KR20020093966A - 항균제로서의 크로메닐메틸 피리미딘디아민 - Google Patents
항균제로서의 크로메닐메틸 피리미딘디아민 Download PDFInfo
- Publication number
- KR20020093966A KR20020093966A KR1020027014451A KR20027014451A KR20020093966A KR 20020093966 A KR20020093966 A KR 20020093966A KR 1020027014451 A KR1020027014451 A KR 1020027014451A KR 20027014451 A KR20027014451 A KR 20027014451A KR 20020093966 A KR20020093966 A KR 20020093966A
- Authority
- KR
- South Korea
- Prior art keywords
- chromen
- dimethyl
- ylmethyl
- methoxy
- compound
- 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.)
- Ceased
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- 239000003242 anti bacterial agent Substances 0.000 title 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 239000003814 drug Substances 0.000 claims abstract description 13
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 150000008371 chromenes Chemical class 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 229940124530 sulfonamide Drugs 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- BAYDPQRUPRTXJV-UHFFFAOYSA-N 5-[(4-bromo-8-ethoxy-2,2-dimethylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(Br)=CC(C)(C)OC=2C(OCC)=CC=1CC1=CN=C(N)N=C1N BAYDPQRUPRTXJV-UHFFFAOYSA-N 0.000 claims description 3
- CIEOBODUUABEGI-UHFFFAOYSA-N 5-[(4-bromo-8-methoxy-2,2-dimethylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(Br)=CC(C)(C)OC=2C(OC)=CC=1CC1=CN=C(N)N=C1N CIEOBODUUABEGI-UHFFFAOYSA-N 0.000 claims description 3
- VSJGJTFTPPQZRO-UHFFFAOYSA-N 5-[(4-chloro-8-methoxy-2,2-dimethylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(Cl)=CC(C)(C)OC=2C(OC)=CC=1CC1=CN=C(N)N=C1N VSJGJTFTPPQZRO-UHFFFAOYSA-N 0.000 claims description 3
- SWJJNJQGSMROBJ-UHFFFAOYSA-N 5-[(8-ethoxy-2,2,4-trimethylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(C)=CC(C)(C)OC=2C(OCC)=CC=1CC1=CN=C(N)N=C1N SWJJNJQGSMROBJ-UHFFFAOYSA-N 0.000 claims description 3
- XXUYEERDOBVMTA-UHFFFAOYSA-N 5-[(8-ethoxy-2,2-dimethyl-4-propylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C2C(CCC)=CC(C)(C)OC2=C(OCC)C=C1CC1=CN=C(N)N=C1N XXUYEERDOBVMTA-UHFFFAOYSA-N 0.000 claims description 3
- RICKLMXZWGPFEH-UHFFFAOYSA-N 5-[(8-ethoxy-4-ethyl-2,2-dimethylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(CC)=CC(C)(C)OC=2C(OCC)=CC=1CC1=CN=C(N)N=C1N RICKLMXZWGPFEH-UHFFFAOYSA-N 0.000 claims description 3
- UXGWEACVEQDIIR-UHFFFAOYSA-N 5-[(8-methoxy-2,2-dimethyl-4-methylsulfanylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(SC)=CC(C)(C)OC=2C(OC)=CC=1CC1=CN=C(N)N=C1N UXGWEACVEQDIIR-UHFFFAOYSA-N 0.000 claims description 3
- LOUYGYYLVYMECR-UHFFFAOYSA-N 5-[[4-(4-fluorophenyl)-8-methoxy-2,2-dimethylchromen-6-yl]methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(C=3C=CC(F)=CC=3)=CC(C)(C)OC=2C(OC)=CC=1CC1=CN=C(N)N=C1N LOUYGYYLVYMECR-UHFFFAOYSA-N 0.000 claims description 3
- DSDHQJZBYGTHTE-UHFFFAOYSA-N 5-[[8-methoxy-4-(3-methoxyprop-1-ynyl)-2,2-dimethylchromen-6-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=C2C(C#CCOC)=CC(C)(C)OC2=C(OC)C=C1CC1=CN=C(N)N=C1N DSDHQJZBYGTHTE-UHFFFAOYSA-N 0.000 claims description 3
- 208000035473 Communicable disease Diseases 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
- KCEXTTYEVBQAAE-UHFFFAOYSA-N 5-[(4-bromo-8-methoxyspiro[chromene-2,4'-oxane]-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(Br)=CC3(CCOCC3)OC=2C(OC)=CC=1CC1=CN=C(N)N=C1N KCEXTTYEVBQAAE-UHFFFAOYSA-N 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 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 claims 2
- 238000001311 chemical methods and process Methods 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 20
- 239000000543 intermediate Substances 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 8
- 239000013543 active substance Substances 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 109
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 88
- -1 methoxy, n-butoxy Chemical group 0.000 description 67
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000013078 crystal Substances 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 44
- 235000019341 magnesium sulphate Nutrition 0.000 description 44
- 239000012267 brine Substances 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 38
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
- 229910004298 SiO 2 Inorganic materials 0.000 description 34
- 238000003818 flash chromatography Methods 0.000 description 34
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
- 239000002904 solvent Substances 0.000 description 30
- 239000000460 chlorine Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 28
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 25
- 235000002639 sodium chloride Nutrition 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 239000012043 crude product Substances 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 14
- FENJKTQEFUPECW-UHFFFAOYSA-N 3-anilinopropanenitrile Chemical compound N#CCCNC1=CC=CC=C1 FENJKTQEFUPECW-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 229960000789 guanidine hydrochloride Drugs 0.000 description 12
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 12
- 239000013067 intermediate product Substances 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 150000001241 acetals Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 10
- 239000012300 argon atmosphere Substances 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 108010022394 Threonine synthase Proteins 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 102000004419 dihydrofolate reductase Human genes 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 9
- INLHTZSEHJMMLW-UHFFFAOYSA-N 4-bromo-6-(1,3-dioxolan-2-yl)-8-methoxy-2,2-dimethylchromene Chemical compound C=1C=2C(Br)=CC(C)(C)OC=2C(OC)=CC=1C1OCCO1 INLHTZSEHJMMLW-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 230000000845 anti-microbial effect Effects 0.000 description 8
- 239000012876 carrier material Substances 0.000 description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
- 239000006187 pill Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- WPYBRGOPUWRINE-UHFFFAOYSA-N 4-bromo-6-(1,3-dioxolan-2-yl)-8-ethoxy-2,2-dimethylchromene Chemical compound C=1C=2C(Br)=CC(C)(C)OC=2C(OCC)=CC=1C1OCCO1 WPYBRGOPUWRINE-UHFFFAOYSA-N 0.000 description 5
- FBBCSYADXYILEH-UHFFFAOYSA-N 4-hydroxy-3-iodo-5-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(I)=C1O FBBCSYADXYILEH-UHFFFAOYSA-N 0.000 description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 5
- 125000005236 alkanoylamino group Chemical group 0.000 description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 4
- WFAHCDLEWJKPJS-UHFFFAOYSA-N 3-ethoxy-4-hydroxy-5-iodobenzaldehyde Chemical compound CCOC1=CC(C=O)=CC(I)=C1O WFAHCDLEWJKPJS-UHFFFAOYSA-N 0.000 description 4
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 4
- 101100366271 Drosophila melanogaster Spn42Dd gene Proteins 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 241000193998 Streptococcus pneumoniae Species 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 229960004198 guanidine Drugs 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 4
- 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 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- JQGKGZPSTIGWGQ-UHFFFAOYSA-N 4-bromo-8-ethoxy-2,2-dimethylchromene-6-carbaldehyde Chemical compound BrC1=CC(C)(C)OC2=C1C=C(C=O)C=C2OCC JQGKGZPSTIGWGQ-UHFFFAOYSA-N 0.000 description 3
- ONKWEGUKYJSTJW-UHFFFAOYSA-N 4-bromo-8-methoxy-2,2-dimethylchromene-6-carbaldehyde Chemical compound BrC1=CC(C)(C)OC2=C1C=C(C=O)C=C2OC ONKWEGUKYJSTJW-UHFFFAOYSA-N 0.000 description 3
- RODLPDCALOUSDI-UHFFFAOYSA-N 8-ethoxy-2,2-dimethylchromene-6-carbaldehyde Chemical compound C1=CC(C)(C)OC2=C1C=C(C=O)C=C2OCC RODLPDCALOUSDI-UHFFFAOYSA-N 0.000 description 3
- IRMONAYMIVIKDK-UHFFFAOYSA-N 8-methoxy-2,2-dimethylchromene-6-carbaldehyde Chemical compound C1=CC(C)(C)OC2=C1C=C(C=O)C=C2OC IRMONAYMIVIKDK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 239000007819 coupling partner Substances 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000007306 functionalization reaction Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000006303 iodophenyl group Chemical group 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical group 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- MJKIOYOGCSQRQO-UHFFFAOYSA-N n-[3-[6-[(2,4-diaminopyrimidin-5-yl)methyl]-8-ethoxy-2,2-dimethylchromen-4-yl]phenyl]acetamide Chemical class C=1C=2C(C=3C=C(NC(C)=O)C=CC=3)=CC(C)(C)OC=2C(OCC)=CC=1CC1=CN=C(N)N=C1N MJKIOYOGCSQRQO-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 229940024898 povidone k30 Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003195 pteridines Chemical class 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
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- FXJZOUPFQNMFOR-UHFFFAOYSA-N pyrimidin-2-ylboronic acid Chemical compound OB(O)C1=NC=CC=N1 FXJZOUPFQNMFOR-UHFFFAOYSA-N 0.000 description 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical group NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 1
- 229960000973 sulfadimethoxine Drugs 0.000 description 1
- 229960000654 sulfafurazole Drugs 0.000 description 1
- 229940101590 sulfamethoxazole 400 mg Drugs 0.000 description 1
- 229960003097 sulfaquinoxaline Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- IKOAXBSGGKQNRC-UHFFFAOYSA-N tert-butyl 4-(4-cyanophenyl)-8-ethoxy-6-formylspiro[chromene-2,4'-piperidine]-1'-carboxylate Chemical compound O1C=2C(OCC)=CC(C=O)=CC=2C(C=2C=CC(=CC=2)C#N)=CC21CCN(C(=O)OC(C)(C)C)CC2 IKOAXBSGGKQNRC-UHFFFAOYSA-N 0.000 description 1
- XJJAWWJTJYLQFO-UHFFFAOYSA-N tert-butyl 4-bromo-6-(1,3-dioxolan-2-yl)-8-ethoxyspiro[chromene-2,4'-piperidine]-1'-carboxylate Chemical compound O1C=2C(OCC)=CC(C3OCCO3)=CC=2C(Br)=CC21CCN(C(=O)OC(C)(C)C)CC2 XJJAWWJTJYLQFO-UHFFFAOYSA-N 0.000 description 1
- MYJYCFVTTXVRIR-UHFFFAOYSA-N tert-butyl 4-bromo-8-ethoxy-6-formylspiro[chromene-2,4'-piperidine]-1'-carboxylate Chemical compound O1C=2C(OCC)=CC(C=O)=CC=2C(Br)=CC21CCN(C(=O)OC(C)(C)C)CC2 MYJYCFVTTXVRIR-UHFFFAOYSA-N 0.000 description 1
- UCKGFQVBALEERS-UHFFFAOYSA-N tert-butyl 8-ethoxy-6-formylspiro[chromene-2,4'-piperidine]-1'-carboxylate Chemical compound O1C=2C(OCC)=CC(C=O)=CC=2C=CC21CCN(C(=O)OC(C)(C)C)CC2 UCKGFQVBALEERS-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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCHASIUOFGDRIO-UHFFFAOYSA-N trimethylsilyl methanesulfonate Chemical compound C[Si](C)(C)OS(C)(=O)=O BCHASIUOFGDRIO-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00108945.7 | 2000-04-27 | ||
| EP00108945 | 2000-04-27 | ||
| PCT/EP2001/004541 WO2001083476A1 (en) | 2000-04-27 | 2001-04-20 | Chromenylmethyl pyrimidinediamines as antibacterial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20020093966A true KR20020093966A (ko) | 2002-12-16 |
Family
ID=8168565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020027014451A Ceased KR20020093966A (ko) | 2000-04-27 | 2001-04-20 | 항균제로서의 크로메닐메틸 피리미딘디아민 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6818649B2 (https=) |
| EP (1) | EP1278742B1 (https=) |
| JP (1) | JP4033676B2 (https=) |
| KR (1) | KR20020093966A (https=) |
| CN (1) | CN1249057C (https=) |
| AT (1) | ATE284882T1 (https=) |
| AU (1) | AU2001252269A1 (https=) |
| BR (1) | BR0110255A (https=) |
| CA (1) | CA2405614A1 (https=) |
| DE (1) | DE60107832T2 (https=) |
| ES (1) | ES2232614T3 (https=) |
| MX (1) | MXPA02010518A (https=) |
| WO (1) | WO2001083476A1 (https=) |
| ZA (1) | ZA200208271B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI243173B (en) | 1999-11-17 | 2005-11-11 | Akzo Nobel Nv | Spiro[2H-1-benzopyran-2,4'-piperidine] derivatives |
| NZ546834A (en) * | 2003-10-01 | 2010-03-26 | Adolor Corp | Spirocyclic heterocyclic derivatives and methods of their use |
| AU2006206458B2 (en) * | 2005-01-19 | 2012-10-25 | Rigel Pharmaceuticals, Inc. | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
| US7598261B2 (en) | 2005-03-31 | 2009-10-06 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| EP1770089A1 (en) * | 2005-10-03 | 2007-04-04 | Institut Pasteur | Pyranodibenzofuran derivatives with antifungal and antibacterial activity |
| US7855194B2 (en) | 2006-03-27 | 2010-12-21 | Hoffmann-La Roche Inc. | Pyrimidine, quinazoline, pteridine and triazine derivatives |
| US7576207B2 (en) | 2006-04-06 | 2009-08-18 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| CN109134493A (zh) * | 2018-09-19 | 2019-01-04 | 浙江师范大学 | 一种具有抗菌活性的2-氧代色烯并噻吩衍生物及其合成方法和应用 |
| CN109988156B (zh) * | 2019-03-12 | 2021-12-28 | 广东中科药物研究有限公司 | 一种氨基嘧啶化合物 |
| CN112824412B (zh) * | 2019-11-21 | 2022-09-16 | 中国科学院大连化学物理研究所 | 手性1′H-螺[吲哚啉-3,4′-吡喃并[2,3-c]吡唑]-2-酮类化合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0866791T3 (da) * | 1995-12-04 | 2002-04-22 | Arpida Ag | Diaminopyrimidiner, farmaceutiske præparater indeholdende disse og deres anvendelse som antibakterielle midler |
-
2001
- 2001-04-20 KR KR1020027014451A patent/KR20020093966A/ko not_active Ceased
- 2001-04-20 CN CNB018085962A patent/CN1249057C/zh not_active Expired - Fee Related
- 2001-04-20 EP EP01925562A patent/EP1278742B1/en not_active Expired - Lifetime
- 2001-04-20 JP JP2001580904A patent/JP4033676B2/ja not_active Expired - Fee Related
- 2001-04-20 DE DE60107832T patent/DE60107832T2/de not_active Expired - Lifetime
- 2001-04-20 AT AT01925562T patent/ATE284882T1/de not_active IP Right Cessation
- 2001-04-20 AU AU2001252269A patent/AU2001252269A1/en not_active Abandoned
- 2001-04-20 MX MXPA02010518A patent/MXPA02010518A/es unknown
- 2001-04-20 ES ES01925562T patent/ES2232614T3/es not_active Expired - Lifetime
- 2001-04-20 WO PCT/EP2001/004541 patent/WO2001083476A1/en not_active Ceased
- 2001-04-20 US US10/258,777 patent/US6818649B2/en not_active Expired - Fee Related
- 2001-04-20 CA CA002405614A patent/CA2405614A1/en not_active Abandoned
- 2001-04-20 BR BR0110255-9A patent/BR0110255A/pt not_active IP Right Cessation
-
2002
- 2002-10-14 ZA ZA200208271A patent/ZA200208271B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001252269A1 (en) | 2001-11-12 |
| ZA200208271B (en) | 2004-01-26 |
| EP1278742A1 (en) | 2003-01-29 |
| US20030144246A1 (en) | 2003-07-31 |
| WO2001083476A1 (en) | 2001-11-08 |
| CN1249057C (zh) | 2006-04-05 |
| JP4033676B2 (ja) | 2008-01-16 |
| ATE284882T1 (de) | 2005-01-15 |
| DE60107832D1 (en) | 2005-01-20 |
| CN1507445A (zh) | 2004-06-23 |
| MXPA02010518A (es) | 2003-03-10 |
| EP1278742B1 (en) | 2004-12-15 |
| BR0110255A (pt) | 2003-01-07 |
| DE60107832T2 (de) | 2005-06-16 |
| US6818649B2 (en) | 2004-11-16 |
| JP2004509839A (ja) | 2004-04-02 |
| ES2232614T3 (es) | 2005-06-01 |
| CA2405614A1 (en) | 2001-11-08 |
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