TW200533666A - Chemical compounds - Google Patents
Chemical compounds Download PDFInfo
- Publication number
- TW200533666A TW200533666A TW093109096A TW93109096A TW200533666A TW 200533666 A TW200533666 A TW 200533666A TW 093109096 A TW093109096 A TW 093109096A TW 93109096 A TW93109096 A TW 93109096A TW 200533666 A TW200533666 A TW 200533666A
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- ring
- alkoxy
- group
- substituents
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 263
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 481
- 239000000203 mixture Substances 0.000 claims abstract description 131
- 150000003839 salts Chemical class 0.000 claims abstract description 116
- 150000002148 esters Chemical class 0.000 claims abstract description 113
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 109
- 238000001727 in vivo Methods 0.000 claims abstract description 109
- 238000000034 method Methods 0.000 claims abstract description 56
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 49
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 16
- -1 substituted Chemical group 0.000 claims description 369
- 125000001424 substituent group Chemical group 0.000 claims description 152
- 125000003545 alkoxy group Chemical group 0.000 claims description 135
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 108
- 239000001257 hydrogen Substances 0.000 claims description 101
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 71
- 229910052757 nitrogen Inorganic materials 0.000 claims description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 47
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 44
- 125000003282 alkyl amino group Chemical group 0.000 claims description 41
- 150000001412 amines Chemical class 0.000 claims description 39
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 32
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 31
- 125000005842 heteroatom Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 26
- 150000001721 carbon Chemical group 0.000 claims description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 23
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 23
- 239000002585 base Substances 0.000 claims description 23
- 238000006467 substitution reaction Methods 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000006239 protecting group Chemical group 0.000 claims description 19
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 19
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 16
- 125000000468 ketone group Chemical group 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 229930194542 Keto Natural products 0.000 claims description 15
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 238000005859 coupling reaction Methods 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 235000021419 vinegar Nutrition 0.000 claims description 12
- 230000000844 anti-bacterial effect Effects 0.000 claims description 11
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000005323 thioketone group Chemical group 0.000 claims description 11
- 239000000052 vinegar Substances 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 239000007983 Tris buffer Substances 0.000 claims description 9
- 150000003852 triazoles Chemical class 0.000 claims description 9
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical class C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000005418 aryl aryl group Chemical group 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 150000007857 hydrazones Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 8
- 241000894006 Bacteria Species 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 150000001540 azides Chemical class 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 230000036961 partial effect Effects 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 5
- 150000005347 biaryls Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 230000000295 complement effect Effects 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000003003 spiro group Chemical group 0.000 claims description 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
- 241000192125 Firmicutes Species 0.000 claims description 3
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 claims description 3
- 229930003270 Vitamin B Natural products 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 claims description 3
- 235000019157 thiamine Nutrition 0.000 claims description 3
- 229960003495 thiamine Drugs 0.000 claims description 3
- 239000011721 thiamine Substances 0.000 claims description 3
- 235000019156 vitamin B Nutrition 0.000 claims description 3
- 239000011720 vitamin B Substances 0.000 claims description 3
- BTANPKGHNRNSDV-UHFFFAOYSA-N 2-(trifluoromethoxy)benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC=C1OC(F)(F)F BTANPKGHNRNSDV-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 206010047700 Vomiting Diseases 0.000 claims description 2
- 150000001345 alkine derivatives Chemical group 0.000 claims description 2
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
- 238000006352 cycloaddition reaction Methods 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 229940050176 methyl chloride Drugs 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 238000005956 quaternization reaction Methods 0.000 claims description 2
- 239000012048 reactive intermediate Substances 0.000 claims description 2
- 230000008673 vomiting Effects 0.000 claims description 2
- 201000006747 infectious mononucleosis Diseases 0.000 claims 6
- NVZIFMAZKAYQJR-UHFFFAOYSA-N 3-(aminomethyl)-1,3-oxazolidin-2-one Chemical compound NCN1CCOC1=O NVZIFMAZKAYQJR-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- SCNYYDMQJXFDHV-UHFFFAOYSA-N chloroethane;sulfuryl dichloride Chemical class CCCl.ClS(Cl)(=O)=O SCNYYDMQJXFDHV-UHFFFAOYSA-N 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 150000003009 phosphonic acids Chemical class 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000011782 vitamin Substances 0.000 claims 1
- 229930003231 vitamin Natural products 0.000 claims 1
- 235000013343 vitamin Nutrition 0.000 claims 1
- 229940088594 vitamin Drugs 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 abstract description 12
- 125000003831 tetrazolyl group Chemical group 0.000 abstract description 5
- 125000001425 triazolyl group Chemical group 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 326
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 219
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 170
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 129
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 122
- 235000019439 ethyl acetate Nutrition 0.000 description 110
- 239000007787 solid Substances 0.000 description 101
- 239000000243 solution Substances 0.000 description 93
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 83
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
- 238000005481 NMR spectroscopy Methods 0.000 description 55
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
- 239000000047 product Substances 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
- 239000000543 intermediate Substances 0.000 description 40
- 239000000741 silica gel Substances 0.000 description 40
- 229910002027 silica gel Inorganic materials 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
- 239000011737 fluorine Substances 0.000 description 36
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 35
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 35
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- 229910052938 sodium sulfate Inorganic materials 0.000 description 34
- 235000011152 sodium sulphate Nutrition 0.000 description 34
- 239000003921 oil Substances 0.000 description 32
- 235000019198 oils Nutrition 0.000 description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 29
- 239000011541 reaction mixture Substances 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 24
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 23
- 238000003818 flash chromatography Methods 0.000 description 23
- 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 23
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 22
- 239000012074 organic phase Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000011181 potassium carbonates Nutrition 0.000 description 19
- 238000004587 chromatography analysis Methods 0.000 description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 18
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 18
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 16
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 16
- 235000019341 magnesium sulphate Nutrition 0.000 description 16
- 239000000651 prodrug Substances 0.000 description 16
- 229940002612 prodrug Drugs 0.000 description 16
- 125000004849 alkoxymethyl group Chemical group 0.000 description 15
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 13
- VWIIJDNADIEEDB-UHFFFAOYSA-N 3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CCOC1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 125000003971 isoxazolinyl group Chemical group 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 125000001246 bromo group Chemical group Br* 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- 102100026459 POU domain, class 3, transcription factor 2 Human genes 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 108010072897 transcription factor Brn-2 Proteins 0.000 description 9
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 125000005997 bromomethyl group Chemical group 0.000 description 8
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound 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 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
- JUDXOKKZTISQDJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound Cl.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 JUDXOKKZTISQDJ-UHFFFAOYSA-N 0.000 description 1
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
- 238000005533 tritiation Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000008433 xiaoji Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0227702A GB0227702D0 (en) | 2002-11-28 | 2002-11-28 | Chemical compounds |
| GB0304725A GB0304725D0 (en) | 2003-03-01 | 2003-03-01 | Chemical compounds |
| GB0318608A GB0318608D0 (en) | 2003-08-08 | 2003-08-08 | Chemical compounds |
| PCT/GB2003/005087 WO2004048392A1 (en) | 2002-11-28 | 2003-11-24 | Oxazolidinone and / or isoxazoline derivatives as antibacterial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200533666A true TW200533666A (en) | 2005-10-16 |
Family
ID=32397650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093109096A TW200533666A (en) | 2002-11-28 | 2004-04-01 | Chemical compounds |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20060116400A1 (enExample) |
| EP (1) | EP1567532A1 (enExample) |
| JP (1) | JP2006508192A (enExample) |
| KR (1) | KR20050085193A (enExample) |
| AU (1) | AU2003302404B2 (enExample) |
| BR (1) | BR0316688A (enExample) |
| CA (1) | CA2507468A1 (enExample) |
| HK (1) | HK1079794A1 (enExample) |
| IL (1) | IL168747A0 (enExample) |
| MX (1) | MXPA05005651A (enExample) |
| NO (1) | NO20052534L (enExample) |
| NZ (1) | NZ540147A (enExample) |
| SA (1) | SA04250088A (enExample) |
| TW (1) | TW200533666A (enExample) |
| WO (1) | WO2004048392A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002329393B2 (en) * | 2001-09-11 | 2008-06-12 | Astrazeneca Ab | Oxazolidinone and/or isoxazoline as antibacterial agents |
| NZ535592A (en) | 2002-02-28 | 2006-07-28 | Astrazeneca Ab | 3-cyclyl-5-(nitrogen-containing 5-membered ring) methyl-oxazolidinone derivatives and their use as antibacterial agents |
| WO2003072576A2 (en) | 2002-02-28 | 2003-09-04 | Astrazeneca Ab | Oxazolidinone derivatives, processes for their preparation, and pharmaceutical compositions containing them |
| US7091196B2 (en) | 2002-09-26 | 2006-08-15 | Rib-X Pharmaceuticals, Inc. | Bifunctional heterocyclic compounds and methods of making and using same |
| CA2507628A1 (en) | 2002-11-28 | 2004-06-10 | Astrazeneca Ab | Oxazolidinones as antibacterial agents |
| GB0227701D0 (en) * | 2002-11-28 | 2003-01-08 | Astrazeneca Ab | Chemical compounds |
| TW200500360A (en) * | 2003-03-01 | 2005-01-01 | Astrazeneca Ab | Hydroxymethyl compounds |
| US8324398B2 (en) | 2003-06-03 | 2012-12-04 | Rib-X Pharmaceuticals, Inc. | Process for the synthesis of biaryl oxazolidinones |
| WO2005012271A2 (en) * | 2003-07-29 | 2005-02-10 | Rib-X Pharmaceuticals, Inc. | Process for the synthesis of biaryl oxazolidinones |
| TWI378092B (en) | 2003-06-03 | 2012-12-01 | Rib X Pharmaceuticals Inc | Biaryl heterocyclic compounds and methods of making and using the same |
| JP4777246B2 (ja) * | 2003-07-29 | 2011-09-21 | リブ−エックス ファーマシューティカルズ，インコーポレイテッド | ビアリールオキサゾリジノンの合成方法 |
| JP2007514782A (ja) | 2003-12-17 | 2007-06-07 | リブ−エックス ファーマシューティカルズ，インコーポレイテッド | ハロゲン化ビアリール複素環式化合物ならびにその作製方法および使用方法 |
| KR100854211B1 (ko) | 2003-12-18 | 2008-08-26 | 동아제약주식회사 | 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물 |
| EP2716647A3 (en) | 2004-02-27 | 2014-08-20 | Rib-X Pharmaceuticals, Inc. | Macrocyclic compounds and methods of making and using the same |
| US20070208062A1 (en) * | 2004-05-25 | 2007-09-06 | Astrazeneca Ab | 3-(4-(2-dihydroisoxazol-3-ylpyridin-5-yl)phenyl)-5-triazol-1-ylmethyloxazolidin-2-one derivatives as mao inhibitors for the treatment of bacterial infections |
| US20080064689A1 (en) * | 2004-05-25 | 2008-03-13 | Astrazeneca Ab | 3-[4-(6-Pyridin-3-Yl)-3-Phenyl] -5-(1H-1,2,3-Triazol-1-Ylmethyl)-1,3-Oxazolidin-2-Ones as Antibacterial Agents |
| EP1904489B1 (en) | 2005-06-08 | 2011-01-26 | Rib-X Pharmaceuticals, Inc. | Process for the synthesis of triazoles |
| RU2659792C1 (ru) | 2008-10-10 | 2018-07-04 | Мерк Шарп Энд Домэ Корп. | Оксазолидиноны и способ их очистки |
| MX384300B (es) | 2009-02-03 | 2025-03-14 | Merck Sharp & Dohme Llc | Forma cristalina del fosfato de dihidrogeno r) -3- (4- (2- (2-metiltetrazol-5-il) piridin-5-il) -3-fluorofenil) -5-hidroximetil oxazolidin-2-ona. |
| US8580767B2 (en) * | 2009-05-28 | 2013-11-12 | Trius Therapeutics, Inc. | Oxazolidinone containing dimer compounds, compositions and methods to make and use |
| US9000200B2 (en) * | 2011-12-19 | 2015-04-07 | Saudi Basic Industries Corporation | Process for the preparation of metallocene complexes |
| CN104093730A (zh) * | 2011-12-19 | 2014-10-08 | 沙特基础工业公司 | 用于制备茂金属络合物的方法 |
| WO2017066964A1 (en) * | 2015-10-22 | 2017-04-27 | Merck Sharp & Dohme Corp. | Oxazolidinone compounds and methods of use thereof as antibacterial agents |
| WO2021000297A1 (en) | 2019-07-03 | 2021-01-07 | Merck Sharp & Dohme Corp. | Compounds and methods of use thereof as antibacterial agents |
| CN113149924B (zh) * | 2021-03-29 | 2023-11-03 | 苏州大学 | 一种异噁唑啉的简单制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4948801A (en) * | 1988-07-29 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| DE4425613A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | 5-gliedrige Heteroaryl-oxazolidinone |
| NZ522990A (en) * | 2000-06-05 | 2003-08-29 | Dong A Pharm | Novel oxazolidinone derivatives and a process for the preparation thereof |
| AU2002329393B2 (en) * | 2001-09-11 | 2008-06-12 | Astrazeneca Ab | Oxazolidinone and/or isoxazoline as antibacterial agents |
| GB0227701D0 (en) * | 2002-11-28 | 2003-01-08 | Astrazeneca Ab | Chemical compounds |
-
2003
- 2003-11-24 NZ NZ540147A patent/NZ540147A/en unknown
- 2003-11-24 KR KR1020057009644A patent/KR20050085193A/ko not_active Ceased
- 2003-11-24 EP EP03811807A patent/EP1567532A1/en not_active Withdrawn
- 2003-11-24 WO PCT/GB2003/005087 patent/WO2004048392A1/en not_active Ceased
- 2003-11-24 MX MXPA05005651A patent/MXPA05005651A/es unknown
- 2003-11-24 CA CA002507468A patent/CA2507468A1/en not_active Abandoned
- 2003-11-24 US US10/536,686 patent/US20060116400A1/en not_active Abandoned
- 2003-11-24 AU AU2003302404A patent/AU2003302404B2/en not_active Ceased
- 2003-11-24 HK HK05112116.9A patent/HK1079794A1/zh unknown
- 2003-11-24 JP JP2005510253A patent/JP2006508192A/ja active Pending
- 2003-11-24 BR BR0316688-0A patent/BR0316688A/pt not_active IP Right Cessation
-
2004
- 2004-04-01 TW TW093109096A patent/TW200533666A/zh unknown
- 2004-04-25 SA SA04250088A patent/SA04250088A/ar unknown
-
2005
- 2005-05-23 IL IL168747A patent/IL168747A0/en unknown
- 2005-05-26 NO NO20052534A patent/NO20052534L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BR0316688A (pt) | 2005-10-18 |
| SA04250088A (ar) | 2005-12-03 |
| IL168747A0 (en) | 2009-02-11 |
| JP2006508192A (ja) | 2006-03-09 |
| CA2507468A1 (en) | 2004-06-10 |
| KR20050085193A (ko) | 2005-08-29 |
| NO20052534L (no) | 2005-08-22 |
| US20060116400A1 (en) | 2006-06-01 |
| NO20052534D0 (no) | 2005-05-26 |
| WO2004048392A1 (en) | 2004-06-10 |
| NZ540147A (en) | 2008-03-28 |
| AU2003302404B2 (en) | 2008-06-19 |
| MXPA05005651A (es) | 2005-07-27 |
| EP1567532A1 (en) | 2005-08-31 |
| HK1079794A1 (zh) | 2006-04-13 |
| AU2003302404A1 (en) | 2004-06-18 |
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