CN1328277C - 取代的嘧啶酮和吡啶酮化合物和它们的应用 - Google Patents
取代的嘧啶酮和吡啶酮化合物和它们的应用 Download PDFInfo
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- CN1328277C CN1328277C CNB971815585A CN97181558A CN1328277C CN 1328277 C CN1328277 C CN 1328277C CN B971815585 A CNB971815585 A CN B971815585A CN 97181558 A CN97181558 A CN 97181558A CN 1328277 C CN1328277 C CN 1328277C
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- Prior art keywords
- amino
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- alkyl
- pyridyl
- phenyl
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- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title claims abstract description 144
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 title abstract description 8
- 150000005299 pyridinones Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 108090001007 Interleukin-8 Proteins 0.000 claims abstract description 18
- 108090001005 Interleukin-6 Proteins 0.000 claims abstract description 14
- 206010061218 Inflammation Diseases 0.000 claims abstract description 9
- 230000004054 inflammatory process Effects 0.000 claims abstract description 9
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- -1 heterocyclic radical Chemical class 0.000 claims description 1885
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 607
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 244
- 229910052736 halogen Inorganic materials 0.000 claims description 233
- 150000002367 halogens Chemical class 0.000 claims description 233
- 125000001072 heteroaryl group Chemical group 0.000 claims description 175
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 160
- 125000000217 alkyl group Chemical group 0.000 claims description 118
- 125000003118 aryl group Chemical group 0.000 claims description 109
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 106
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 91
- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- 238000002360 preparation method Methods 0.000 claims description 89
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 86
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 84
- 238000006243 chemical reaction Methods 0.000 claims description 79
- 125000003368 amide group Chemical group 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims description 61
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 60
- 125000001188 haloalkyl group Chemical group 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 55
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 49
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 38
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 34
- 125000004414 alkyl thio group Chemical group 0.000 claims description 33
- 125000005418 aryl aryl group Chemical group 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 30
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- 108010002352 Interleukin-1 Proteins 0.000 claims description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 19
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 11
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 9
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- 239000005864 Sulphur Substances 0.000 claims description 8
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 8
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
- CCMHVACSTGTQTB-NRFANRHFSA-N 2-[[(2s)-2-amino-3-phenylpropyl]amino]-5-(4-fluorophenyl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical class C([C@H](N)CNC=1N(C(C(C=2C=CC(F)=CC=2)=C(C=2C=CN=CC=2)N=1)=O)C)C1=CC=CC=C1 CCMHVACSTGTQTB-NRFANRHFSA-N 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
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- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 208000004232 Enteritis Diseases 0.000 claims description 5
- 102000051325 Glucagon Human genes 0.000 claims description 5
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- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 208000026500 emaciation Diseases 0.000 claims description 5
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 claims description 5
- 229960004666 glucagon Drugs 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
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- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 208000031886 HIV Infections Diseases 0.000 claims description 4
- 206010020164 HIV infection CDC Group III Diseases 0.000 claims description 4
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims description 4
- 241000713340 Human immunodeficiency virus 2 Species 0.000 claims description 4
- 206010031252 Osteomyelitis Diseases 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 4
- 208000033464 Reiter syndrome Diseases 0.000 claims description 4
- 206010040047 Sepsis Diseases 0.000 claims description 4
- 206010044248 Toxic shock syndrome Diseases 0.000 claims description 4
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 208000019664 bone resorption disease Diseases 0.000 claims description 4
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- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
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- 230000036303 septic shock Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 3
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- OEUZJGSBWARDHK-UHFFFAOYSA-N 2-(2-anilinoethylamino)-5-(4-fluorophenyl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical class N=1C(C=2C=CN=CC=2)=C(C=2C=CC(F)=CC=2)C(=O)N(C)C=1NCCNC1=CC=CC=C1 OEUZJGSBWARDHK-UHFFFAOYSA-N 0.000 claims description 2
- AKCSCNNVLSSWOX-UHFFFAOYSA-N 2-(benzylamino)-5-(4-fluorophenyl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical class N=1C(C=2C=CN=CC=2)=C(C=2C=CC(F)=CC=2)C(=O)N(C)C=1NCC1=CC=CC=C1 AKCSCNNVLSSWOX-UHFFFAOYSA-N 0.000 claims description 2
- DDVPIZNSURFYGG-NRFANRHFSA-N 2-[[(3s)-3-amino-3-phenylpropyl]amino]-5-(4-fluorophenyl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical class C1([C@@H](N)CCNC=2N(C(C(C=3C=CC(F)=CC=3)=C(C=3C=CN=CC=3)N=2)=O)C)=CC=CC=C1 DDVPIZNSURFYGG-NRFANRHFSA-N 0.000 claims description 2
- HFNYLNWRGDTVAI-UHFFFAOYSA-N 5-(4-fluorophenyl)-2-[(3-hydroxy-3-phenylpropyl)amino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical class N=1C(C=2C=CN=CC=2)=C(C=2C=CC(F)=CC=2)C(=O)N(C)C=1NCCC(O)C1=CC=CC=C1 HFNYLNWRGDTVAI-UHFFFAOYSA-N 0.000 claims description 2
- ZDWDPACJGPUXFV-UHFFFAOYSA-N 5-(4-fluorophenyl)-2-[2-(4-fluorophenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical class N=1C(C=2C=CN=CC=2)=C(C=2C=CC(F)=CC=2)C(=O)N(C)C=1NCCC1=CC=C(F)C=C1 ZDWDPACJGPUXFV-UHFFFAOYSA-N 0.000 claims description 2
- NKBHQDAYDPJEHQ-QFIPXVFZSA-N N[C@H](CNC1=NC(=C(C(N1C)=O)C1=CC(=CC=C1)CN)C1=CC=NC=C1)CC1=CC=CC=C1 Chemical class N[C@H](CNC1=NC(=C(C(N1C)=O)C1=CC(=CC=C1)CN)C1=CC=NC=C1)CC1=CC=CC=C1 NKBHQDAYDPJEHQ-QFIPXVFZSA-N 0.000 claims description 2
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- LIUSGUDNCQIOFR-QFIPXVFZSA-N n-[(2s)-1-[[5-(4-fluorophenyl)-1-methyl-6-oxo-4-pyridin-4-ylpyrimidin-2-yl]amino]-3-phenylpropan-2-yl]-2-hydroxyacetamide Chemical class C([C@@H](CNC=1N(C(C(C=2C=CC(F)=CC=2)=C(C=2C=CN=CC=2)N=1)=O)C)NC(=O)CO)C1=CC=CC=C1 LIUSGUDNCQIOFR-QFIPXVFZSA-N 0.000 claims description 2
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- DDVPIZNSURFYGG-UHFFFAOYSA-N 2-[(3-amino-3-phenylpropyl)amino]-5-(4-fluorophenyl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical class N=1C(C=2C=CN=CC=2)=C(C=2C=CC(F)=CC=2)C(=O)N(C)C=1NCCC(N)C1=CC=CC=C1 DDVPIZNSURFYGG-UHFFFAOYSA-N 0.000 claims 1
- CCMHVACSTGTQTB-OAQYLSRUSA-N 2-[[(2r)-2-amino-3-phenylpropyl]amino]-5-(4-fluorophenyl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical class C([C@@H](N)CNC=1N(C(C(C=2C=CC(F)=CC=2)=C(C=2C=CN=CC=2)N=1)=O)C)C1=CC=CC=C1 CCMHVACSTGTQTB-OAQYLSRUSA-N 0.000 claims 1
- ZNVSAAACVGXBTD-UZUQRXQVSA-N 2-[[(2r,3r)-3-amino-2-methyl-3-phenylpropyl]amino]-5-(4-fluorophenyl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical class C([C@@H](C)[C@@H](N)C=1C=CC=CC=1)NC(N(C(=O)C=1C=2C=CC(F)=CC=2)C)=NC=1C1=CC=NC=C1 ZNVSAAACVGXBTD-UZUQRXQVSA-N 0.000 claims 1
- FVKOZHOHAXIKKN-QFIPXVFZSA-N 2-[[(2s)-2-amino-3-phenylpropyl]amino]-3-ethyl-5-(4-fluorophenyl)-6-pyridin-4-ylpyrimidin-4-one Chemical class C([C@H](N)CNC=1N(C(C(C=2C=CC(F)=CC=2)=C(C=2C=CN=CC=2)N=1)=O)CC)C1=CC=CC=C1 FVKOZHOHAXIKKN-QFIPXVFZSA-N 0.000 claims 1
- SRTMKYZQMSTUPY-DEOSSOPVSA-N 2-[[(2s)-2-amino-3-phenylpropyl]amino]-3-methyl-5-(3-propan-2-ylphenyl)-6-pyridin-4-ylpyrimidin-4-one Chemical class CC(C)C1=CC=CC(C=2C(N(C)C(NC[C@@H](N)CC=3C=CC=CC=3)=NC=2C=2C=CN=CC=2)=O)=C1 SRTMKYZQMSTUPY-DEOSSOPVSA-N 0.000 claims 1
- CVFGZFPGZQTSNR-QFIPXVFZSA-N 2-[[(2s)-2-amino-3-phenylpropyl]amino]-3-methyl-5-(4-methylphenyl)-6-pyridin-4-ylpyrimidin-4-one Chemical class C1=CC(C)=CC=C1C(C(N1C)=O)=C(C=2C=CN=CC=2)N=C1NC[C@@H](N)CC1=CC=CC=C1 CVFGZFPGZQTSNR-QFIPXVFZSA-N 0.000 claims 1
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- YLBDKLMQLYSQOY-UHFFFAOYSA-N 2-[[2-(aminomethyl)-3-phenylpropyl]amino]-5-(4-fluorophenyl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical class N=1C(C=2C=CN=CC=2)=C(C=2C=CC(F)=CC=2)C(=O)N(C)C=1NCC(CN)CC1=CC=CC=C1 YLBDKLMQLYSQOY-UHFFFAOYSA-N 0.000 claims 1
- XNTSQSMGVQDMIQ-UHFFFAOYSA-N 3-ethyl-5-(4-fluorophenyl)-2-[(2-methyl-3-phenylpropyl)amino]-6-pyridin-4-ylpyrimidin-4-one Chemical class N=1C(C=2C=CN=CC=2)=C(C=2C=CC(F)=CC=2)C(=O)N(CC)C=1NCC(C)CC1=CC=CC=C1 XNTSQSMGVQDMIQ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D213/62—Oxygen or sulfur atoms
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Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
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| US3212896P | 1996-12-05 | 1996-12-05 | |
| US60/032,128 | 1996-12-05 | ||
| US5095097P | 1997-06-13 | 1997-06-13 | |
| US60/050,950 | 1997-06-13 | ||
| US97605397A | 1997-11-21 | 1997-11-21 | |
| US08/976,053 | 1997-11-21 |
Publications (2)
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| CN1246857A CN1246857A (zh) | 2000-03-08 |
| CN1328277C true CN1328277C (zh) | 2007-07-25 |
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| CNB971815585A Expired - Fee Related CN1328277C (zh) | 1996-12-05 | 1997-12-04 | 取代的嘧啶酮和吡啶酮化合物和它们的应用 |
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| EP (1) | EP0948496A2 (hu) |
| JP (1) | JP2002514196A (hu) |
| KR (1) | KR100476586B1 (hu) |
| CN (1) | CN1328277C (hu) |
| AU (1) | AU735901C (hu) |
| BG (1) | BG65129B1 (hu) |
| BR (1) | BR9713863A (hu) |
| CA (1) | CA2274093C (hu) |
| CZ (1) | CZ9902016A3 (hu) |
| HU (1) | HUP0001140A3 (hu) |
| IL (1) | IL130181A0 (hu) |
| NZ (1) | NZ335992A (hu) |
| WO (1) | WO1998024780A2 (hu) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110078674A (zh) * | 2019-04-10 | 2019-08-02 | 昆明理工大学 | 一种2-烃基胺基嘧啶酮的制备方法 |
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| ES2857649T3 (es) | 2012-03-01 | 2021-09-29 | Array Biopharma Inc | Inhibidores de serina/treonina cinasa |
| KR20150047597A (ko) | 2012-08-27 | 2015-05-04 | 어레이 바이오파마 인크. | 과증식성 질환의 치료를 위한 세린/트레오닌 키나아제 억제제 |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| HUE053734T2 (hu) | 2014-01-21 | 2021-07-28 | Janssen Pharmaceutica Nv | 2-es altípusú metabotróp glutamáterg receptor pozitív allosztérikus modulátorait tartalmazó kombinációk és alkalmazásuk |
| EA201891617A3 (ru) | 2014-01-21 | 2019-04-30 | Янссен Фармацевтика Нв | Комбинации, содержащие положительные аллостерические модуляторы или ортостерические агонисты метаботропного глутаматергического рецептора 2 подтипа, и их применение |
| KR101693781B1 (ko) * | 2014-10-06 | 2017-01-09 | 한양대학교 에리카산학협력단 | 다이플루오로알킬기가 도입된 방향족 화합물의 제조 방법 |
| TN2017000461A1 (en) | 2015-05-05 | 2019-04-12 | Pfizer | 2-thiopyrimidinones |
| CN107200731B (zh) * | 2017-06-11 | 2020-10-23 | 湖南科技大学 | 一种含噻唑环吡啶酮衍生物及其制备方法和应用 |
| CR20220308A (es) | 2019-11-25 | 2022-08-04 | Amgen Inc | Compuestos heterocíclicos como inhibidores de delta-5 desaturasa y métodos de uso |
| CN115650906A (zh) * | 2022-11-04 | 2023-01-31 | 苏州艾缇克药物化学有限公司 | 一种2-氨基异烟酸的制备方法 |
| US11993580B1 (en) | 2022-12-02 | 2024-05-28 | Neumora Therapeutics, Inc. | Methods of treating neurological disorders |
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| US5620999A (en) * | 1994-07-28 | 1997-04-15 | Weier; Richard M. | Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation |
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| DE1271116B (de) * | 1965-05-04 | 1968-06-27 | Bayer Ag | Verfahren zur Herstellung von 4-Hydroxypyrimidinen |
| JPS6163680A (ja) * | 1984-09-05 | 1986-04-01 | Kanto Ishi Pharma Co Ltd | ピリミド〔１，２−ａ〕ベンズイミダゾ−ル誘導体及びその製造方法 |
| KR19990064117A (ko) * | 1995-10-06 | 1999-07-26 | 폴락 돈나 엘. | 항암 활성과 사이토킨 억제 활성을 갖는 치환된 이미다졸 |
| EP0859771A4 (en) * | 1995-10-31 | 2000-03-15 | Merck & Co Inc | SUBSTITUTED PYRIDYL PYRROLES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHOD OF USE |
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1997
- 1997-12-04 WO PCT/US1997/022949 patent/WO1998024780A2/en not_active Application Discontinuation
- 1997-12-04 CZ CZ992016A patent/CZ9902016A3/cs unknown
- 1997-12-04 HU HU0001140A patent/HUP0001140A3/hu unknown
- 1997-12-04 EP EP97951678A patent/EP0948496A2/en not_active Withdrawn
- 1997-12-04 JP JP52590298A patent/JP2002514196A/ja active Pending
- 1997-12-04 CN CNB971815585A patent/CN1328277C/zh not_active Expired - Fee Related
- 1997-12-04 AU AU55254/98A patent/AU735901C/en not_active Ceased
- 1997-12-04 CA CA002274093A patent/CA2274093C/en not_active Expired - Fee Related
- 1997-12-04 KR KR10-1999-7005022A patent/KR100476586B1/ko not_active IP Right Cessation
- 1997-12-04 NZ NZ335992A patent/NZ335992A/xx unknown
- 1997-12-04 BR BR9713863-0A patent/BR9713863A/pt not_active Application Discontinuation
- 1997-12-04 IL IL13018197A patent/IL130181A0/xx unknown
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1999
- 1999-06-23 BG BG103521A patent/BG65129B1/bg unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5620999A (en) * | 1994-07-28 | 1997-04-15 | Weier; Richard M. | Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110078674A (zh) * | 2019-04-10 | 2019-08-02 | 昆明理工大学 | 一种2-烃基胺基嘧啶酮的制备方法 |
| CN110078674B (zh) * | 2019-04-10 | 2022-11-01 | 昆明理工大学 | 一种2-烃基胺基嘧啶酮的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0001140A3 (en) | 2002-05-28 |
| AU735901C (en) | 2004-02-12 |
| CN1246857A (zh) | 2000-03-08 |
| HUP0001140A2 (hu) | 2001-04-28 |
| WO1998024780A3 (en) | 1998-07-30 |
| AU735901B2 (en) | 2001-07-19 |
| NZ335992A (en) | 2001-09-28 |
| IL130181A0 (en) | 2000-06-01 |
| CZ9902016A3 (cs) | 1999-11-17 |
| BG103521A (en) | 2000-07-31 |
| KR20000069329A (ko) | 2000-11-25 |
| JP2002514196A (ja) | 2002-05-14 |
| WO1998024780A2 (en) | 1998-06-11 |
| CA2274093A1 (en) | 1998-06-11 |
| CA2274093C (en) | 2006-11-07 |
| AU5525498A (en) | 1998-06-29 |
| BR9713863A (pt) | 2000-03-14 |
| KR100476586B1 (ko) | 2005-03-18 |
| EP0948496A2 (en) | 1999-10-13 |
| BG65129B1 (bg) | 2007-03-30 |
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