CA2405132A1 - 2-hydroxy-mutilin carbamate derivatives for antibacterial use - Google Patents
2-hydroxy-mutilin carbamate derivatives for antibacterial use Download PDFInfo
- Publication number
- CA2405132A1 CA2405132A1 CA002405132A CA2405132A CA2405132A1 CA 2405132 A1 CA2405132 A1 CA 2405132A1 CA 002405132 A CA002405132 A CA 002405132A CA 2405132 A CA2405132 A CA 2405132A CA 2405132 A1 CA2405132 A1 CA 2405132A1
- Authority
- CA
- Canada
- Prior art keywords
- ester
- hydroxymutilin
- carbamic acid
- compound
- amino
- 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.)
- Abandoned
Links
- 229960002771 retapamulin Drugs 0.000 title description 15
- 230000000844 anti-bacterial effect Effects 0.000 title description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 8
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 153
- -1 (5-Amino-5-methoxy-3-pyridinylcarbonyl)carbamic acid Chemical compound 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 37
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- MWYWFTWLVGGYTR-UHFFFAOYSA-N (5-amino-6-methoxypyridine-3-carbonyl)carbamic acid Chemical compound COC1=NC=C(C(=O)NC(O)=O)C=C1N MWYWFTWLVGGYTR-UHFFFAOYSA-N 0.000 claims description 8
- RPJLBABLHVHARI-UHFFFAOYSA-N (6-aminopyridine-3-carbonyl)carbamic acid Chemical compound NC1=CC=C(C(=O)NC(O)=O)C=N1 RPJLBABLHVHARI-UHFFFAOYSA-N 0.000 claims description 8
- PDFCJGXLMSPJFC-UHFFFAOYSA-N (6-amino-5-cyanopyridine-3-carbonyl)carbamic acid Chemical compound NC1=NC=C(C(=O)NC(O)=O)C=C1C#N PDFCJGXLMSPJFC-UHFFFAOYSA-N 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- DMRODRMVBHJWTM-UHFFFAOYSA-N (6-aminopyridazine-3-carbonyl)carbamic acid Chemical compound NC1=CC=C(C(=O)NC(O)=O)N=N1 DMRODRMVBHJWTM-UHFFFAOYSA-N 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- RBVCOOCJPMGIIF-UHFFFAOYSA-N (2-amino-1,3-thiazole-5-carbonyl)carbamic acid Chemical compound NC1=NC=C(C(=O)NC(O)=O)S1 RBVCOOCJPMGIIF-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- MZLDNTTWPFHOCQ-UHFFFAOYSA-N (6-amino-5-nitropyridine-3-carbonyl)carbamic acid Chemical compound NC1=NC=C(C(=O)NC(O)=O)C=C1[N+]([O-])=O MZLDNTTWPFHOCQ-UHFFFAOYSA-N 0.000 claims description 3
- JDJZUWBSVRBOHI-UHFFFAOYSA-N (6-aminopyridine-2-carbonyl)carbamic acid Chemical compound NC1=CC=CC(C(=O)NC(O)=O)=N1 JDJZUWBSVRBOHI-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- LNHYWIJUQBOCHC-UHFFFAOYSA-N [6-(dimethylamino)pyridine-3-carbonyl]carbamic acid Chemical compound CN(C)C1=CC=C(C(=O)NC(O)=O)C=N1 LNHYWIJUQBOCHC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- CPXYIAFTBKDAJN-UHFFFAOYSA-N (2-amino-6-methoxypyrimidine-4-carbonyl)carbamic acid Chemical compound COC1=CC(C(=O)NC(O)=O)=NC(N)=N1 CPXYIAFTBKDAJN-UHFFFAOYSA-N 0.000 claims description 2
- XUWVDYHVAATWCW-UHFFFAOYSA-N (3-oxo-4h-pyrido[2,3-b]pyrazine-7-carbonyl)carbamic acid Chemical compound N1C(=O)C=NC2=CC(C(=O)NC(=O)O)=CN=C21 XUWVDYHVAATWCW-UHFFFAOYSA-N 0.000 claims description 2
- PLPDKZUROYQXGZ-UHFFFAOYSA-N (5-aminopyridine-3-carbonyl)carbamic acid Chemical compound NC1=CN=CC(C(=O)NC(O)=O)=C1 PLPDKZUROYQXGZ-UHFFFAOYSA-N 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
- LMJJEQQMLOQOON-UHFFFAOYSA-N 4h-pyrido[2,3-b]pyrazin-3-one Chemical compound C1=CN=C2NC(=O)C=NC2=C1 LMJJEQQMLOQOON-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- VZZKHXICDMHUML-UHFFFAOYSA-N [2-[1-(cyanomethyl)piperidin-4-yl]-1,3-thiazole-4-carbonyl]carbamic acid Chemical compound OC(=O)NC(=O)C1=CSC(C2CCN(CC#N)CC2)=N1 VZZKHXICDMHUML-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 7
- 208000035143 Bacterial infection Diseases 0.000 abstract description 2
- 208000022362 bacterial infectious disease Diseases 0.000 abstract description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 description 96
- 238000002360 preparation method Methods 0.000 description 74
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
- 239000000203 mixture Substances 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 40
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 235000019439 ethyl acetate Nutrition 0.000 description 27
- 150000003839 salts Chemical class 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- 238000000451 chemical ionisation Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 17
- 229910052708 sodium Inorganic materials 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 230000000306 recurrent effect Effects 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000006071 cream Substances 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- OBUUFWIMEGVAQS-UHFFFAOYSA-N Pleuromutenol Natural products CC1C(O)C(C)(C=C)CC(O)C2(C)C(C)CCC31C2C(=O)CC3 OBUUFWIMEGVAQS-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 210000001989 nasopharynx Anatomy 0.000 description 9
- STZYTFJPGGDRJD-NHUWBDDWSA-N retapamulin Chemical compound C([C@H]([C@@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CS[C@@H]3C[C@H]4CC[C@H](N4C)C3)C)C[C@]32[C@H]1C(=O)CC3 STZYTFJPGGDRJD-NHUWBDDWSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 239000008186 active pharmaceutical agent Substances 0.000 description 7
- 229940088679 drug related substance Drugs 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 241000282412 Homo Species 0.000 description 6
- 206010033078 Otitis media Diseases 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 201000009890 sinusitis Diseases 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000011321 prophylaxis Methods 0.000 description 5
- DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- YPFOIFPYGILOBV-UHFFFAOYSA-N [6-[(2-methylpropan-2-yl)oxycarbonylamino]pyridine-3-carbonyl]carbamic acid Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C(=O)NC(O)=O)C=N1 YPFOIFPYGILOBV-UHFFFAOYSA-N 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001647372 Chlamydia pneumoniae Species 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- 241000588655 Moraxella catarrhalis Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000193998 Streptococcus pneumoniae Species 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229940120124 dichloroacetate Drugs 0.000 description 3
- 229960005215 dichloroacetic acid Drugs 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 210000003928 nasal cavity Anatomy 0.000 description 3
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical compound C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
- 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 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- BLMXHXSCDYUYAW-UHFFFAOYSA-N (2-methoxypyrimidine-5-carbonyl)carbamic acid Chemical compound COC1=NC=C(C(=O)NC(O)=O)C=N1 BLMXHXSCDYUYAW-UHFFFAOYSA-N 0.000 description 2
- WSUYAJLYJNJPES-UHFFFAOYSA-N 2,2,2-trifluoro-1-(1h-imidazol-2-yl)ethanone Chemical compound FC(F)(F)C(=O)C1=NC=CN1 WSUYAJLYJNJPES-UHFFFAOYSA-N 0.000 description 2
- QNFLEDLPOVONCN-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazole-5-carboxylic acid Chemical compound CC(C)(C)OC(=O)NC1=NC=C(C(O)=O)S1 QNFLEDLPOVONCN-UHFFFAOYSA-N 0.000 description 2
- GKFPFLBDQJVJIH-UHFFFAOYSA-N 2-aminopyrimidine-4-carboxylic acid Chemical compound NC1=NC=CC(C(O)=O)=N1 GKFPFLBDQJVJIH-UHFFFAOYSA-N 0.000 description 2
- STXYMSGJQJBIHL-UHFFFAOYSA-N 6-[(2-methylpropan-2-yl)oxycarbonylamino]pyridine-3-carboxylic acid Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C(O)=O)C=N1 STXYMSGJQJBIHL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- ZRZNJUXESFHSIO-UHFFFAOYSA-N Pleuromutilin Natural products CC1C(O)C(C)(C=C)CC(OC(=O)CO)C2(C)C(C)CCC31C2C(=O)CC3 ZRZNJUXESFHSIO-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 206010062255 Soft tissue infection Diseases 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- BLVXKGPKFNRLSR-UHFFFAOYSA-N [2-(methylamino)pyrimidine-5-carbonyl]carbamic acid Chemical compound CNC1=NC=C(C(=O)NC(O)=O)C=N1 BLVXKGPKFNRLSR-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229960005110 cerivastatin Drugs 0.000 description 2
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000010931 ester hydrolysis Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 210000001853 liver microsome Anatomy 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000007922 nasal spray Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 2
- 206010040872 skin infection Diseases 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- JRAKWEXFESTHLG-UHFFFAOYSA-M sodium;6-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-cyanopyridine-3-carboxylate Chemical compound [Na+].CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C([O-])=O)C=C1C#N JRAKWEXFESTHLG-UHFFFAOYSA-M 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- POAZJBXYJYANLG-UHFFFAOYSA-N (2,6-diaminopyrimidine-4-carbonyl)carbamic acid Chemical compound NC1=CC(C(=O)NC(O)=O)=NC(N)=N1 POAZJBXYJYANLG-UHFFFAOYSA-N 0.000 description 1
- ACXBEZAABDGTSB-UHFFFAOYSA-N (2-amino-1,3-thiazole-4-carbonyl)carbamic acid Chemical compound NC1=NC(C(=O)NC(O)=O)=CS1 ACXBEZAABDGTSB-UHFFFAOYSA-N 0.000 description 1
- GTRMHRFSKSVRIP-UHFFFAOYSA-N (2-aminopyrimidine-5-carbonyl)carbamic acid Chemical compound NC1=NC=C(C(=O)NC(O)=O)C=N1 GTRMHRFSKSVRIP-UHFFFAOYSA-N 0.000 description 1
- VOHOTSWQMACKQJ-UHFFFAOYSA-N (2-piperidin-4-yl-1,3-thiazole-4-carbonyl)carbamic acid Chemical compound OC(=O)NC(=O)C1=CSC(C2CCNCC2)=N1 VOHOTSWQMACKQJ-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- SIGYGMXLAAMHIP-UHFFFAOYSA-N (5,6-diaminopyridine-3-carbonyl)carbamic acid Chemical compound NC1=CC(C(=O)NC(O)=O)=CN=C1N SIGYGMXLAAMHIP-UHFFFAOYSA-N 0.000 description 1
- JRAYPJVANZWIOB-UHFFFAOYSA-N (6-amino-5-methoxypyridine-3-carbonyl)carbamic acid Chemical compound COC1=CC(C(=O)NC(O)=O)=CN=C1N JRAYPJVANZWIOB-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- ZGMSLRPPUJSIGP-UHFFFAOYSA-N 1h-indol-2-ylurea Chemical class C1=CC=C2NC(NC(=O)N)=CC2=C1 ZGMSLRPPUJSIGP-UHFFFAOYSA-N 0.000 description 1
- RVGWKFBYZGWODT-UHFFFAOYSA-N 2,6-diaminopyrimidine-4-carboxylic acid;methyl 2,6-diaminopyrimidine-4-carboxylate Chemical compound NC1=CC(C(O)=O)=NC(N)=N1.COC(=O)C1=CC(N)=NC(N)=N1 RVGWKFBYZGWODT-UHFFFAOYSA-N 0.000 description 1
- PIWSRJPUYPNQJE-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazole-4-carboxylic acid Chemical compound CC(C)(C)OC(=O)NC1=NC(C(O)=O)=CS1 PIWSRJPUYPNQJE-UHFFFAOYSA-N 0.000 description 1
- KIRRXZPLONWSFO-UHFFFAOYSA-N 2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]-1,3-thiazole-4-carboxylic acid Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NC(C(O)=O)=CS1 KIRRXZPLONWSFO-UHFFFAOYSA-N 0.000 description 1
- FGJHMYMBXPJUQT-UHFFFAOYSA-N 2-aminopyrimidine-5-carbonyl chloride;hydrochloride Chemical compound Cl.NC1=NC=C(C(Cl)=O)C=N1 FGJHMYMBXPJUQT-UHFFFAOYSA-N 0.000 description 1
- CBRLWSXYXSFYSP-UHFFFAOYSA-N 2-aminopyrimidine-5-carboxylic acid Chemical compound NC1=NC=C(C(O)=O)C=N1 CBRLWSXYXSFYSP-UHFFFAOYSA-N 0.000 description 1
- JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
- VZSPKIQKRMTWRO-UHFFFAOYSA-N 2-methoxypyrimidine-5-carboxylic acid Chemical compound COC1=NC=C(C(O)=O)C=N1 VZSPKIQKRMTWRO-UHFFFAOYSA-N 0.000 description 1
- TYEYBOSBBBHJIV-UHFFFAOYSA-M 2-oxobutanoate Chemical compound CCC(=O)C([O-])=O TYEYBOSBBBHJIV-UHFFFAOYSA-M 0.000 description 1
- FDVCTOXWRVZQRP-UHFFFAOYSA-N 5-aminopyridine-3-carboxylic acid;ethyl 5-aminopyridine-3-carboxylate Chemical compound NC1=CN=CC(C(O)=O)=C1.CCOC(=O)C1=CN=CC(N)=C1 FDVCTOXWRVZQRP-UHFFFAOYSA-N 0.000 description 1
- NFBIWMFMHLPVLT-UHFFFAOYSA-N 5-bromo-3-methoxypyridin-2-amine Chemical compound COC1=CC(Br)=CN=C1N NFBIWMFMHLPVLT-UHFFFAOYSA-N 0.000 description 1
- CCVDDABLPJDPDU-UHFFFAOYSA-N 5-iodo-6-oxo-1h-pyridine-3-carboxylic acid;6-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C=1C=CC(=O)NC=1.OC(=O)C1=CNC(=O)C(I)=C1 CCVDDABLPJDPDU-UHFFFAOYSA-N 0.000 description 1
- IPMMVHLXFCSAAA-UHFFFAOYSA-N 5-iodo-6-oxo-1h-pyridine-3-carboxylic acid;methyl 6-chloro-5-iodopyridine-3-carboxylate Chemical compound OC(=O)C1=CN=C(O)C(I)=C1.COC(=O)C1=CN=C(Cl)C(I)=C1 IPMMVHLXFCSAAA-UHFFFAOYSA-N 0.000 description 1
- XWMLEYINWKGSAC-UHFFFAOYSA-N 6-(dimethylamino)pyridine-3-carboxylic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=N1 XWMLEYINWKGSAC-UHFFFAOYSA-N 0.000 description 1
- UAPWECHJYPNTAC-UHFFFAOYSA-N 6-(methylamino)pyridazine-3-carboxylic acid Chemical compound CNC1=CC=C(C(O)=O)N=N1 UAPWECHJYPNTAC-UHFFFAOYSA-N 0.000 description 1
- WCQCLEPPOCKUTK-UHFFFAOYSA-N 6-(methylamino)pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.CNC1=CC=C(C(O)=O)C=N1.CNC1=CC=C(C(O)=O)C=N1 WCQCLEPPOCKUTK-UHFFFAOYSA-N 0.000 description 1
- JDDGLUVPISQPKN-UHFFFAOYSA-N 6-amino-5-nitropyridine-3-carboxylic acid Chemical compound NC1=NC=C(C(O)=O)C=C1[N+]([O-])=O JDDGLUVPISQPKN-UHFFFAOYSA-N 0.000 description 1
- HHGZQZULOHYEOH-UHFFFAOYSA-N 6-chloropyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)N=N1 HHGZQZULOHYEOH-UHFFFAOYSA-N 0.000 description 1
- QHKFPOWHXBOUGV-UHFFFAOYSA-N 6-chloropyridazine-3-carboxylic acid;6-(methylamino)pyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)N=N1.CNC1=CC=C(C(O)=O)N=N1 QHKFPOWHXBOUGV-UHFFFAOYSA-N 0.000 description 1
- NDRREPCTSIPTPF-UHFFFAOYSA-N 6-chloropyridine-3-carboxylic acid;6-(methylamino)pyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=C(Cl)N=C1.CNC1=CC=C(C(O)=O)C=N1 NDRREPCTSIPTPF-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001495184 Chlamydia sp. Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- XMBZUNHETOKKBH-UHFFFAOYSA-N Dihydro-Mutilin Natural products CC1C(O)C(CC)(C)CC(O)C2(C)C(C)CCC31CCC(=O)C32 XMBZUNHETOKKBH-UHFFFAOYSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 241000606841 Haemophilus sp. Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000589268 Legionella sp. Species 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 241001430197 Mollicutes Species 0.000 description 1
- 241000204022 Mycoplasma gallisepticum Species 0.000 description 1
- 241000202934 Mycoplasma pneumoniae Species 0.000 description 1
- 241001440871 Neisseria sp. Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 241000193985 Streptococcus agalactiae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 206010062910 Vascular infections Diseases 0.000 description 1
- GOZPBMOFGLRYAE-UHFFFAOYSA-N [2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazole-5-carbonyl]carbamic acid Chemical compound CC(C)(C)OC(=O)NC1=NC=C(C(=O)NC(O)=O)S1 GOZPBMOFGLRYAE-UHFFFAOYSA-N 0.000 description 1
- ZTECYPPGYSIIAV-UHFFFAOYSA-N [6-(methylamino)pyridine-3-carbonyl]carbamic acid Chemical compound CNC1=CC=C(C(=O)NC(O)=O)C=N1 ZTECYPPGYSIIAV-UHFFFAOYSA-N 0.000 description 1
- WBDULCPABNSJIT-UHFFFAOYSA-N [6-[(triphenyl-$l^{5}-phosphanylidene)amino]pyridazine-3-carbonyl]carbamic acid Chemical compound N1=NC(C(=O)NC(=O)O)=CC=C1N=P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WBDULCPABNSJIT-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002725 anti-mycoplasma Effects 0.000 description 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229960005370 atorvastatin Drugs 0.000 description 1
- SHZPNDRIDUBNMH-NIJVSVLQSA-L atorvastatin calcium trihydrate Chemical compound O.O.O.[Ca+2].C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1.C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 SHZPNDRIDUBNMH-NIJVSVLQSA-L 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 125000005501 benzalkonium group Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 230000021235 carbamoylation Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- BLPDHDYKCBRILY-UHFFFAOYSA-N ethyl 5-aminopyrazine-2-carboxylate Chemical compound CCOC(=O)C1=CN=C(N)C=N1 BLPDHDYKCBRILY-UHFFFAOYSA-N 0.000 description 1
- VKVSFDPQJVUTAM-UHFFFAOYSA-N ethyl 5-aminopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(N)=C1 VKVSFDPQJVUTAM-UHFFFAOYSA-N 0.000 description 1
- MBRXPNIOOHRVMY-UHFFFAOYSA-N ethyl 6-(methylamino)pyridazine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(NC)N=N1 MBRXPNIOOHRVMY-UHFFFAOYSA-N 0.000 description 1
- WENPLWCFUSGOHX-UHFFFAOYSA-N ethyl 6-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pyridazine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(N(C)C(=O)OC(C)(C)C)N=N1 WENPLWCFUSGOHX-UHFFFAOYSA-N 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000003885 eye ointment Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229940002661 lipitor Drugs 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 238000013160 medical therapy Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- UJNNCGWBDJHCEM-UHFFFAOYSA-N methyl 2-amino-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C1=CN=C(N)S1 UJNNCGWBDJHCEM-UHFFFAOYSA-N 0.000 description 1
- WSZAYLCQMYIFGC-UHFFFAOYSA-N methyl 2-amino-6-methoxypyrimidine-4-carboxylate Chemical compound COC(=O)C1=CC(OC)=NC(N)=N1 WSZAYLCQMYIFGC-UHFFFAOYSA-N 0.000 description 1
- SVWWNEYBEFASMP-UHFFFAOYSA-N methyl 2-aminopyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(N)=C1 SVWWNEYBEFASMP-UHFFFAOYSA-N 0.000 description 1
- OBFFZLIOVNLYIL-UHFFFAOYSA-N methyl 2-chloro-6-methoxypyrimidine-4-carboxylate Chemical compound COC(=O)C1=CC(OC)=NC(Cl)=N1 OBFFZLIOVNLYIL-UHFFFAOYSA-N 0.000 description 1
- GSTFIRZTVXFZMG-UHFFFAOYSA-N methyl 2-chloro-6-methoxypyrimidine-4-carboxylate;sodium Chemical compound [Na].COC(=O)C1=CC(OC)=NC(Cl)=N1 GSTFIRZTVXFZMG-UHFFFAOYSA-N 0.000 description 1
- YHOVYZINCVIRGK-UHFFFAOYSA-N methyl 4-aminopyridine-2-carboxylate Chemical compound COC(=O)C1=CC(N)=CC=N1 YHOVYZINCVIRGK-UHFFFAOYSA-N 0.000 description 1
- CPBOTXGXHPDXBZ-UHFFFAOYSA-N methyl 4-nitropyridine-2-carboxylate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC=N1 CPBOTXGXHPDXBZ-UHFFFAOYSA-N 0.000 description 1
- MBHLSPAJNLINIC-UHFFFAOYSA-N methyl 5-amino-6-methoxypyridine-3-carboxylate Chemical compound COC(=O)C1=CN=C(OC)C(N)=C1 MBHLSPAJNLINIC-UHFFFAOYSA-N 0.000 description 1
- LJYSUEZSIXOJFK-UHFFFAOYSA-N methyl 5-aminopyridine-2-carboxylate Chemical compound COC(=O)C1=CC=C(N)C=N1 LJYSUEZSIXOJFK-UHFFFAOYSA-N 0.000 description 1
- KHMRKCRGUHPQLA-UHFFFAOYSA-N methyl 6-[(2-methylpropan-2-yl)oxycarbonylamino]pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(NC(=O)OC(C)(C)C)N=C1 KHMRKCRGUHPQLA-UHFFFAOYSA-N 0.000 description 1
- UZOLXXKNCKNJFU-UHFFFAOYSA-N methyl 6-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-cyanopyridine-3-carboxylate Chemical compound COC(=O)C1=CN=C(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(C#N)=C1 UZOLXXKNCKNJFU-UHFFFAOYSA-N 0.000 description 1
- QLNFTTYJNDCOEP-UHFFFAOYSA-N methyl 6-amino-5-cyanopyridine-3-carboxylate Chemical compound COC(=O)C1=CN=C(N)C(C#N)=C1 QLNFTTYJNDCOEP-UHFFFAOYSA-N 0.000 description 1
- CJSCVGMGFVSANX-UHFFFAOYSA-N methyl 6-amino-5-iodopyridine-3-carboxylate Chemical compound COC(=O)C1=CN=C(N)C(I)=C1 CJSCVGMGFVSANX-UHFFFAOYSA-N 0.000 description 1
- BUEPHLMDJNETDF-UHFFFAOYSA-N methyl 6-amino-5-methoxypyridine-3-carboxylate Chemical compound COC(=O)C1=CN=C(N)C(OC)=C1 BUEPHLMDJNETDF-UHFFFAOYSA-N 0.000 description 1
- JACPDLJUQLKABC-UHFFFAOYSA-N methyl 6-aminopyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(N)N=C1 JACPDLJUQLKABC-UHFFFAOYSA-N 0.000 description 1
- OVLDWZNVBDRZNN-UHFFFAOYSA-N methyl 6-methoxypyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(OC)N=C1 OVLDWZNVBDRZNN-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QJPQVXSHYBGQGM-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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940089484 pravachol Drugs 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HNYVPKNVKSTVJO-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC=NC2=C(C(=O)O)C=NN21 HNYVPKNVKSTVJO-UHFFFAOYSA-N 0.000 description 1
- XDMBVWSTOMJJOR-UHFFFAOYSA-N pyridazine-3-carbonylcarbamic acid Chemical compound OC(=O)NC(=O)C1=CC=CN=N1 XDMBVWSTOMJJOR-UHFFFAOYSA-N 0.000 description 1
- RUUOPSRRIKJHNH-UHFFFAOYSA-N pyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=N1 RUUOPSRRIKJHNH-UHFFFAOYSA-N 0.000 description 1
- YPOXGDJGKBXRFP-UHFFFAOYSA-M pyrimidine-4-carboxylate Chemical compound [O-]C(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-M 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- MSWBSAIVJOPOBW-UHFFFAOYSA-M sodium;2-chloro-6-methoxypyrimidine-4-carboxylate Chemical compound [Na+].COC1=CC(C([O-])=O)=NC(Cl)=N1 MSWBSAIVJOPOBW-UHFFFAOYSA-M 0.000 description 1
- DPGYVSSOZKWHON-UHFFFAOYSA-M sodium;6-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pyridazine-3-carboxylate Chemical compound [Na+].CC(C)(C)OC(=O)N(C)C1=CC=C(C([O-])=O)N=N1 DPGYVSSOZKWHON-UHFFFAOYSA-M 0.000 description 1
- JNQNCRBTFYOMLO-UHFFFAOYSA-M sodium;6-chloro-5-iodopyridine-3-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CN=C(Cl)C(I)=C1 JNQNCRBTFYOMLO-UHFFFAOYSA-M 0.000 description 1
- CTYUGETYSYCSMK-UHFFFAOYSA-M sodium;6-chloro-5-iodopyridine-3-carboxylate;methyl 6-amino-5-iodopyridine-3-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CN=C(Cl)C(I)=C1.COC(=O)C1=CN=C(N)C(I)=C1 CTYUGETYSYCSMK-UHFFFAOYSA-M 0.000 description 1
- NWVGFZLJTFZNMB-UHFFFAOYSA-M sodium;6-methoxypyridine-3-carboxylate Chemical compound [Na+].COC1=CC=C(C([O-])=O)C=N1 NWVGFZLJTFZNMB-UHFFFAOYSA-M 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UURAUHCOJAIIRQ-QGLSALSOSA-N tiamulin Chemical compound CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 UURAUHCOJAIIRQ-QGLSALSOSA-N 0.000 description 1
- 229960004885 tiamulin Drugs 0.000 description 1
- 239000008181 tonicity modifier Substances 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 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
- 238000011269 treatment regimen Methods 0.000 description 1
- YGUNDMHXMXDGII-UHFFFAOYSA-N tributyl(isocyanato)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)N=C=O YGUNDMHXMXDGII-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
- 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
- 238000009827 uniform distribution Methods 0.000 description 1
Classifications
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0008260.2A GB0008260D0 (en) | 2000-04-04 | 2000-04-04 | Novel compounds |
| GB0008260.2 | 2000-04-04 | ||
| GB0027182A GB0027182D0 (en) | 2000-11-04 | 2000-11-04 | Novel comounds |
| GB0027182.5 | 2000-11-04 | ||
| PCT/EP2001/003594 WO2001074788A1 (en) | 2000-04-04 | 2001-03-29 | 2-hydroxy-mutilin carbamate derivatives for antibacterial use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2405132A1 true CA2405132A1 (en) | 2001-10-11 |
Family
ID=26244040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002405132A Abandoned CA2405132A1 (en) | 2000-04-04 | 2001-03-29 | 2-hydroxy-mutilin carbamate derivatives for antibacterial use |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6972297B2 (enExample) |
| EP (1) | EP1268443B1 (enExample) |
| JP (1) | JP2003529593A (enExample) |
| KR (1) | KR100758441B1 (enExample) |
| CN (1) | CN1210267C (enExample) |
| AR (1) | AR030203A1 (enExample) |
| AT (1) | ATE437860T1 (enExample) |
| AU (2) | AU2001263827B2 (enExample) |
| BR (1) | BR0109809A (enExample) |
| CA (1) | CA2405132A1 (enExample) |
| CO (1) | CO5280223A1 (enExample) |
| CZ (1) | CZ20023290A3 (enExample) |
| DE (1) | DE60139382D1 (enExample) |
| ES (1) | ES2328109T3 (enExample) |
| HU (1) | HUP0300370A3 (enExample) |
| IL (1) | IL151887A0 (enExample) |
| MX (1) | MXPA02009816A (enExample) |
| NO (1) | NO324229B1 (enExample) |
| NZ (1) | NZ521536A (enExample) |
| PL (1) | PL358666A1 (enExample) |
| WO (1) | WO2001074788A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0024811D0 (en) | 2000-10-10 | 2000-11-22 | Smithkline Beecham Plc | Novel compounds |
| US7176310B1 (en) | 2002-04-09 | 2007-02-13 | Ucb Sa | Pyrimidinecarboxamide derivatives and their use as anti-inflammatory agents |
| GB0209262D0 (en) * | 2002-04-23 | 2002-06-05 | Biochemie Gmbh | Organic compounds |
| AU2003257493A1 (en) * | 2002-07-24 | 2004-02-16 | Sandoz Ag | Pleuromutilin derivatives as antimicrobbials |
| GB0218578D0 (en) * | 2002-08-09 | 2002-09-18 | Glaxo Group Ltd | Novel method |
| GB0308114D0 (en) * | 2003-04-08 | 2003-05-14 | Glaxo Group Ltd | Novel compounds |
| FR2856685B1 (fr) * | 2003-06-25 | 2005-09-23 | Merck Sante Sas | Derives de thiazolylpiperidine, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| JP2008523016A (ja) * | 2004-12-13 | 2008-07-03 | グラクソ グループ リミテッド | （５−アミノ−６−メトキシ−３−ピリジンカルボニル）カルバミン酸２−（ｓ）−ヒドロキシムチリン１４−エステルの新規の多形 |
| EP1832591A1 (en) * | 2004-12-27 | 2007-09-12 | Kyorin Pharmaceutical Co., Ltd. | 12-position substituted mutilin derivative |
| US20080139626A1 (en) * | 2005-03-10 | 2008-06-12 | Rittenhouse Stephen F | Novel Method |
| TW200738701A (en) | 2005-07-26 | 2007-10-16 | Du Pont | Fungicidal carboxamides |
| KR100695541B1 (ko) * | 2005-10-31 | 2007-03-16 | 한국단자공업 주식회사 | 연결터미널 |
| WO2007079173A2 (en) * | 2005-12-30 | 2007-07-12 | Emergent Biosolutions Inc. | Novel 2-heteroaryloxy-phenol derivatives as antibacterial agents |
| EP2149571A4 (en) * | 2007-05-24 | 2010-09-01 | Kyorin Seiyaku Kk | MUTILINE DERIVATIVE WITH A RINGED, HETEROCYCLIC AND AROMATIC CARBOXYLIC ACID STRUCTURE IN A SUBSTITUTE AT POSITION 14 |
| EP2014640A1 (en) * | 2007-07-13 | 2009-01-14 | Nabriva Therapeutics AG | Pleuromutilin derivatives |
| JP2010100582A (ja) * | 2008-10-24 | 2010-05-06 | Kyorin Pharmaceut Co Ltd | １４位置換基に複素芳香環カルボン酸構造を有するムチリン誘導体 |
| EP2184273A1 (de) | 2008-11-05 | 2010-05-12 | Bayer CropScience AG | Halogen-substituierte Verbindungen als Pestizide |
| EP2253617A1 (de) | 2009-05-20 | 2010-11-24 | Bayer CropScience AG | Halogen-substituierte Verbindungen als Pestizide |
| JP6818019B2 (ja) * | 2015-06-17 | 2021-01-20 | ナブリヴァ セラピュティクス ゲーエムベーハー | レファムリンの注射可能医薬組成物 |
| CA3130138A1 (en) * | 2019-02-27 | 2020-09-03 | Oticara, Inc. | Method for treating nasal, sinonasal, and nasopharyngeal tissue infection and/or inflammation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP9900973A3 (en) * | 1996-01-03 | 2000-04-28 | Smithkline Beecham Plc | Carbamoyloxy derivatives of mutiline with antibacterial activity, pharmaceutical compns. contg. them and process for preparing the said compds. |
| HUP0001741A3 (en) * | 1996-08-02 | 2000-11-28 | Smithkline Beecham Plc | Azabicyclic carbamoyloxy mutilin derivatives for antibacterial use, process for preparing them, pharmaceuticals contg. them and their use |
| UY25225A1 (es) | 1997-10-29 | 2000-12-29 | Smithkline Beecham Plc | Derivados de pleuromutilina utiles como agentes antimicrobianos |
| FR2771008B1 (fr) | 1997-11-17 | 2000-04-28 | Hoechst Marion Roussel Inc | Utilisation des ketolides pour la preparation de compositions pharmaceutiques destinees a prevenir les complications thrombotiques arterielles liees a l'atherosclerose |
| GB9817029D0 (en) * | 1998-08-05 | 1998-09-30 | Smithkline Beecham Plc | Novel compounds |
-
2001
- 2001-03-29 CA CA002405132A patent/CA2405132A1/en not_active Abandoned
- 2001-03-29 AT AT01938069T patent/ATE437860T1/de not_active IP Right Cessation
- 2001-03-29 CN CNB018091989A patent/CN1210267C/zh not_active Expired - Fee Related
- 2001-03-29 HU HU0300370A patent/HUP0300370A3/hu unknown
- 2001-03-29 AU AU2001263827A patent/AU2001263827B2/en not_active Ceased
- 2001-03-29 WO PCT/EP2001/003594 patent/WO2001074788A1/en not_active Ceased
- 2001-03-29 NZ NZ521536A patent/NZ521536A/en unknown
- 2001-03-29 PL PL01358666A patent/PL358666A1/xx not_active Application Discontinuation
- 2001-03-29 US US10/240,908 patent/US6972297B2/en not_active Expired - Fee Related
- 2001-03-29 BR BR0109809-8A patent/BR0109809A/pt not_active Application Discontinuation
- 2001-03-29 CZ CZ20023290A patent/CZ20023290A3/cs unknown
- 2001-03-29 AU AU6382701A patent/AU6382701A/xx not_active Withdrawn
- 2001-03-29 ES ES01938069T patent/ES2328109T3/es not_active Expired - Lifetime
- 2001-03-29 DE DE60139382T patent/DE60139382D1/de not_active Expired - Lifetime
- 2001-03-29 JP JP2001572483A patent/JP2003529593A/ja active Pending
- 2001-03-29 IL IL15188701A patent/IL151887A0/xx unknown
- 2001-03-29 EP EP01938069A patent/EP1268443B1/en not_active Expired - Lifetime
- 2001-03-29 MX MXPA02009816A patent/MXPA02009816A/es active IP Right Grant
- 2001-03-29 KR KR1020027013202A patent/KR100758441B1/ko not_active Expired - Fee Related
- 2001-03-30 AR ARP010101559A patent/AR030203A1/es not_active Application Discontinuation
- 2001-03-30 CO CO01025487A patent/CO5280223A1/es not_active Application Discontinuation
-
2002
- 2002-10-02 NO NO20024745A patent/NO324229B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA02009816A (es) | 2003-03-27 |
| ATE437860T1 (de) | 2009-08-15 |
| HUP0300370A3 (en) | 2005-07-28 |
| PL358666A1 (en) | 2004-08-09 |
| CO5280223A1 (es) | 2003-05-30 |
| CN1427827A (zh) | 2003-07-02 |
| HUP0300370A2 (hu) | 2003-06-28 |
| KR100758441B1 (ko) | 2007-09-14 |
| US6972297B2 (en) | 2005-12-06 |
| NO20024745D0 (no) | 2002-10-02 |
| AR030203A1 (es) | 2003-08-13 |
| NO20024745L (no) | 2002-11-19 |
| JP2003529593A (ja) | 2003-10-07 |
| WO2001074788A1 (en) | 2001-10-11 |
| CN1210267C (zh) | 2005-07-13 |
| DE60139382D1 (de) | 2009-09-10 |
| KR20030011815A (ko) | 2003-02-11 |
| US20030114674A1 (en) | 2003-06-19 |
| CZ20023290A3 (cs) | 2003-03-12 |
| NO324229B1 (no) | 2007-09-10 |
| ES2328109T3 (es) | 2009-11-10 |
| NZ521536A (en) | 2004-05-28 |
| AU6382701A (en) | 2001-10-15 |
| WO2001074788A8 (en) | 2001-12-20 |
| IL151887A0 (en) | 2003-04-10 |
| AU2001263827B2 (en) | 2004-06-17 |
| BR0109809A (pt) | 2003-01-21 |
| EP1268443B1 (en) | 2009-07-29 |
| EP1268443A1 (en) | 2003-01-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1268443B1 (en) | 2-hydroxy-mutilin carbamate derivatives for antibacterial use | |
| AU2001263827A1 (en) | 2-hydroxy-mutilin carbamate derivatives for antibacterial use | |
| SK91098A3 (en) | Carbamoyloxy derivatives of mutiline and their use as antibacterials | |
| WO2000027790A1 (en) | Mutilin compounds | |
| EP1351959B1 (en) | Novel pleuromutilin derivatives | |
| US6878704B2 (en) | Heterocyclic mutilin esters and their use as antibacterials | |
| EP1355873B1 (en) | Pleuromutilin derivatives with antimicrobial activity | |
| WO2000007974A1 (en) | 2-fluoro mutilin derivatives | |
| ZA200207912B (en) | 2-hydroxy-mitilin carbamate derivatives for antibacterial use. | |
| WO2001014310A1 (en) | PLEUROMUTILIN β-KETOESTERS | |
| HK1078865A (en) | Novel pleuromutilin derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |