHFFFAOYSA-N 0.000 description 1
- BLFAQVDMGROPLP-UHFFFAOYSA-N 6-formylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C=O)C=NC2=C(C(=O)O)C=NN21 BLFAQVDMGROPLP-UHFFFAOYSA-N 0.000 description 1
- ZVUKRBPCNITCOH-UHFFFAOYSA-N 6-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(O)C=NC2=C(C(=O)O)C=NN21 ZVUKRBPCNITCOH-UHFFFAOYSA-N 0.000 description 1
- JMLBPVQSGMQBAF-UHFFFAOYSA-N 6-phenylmethoxypyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=NC2=C(C(=O)O)C=NN2C=C1OCC1=CC=CC=C1 JMLBPVQSGMQBAF-UHFFFAOYSA-N 0.000 description 1
- HQXDTADTVSWAQX-UHFFFAOYSA-N 7-[3-[tert-butyl(dimethyl)silyl]oxycyclopentyl]oxyquinolin-6-amine Chemical compound C1C(O[Si](C)(C)C(C)(C)C)CCC1OC1=CC2=NC=CC=C2C=C1N HQXDTADTVSWAQX-UHFFFAOYSA-N 0.000 description 1
- XZWXQSGFZHRDNB-UHFFFAOYSA-N 7-bromo-3-hydroxynaphthalene-2-carboxylic acid Chemical compound BrC1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 XZWXQSGFZHRDNB-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
- 208000005676 Adrenogenital syndrome Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010001889 Alveolitis Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 208000028185 Angioedema Diseases 0.000 description 1
- 206010053555 Arthritis bacterial Diseases 0.000 description 1
- 206010003267 Arthritis reactive Diseases 0.000 description 1
- 241001133287 Artocarpus hirsutus Species 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- UUYRCMPJDHVQDQ-UHFFFAOYSA-N B(F)(F)F.COC(C1=CC(=C(C=C1)[N+](=O)[O-])OC)=O Chemical compound B(F)(F)F.COC(C1=CC(=C(C=C1)[N+](=O)[O-])OC)=O UUYRCMPJDHVQDQ-UHFFFAOYSA-N 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 206010004663 Biliary colic Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 206010006417 Bronchial carcinoma Diseases 0.000 description 1
- DPKCFUBZGIWDPL-UHFFFAOYSA-N C(C)(=O)OC(C)=O.C(C)(=O)NC=1C=C(C=CC1)OC(C)=O Chemical compound C(C)(=O)OC(C)=O.C(C)(=O)NC=1C=C(C=CC1)OC(C)=O DPKCFUBZGIWDPL-UHFFFAOYSA-N 0.000 description 1
- OAIZIGCYCZQOBC-UHFFFAOYSA-N C(C)(=O)OC(C)=O.C(C)C1=CC=C(C=C1)NC(C)=O Chemical compound C(C)(=O)OC(C)=O.C(C)C1=CC=C(C=C1)NC(C)=O OAIZIGCYCZQOBC-UHFFFAOYSA-N 0.000 description 1
- WZMUSNWTWQKSED-UHFFFAOYSA-N COC=1C=C(C=CC1[N+](=O)[O-])C1=CC=CC=C1.COC=1C=C(C=CC1N)C1=CC=CC=C1 Chemical group COC=1C=C(C=CC1[N+](=O)[O-])C1=CC=CC=C1.COC=1C=C(C=CC1N)C1=CC=CC=C1 WZMUSNWTWQKSED-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 102100038916 Caspase-5 Human genes 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 102000000844 Cell Surface Receptors Human genes 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 102000019034 Chemokines Human genes 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- 208000002691 Choroiditis Diseases 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- RISSLRPXGCNRKM-UHFFFAOYSA-N ClC(C(=O)N=C=O)(Cl)Cl.CC1=CSC2=C1NC(NC2=O)=O Chemical compound ClC(C(=O)N=C=O)(Cl)Cl.CC1=CSC2=C1NC(NC2=O)=O RISSLRPXGCNRKM-UHFFFAOYSA-N 0.000 description 1
- MXQNMVWVIQRTKP-UHFFFAOYSA-N ClC1=C(C=CC(=C1)C)[N+](=O)[O-].ClC=1C=C(C(=O)O)C=CC1[N+](=O)[O-] Chemical compound ClC1=C(C=CC(=C1)C)[N+](=O)[O-].ClC=1C=C(C(=O)O)C=CC1[N+](=O)[O-] MXQNMVWVIQRTKP-UHFFFAOYSA-N 0.000 description 1
- MUYFQIQEBJQOGI-JOCQHMNTSA-N ClC=1C=CC(=C(C=1)NC(=O)C1=CSC2=C1N=CN=C2)O[C@@H]1CC[C@H](CC1)O Chemical compound ClC=1C=CC(=C(C=1)NC(=O)C1=CSC2=C1N=CN=C2)O[C@@H]1CC[C@H](CC1)O MUYFQIQEBJQOGI-JOCQHMNTSA-N 0.000 description 1
- 208000015943 Coeliac disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 102000010170 Death domains Human genes 0.000 description 1
- 108050001718 Death domains Proteins 0.000 description 1
- 206010012434 Dermatitis allergic Diseases 0.000 description 1
- 206010012441 Dermatitis bullous Diseases 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 102100039658 E3 ubiquitin-protein ligase pellino homolog 2 Human genes 0.000 description 1
- 101710150161 E3 ubiquitin-protein ligase pellino homolog 2 Proteins 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 206010060742 Endocrine ophthalmopathy Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 206010015218 Erythema multiforme Diseases 0.000 description 1
- 206010015226 Erythema nodosum Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 208000005577 Gastroenteritis Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 206010018498 Goitre Diseases 0.000 description 1
- 208000009329 Graft vs Host Disease Diseases 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 208000003807 Graves Disease Diseases 0.000 description 1
- 208000015023 Graves' disease Diseases 0.000 description 1
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 1
- 208000001204 Hashimoto Disease Diseases 0.000 description 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 241001272567 Hominoidea Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- 101000852483 Homo sapiens Interleukin-1 receptor-associated kinase 1 Proteins 0.000 description 1
- 101000977771 Homo sapiens Interleukin-1 receptor-associated kinase 4 Proteins 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
- 206010021750 Infantile Spasms Diseases 0.000 description 1
- 208000004575 Infectious Arthritis Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- 102000004557 Interleukin-18 Receptors Human genes 0.000 description 1
- 108010017537 Interleukin-18 Receptors Proteins 0.000 description 1
- 208000029523 Interstitial Lung disease Diseases 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 description 1
- 208000012659 Joint disease Diseases 0.000 description 1
- 208000003456 Juvenile Arthritis Diseases 0.000 description 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 102100020870 La-related protein 6 Human genes 0.000 description 1
- 108050008265 La-related protein 6 Proteins 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 108091054455 MAP kinase family Proteins 0.000 description 1
- 102000043136 MAP kinase family Human genes 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 102000003945 NF-kappa B Human genes 0.000 description 1
- 108010057466 NF-kappa B Proteins 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 101000881330 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) Dynein heavy chain, cytoplasmic Proteins 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 208000025047 Non-histaminic angioedema Diseases 0.000 description 1
- 208000011623 Obstructive Lung disease Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- 206010033078 Otitis media Diseases 0.000 description 1
- 241000282579 Pan Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 201000011152 Pemphigus Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 208000007048 Polymyalgia Rheumatica Diseases 0.000 description 1
- 208000003971 Posterior uveitis Diseases 0.000 description 1
- 206010052381 Primary adrenal insufficiency Diseases 0.000 description 1
- 206010036774 Proctitis Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 206010037765 Radiation pneumonitis Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010038419 Renal colic Diseases 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000030934 Restrictive pulmonary disease Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241001303601 Rosacea Species 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 206010042742 Sympathetic ophthalmia Diseases 0.000 description 1
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 201000002015 Thyroid Crisis Diseases 0.000 description 1
- 206010043784 Thyroiditis subacute Diseases 0.000 description 1
- 206010043786 Thyrotoxic crisis Diseases 0.000 description 1
- 206010048873 Traumatic arthritis Diseases 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- LLPMCUWLYAMILW-UHFFFAOYSA-N [4-(3-aminonaphthalen-2-yl)oxycyclohexyl] 2,2,2-trifluoroacetate Chemical compound NC1=CC2=CC=CC=C2C=C1OC1CCC(OC(=O)C(F)(F)F)CC1 LLPMCUWLYAMILW-UHFFFAOYSA-N 0.000 description 1
- PZRPBPMLSSNFOM-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]boronic acid Chemical compound OCC1=CC=C(B(O)O)C=C1 PZRPBPMLSSNFOM-UHFFFAOYSA-N 0.000 description 1
- ILWMFSFXGTWKQW-UHFFFAOYSA-N [5-[(4-chloro-2-nitrophenoxy)methyl]-1,3-oxazol-2-yl]-tri(propan-2-yl)silane Chemical compound O1C([Si](C(C)C)(C(C)C)C(C)C)=NC=C1COC1=CC=C(Cl)C=C1[N+]([O-])=O ILWMFSFXGTWKQW-UHFFFAOYSA-N 0.000 description 1
- UHOPCVRVULFABT-UHFFFAOYSA-N [5-[(4-chloro-2-nitrophenoxy)methyl]-1,3-oxazol-2-yl]-tri(propan-2-yl)silane 5-chloro-2-[[2-tri(propan-2-yl)silyl-1,3-oxazol-5-yl]methoxy]aniline Chemical compound ClC1=CC(=C(OCC2=CN=C(O2)[Si](C(C)C)(C(C)C)C(C)C)C=C1)[N+](=O)[O-].ClC=1C=CC(=C(C1)N)OCC1=CN=C(O1)[Si](C(C)C)(C(C)C)C(C)C UHOPCVRVULFABT-UHFFFAOYSA-N 0.000 description 1
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 231100000354 acute hepatitis Toxicity 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000000033 alkoxyamino group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 208000004631 alopecia areata Diseases 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
- 229910052782 aluminium Inorganic materials 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 125000002431 aminoalkoxy group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000030741 antigen processing and presentation Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 206010003230 arteritis Diseases 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
- 230000005784 autoimmunity Effects 0.000 description 1
- 230000035578 autophosphorylation Effects 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000002479 balanitis Diseases 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 239000004305 biphenyl Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 208000010217 blepharitis Diseases 0.000 description 1
- 239000003914 blood derivative Substances 0.000 description 1
- 208000019664 bone resorption disease Diseases 0.000 description 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N boron trifluoride etherate Substances FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 201000008275 breast carcinoma Diseases 0.000 description 1
- 201000009267 bronchiectasis Diseases 0.000 description 1
- 208000003362 bronchogenic carcinoma Diseases 0.000 description 1
- 239000000872 buffer 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000007887 coronary angioplasty Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
- 230000004041 dendritic cell maturation Effects 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 201000001981 dermatomyositis Diseases 0.000 description 1
- 230000000368 destabilizing effect Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 description 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 208000030172 endocrine system disease Diseases 0.000 description 1
- 239000006274 endogenous ligand Substances 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 208000010227 enterocolitis Diseases 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- FPNWHTWMWSMZFO-UHFFFAOYSA-N ethyl 2-(2,4-diamino-5-piperidin-1-ylphenyl)acetate Chemical compound C1=C(N)C(CC(=O)OCC)=CC(N2CCCCC2)=C1N FPNWHTWMWSMZFO-UHFFFAOYSA-N 0.000 description 1
- KAFOSVOBHQJJOQ-UHFFFAOYSA-N ethyl 2-(5-chloro-2,4-dinitrophenyl)acetate Chemical compound CCOC(=O)CC1=CC(Cl)=C([N+]([O-])=O)C=C1[N+]([O-])=O KAFOSVOBHQJJOQ-UHFFFAOYSA-N 0.000 description 1
- PEOQPQHZHDFVIL-UHFFFAOYSA-N ethyl 3-hydroxycyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCC(O)C1 PEOQPQHZHDFVIL-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 208000027096 gram-negative bacterial infections Diseases 0.000 description 1
- 208000027136 gram-positive bacterial infections Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 230000000322 hemodialysis Effects 0.000 description 1
- 208000007475 hemolytic anemia Diseases 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 1
- 125000004476 heterocycloamino group Chemical group 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000005181 hydroxyalkylaminoalkyl group Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 230000006951 hyperphosphorylation Effects 0.000 description 1
- 230000004047 hyperresponsiveness Effects 0.000 description 1
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 description 1
- 238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
- WHOCKNWCRFHEMH-UHFFFAOYSA-N imidazo[1,2-a]pyridine-8-carboxylic acid Chemical compound OC(=O)C1=CC=CN2C=CN=C12 WHOCKNWCRFHEMH-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000012739 integrated shape imaging system Methods 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 201000004614 iritis Diseases 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 208000025036 lymphosarcoma Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- LJNKREYVJAYXIC-GQCTYLIASA-N methyl (e)-3-(3-amino-4-methoxyphenyl)prop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=C(OC)C(N)=C1 LJNKREYVJAYXIC-GQCTYLIASA-N 0.000 description 1
- NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
- XEHGOHFMQFJUDW-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=CC(OC)=CC=C1NC(=O)C1=C2N=CC=CN2N=C1 XEHGOHFMQFJUDW-UHFFFAOYSA-N 0.000 description 1
- ZLJPDSYSFMDJCB-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-methoxy-4-nitrobenzamide Chemical compound COC1=CC(C(=O)NCCO)=CC=C1[N+]([O-])=O ZLJPDSYSFMDJCB-UHFFFAOYSA-N 0.000 description 1
- RNXQSPMVEIEHGZ-UHFFFAOYSA-N n-(2-methoxy-4-methylphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=CC(C)=CC=C1NC(=O)C1=C2N=CC=CN2N=C1 RNXQSPMVEIEHGZ-UHFFFAOYSA-N 0.000 description 1
- FIUJLVQYVUCBLW-UHFFFAOYSA-N n-(2-methoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)C1=CSC2=CN=CN=C12 FIUJLVQYVUCBLW-UHFFFAOYSA-N 0.000 description 1
- ZKMUGSIXUVCRLU-UHFFFAOYSA-N n-(3-amino-2-methoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=C(N)C=CC=C1NC(=O)C1=C2N=CC=CN2N=C1 ZKMUGSIXUVCRLU-UHFFFAOYSA-N 0.000 description 1
- FULKEVNWMGUXNQ-UHFFFAOYSA-N n-(3-hydroxy-4-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C(O)=C1 FULKEVNWMGUXNQ-UHFFFAOYSA-N 0.000 description 1
- HOPWGOFWAPWHDS-UHFFFAOYSA-N n-(4-ethylphenyl)acetamide Chemical compound CCC1=CC=C(NC(C)=O)C=C1 HOPWGOFWAPWHDS-UHFFFAOYSA-N 0.000 description 1
- SXLHIROETAWJJQ-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)-5-(2-hydroxyethylamino)thieno[3,2-b]pyridine-3-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1=CSC2=CC=C(NCCO)N=C12 SXLHIROETAWJJQ-UHFFFAOYSA-N 0.000 description 1
- JSNBIIURKPLWEV-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1=C2N=CC=CN2N=C1 JSNBIIURKPLWEV-UHFFFAOYSA-N 0.000 description 1
- UPLGLZRLZZMGKV-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)thieno[3,2-b]pyridine-3-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1=CSC2=CC=CN=C12 UPLGLZRLZZMGKV-UHFFFAOYSA-N 0.000 description 1
- OMGFERVXHMERQL-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1=CSC2=CN=CN=C12 OMGFERVXHMERQL-UHFFFAOYSA-N 0.000 description 1
- UNGJDCICXXTFHD-UHFFFAOYSA-N n-(5-methoxy-2-methyl-4-nitrophenyl)acetamide Chemical compound COC1=CC(NC(C)=O)=C(C)C=C1[N+]([O-])=O UNGJDCICXXTFHD-UHFFFAOYSA-N 0.000 description 1
- JIUDGHSGSAGAQX-UHFFFAOYSA-N n-[2-[4-[tert-butyl(dimethyl)silyl]oxycyclohexyl]oxy-5-chlorophenyl]-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=12N=C(C)C=CN2N=CC=1C(=O)NC1=CC(Cl)=CC=C1OC1CCC(O[Si](C)(C)C(C)(C)C)CC1 JIUDGHSGSAGAQX-UHFFFAOYSA-N 0.000 description 1
- WYNYDUMRWMWAFF-UHFFFAOYSA-N n-[2-[4-[tert-butyl(dimethyl)silyl]oxycyclohexyl]oxy-5-chlorophenyl]-6-(hydroxymethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1CC(O[Si](C)(C)C(C)(C)C)CCC1OC1=CC=C(Cl)C=C1NC(=O)C1=C2N=CC(CO)=CN2N=C1 WYNYDUMRWMWAFF-UHFFFAOYSA-N 0.000 description 1
- PYKORXQGTHXNPW-UHFFFAOYSA-N n-[2-[4-[tert-butyl(dimethyl)silyl]oxycyclohexyl]oxy-5-chlorophenyl]-6-formylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1CC(O[Si](C)(C)C(C)(C)C)CCC1OC1=CC=C(Cl)C=C1NC(=O)C1=C2N=CC(C=O)=CN2N=C1 PYKORXQGTHXNPW-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- LTPIGZKMKGKCLS-UHFFFAOYSA-N n-[4-[2-[tert-butyl(dimethyl)silyl]oxyethylcarbamoyl]-2-methoxyphenyl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound COC1=CC(C(=O)NCCO[Si](C)(C)C(C)(C)C)=CC=C1NC(=O)C1=CSC2=CN=CN=C12 LTPIGZKMKGKCLS-UHFFFAOYSA-N 0.000 description 1
- SJNZPBUGPXFCMF-UHFFFAOYSA-N n-[4-[3-[tert-butyl(dimethyl)silyl]oxypropylcarbamoyl]-2-methoxyphenyl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound COC1=CC(C(=O)NCCCO[Si](C)(C)C(C)(C)C)=CC=C1NC(=O)C1=CSC2=CN=CN=C12 SJNZPBUGPXFCMF-UHFFFAOYSA-N 0.000 description 1
- CZYRNCFEHFTAFU-UHFFFAOYSA-N n-[5-chloro-2-(2-methoxyethoxy)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COCCOC1=CC=C(Cl)C=C1NC(=O)C1=C2N=CC=CN2N=C1 CZYRNCFEHFTAFU-UHFFFAOYSA-N 0.000 description 1
- PWPFIWWDNIBEBU-UHFFFAOYSA-N n-[5-chloro-2-(4-hydroxycyclohexyl)oxyphenyl]-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide Chemical compound C1CC(O)CCC1OC1=CC=C(Cl)C=C1NC(=O)C1=CC=CN2C1=NN=C2 PWPFIWWDNIBEBU-UHFFFAOYSA-N 0.000 description 1
- GCWWFULDZVZOHD-UHFFFAOYSA-N n-[5-chloro-2-(4-hydroxyphenoxy)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1NC(=O)C1=C2N=CC=CN2N=C1 GCWWFULDZVZOHD-UHFFFAOYSA-N 0.000 description 1
- WRORDPRTLRAARE-UHFFFAOYSA-N n-[5-chloro-2-[(4-methyl-1,3-oxazol-5-yl)methoxy]phenyl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N1=COC(COC=2C(=CC(Cl)=CC=2)NC(=O)C=2C3=NC=NC=C3SC=2)=C1C WRORDPRTLRAARE-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RRPKGUUYTHFUPN-UHFFFAOYSA-N n-hydroxy-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=C(S(=O)(=O)NO)C(C)=C1 RRPKGUUYTHFUPN-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 208000028931 non-acquired combined pituitary hormone deficiency Diseases 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 231100001143 noxa Toxicity 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 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
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 201000001976 pemphigus vulgaris Diseases 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 208000000689 peptic esophagitis Diseases 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 1
- 206010035116 pityriasis rubra pilaris Diseases 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 208000005987 polymyositis Diseases 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000004063 proteosomal degradation Effects 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 201000003651 pulmonary sarcoidosis Diseases 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- XPPZAORQJNABAD-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=C=C[CH]N2N=CC=C21 XPPZAORQJNABAD-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006042 reductive dechlorination reaction Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 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
- 201000001223 septic arthritis Diseases 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- HPCQQAHJYKEGJS-UHFFFAOYSA-M sodium 7-amino-6-methoxynaphthalene-2-carboxylic acid hydroxide Chemical compound [OH-].[Na+].NC1=C(C=C2C=CC(=CC2=C1)C(=O)O)OC HPCQQAHJYKEGJS-UHFFFAOYSA-M 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 201000007497 subacute thyroiditis Diseases 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 208000020408 systemic-onset juvenile idiopathic arthritis Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- OBQVQGZTFXIGLW-UHFFFAOYSA-N tert-butyl 3-(1-hydroxyethyl)pyrrolidine-1-carboxylate Chemical compound CC(O)C1CCN(C(=O)OC(C)(C)C)C1 OBQVQGZTFXIGLW-UHFFFAOYSA-N 0.000 description 1
- UMXWTCYHDBMXRT-UHFFFAOYSA-N tert-butyl 4-(2-amino-4-chlorophenoxy)piperidine-1-carboxylate;tert-butyl 4-(4-chloro-2-nitrophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C(Cl)C=C1N.C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C(Cl)C=C1[N+]([O-])=O UMXWTCYHDBMXRT-UHFFFAOYSA-N 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- CKVGXEYBCUEUGN-UHFFFAOYSA-N tert-butyl n-[4-(2-amino-4-chlorophenoxy)cyclohexyl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCC1OC1=CC=C(Cl)C=C1N CKVGXEYBCUEUGN-UHFFFAOYSA-N 0.000 description 1
- UJIIRKKGCOZQBM-UHFFFAOYSA-N tert-butyl-[3-(4-chloro-2-nitrophenyl)phenoxy]-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC(C=2C(=CC(Cl)=CC=2)[N+]([O-])=O)=C1 UJIIRKKGCOZQBM-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- AROWMXGGAHTZPG-UHFFFAOYSA-N thieno[3,2-d]pyrimidine-7-carbaldehyde Chemical compound N1=CN=C2C(C=O)=CSC2=C1 AROWMXGGAHTZPG-UHFFFAOYSA-N 0.000 description 1
- UAVRRNWMMUYYOK-UHFFFAOYSA-N thieno[3,2-d]pyrimidine-7-carbaldehyde thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound N1=CN=CC2=C1C(=CS2)C=O.N2=CN=CC1=C2C(=CS1)C(=O)O UAVRRNWMMUYYOK-UHFFFAOYSA-N 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000010798 ubiquitination Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 208000002003 vulvitis Diseases 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic 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
-
- 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
- A61P1/12—Antidiarrhoeals
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial 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
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Gastroenterology & Hepatology (AREA)
- Transplantation (AREA)
- Virology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36385510P | 2010-07-13 | 2010-07-13 | |
| US61/363,855 | 2010-07-13 | ||
| US201161485145P | 2011-05-12 | 2011-05-12 | |
| US61/485,145 | 2011-05-12 | ||
| PCT/EP2011/061598 WO2012007375A1 (en) | 2010-07-13 | 2011-07-08 | Pyrazolo [1, 5a] pyrimidine and thieno [3, 2b] pyrimidine derivatives as irak4 modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2802641A1 CA2802641A1 (en) | 2012-01-19 |
| CA2802641C true CA2802641C (en) | 2019-03-12 |
Family
ID=45467432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2802641A Expired - Fee Related CA2802641C (en) | 2010-07-13 | 2011-07-08 | Pyrazolo [1, 5a] pyrimidine and thieno [3, 2b] pyrimidine derivatives as irak4 modulators |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US20120015962A1 (OSRAM) |
| EP (2) | EP3252054A1 (OSRAM) |
| JP (3) | JP5985473B2 (OSRAM) |
| KR (2) | KR101995013B1 (OSRAM) |
| CN (3) | CN110003219A (OSRAM) |
| AR (1) | AR082154A1 (OSRAM) |
| BR (1) | BR112013000868A2 (OSRAM) |
| CA (1) | CA2802641C (OSRAM) |
| MX (2) | MX340490B (OSRAM) |
| RU (1) | RU2604062C2 (OSRAM) |
| WO (1) | WO2012007375A1 (OSRAM) |
Families Citing this family (107)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101483215B1 (ko) * | 2010-01-29 | 2015-01-16 | 한미약품 주식회사 | 단백질 키나아제 저해활성을 갖는 비시클릭 헤테로아릴 유도체 |
| KR101995013B1 (ko) | 2010-07-13 | 2019-07-02 | 에프. 호프만-라 로슈 아게 | Irak4 조절제로서 피라졸로[1,5a]피리미딘 및 티에노[3,2b]피리미딘 유도체 |
| EP2663312B1 (en) * | 2011-01-10 | 2017-10-11 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| EP2688872A4 (en) * | 2011-03-22 | 2014-08-27 | Merck Sharp & Dohme | AMIDOPYRAZOLHEMMER OF INTERLEUKIN RECEPTOR-MEDIATED KINASES |
| JP2014517079A (ja) | 2011-06-22 | 2014-07-17 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｒキナーゼ阻害剤として有用な化合物 |
| BR112014015720B1 (pt) * | 2011-12-30 | 2020-03-17 | Hanmi Pharm. Co., Ltd. | Derivados de tieno[3,2-d]pirimidina, composição farmacêutica e uso dos mesmos para a prevenção ou tratamento de uma doença causada por ativação anormal de uma proteína quinase |
| CN104582705A (zh) * | 2012-01-10 | 2015-04-29 | 林伯士艾瑞斯公司 | 白介素-1受体相关激酶(irak)抑制剂和其用途 |
| JP6109193B2 (ja) * | 2012-01-10 | 2017-04-05 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | チエノピリミジン化合物 |
| WO2014003483A1 (en) * | 2012-06-29 | 2014-01-03 | Hanmi Pharm. Co., Ltd. | Fused pyrimidine derivatives having inhibitory activity on fms kinases |
| US9216991B2 (en) * | 2012-07-10 | 2015-12-22 | Ares Trading S.A. | Pyrimidine pyrazolyl derivatives |
| CN104902959A (zh) | 2012-07-11 | 2015-09-09 | 林伯士艾瑞斯公司 | Irak抑制剂和其用途 |
| EP2872144A4 (en) | 2012-07-11 | 2015-12-02 | Nimbus Iris Inc | IRAQ INHIBITOR AND USES THEREOF |
| US20140018361A1 (en) * | 2012-07-11 | 2014-01-16 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| PT4190786T (pt) | 2012-12-07 | 2025-05-29 | Vertex Pharma | Compostos úteis como inibidores da quinase atr |
| AU2014205577A1 (en) | 2013-01-10 | 2015-05-28 | Nimbus Iris, Inc. | IRAK inhibitors and uses thereof |
| JP6437452B2 (ja) | 2013-01-14 | 2018-12-12 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｐｉｍキナーゼ阻害剤として有用な二環式芳香族カルボキサミド化合物 |
| LT2945939T (lt) | 2013-01-15 | 2020-07-27 | Incyte Holdings Corporation | Triazolkarboksamidai ir piridinkarboksamido junginiai, naudotini kaip pim kinazės inhibitoriai |
| US8778365B1 (en) | 2013-01-31 | 2014-07-15 | Merz Pharmaceuticals, Llc | Topical compositions and methods for making and using same |
| JP2016512239A (ja) | 2013-03-15 | 2016-04-25 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Ａｔｒキナーゼの阻害剤として有用な化合物 |
| JP2016512816A (ja) * | 2013-03-15 | 2016-05-09 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Ａｔｒキナーゼの阻害剤として有用な化合物 |
| EP2970286A1 (en) | 2013-03-15 | 2016-01-20 | Vertex Pharmaceuticals Inc. | Fused pyrazolopyrimidine derivatives useful as inhibitors of atr kinase |
| GB201311891D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| GB201311888D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| US20160166576A1 (en) * | 2013-07-11 | 2016-06-16 | Merck Sharp & Dohme Corp. | Substituted amidopyrazole inhibitors of interleukin receptor-associated kinases (irak-4) |
| EP3036238A1 (en) * | 2013-08-23 | 2016-06-29 | Incyte Corporation | Furo- and thieno-pyridine carboxamide compounds useful as pim kinase inhibitors |
| EP3049086A4 (en) | 2013-09-27 | 2017-02-22 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| CA2932757C (en) | 2013-12-06 | 2023-10-31 | Vertex Pharmaceuticals Incorporated | 2-amino-6-fluoro-n-[5-fluoro-pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-3-carboxamide compound useful as atr kinase inhibitor, its preparation, different solid forms and radiolabelled derivatives thereof |
| US9908872B2 (en) | 2013-12-13 | 2018-03-06 | Dana-Farber Cancer Institute, Inc. | Methods to treat lymphoplasmacytic lymphoma |
| AU2014361798B2 (en) | 2013-12-13 | 2020-06-11 | Dana-Farber Cancer Institute, Inc. | Methods to treat lymphoplasmacytic lymphoma |
| TWI667233B (zh) | 2013-12-19 | 2019-08-01 | 德商拜耳製藥公司 | 新穎吲唑羧醯胺，其製備方法、含彼等之醫藥製劑及其製造醫藥之用途 |
| KR20160115933A (ko) * | 2014-01-10 | 2016-10-06 | 오리진 디스커버리 테크놀로지스 리미티드 | Irak4 억제제로서의 인다졸 화합물 |
| HRP20181795T1 (hr) | 2014-01-13 | 2019-01-25 | Aurigene Discovery Technologies Limited | Biciklički heterociklilni derivati kao inhibitori irak4 |
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| HUE054784T2 (hu) | 2014-05-23 | 2021-09-28 | Hoffmann La Roche | 5-klór-2-difluor-metoxifenil-pirazolopirimidin vegyületek, amelyek JAK-gátlók |
| KR102575125B1 (ko) | 2014-06-05 | 2023-09-07 | 버텍스 파마슈티칼스 인코포레이티드 | Atr 키나제의 저해제로서 유용한 2-아미노-6-플루오로-n-[5-플루오로-피리딘-3-일]-피라졸로[1,5-a]피리미딘-3-카복스아미드 화합물의 방사성표지된 유도체, 상기 화합물의 제조 및 이의 다양한 고체 형태 |
| RU2736219C2 (ru) | 2014-06-17 | 2020-11-12 | Вертекс Фармасьютикалз Инкорпорейтед | Способ лечения рака с использованием комбинации ингибиторов снк1 и atr |
| US9822124B2 (en) | 2014-07-14 | 2017-11-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as Pim kinase inhibitors |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| EP3715346B1 (en) | 2014-10-22 | 2024-01-03 | Dana-Farber Cancer Institute, Inc. | Thiazolyl-containing compounds for treating proliferative diseases |
| KR102662215B1 (ko) * | 2014-11-06 | 2024-05-02 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 치환된 피라졸로(1,5-a)피리미딘 및 의학적 장애의 치료에서의 그의 용도 |
| US20180185368A1 (en) | 2014-11-06 | 2018-07-05 | Lysosomal Therapeutics Inc. | Substituted pyrrolo[1,2-a]pyrimidines and their use in the treatment of medical disorders |
| ES2958391T3 (es) | 2014-11-06 | 2024-02-08 | Bial R&D Invest S A | Imidazo[1,5-a]pirimidinas sustituidas y su uso en el tratamiento de trastornos médicos |
| EP3221306B1 (en) * | 2014-11-20 | 2019-11-13 | Merck Patent GmbH | Heteroaryl compounds as irak inhibitors and uses thereof |
| US10040802B2 (en) | 2015-03-12 | 2018-08-07 | Merck Sharp & Dohme Corp. | Thienopyrazine inhibitors of IRAK4 activity |
| WO2016144848A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Pyrrolotriazine inhibitors of irak4 activity |
| US10040798B2 (en) | 2015-03-12 | 2018-08-07 | Merck Sharp & Dohme Corp. | Pyrrolopyridazine inhibitors of IRAK4 activity |
| WO2016144846A1 (en) * | 2015-03-12 | 2016-09-15 | Merck Sharp & Dohme Corp. | Pyrazolopyrimidine inhibitors of irak4 activity |
| EP3268367B8 (en) | 2015-03-12 | 2022-11-16 | Merck Sharp & Dohme LLC | Carboxamide inhibitors of irak4 activity |
| US9540347B2 (en) | 2015-05-29 | 2017-01-10 | Incyte Corporation | Pyridineamine compounds useful as Pim kinase inhibitors |
| WO2017004134A1 (en) * | 2015-06-29 | 2017-01-05 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| EA201890307A1 (ru) * | 2015-07-15 | 2018-10-31 | Ориджин Дискавери Текнолоджиз Лимитед | Индазольные и азаиндазольные соединения как ингибиторы irak-4 |
| AR105967A1 (es) | 2015-09-09 | 2017-11-29 | Incyte Corp | Sales de un inhibidor de pim quinasa |
| US10550070B2 (en) | 2015-09-17 | 2020-02-04 | City Of Hope | PCNA inhibitors |
| AU2016331955B2 (en) | 2015-09-30 | 2022-07-21 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors |
| CN105237414B (zh) * | 2015-09-30 | 2017-03-22 | 浙江永宁药业股份有限公司 | ivacaftor中间体及其制备方法和用途 |
| WO2017059251A1 (en) | 2015-10-02 | 2017-04-06 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| CN108473498B (zh) * | 2015-12-22 | 2021-11-02 | 豪夫迈·罗氏有限公司 | 作为IRAK4调节剂的吡唑并[1,5a]嘧啶衍生物 |
| CA3020310A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics Inc. | Pyrrolo[1,2-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| US10787454B2 (en) | 2016-04-06 | 2020-09-29 | BIAL—BioTech Investments, Inc. | Imidazo[1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| KR20230104752A9 (ko) | 2016-04-06 | 2024-11-15 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 피라졸로[1,5-a]피리미디닐 카르복스아미드 화합물및 의학적 장애의 치료에서의 그의 용도 |
| WO2017192841A1 (en) * | 2016-05-04 | 2017-11-09 | Lysosomal Therapeutics Inc. | Methods of treatment and combination therapies using gcase activator heterobicyclic and related compounds |
| EP3452455A4 (en) | 2016-05-05 | 2019-11-13 | Lysosomal Therapeutics Inc. | SUBSTITUTED IMDAZO [1,2-] PYRIDINES, SUBSTITUTED IMIDAZO [1,2-] PYRAZINES, RELATED COMPOUNDS AND THEIR USE IN THE TREATMENT OF ILLNESSES |
| JP7164774B2 (ja) | 2016-05-05 | 2022-11-02 | ビアル－アール・アンド・ディ・インベストメンツ・ソシエダーデ・アノニマ | 置換イミダゾ［１，２－ｂ］ピリダジン、置換イミダゾ［１，５－ｂ］ピリダジン、関連化合物、および医学的障害の治療におけるその使用 |
| CN106222183B (zh) * | 2016-07-25 | 2019-11-08 | 南通大学 | 靶向人irak1基因的小干扰rna及其应用 |
| EP3535273A1 (en) * | 2016-11-02 | 2019-09-11 | H. Hoffnabb-La Roche Ag | PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS |
| US11072599B2 (en) | 2017-02-01 | 2021-07-27 | Biotheryx, Inc. | Pyrazole compounds and uses thereof |
| JOP20180011A1 (ar) | 2017-02-16 | 2019-01-30 | Gilead Sciences Inc | مشتقات بيرولو [1، 2-b]بيريدازين |
| US11419875B2 (en) | 2017-03-31 | 2022-08-23 | Aurigene Discovery Technologies Limited | Compounds and compositions for treating hematological disorders |
| CN106946890A (zh) * | 2017-04-26 | 2017-07-14 | 中国药科大学 | 吡啶类irak4抑制剂、其制备方法及应用 |
| JP7256757B2 (ja) | 2017-05-22 | 2023-04-12 | エフ． ホフマン－ラ ロシュ アーゲー | 処置用化合物及び組成物、並びにその使用方法 |
| WO2018234342A1 (en) * | 2017-06-21 | 2018-12-27 | F. Hoffmann-La Roche Ag | Isoindolinone derivatives as irak4 modulators |
| WO2018234343A1 (en) | 2017-06-21 | 2018-12-27 | F. Hoffmann-La Roche Ag | Benzofurans as irak4 modulators |
| EP3642204A1 (en) * | 2017-06-21 | 2020-04-29 | H. Hoffnabb-La Roche Ag | PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS |
| WO2019001460A1 (zh) * | 2017-06-27 | 2019-01-03 | 南京明德新药研发股份有限公司 | 作为 irak4 抑制剂的稠环化合物 |
| JP7114394B2 (ja) * | 2017-08-18 | 2022-08-08 | 住友化学株式会社 | 化合物、レジスト組成物及びレジストパターンの製造方法 |
| EP3684366A4 (en) | 2017-09-22 | 2021-09-08 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES OF THE LATEST |
| WO2019060742A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc | AGENTS FOR DEGRADING PROTEINS AND USES THEREOF |
| EP3704108B1 (en) | 2017-10-31 | 2024-04-24 | Curis, Inc. | Irak4 inhibitor in combination with a bcl-2 inhibitor for use in treating cancer |
| US11065231B2 (en) | 2017-11-17 | 2021-07-20 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of interleukin-1 receptor- associated kinase 4 polypeptides |
| WO2019107987A1 (en) * | 2017-11-30 | 2019-06-06 | Hanmi Pharm. Co., Ltd. | THIENO[3,2-d]PYRIMIDINE COMPOUND HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASE |
| WO2019111218A1 (en) | 2017-12-08 | 2019-06-13 | Cadila Healthcare Limited | Novel heterocyclic compounds as irak4 inhibitors |
| TW201924683A (zh) | 2017-12-08 | 2019-07-01 | 美商英塞特公司 | 用於治療骨髓增生性贅瘤的低劑量組合療法 |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| EP3737675A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | Crbn ligands and uses thereof |
| WO2019140380A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| IL277408B2 (en) * | 2018-04-05 | 2024-08-01 | Merck Patent Gmbh | Heteroaryl compounds as type ii irak inhibitors and uses thereof |
| US11292792B2 (en) | 2018-07-06 | 2022-04-05 | Kymera Therapeutics, Inc. | Tricyclic CRBN ligands and uses thereof |
| WO2020010227A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| TWI842978B (zh) | 2018-07-13 | 2024-05-21 | 美商基利科學股份有限公司 | 衍生物 |
| CN110862375B (zh) * | 2018-08-27 | 2022-10-25 | 深圳铂立健医药有限公司 | 吡唑化合物及其药物组合物和应用 |
| JP7385658B2 (ja) | 2018-10-30 | 2023-11-22 | クロノス バイオ インコーポレイテッド | Ｃｄｋ９活性を調節するための化合物、組成物、および方法 |
| US11352350B2 (en) | 2018-11-30 | 2022-06-07 | Kymera Therapeutics, Inc. | IRAK degraders and uses thereof |
| KR20220027196A (ko) * | 2019-06-27 | 2022-03-07 | 바이오젠 엠에이 인코포레이티드 | 이미다조[1,2-a]피리디닐 유도체 및 질병의 치료에서 이것들의 용도 |
| JP7386576B2 (ja) | 2019-10-02 | 2023-11-27 | カイノス・メディスン・インコーポレイテッド | Ｎ－（１ｈ－イミダゾール－２－イル）ベンズアミド化合物および該化合物を活性成分として含む医薬組成物 |
| EP4076520A4 (en) | 2019-12-17 | 2024-03-27 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| WO2021127283A2 (en) | 2019-12-17 | 2021-06-24 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| WO2021198980A1 (en) | 2020-04-04 | 2021-10-07 | Pfizer Inc. | Methods of treating coronavirus disease 2019 |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| EP4223750B1 (en) * | 2020-09-30 | 2025-06-25 | Asahi Kasei Pharma Corporation | Nitrogen-containing bicyclic compounds which contain pyrimidine as interleukin 1 receptor-associated kinase 4 (irak-4) inhibitors to be used in the treatment of inflammatory or autoimmune diseases |
| US11866405B2 (en) | 2020-12-10 | 2024-01-09 | Astrazeneca Ab | Substituted indazoles as IRAK4 inhibitors |
| TW202241891A (zh) | 2020-12-30 | 2022-11-01 | 美商凱麥拉醫療公司 | Irak降解劑及其用途 |
| JP2024506656A (ja) | 2021-02-15 | 2024-02-14 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ４分解剤およびその使用 |
| KR20240004476A (ko) | 2021-04-08 | 2024-01-11 | 쿠리스 인코퍼레이션 | 암 치료를 위한 병용 요법 |
| US12097261B2 (en) | 2021-05-07 | 2024-09-24 | Kymera Therapeutics, Inc. | CDK2 degraders and uses thereof |
| KR102869914B1 (ko) * | 2021-10-28 | 2025-10-13 | 재단법인 대구경북첨단의료산업진흥재단 | 신규한 티에노[2,3-d]피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 포함하는 암 또는 자가면역질환의 예방 또는 치료용 약학적 조성물 |
| WO2023076556A1 (en) | 2021-10-29 | 2023-05-04 | Kymera Therapeutics, Inc. | Irak4 degraders and synthesis thereof |
| JP2025504059A (ja) | 2022-01-31 | 2025-02-06 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋデグレーダー及びその使用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6436628B1 (en) * | 1998-06-19 | 2002-08-20 | The Rockefeller University | Methods of identifying an agent which modulates period and doubletime protein interaction |
| ATE511840T1 (de) | 2001-10-09 | 2011-06-15 | Amgen Inc | Imidazolderivate als entzündungshemmende mittel |
| AR038118A1 (es) | 2002-01-14 | 2004-12-29 | Upjohn Co | Compuestos derivados de la bencinamida del acido 7-oxo-4,7-dihidrotien[2,3-b[piridin-6-carboxilico 3-sustituido que son utiles como antivirales |
| WO2005004810A2 (en) * | 2003-07-02 | 2005-01-20 | Merck & Co., Inc. | Arylsulfonamide derivatives |
| TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| GB0329214D0 (en) * | 2003-12-17 | 2004-01-21 | Glaxo Group Ltd | Novel compounds |
| EP1720874A4 (en) | 2004-02-24 | 2010-03-03 | Bioaxone Therapeutique Inc | 4-SUBSTITUTED PIPERIDINE DERIVATIVES |
| US20070197836A1 (en) | 2004-03-31 | 2007-08-23 | Kuraray Co., Ltd. | Method for producing halogenated unsaturated carbonyl compound |
| JP2008013527A (ja) | 2006-07-10 | 2008-01-24 | Sankyo Co Ltd | チエノ［３，２−ｄ］ピリミジン−２，４−ジアミン誘導体 |
| EP2102211A2 (en) * | 2006-11-20 | 2009-09-23 | Alantos Pharmaceuticals Holding, Inc. | Heterobicyclic metalloprotease inhibitors |
| NZ584454A (en) * | 2007-10-12 | 2011-09-30 | Ingenium Pharmaceuticals Gmbh | N-[6-phenyl-pyrimidin-4-yl]-amides and urea derivatives as inhibitors of protein kinases |
| US8853125B2 (en) * | 2008-09-24 | 2014-10-07 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| CA2740792C (en) * | 2008-10-31 | 2016-06-21 | Genentech, Inc. | Pyrazolopyrimidine jak inhibitor compounds and methods |
| IT1392824B1 (it) * | 2009-02-13 | 2012-03-23 | Sacmi | Apparato per formare oggetti |
| CN101537007A (zh) * | 2009-03-18 | 2009-09-23 | 中国医学科学院血液病医院（血液学研究所） | N-(噻吩-2)吡唑并[1,5-a]嘧啶-3-甲酰胺类化合物在制备抗恶性肿瘤药物方面的应用 |
| UA110324C2 (en) * | 2009-07-02 | 2015-12-25 | Genentech Inc | Jak inhibitory compounds based on pyrazolo pyrimidine |
| JP2013503188A (ja) * | 2009-08-28 | 2013-01-31 | アレイ バイオファーマ、インコーポレイテッド | Ｒａｆ阻害化合物およびその使用方法 |
| KR101483215B1 (ko) * | 2010-01-29 | 2015-01-16 | 한미약품 주식회사 | 단백질 키나아제 저해활성을 갖는 비시클릭 헤테로아릴 유도체 |
| EP2528925B1 (en) * | 2010-01-29 | 2017-07-05 | Hanmi Science Co., Ltd. | THIENO[3,2-d]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY ON PROTEIN KINASES |
| KR101995013B1 (ko) * | 2010-07-13 | 2019-07-02 | 에프. 호프만-라 로슈 아게 | Irak4 조절제로서 피라졸로[1,5a]피리미딘 및 티에노[3,2b]피리미딘 유도체 |
-
2011
- 2011-07-08 KR KR1020137003548A patent/KR101995013B1/ko not_active Expired - Fee Related
- 2011-07-08 CN CN201910238769.XA patent/CN110003219A/zh active Pending
- 2011-07-08 CA CA2802641A patent/CA2802641C/en not_active Expired - Fee Related
- 2011-07-08 KR KR1020197018324A patent/KR20190077610A/ko not_active Withdrawn
- 2011-07-08 EP EP17174156.4A patent/EP3252054A1/en not_active Withdrawn
- 2011-07-08 MX MX2013000390A patent/MX340490B/es active IP Right Grant
- 2011-07-08 CN CN201180034712.XA patent/CN102985426B/zh not_active Expired - Fee Related
- 2011-07-08 EP EP11736028.9A patent/EP2593457B1/en not_active Not-in-force
- 2011-07-08 WO PCT/EP2011/061598 patent/WO2012007375A1/en not_active Ceased
- 2011-07-08 JP JP2013519044A patent/JP5985473B2/ja not_active Expired - Fee Related
- 2011-07-08 MX MX2016007068A patent/MX358682B/es unknown
- 2011-07-08 RU RU2013103539/04A patent/RU2604062C2/ru not_active IP Right Cessation
- 2011-07-08 BR BR112013000868A patent/BR112013000868A2/pt not_active Application Discontinuation
- 2011-07-08 CN CN201510559974.8A patent/CN105367577B/zh not_active Expired - Fee Related
- 2011-07-12 US US13/180,589 patent/US20120015962A1/en not_active Abandoned
- 2011-07-12 AR ARP110102497A patent/AR082154A1/es unknown
-
2014
- 2014-04-02 US US14/243,074 patent/US9255110B2/en not_active Expired - Fee Related
-
2015
- 2015-12-18 US US14/975,004 patent/US10023589B2/en not_active Expired - Fee Related
-
2016
- 2016-08-01 JP JP2016151041A patent/JP6396376B2/ja not_active Expired - Fee Related
-
2018
- 2018-06-18 US US16/011,018 patent/US20180298026A1/en not_active Abandoned
- 2018-08-29 JP JP2018159947A patent/JP2018199703A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN105367577B (zh) | 2019-04-23 |
| JP6396376B2 (ja) | 2018-09-26 |
| KR20190077610A (ko) | 2019-07-03 |
| US20140303149A1 (en) | 2014-10-09 |
| KR20130132396A (ko) | 2013-12-04 |
| CN102985426B (zh) | 2015-10-07 |
| US20120015962A1 (en) | 2012-01-19 |
| JP2016222707A (ja) | 2016-12-28 |
| AR082154A1 (es) | 2012-11-14 |
| KR101995013B1 (ko) | 2019-07-02 |
| CN102985426A (zh) | 2013-03-20 |
| CN110003219A (zh) | 2019-07-12 |
| EP2593457A1 (en) | 2013-05-22 |
| MX2013000390A (es) | 2013-03-08 |
| RU2013103539A (ru) | 2014-08-20 |
| JP5985473B2 (ja) | 2016-09-06 |
| JP2018199703A (ja) | 2018-12-20 |
| US10023589B2 (en) | 2018-07-17 |
| HK1183029A1 (zh) | 2013-12-13 |
| US20160207936A1 (en) | 2016-07-21 |
| MX340490B (es) | 2016-07-11 |
| CN105367577A (zh) | 2016-03-02 |
| EP2593457B1 (en) | 2017-08-23 |
| BR112013000868A2 (pt) | 2016-05-17 |
| WO2012007375A1 (en) | 2012-01-19 |
| JP2013531018A (ja) | 2013-08-01 |
| MX358682B (es) | 2018-08-31 |
| CA2802641A1 (en) | 2012-01-19 |
| RU2604062C2 (ru) | 2016-12-10 |
| EP3252054A1 (en) | 2017-12-06 |
| US9255110B2 (en) | 2016-02-09 |
| US20180298026A1 (en) | 2018-10-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2802641C (en) | Pyrazolo [1, 5a] pyrimidine and thieno [3, 2b] pyrimidine derivatives as irak4 modulators | |
| ES2294189T3 (es) | Derivados de pirazolopirimidinona que tienen accion inhibidora de pde7. | |
| US7456185B2 (en) | Substituted quinazoline compounds useful as p38 kinase inhibitors | |
| US8871760B2 (en) | [1,2,4]triazolo[3,4-C][1,4]oxazines as P2X7 modulators | |
| AU2006283940A1 (en) | P38 MAP kinase inhibitors and methods for using the same | |
| US10300067B2 (en) | Tetrahydropyridopyrimidine compound or salt thereof | |
| AU2019237991B2 (en) | JAK inhibitors | |
| AU2004295050A1 (en) | Pyrazolyl and imidazolyl pyrimidines | |
| US20080207684A1 (en) | Kinase inhibitors and methods for using the same | |
| RU2378275C2 (ru) | ПРОИЗВОДНЫЕ ПИРРОЛО[3,2-c]ПИРИДИНА И СПОСОБ ИХ ПОЛУЧЕНИЯ | |
| CA2672719A1 (en) | Pyrazolo [3, 4 -d] pyrimidine p38 map kinase inhibitors | |
| HK1183029B (en) | Pyrazolo [1, 5a] pyrimidine and thieno [3, 2b] pyrimidine derivatives as irak4 modulators | |
| TW201217379A (en) | Pyrazolo[1,5a]pyrimidine derivatives as IRAK4 modulators |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160705 |
|
| MKLA | Lapsed |
Effective date: 20220301 |
|
| MKLA | Lapsed |
Effective date: 20200831 |