ES2265365T3 - Piperidiniloxi y pirrolidiniloxifenil-oxazolidinona que tienen actividad antibacteriana. - Google Patents
Piperidiniloxi y pirrolidiniloxifenil-oxazolidinona que tienen actividad antibacteriana. Download PDFInfo
- Publication number
- ES2265365T3 ES2265365T3 ES00986365T ES00986365T ES2265365T3 ES 2265365 T3 ES2265365 T3 ES 2265365T3 ES 00986365 T ES00986365 T ES 00986365T ES 00986365 T ES00986365 T ES 00986365T ES 2265365 T3 ES2265365 T3 ES 2265365T3
- Authority
- ES
- Spain
- Prior art keywords
- oxy
- mmol
- phenyl
- piperidinyl
- oxo
- 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.)
- Expired - Lifetime
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- 230000000844 anti-bacterial effect Effects 0.000 title description 7
- -1 cyclic amino derivative Chemical class 0.000 claims abstract description 217
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
- 125000006413 ring segment Chemical group 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000002252 acyl group Chemical group 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 230000003287 optical effect Effects 0.000 claims abstract description 6
- 150000007524 organic acids Chemical class 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000003106 haloaryl group Chemical group 0.000 claims abstract description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 275
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 151
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 11
- 208000035143 Bacterial infection Diseases 0.000 claims description 7
- 239000003242 anti bacterial agent Substances 0.000 claims description 7
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 206010005940 Bone and joint infections Diseases 0.000 claims description 2
- 241000606768 Haemophilus influenzae Species 0.000 claims description 2
- 206010024971 Lower respiratory tract infections Diseases 0.000 claims description 2
- 208000032376 Lung infection Diseases 0.000 claims description 2
- 241000588655 Moraxella catarrhalis Species 0.000 claims description 2
- 206010035664 Pneumonia Diseases 0.000 claims description 2
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 2
- 206010062255 Soft tissue infection Diseases 0.000 claims description 2
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 2
- 206010046306 Upper respiratory tract infection Diseases 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 208000020029 respiratory tract infectious disease Diseases 0.000 claims description 2
- 206010040872 skin infection Diseases 0.000 claims description 2
- 235000013162 Cocos nucifera Nutrition 0.000 claims 2
- 244000060011 Cocos nucifera Species 0.000 claims 2
- 241000194033 Enterococcus Species 0.000 claims 1
- 125000004429 atom Chemical group 0.000 abstract description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 192
- 238000006243 chemical reaction Methods 0.000 description 181
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 162
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 150
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 146
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 104
- 239000000243 solution Substances 0.000 description 89
- 239000002904 solvent Substances 0.000 description 82
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 78
- 235000019439 ethyl acetate Nutrition 0.000 description 75
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 73
- 235000019341 magnesium sulphate Nutrition 0.000 description 73
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 65
- 239000000460 chlorine Substances 0.000 description 56
- 239000007787 solid Substances 0.000 description 55
- 230000002829 reductive effect Effects 0.000 description 49
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 49
- 239000012044 organic layer Substances 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- 238000002390 rotary evaporation Methods 0.000 description 44
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 41
- 239000003921 oil Substances 0.000 description 34
- 235000019198 oils Nutrition 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
- 239000006260 foam Substances 0.000 description 24
- 238000004587 chromatography analysis Methods 0.000 description 23
- 239000003039 volatile agent Substances 0.000 description 23
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 19
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 238000000746 purification Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- PBTHJVDBCFJQGG-UHFFFAOYSA-N methyl azide Chemical compound CN=[N+]=[N-] PBTHJVDBCFJQGG-UHFFFAOYSA-N 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 238000010898 silica gel chromatography Methods 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 14
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 14
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 229940125782 compound 2 Drugs 0.000 description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 10
- 150000001412 amines Chemical group 0.000 description 10
- 230000003197 catalytic effect Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229940022682 acetone Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 241001465754 Metazoa Species 0.000 description 7
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 7
- 239000012346 acetyl chloride Substances 0.000 description 7
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- QISAUDWTBBNJIR-UHFFFAOYSA-N 2-phenylmethoxyacetyl chloride Chemical compound ClC(=O)COCC1=CC=CC=C1 QISAUDWTBBNJIR-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 description 6
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229960000281 trometamol Drugs 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 235000019502 Orange oil Nutrition 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000010502 orange oil Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 5
- RUBQQRMAWLSCCJ-UHFFFAOYSA-N 1,2-difluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1 RUBQQRMAWLSCCJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000007832 Na2SO4 Substances 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
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- UIJXHKXIOCDSEB-UHFFFAOYSA-N tert-butyl 3-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(O)C1 UIJXHKXIOCDSEB-UHFFFAOYSA-N 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- HEXUYIFKISYJAA-UHFFFAOYSA-N 1-(3-hydroxypyrrolidin-1-yl)-2-phenylmethoxyethanone Chemical compound C1C(O)CCN1C(=O)COCC1=CC=CC=C1 HEXUYIFKISYJAA-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 2
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 2
- KPISTRILDWVIKF-UHFFFAOYSA-N 4-pyridin-3-ylbutanenitrile Chemical compound N#CCCCC1=CC=CN=C1 KPISTRILDWVIKF-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 description 2
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- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 108010059993 Vancomycin Proteins 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
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- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C07D413/02—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
- C07D413/12—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 chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- C07D413/14—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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17292399P | 1999-12-21 | 1999-12-21 | |
| US172923P | 1999-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2265365T3 true ES2265365T3 (es) | 2007-02-16 |
Family
ID=22629768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00986365T Expired - Lifetime ES2265365T3 (es) | 1999-12-21 | 2000-12-14 | Piperidiniloxi y pirrolidiniloxifenil-oxazolidinona que tienen actividad antibacteriana. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6518285B2 (https=) |
| EP (1) | EP1246810B1 (https=) |
| JP (1) | JP2003518106A (https=) |
| CN (1) | CN1227238C (https=) |
| AR (1) | AR029420A1 (https=) |
| AT (1) | ATE326452T1 (https=) |
| AU (1) | AU784314B2 (https=) |
| CA (1) | CA2395204C (https=) |
| CO (1) | CO5280081A1 (https=) |
| CY (1) | CY1106124T1 (https=) |
| DE (1) | DE60028085T2 (https=) |
| DK (1) | DK1246810T3 (https=) |
| ES (1) | ES2265365T3 (https=) |
| MX (1) | MXPA02006323A (https=) |
| MY (1) | MY127677A (https=) |
| PT (1) | PT1246810E (https=) |
| WO (1) | WO2001046164A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| GB0009803D0 (en) | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| WO2003031443A1 (en) | 2001-10-04 | 2003-04-17 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Dual actions antibiotics comprising a oxazoldinone and a quinolone or naphthyridinone moiety |
| US6940748B2 (en) | 2002-05-16 | 2005-09-06 | Micron Technology, Inc. | Stacked 1T-nMTJ MRAM structure |
| EP1594852A1 (en) * | 2003-02-07 | 2005-11-16 | Ranbaxy Laboratories, Ltd. | Oxazolidinone derivatives as antimicrobials |
| JP4805139B2 (ja) | 2003-04-30 | 2011-11-02 | モルホケム アクツィエンゲゼルシャフト フューア コンビナートリッシュ ヒェミー | 炭疽および他の感染を治療するためのオキサゾリジノン‐キノリンハイブリッド抗生物質の使用 |
| DE10340485B4 (de) | 2003-09-03 | 2015-05-13 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Verfahren zur Herstellung von Oxazolidinon-Chinolon Hybriden |
| US8158797B2 (en) | 2003-12-18 | 2012-04-17 | Morphochem Aktiengesellschaft Fur Kombinatorische Chemie | Oxazolidinone-quinolone hybrid antibiotics |
| BRPI0417193B8 (pt) | 2003-12-18 | 2021-05-25 | Morphochem Ag Fuer Komb Chemie | antibióticos híbridos de oxazolidinona-quinolona, seus sais monossódicos, dissódicos ou trissódicos e seus pró-fármacos, composições farmacêuticas, e seu uso |
| MX2007003318A (es) | 2004-09-20 | 2007-05-18 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| BRPI0515482A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e seus usos como agentes terapêuticos |
| MX2007003332A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de estearoil-coa-desaturasa. |
| BRPI0515500A (pt) * | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados piridazina para inibição de estearoil-coa-desaturase |
| AU2005286728A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| CA2618646A1 (en) | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| EP2407459A1 (en) | 2005-09-27 | 2012-01-18 | Shionogi & Co., Ltd. | Synthetic intermediate in the production of a sulfonamide derivative having PGD2 receptor antagonistic activity |
| JP5209254B2 (ja) * | 2007-08-30 | 2013-06-12 | 日本曹達株式会社 | 置換フェノキシアザビシクロオクタン誘導体の製造方法 |
| CN108785728A (zh) * | 2017-05-05 | 2018-11-13 | 国家纳米科学中心 | 含药物中间体修饰的纳米金的抗菌敷料、其制备方法及应用 |
| CN109503569B (zh) * | 2019-01-03 | 2021-01-15 | 山东大学 | 噻唑类衍生物及其制备方法和应用 |
| JP2024538778A (ja) * | 2021-10-12 | 2024-10-23 | エフ． ホフマン－ラ ロシュ アーゲー | 細菌感染症の処置のためのスルホニルピペラジニル化合物 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES533097A0 (es) | 1983-06-07 | 1985-08-01 | Du Pont | Un procedimiento para la preparacion de nuevos derivados del amino-metil-oxooxazolidinil-benzeno. |
| US4705799A (en) | 1983-06-07 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents |
| JPS608277A (ja) * | 1983-06-07 | 1985-01-17 | ザ・デュポン・メルク・ファーマシュウティカル・カンパニー | アミノメチルオキソオキサゾリジニルベンゼン誘導体 |
| CA1260948A (en) * | 1984-12-05 | 1989-09-26 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| EP0610265B1 (en) | 1991-11-01 | 1996-12-27 | PHARMACIA & UPJOHN COMPANY | Substituted aryl- and heteroarylphenyloxazolidinones useful as antibacterial agents |
| MY115155A (en) * | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| PT792273E (pt) | 1994-11-15 | 2003-06-30 | Upjohn Co | Produtos antibacterianos de oxazolidinona substituida com oxazina e tiazina biciclicas |
| ATE205205T1 (de) | 1995-02-03 | 2001-09-15 | Upjohn Co | Durch hetero-aromatische ring substituierte phenyloxazolidinone als antimikrobielles mittel |
| US6124334A (en) | 1995-02-03 | 2000-09-26 | Pharmacia & Upjohn Company | Hetero-aromatic ring substituted phenyloxazolidinone antimicrobials |
| HRP960159A2 (en) * | 1995-04-21 | 1997-08-31 | Bayer Ag | Benzocyclopentane oxazolidinones containing heteroatoms |
| DE69614847T2 (de) | 1995-05-11 | 2002-04-04 | Pharmacia & Upjohn Co., Kalamazoo | Spirocyclische und bicyclische diazinyl- und carbazinyloxazolidinone |
| US5883093A (en) | 1995-09-12 | 1999-03-16 | Pharmacia & Upjohn Company | Phenyloxazolidinone antimicrobials |
| DE19601264A1 (de) | 1996-01-16 | 1997-07-17 | Bayer Ag | Pyrido-annellierte Thienyl- und Furanyl-Oxazolidinone |
| DE19604223A1 (de) | 1996-02-06 | 1997-08-07 | Bayer Ag | Neue substituierte Oxazolidinone |
| DK1114819T3 (da) | 1996-04-11 | 2008-04-14 | Pharmacia & Upjohn Co Llc | Fremgangsmåde til fremstilling af oxazolidinoner |
| SK156499A3 (en) | 1997-05-30 | 2000-06-12 | Upjohn Co | Oxazolidinone antibacterial agents having a thiocarbonyl functionality |
| GB9717807D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| AU9001598A (en) | 1997-09-11 | 1999-03-29 | Hokuriku Seiyaku Co. Ltd | Thiourea derivatives |
| JPH11322729A (ja) | 1998-03-09 | 1999-11-24 | Hokuriku Seiyaku Co Ltd | ジチオカルバミド酸誘導体 |
| JP2000204084A (ja) * | 1998-11-11 | 2000-07-25 | Hokuriku Seiyaku Co Ltd | チオカルバミド酸誘導体 |
-
2000
- 2000-12-05 US US09/729,342 patent/US6518285B2/en not_active Expired - Lifetime
- 2000-12-14 MX MXPA02006323A patent/MXPA02006323A/es active IP Right Grant
- 2000-12-14 DE DE60028085T patent/DE60028085T2/de not_active Expired - Fee Related
- 2000-12-14 EP EP00986365A patent/EP1246810B1/en not_active Expired - Lifetime
- 2000-12-14 PT PT00986365T patent/PT1246810E/pt unknown
- 2000-12-14 WO PCT/US2000/033835 patent/WO2001046164A1/en not_active Ceased
- 2000-12-14 CA CA002395204A patent/CA2395204C/en not_active Expired - Fee Related
- 2000-12-14 DK DK00986365T patent/DK1246810T3/da active
- 2000-12-14 AT AT00986365T patent/ATE326452T1/de not_active IP Right Cessation
- 2000-12-14 CN CNB008189803A patent/CN1227238C/zh not_active Expired - Fee Related
- 2000-12-14 ES ES00986365T patent/ES2265365T3/es not_active Expired - Lifetime
- 2000-12-14 JP JP2001547075A patent/JP2003518106A/ja active Pending
- 2000-12-14 AU AU22617/01A patent/AU784314B2/en not_active Ceased
- 2000-12-20 MY MYPI20006020A patent/MY127677A/en unknown
- 2000-12-20 AR ARP000106796A patent/AR029420A1/es unknown
- 2000-12-21 CO CO00097143A patent/CO5280081A1/es not_active Application Discontinuation
-
2006
- 2006-07-21 CY CY20061101016T patent/CY1106124T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20020103377A1 (en) | 2002-08-01 |
| MXPA02006323A (es) | 2003-09-22 |
| CA2395204A1 (en) | 2001-06-28 |
| EP1246810A1 (en) | 2002-10-09 |
| DE60028085D1 (de) | 2006-06-22 |
| PT1246810E (pt) | 2006-08-31 |
| AU784314B2 (en) | 2006-03-09 |
| CN1434810A (zh) | 2003-08-06 |
| DE60028085T2 (de) | 2006-12-07 |
| CN1227238C (zh) | 2005-11-16 |
| AR029420A1 (es) | 2003-06-25 |
| CA2395204C (en) | 2008-02-05 |
| ATE326452T1 (de) | 2006-06-15 |
| CO5280081A1 (es) | 2003-05-30 |
| DK1246810T3 (da) | 2006-09-18 |
| CY1106124T1 (el) | 2011-06-08 |
| EP1246810B1 (en) | 2006-05-17 |
| WO2001046164A1 (en) | 2001-06-28 |
| AU2261701A (en) | 2001-07-03 |
| US6518285B2 (en) | 2003-02-11 |
| MY127677A (en) | 2006-12-29 |
| JP2003518106A (ja) | 2003-06-03 |
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