TW200806667A - New compounds - Google Patents
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- TW200806667A TW200806667A TW096112534A TW96112534A TW200806667A TW 200806667 A TW200806667 A TW 200806667A TW 096112534 A TW096112534 A TW 096112534A TW 96112534 A TW96112534 A TW 96112534A TW 200806667 A TW200806667 A TW 200806667A
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- compound
- alkoxy
- alkyl
- phenoxy
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 317
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 102000004190 Enzymes Human genes 0.000 claims abstract description 14
- 108090000790 Enzymes Proteins 0.000 claims abstract description 14
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 162
- 125000000217 alkyl group Chemical group 0.000 claims description 161
- 201000006417 multiple sclerosis Diseases 0.000 claims description 145
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 136
- 229920006395 saturated elastomer Polymers 0.000 claims description 126
- -1 phenoxymethylene Chemical group 0.000 claims description 121
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 114
- 125000003118 aryl group Chemical group 0.000 claims description 103
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 94
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 74
- 125000005842 heteroatom Chemical group 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 62
- 150000002367 halogens Chemical class 0.000 claims description 61
- 229910052757 nitrogen Inorganic materials 0.000 claims description 60
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 57
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 57
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 46
- 125000004429 atom Chemical group 0.000 claims description 42
- 201000010099 disease Diseases 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000002950 monocyclic group Chemical group 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 150000002923 oximes Chemical class 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000004122 cyclic group Chemical group 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 239000001301 oxygen Substances 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 23
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 23
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 150000002576 ketones Chemical class 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- 201000001320 Atherosclerosis Diseases 0.000 claims description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 14
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 14
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- 125000001041 indolyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 102100022631 Glutamate receptor ionotropic, NMDA 2C Human genes 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 230000003959 neuroinflammation Effects 0.000 claims description 6
- 108091008646 testicular receptors Proteins 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 5
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 230000000241 respiratory effect Effects 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 230000008901 benefit Effects 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 206010006451 bronchitis Diseases 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 229910052762 osmium Inorganic materials 0.000 claims description 4
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 4
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 3
- 206010014561 Emphysema Diseases 0.000 claims description 3
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims description 3
- 235000003140 Panax quinquefolius Nutrition 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000006612 decyloxy group Chemical group 0.000 claims description 3
- 235000008434 ginseng Nutrition 0.000 claims description 3
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003544 oxime group Chemical group 0.000 claims description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 102000016736 Cyclin Human genes 0.000 claims description 2
- 108050006400 Cyclin Proteins 0.000 claims description 2
- 206010065563 Eosinophilic bronchitis Diseases 0.000 claims description 2
- 108091008648 NR7C Proteins 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 claims description 2
- 230000001771 impaired effect Effects 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 230000002458 infectious effect Effects 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical group [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 241000208340 Araliaceae Species 0.000 claims 2
- 235000015170 shellfish Nutrition 0.000 claims 2
- 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 claims 1
- UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052684 Cerium Inorganic materials 0.000 claims 1
- 102000012004 Ghrelin Human genes 0.000 claims 1
- 101800001586 Ghrelin Proteins 0.000 claims 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims 1
- 244000046052 Phaseolus vulgaris Species 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 claims 1
- 241000239226 Scorpiones Species 0.000 claims 1
- HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 claims 1
- 241001061127 Thione Species 0.000 claims 1
- BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 claims 1
- 229960005370 atorvastatin Drugs 0.000 claims 1
- SHZPNDRIDUBNMH-NIJVSVLQSA-L atorvastatin calcium trihydrate Chemical group O.O.O.[Ca+2].C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1.C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 SHZPNDRIDUBNMH-NIJVSVLQSA-L 0.000 claims 1
- 230000037429 base substitution Effects 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 230000007883 bronchodilation Effects 0.000 claims 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical group [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 1
- 229940109275 cyclamate Drugs 0.000 claims 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 229960003883 furosemide Drugs 0.000 claims 1
- GNKDKYIHGQKHHM-RJKLHVOGSA-N ghrelin Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)CN)COC(=O)CCCCCCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C1=CC=CC=C1 GNKDKYIHGQKHHM-RJKLHVOGSA-N 0.000 claims 1
- MQUPWTBHHPUUMC-UHFFFAOYSA-N isoindole Chemical compound C1=CC=C[C]2C=NC=C21 MQUPWTBHHPUUMC-UHFFFAOYSA-N 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- 210000004080 milk Anatomy 0.000 claims 1
- 235000013336 milk Nutrition 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Natural products O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 1
- BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 claims 1
- 125000001725 pyrenyl group Chemical group 0.000 claims 1
- 125000004151 quinonyl group Chemical group 0.000 claims 1
- 238000004611 spectroscopical analysis Methods 0.000 claims 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 94
- 238000000034 method Methods 0.000 abstract description 73
- 230000003143 atherosclerotic effect Effects 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 11
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 350
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 183
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 174
- 235000019439 ethyl acetate Nutrition 0.000 description 159
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 95
- 238000005481 NMR spectroscopy Methods 0.000 description 94
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- 239000011541 reaction mixture Substances 0.000 description 51
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 239000007787 solid Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 30
- 238000007429 general method Methods 0.000 description 29
- 229960000583 acetic acid Drugs 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000012043 crude product Substances 0.000 description 24
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 238000000746 purification Methods 0.000 description 23
- 238000010992 reflux Methods 0.000 description 23
- 229910021529 ammonia Inorganic materials 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 238000001914 filtration Methods 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
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Classifications
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- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
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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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- 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
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/22—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one sulfur atom
Landscapes
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| ES (1) | ES2389266T3 (enExample) |
| MX (1) | MX2008013033A (enExample) |
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| MY140748A (en) | 2004-12-06 | 2010-01-15 | Astrazeneca Ab | Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy |
| CN101472926A (zh) * | 2006-04-13 | 2009-07-01 | 阿斯利康(瑞典)有限公司 | 硫代黄嘌呤衍生物以及它们作为髓过氧化物酶抑制剂的用途 |
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| AR066936A1 (es) * | 2007-06-13 | 2009-09-23 | Astrazeneca Ab | 3 - (2r - tetrahidrofuril - metil) - 2 - tioxantina. composiciones farmaceuticas. |
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| WO2010068171A1 (en) * | 2008-12-12 | 2010-06-17 | Astrazeneca Ab | A process for the preparation of 3- [ (2r) tetrahydrofuran-2- ylmethyl] -2-thioxo-l, 2, 3, 7-tetrahydro-6h-purin-6-one |
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| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
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| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| GEP201706656B (en) | 2011-11-11 | 2017-04-25 | Pfizer | 2-thiopyrimidinones |
| ES2587954T3 (es) * | 2012-03-29 | 2016-10-27 | Basf Se | Compuestos de hetero-bicíclicos N-sustituidos y derivados para combatir plagas animales II |
| WO2016040419A1 (en) | 2014-09-11 | 2016-03-17 | Bristol-Myers Squibb Company | Thioether triazolopyridine and triazolopyrmidine inhibitors of myeloperoxidase |
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| WO2016178113A1 (en) | 2015-05-05 | 2016-11-10 | Pfizer Inc. | 2-thiopyrimidinones |
| WO2017040450A1 (en) * | 2015-09-03 | 2017-03-09 | Bristol-Myers Squibb Company | Triazolopyridine inhibitors of myeloperoxidase |
| US11059818B2 (en) * | 2016-03-14 | 2021-07-13 | Bristol-Myers Squibb Company | Triazolopyridine inhibitors of myeloperoxidase |
| CN115403584B (zh) * | 2021-05-26 | 2024-04-02 | 长春金赛药业有限责任公司 | 2-硫代-2,3-二氢嘧啶-4-酮衍生物、药物组合物及其制备方法和应用 |
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| WO2025172474A1 (en) | 2024-02-15 | 2025-08-21 | Astrazeneca Ab | Inhibitors of myeloperoxidase |
| WO2025190901A1 (en) | 2024-03-13 | 2025-09-18 | Institut National de la Santé et de la Recherche Médicale | Use of myeloperoxidase (mpo) inhibitors for promoting cd8+ t cell responses |
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| GB9312853D0 (en) * | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| AU7331094A (en) * | 1993-07-13 | 1995-02-13 | United States Of America, As Represented By The Secretary, Department Of Health And Human Services, The | A3 adenosine receptor agonists |
| US5708009A (en) * | 1993-12-21 | 1998-01-13 | Eli Lilly And Company | Methods of inhibiting myeloperoxidase activity |
| US6780865B1 (en) * | 1994-02-18 | 2004-08-24 | Cell Therapeutics, Inc. | Compounds having selective hydrolytic potentials |
| WO1996018399A1 (en) * | 1994-12-13 | 1996-06-20 | Euro-Celtique, S.A. | Aryl thioxanthines |
| US6727259B2 (en) * | 1997-09-05 | 2004-04-27 | Kyowa Hakko Kogyo Co., Ltd. | Remedial agent for neural degeneration |
| AR029347A1 (es) * | 1999-04-02 | 2003-06-25 | Euro Celtique Sa | Compuesto de adenina, compuesto de isognanina y 2,6-ditioxantina como precursor del mismo, uso de dichos compuestos para preparar una composicion farmaceutica y dicha composicion farmaceutica |
| AR039385A1 (es) * | 2002-04-19 | 2005-02-16 | Astrazeneca Ab | Derivados de tioxantina como inhibidores de la mieloperoxidasa |
| SE0302756D0 (sv) * | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel Compounds |
| MY140748A (en) * | 2004-12-06 | 2010-01-15 | Astrazeneca Ab | Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy |
| CN101472926A (zh) * | 2006-04-13 | 2009-07-01 | 阿斯利康(瑞典)有限公司 | 硫代黄嘌呤衍生物以及它们作为髓过氧化物酶抑制剂的用途 |
| TW200804383A (en) * | 2006-06-05 | 2008-01-16 | Astrazeneca Ab | New compounds |
| US20090054468A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Use 938 |
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2007
- 2007-04-10 TW TW096112534A patent/TW200806667A/zh unknown
- 2007-04-10 UY UY30267A patent/UY30267A1/es unknown
- 2007-04-12 US US12/295,306 patent/US8026244B2/en not_active Expired - Fee Related
- 2007-04-12 AU AU2007239147A patent/AU2007239147A1/en not_active Abandoned
- 2007-04-12 BR BRPI0711529-6A patent/BRPI0711529A2/pt not_active IP Right Cessation
- 2007-04-12 CA CA002649150A patent/CA2649150A1/en not_active Abandoned
- 2007-04-12 EP EP07748015A patent/EP2010535B1/en active Active
- 2007-04-12 ES ES07748015T patent/ES2389266T3/es active Active
- 2007-04-12 JP JP2009505326A patent/JP2009533427A/ja not_active Ceased
- 2007-04-12 AR ARP070101557A patent/AR060429A1/es unknown
- 2007-04-12 CN CNA200780022184XA patent/CN101466712A/zh active Pending
- 2007-04-12 WO PCT/SE2007/000349 patent/WO2007120098A1/en not_active Ceased
- 2007-04-12 KR KR1020087027662A patent/KR20080109087A/ko not_active Withdrawn
- 2007-04-12 MX MX2008013033A patent/MX2008013033A/es not_active Application Discontinuation
- 2007-04-12 CL CL200701042A patent/CL2007001042A1/es unknown
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2008
- 2008-09-25 ZA ZA200808195A patent/ZA200808195B/xx unknown
- 2008-09-25 KR KR1020097014335A patent/KR20090109087A/ko not_active Ceased
- 2008-10-14 EC EC2008008821A patent/ECSP088821A/es unknown
- 2008-11-11 NO NO20084764A patent/NO20084764L/no not_active Application Discontinuation
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|---|---|
| AU2007239147A1 (en) | 2007-10-25 |
| CL2007001042A1 (es) | 2008-02-08 |
| ZA200808195B (en) | 2009-08-26 |
| MX2008013033A (es) | 2008-10-17 |
| EP2010535A1 (en) | 2009-01-07 |
| ES2389266T3 (es) | 2012-10-24 |
| JP2009533427A (ja) | 2009-09-17 |
| EP2010535B1 (en) | 2012-07-11 |
| CA2649150A1 (en) | 2007-10-25 |
| BRPI0711529A2 (pt) | 2011-11-01 |
| KR20090109087A (ko) | 2009-10-19 |
| WO2007120098A1 (en) | 2007-10-25 |
| ECSP088821A (es) | 2008-11-27 |
| EP2010535A4 (en) | 2011-07-20 |
| CN101466712A (zh) | 2009-06-24 |
| AR060429A1 (es) | 2008-06-18 |
| NO20084764L (no) | 2009-01-06 |
| US20090149475A1 (en) | 2009-06-11 |
| US8026244B2 (en) | 2011-09-27 |
| KR20080109087A (ko) | 2008-12-16 |
| UY30267A1 (es) | 2007-11-30 |
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