KR20190077610A - Irak4 조절제로서 피라졸로[1,5a]피리미딘 및 티에노[3,2b]피리미딘 유도체 - Google Patents
Irak4 조절제로서 피라졸로[1,5a]피리미딘 및 티에노[3,2b]피리미딘 유도체 Download PDFInfo
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- KR20190077610A KR20190077610A KR1020197018324A KR20197018324A KR20190077610A KR 20190077610 A KR20190077610 A KR 20190077610A KR 1020197018324 A KR1020197018324 A KR 1020197018324A KR 20197018324 A KR20197018324 A KR 20197018324A KR 20190077610 A KR20190077610 A KR 20190077610A
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- South Korea
- Prior art keywords
- hydroxy
- amino
- alkyl
- phenyl
- chloro
- 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.)
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- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 43
- 201000010099 disease Diseases 0.000 claims abstract description 36
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 230000001404 mediated effect Effects 0.000 claims abstract description 8
- -1 Hydroxy, amino, amino Chemical group 0.000 claims description 1015
- 125000000217 alkyl group Chemical group 0.000 claims description 393
- 125000003545 alkoxy group Chemical group 0.000 claims description 173
- 238000000034 method Methods 0.000 claims description 120
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 88
- 210000004369 blood Anatomy 0.000 claims description 85
- 239000008280 blood Substances 0.000 claims description 85
- 125000005843 halogen group Chemical group 0.000 claims description 64
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 47
- 238000004519 manufacturing process Methods 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 125000003386 piperidinyl group Chemical group 0.000 claims description 34
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 31
- 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 28
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 28
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 27
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 26
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 26
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 17
- 125000004193 piperazinyl group Chemical group 0.000 claims description 17
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
- 208000027866 inflammatory disease Diseases 0.000 claims description 11
- 208000023275 Autoimmune disease Diseases 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 102000000551 Syk Kinase Human genes 0.000 claims description 8
- 108010016672 Syk Kinase Proteins 0.000 claims description 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
- 102000005962 receptors Human genes 0.000 claims description 8
- 108020003175 receptors Proteins 0.000 claims description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
- 108091000080 Phosphotransferase Proteins 0.000 claims description 7
- 206010003246 arthritis Diseases 0.000 claims description 7
- 102000020233 phosphotransferase Human genes 0.000 claims description 7
- 108050006617 Interleukin-1 receptor Proteins 0.000 claims description 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 5
- 102000019223 Interleukin-1 receptor Human genes 0.000 claims description 5
- 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 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 4
- 208000009079 Bronchial Spasm Diseases 0.000 claims description 3
- 208000014181 Bronchial disease Diseases 0.000 claims description 3
- 206010006482 Bronchospasm Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 105
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 abstract description 18
- 101710199015 Interleukin-1 receptor-associated kinase 1 Proteins 0.000 abstract description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 283
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 263
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 256
- 239000000203 mixture Substances 0.000 description 183
- 230000015572 biosynthetic process Effects 0.000 description 139
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 138
- 238000003786 synthesis reaction Methods 0.000 description 138
- 239000007787 solid Substances 0.000 description 127
- 230000002829 reductive effect Effects 0.000 description 126
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 116
- 239000000243 solution Substances 0.000 description 108
- 235000019439 ethyl acetate Nutrition 0.000 description 106
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 97
- 239000011541 reaction mixture Substances 0.000 description 94
- 239000000843 powder Substances 0.000 description 83
- 206010057190 Respiratory tract infections Diseases 0.000 description 78
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 76
- 238000006243 chemical reaction Methods 0.000 description 70
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
- 238000003818 flash chromatography Methods 0.000 description 52
- 239000012267 brine Substances 0.000 description 47
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 43
- 239000000284 extract Substances 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 239000012044 organic layer Substances 0.000 description 32
- 238000002360 preparation method Methods 0.000 description 32
- 125000002947 alkylene group Chemical group 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- 238000001914 filtration Methods 0.000 description 27
- 239000007858 starting material Substances 0.000 description 26
- 239000000706 filtrate Substances 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 238000000746 purification Methods 0.000 description 22
- 239000007864 aqueous solution Substances 0.000 description 21
- 239000010410 layer Substances 0.000 description 20
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
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- 239000004480 active ingredient Substances 0.000 description 18
- 125000000753 cycloalkyl group Chemical group 0.000 description 18
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 235000011121 sodium hydroxide Nutrition 0.000 description 15
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
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- 229910002027 silica gel Inorganic materials 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
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- 229910052757 nitrogen Inorganic materials 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
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- 125000000623 heterocyclic group Chemical group 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
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- MEFLFWFJDKLBAI-UHFFFAOYSA-N tert-butyl 3-[6-(thieno[3,2-d]pyrimidine-7-carbonylamino)quinolin-7-yl]oxypyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1OC1=CC2=NC=CC=C2C=C1NC(=O)C1=CSC2=CN=CN=C12 MEFLFWFJDKLBAI-UHFFFAOYSA-N 0.000 description 1
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QQDYCGWATBCBMZ-UHFFFAOYSA-N tert-butyl 4-[4-chloro-2-(pyrazolo[1,5-a]pyrimidine-3-carbonylamino)phenoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C(Cl)C=C1NC(=O)C1=C2N=CC=CN2N=C1 QQDYCGWATBCBMZ-UHFFFAOYSA-N 0.000 description 1
- LFXWKTJBELYZGI-UHFFFAOYSA-N tert-butyl 4-[6-(pyrazolo[1,5-a]pyrimidine-3-carbonylamino)quinolin-7-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC2=NC=CC=C2C=C1NC(=O)C1=C2N=CC=CN2N=C1 LFXWKTJBELYZGI-UHFFFAOYSA-N 0.000 description 1
- MTKYTRJNYNUFSK-UHFFFAOYSA-N tert-butyl 4-[6-(thieno[3,2-d]pyrimidine-7-carbonylamino)quinolin-7-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC2=NC=CC=C2C=C1NC(=O)C1=CSC2=CN=CN=C12 MTKYTRJNYNUFSK-UHFFFAOYSA-N 0.000 description 1
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
- OVIRKYYCZVHSRD-UHFFFAOYSA-N tert-butyl n-[1-[4-chloro-2-(pyrazolo[1,5-a]pyrimidine-3-carbonylamino)phenyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1C1=CC=C(Cl)C=C1NC(=O)C1=C2N=CC=CN2N=C1 OVIRKYYCZVHSRD-UHFFFAOYSA-N 0.000 description 1
- WVLVVZXRYMZTEV-UHFFFAOYSA-N tert-butyl n-[3-(6-aminoquinolin-7-yl)oxypropyl]carbamate Chemical compound C1=CC=C2C=C(N)C(OCCCNC(=O)OC(C)(C)C)=CC2=N1 WVLVVZXRYMZTEV-UHFFFAOYSA-N 0.000 description 1
- XYGBDROEPNBABC-UHFFFAOYSA-N tert-butyl n-[3-[6-(thieno[3,2-d]pyrimidine-7-carbonylamino)quinolin-7-yl]oxypropyl]carbamate Chemical compound N1=CN=C2C(C(=O)NC3=CC4=CC=CN=C4C=C3OCCCNC(=O)OC(C)(C)C)=CSC2=C1 XYGBDROEPNBABC-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
- JCMPLWODBVSGLV-UHFFFAOYSA-N tert-butyl n-[4-[4-chloro-2-(thieno[3,2-d]pyrimidine-7-carbonylamino)phenoxy]cyclohexyl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCC1OC1=CC=C(Cl)C=C1NC(=O)C1=CSC2=CN=CN=C12 JCMPLWODBVSGLV-UHFFFAOYSA-N 0.000 description 1
- OWNBKKFTBHNYQY-UHFFFAOYSA-N tert-butyl n-[[1-(2,6-diaminophenyl)piperidin-4-yl]methyl]carbamate Chemical compound C1CC(CNC(=O)OC(C)(C)C)CCN1C1=C(N)C=CC=C1N OWNBKKFTBHNYQY-UHFFFAOYSA-N 0.000 description 1
- IZDLIPUGSDINFS-UHFFFAOYSA-N tert-butyl n-[[1-[2-amino-5-(phenylcarbamoyl)phenyl]piperidin-4-yl]methyl]carbamate Chemical compound C1CC(CNC(=O)OC(C)(C)C)CCN1C1=CC(C(=O)NC=2C=CC=CC=2)=CC=C1N IZDLIPUGSDINFS-UHFFFAOYSA-N 0.000 description 1
- GDKGVOFWJXFYTQ-UHFFFAOYSA-N tert-butyl n-[[1-[2-amino-6-(pyrazolo[1,5-a]pyrimidine-3-carbonylamino)phenyl]piperidin-4-yl]methyl]carbamate Chemical compound C1CC(CNC(=O)OC(C)(C)C)CCN1C1=C(N)C=CC=C1NC(=O)C1=C2N=CC=CN2N=C1 GDKGVOFWJXFYTQ-UHFFFAOYSA-N 0.000 description 1
- RGGPEAUAJMURQC-UHFFFAOYSA-N tert-butyl n-[[1-[6-(thieno[3,2-b]pyridine-3-carbonylamino)quinolin-7-yl]piperidin-4-yl]methyl]carbamate Chemical compound C1CC(CNC(=O)OC(C)(C)C)CCN1C1=CC2=NC=CC=C2C=C1NC(=O)C1=CSC2=CC=CN=C12 RGGPEAUAJMURQC-UHFFFAOYSA-N 0.000 description 1
- DHHITPKHLQZGOB-UHFFFAOYSA-N tert-butyl n-[[1-[6-(thieno[3,2-d]pyrimidine-7-carbonylamino)quinolin-7-yl]piperidin-4-yl]methyl]carbamate Chemical compound C1CC(CNC(=O)OC(C)(C)C)CCN1C1=CC2=NC=CC=C2C=C1NC(=O)C1=CSC2=CN=CN=C12 DHHITPKHLQZGOB-UHFFFAOYSA-N 0.000 description 1
- WJAOZSLVOYBXKN-UHFFFAOYSA-N tert-butyl n-[[4-(2-amino-4-chlorophenyl)phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1C1=CC=C(Cl)C=C1N WJAOZSLVOYBXKN-UHFFFAOYSA-N 0.000 description 1
- MYVBHSKAJCUYHC-UHFFFAOYSA-N tert-butyl n-[[4-[4-chloro-2-(pyrazolo[1,5-a]pyrimidine-3-carbonylamino)phenyl]phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1C1=CC=C(Cl)C=C1NC(=O)C1=C2N=CC=CN2N=C1 MYVBHSKAJCUYHC-UHFFFAOYSA-N 0.000 description 1
- LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-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
- 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
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011285 therapeutic regimen Methods 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
- 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 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001685 thyroid gland Anatomy 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000013271 transdermal drug delivery Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000008733 trauma Effects 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
- 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
- 230000002792 vascular Effects 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
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- 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
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- 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
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- 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
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-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Gastroenterology & Hepatology (AREA)
- Transplantation (AREA)
- Urology & Nephrology (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (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 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137003548A Division KR101995013B1 (ko) | 2010-07-13 | 2011-07-08 | Irak4 조절제로서 피라졸로[1,5a]피리미딘 및 티에노[3,2b]피리미딘 유도체 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20190077610A true KR20190077610A (ko) | 2019-07-03 |
Family
ID=45467432
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137003548A Expired - Fee Related KR101995013B1 (ko) | 2010-07-13 | 2011-07-08 | Irak4 조절제로서 피라졸로[1,5a]피리미딘 및 티에노[3,2b]피리미딘 유도체 |
| KR1020197018324A Withdrawn KR20190077610A (ko) | 2010-07-13 | 2011-07-08 | Irak4 조절제로서 피라졸로[1,5a]피리미딘 및 티에노[3,2b]피리미딘 유도체 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137003548A Expired - Fee Related KR101995013B1 (ko) | 2010-07-13 | 2011-07-08 | Irak4 조절제로서 피라졸로[1,5a]피리미딘 및 티에노[3,2b]피리미딘 유도체 |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US20120015962A1 (enExample) |
| EP (2) | EP2593457B1 (enExample) |
| JP (3) | JP5985473B2 (enExample) |
| KR (2) | KR101995013B1 (enExample) |
| CN (3) | CN102985426B (enExample) |
| AR (1) | AR082154A1 (enExample) |
| BR (1) | BR112013000868A2 (enExample) |
| CA (1) | CA2802641C (enExample) |
| MX (2) | MX340490B (enExample) |
| RU (1) | RU2604062C2 (enExample) |
| WO (1) | WO2012007375A1 (enExample) |
Families Citing this family (108)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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2018
- 2018-06-18 US US16/011,018 patent/US20180298026A1/en not_active Abandoned
- 2018-08-29 JP JP2018159947A patent/JP2018199703A/ja active Pending
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| US9255110B2 (en) | 2016-02-09 |
| CN102985426B (zh) | 2015-10-07 |
| US10023589B2 (en) | 2018-07-17 |
| US20180298026A1 (en) | 2018-10-18 |
| MX358682B (es) | 2018-08-31 |
| JP5985473B2 (ja) | 2016-09-06 |
| JP2016222707A (ja) | 2016-12-28 |
| JP6396376B2 (ja) | 2018-09-26 |
| AR082154A1 (es) | 2012-11-14 |
| CA2802641C (en) | 2019-03-12 |
| KR101995013B1 (ko) | 2019-07-02 |
| EP3252054A1 (en) | 2017-12-06 |
| CN110003219A (zh) | 2019-07-12 |
| CN105367577B (zh) | 2019-04-23 |
| US20120015962A1 (en) | 2012-01-19 |
| RU2604062C2 (ru) | 2016-12-10 |
| CN105367577A (zh) | 2016-03-02 |
| CA2802641A1 (en) | 2012-01-19 |
| EP2593457A1 (en) | 2013-05-22 |
| JP2013531018A (ja) | 2013-08-01 |
| US20160207936A1 (en) | 2016-07-21 |
| RU2013103539A (ru) | 2014-08-20 |
| CN102985426A (zh) | 2013-03-20 |
| US20140303149A1 (en) | 2014-10-09 |
| EP2593457B1 (en) | 2017-08-23 |
| JP2018199703A (ja) | 2018-12-20 |
| MX2013000390A (es) | 2013-03-08 |
| KR20130132396A (ko) | 2013-12-04 |
| HK1183029A1 (zh) | 2013-12-13 |
| WO2012007375A1 (en) | 2012-01-19 |
| MX340490B (es) | 2016-07-11 |
| BR112013000868A2 (pt) | 2016-05-17 |
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