DE19838998A1 - Neue Naturstoffderivate - Google Patents
Neue NaturstoffderivateInfo
- Publication number
- DE19838998A1 DE19838998A1 DE19838998A DE19838998A DE19838998A1 DE 19838998 A1 DE19838998 A1 DE 19838998A1 DE 19838998 A DE19838998 A DE 19838998A DE 19838998 A DE19838998 A DE 19838998A DE 19838998 A1 DE19838998 A1 DE 19838998A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- compounds according
- compounds
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000002796 natural product derivatives Chemical class 0.000 title description 3
- 239000003592 new natural product Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 58
- -1 t-butoxycarbonyl Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 11
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
- 239000007821 HATU Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000007822 coupling agent Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 5
- 241001465754 Metazoa Species 0.000 abstract description 3
- 201000010099 disease Diseases 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 239000005445 natural material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 244000052616 bacterial pathogen Species 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001212 derivatisation Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZMWBCGMRXBPXEU-JGVFFNPUSA-N tan-1057-b Chemical compound NC(N)=NCCC[C@H](N)CC(=O)N(C)[C@@H]1CN=C(NC(N)=O)NC1=O ZMWBCGMRXBPXEU-JGVFFNPUSA-N 0.000 description 3
- LHJJHUUMPVVEBX-IBGZPJMESA-N (3s)-3,6-bis(phenylmethoxycarbonylamino)hexanoic acid Chemical compound C([C@@H](CC(=O)O)NC(=O)OCC=1C=CC=CC=1)CCNC(=O)OCC1=CC=CC=C1 LHJJHUUMPVVEBX-IBGZPJMESA-N 0.000 description 2
- VNWXCGKMEWXYBP-YFKPBYRVSA-N (3s)-3-amino-6-(diaminomethylideneamino)hexanoic acid Chemical group OC(=O)C[C@@H](N)CCCNC(N)=N VNWXCGKMEWXYBP-YFKPBYRVSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- MTVUEWBUJJLDPS-UHFFFAOYSA-N 1h-pyrimidin-2-one;dihydrochloride Chemical compound Cl.Cl.O=C1N=CC=CN1 MTVUEWBUJJLDPS-UHFFFAOYSA-N 0.000 description 2
- UAIUNKRWKOVEES-UHFFFAOYSA-N 3,3',5,5'-tetramethylbenzidine Chemical compound CC1=C(N)C(C)=CC(C=2C=C(C)C(N)=C(C)C=2)=C1 UAIUNKRWKOVEES-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- WHCBOJSNHPKNIF-UHFFFAOYSA-O C[S+]=C(NC(OCC1=CC=CC=C1)=O)NC(OCC1=CC=CC=C1)=O Chemical compound C[S+]=C(NC(OCC1=CC=CC=C1)=O)NC(OCC1=CC=CC=C1)=O WHCBOJSNHPKNIF-UHFFFAOYSA-O 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- LWLLWVAPFKQPRH-UHFFFAOYSA-N methyl 3-(3-aminophenyl)-3-(phenylmethoxycarbonylamino)propanoate Chemical compound C=1C=CC(N)=CC=1C(CC(=O)OC)NC(=O)OCC1=CC=CC=C1 LWLLWVAPFKQPRH-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DMAWWPKESYQPKR-HNNXBMFYSA-N (3s)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(phenylmethoxycarbonylamino)hexanoic acid Chemical compound CC(C)(C)OC(=O)NCCC[C@@H](CC(O)=O)NC(=O)OCC1=CC=CC=C1 DMAWWPKESYQPKR-HNNXBMFYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- PWNQRCRMEYGPNQ-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-d][1,4]diazepine Chemical compound C1CNCCN2CCCC=C21 PWNQRCRMEYGPNQ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- AHXWDLAKCSVNSI-UHFFFAOYSA-N 2-[2-chloro-2-(1,2,2-trichloroethenyl)cyclopropyl]ethoxymethylbenzene Chemical compound ClC(Cl)=C(Cl)C1(Cl)CC1CCOCC1=CC=CC=C1 AHXWDLAKCSVNSI-UHFFFAOYSA-N 0.000 description 1
- VCDUBORCNDFBQK-UHFFFAOYSA-N 3-[3-[carbamimidoyl(phenylmethoxycarbonyl)amino]phenyl]-3-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C=1C=CC(C(CC(O)=O)NC(=O)OCC=2C=CC=CC=2)=CC=1N(C(=N)N)C(=O)OCC1=CC=CC=C1 VCDUBORCNDFBQK-UHFFFAOYSA-N 0.000 description 1
- SJBFILRQMRECCK-UHFFFAOYSA-N 3-amino-3-(3-nitrophenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC=CC([N+]([O-])=O)=C1 SJBFILRQMRECCK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- WCYSVIMUYDWOPM-UHFFFAOYSA-N methyl 3-amino-3-(3-nitrophenyl)propanoate Chemical compound COC(=O)CC(N)C1=CC=CC([N+]([O-])=O)=C1 WCYSVIMUYDWOPM-UHFFFAOYSA-N 0.000 description 1
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- 235000021317 phosphate Nutrition 0.000 description 1
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- 125000005544 phthalimido group Chemical group 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
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- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
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- ZMWBCGMRXBPXEU-YUMQZZPRSA-N tan-1057-a Chemical compound NC(N)=NCCC[C@H](N)CC(=O)N(C)[C@H]1CN=C(NC(N)=O)NC1=O ZMWBCGMRXBPXEU-YUMQZZPRSA-N 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical class C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 231100000041 toxicology testing Toxicity 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 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
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
-
- 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
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (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)
- Bakery Products And Manufacturing Methods Therefor (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19838998A DE19838998A1 (de) | 1998-08-27 | 1998-08-27 | Neue Naturstoffderivate |
| CA002342102A CA2342102C (en) | 1998-08-27 | 1999-08-20 | Tan-1057 derivatives |
| JP2000567514A JP4533535B2 (ja) | 1998-08-27 | 1999-08-20 | Ｔａｎ−１０５７誘導体 |
| EP99968234A EP1117652B1 (de) | 1998-08-27 | 1999-08-20 | Tan-1057 derivate |
| US09/763,711 US6617332B1 (en) | 1998-08-27 | 1999-08-20 | Tan-1057 derivatives |
| ES99968234T ES2219105T3 (es) | 1998-08-27 | 1999-08-20 | Derivados de tan-1057. |
| SK262-2001A SK2622001A3 (en) | 1998-08-27 | 1999-08-20 | Tan-1057 derivatives |
| PCT/EP1999/006124 WO2000012484A1 (de) | 1998-08-27 | 1999-08-20 | Tan-1057 derivate |
| EEP200100125A EE200100125A (et) | 1998-08-27 | 1999-08-20 | TAN-1057 derivaadid |
| BR9913337-7A BR9913337A (pt) | 1998-08-27 | 1999-08-20 | Derivados tan-1057 |
| HR20010135A HRP20010135A2 (en) | 1998-08-27 | 1999-08-20 | Novel natural product derivatives |
| IDW20010483A ID28365A (id) | 1998-08-27 | 1999-08-20 | Turunan produk alami yang baru |
| AU10099/00A AU759618B2 (en) | 1998-08-27 | 1999-08-20 | Tan-1057 derivatives |
| TR2001/00637T TR200100637T2 (tr) | 1998-08-27 | 1999-08-20 | Yeni doğal ürün türevleri |
| KR1020017002417A KR20010099629A (ko) | 1998-08-27 | 1999-08-20 | Ｔａｎ-1057 유도체 |
| AT99968234T ATE267816T1 (de) | 1998-08-27 | 1999-08-20 | Tan-1057 derivate |
| DE59909607T DE59909607D1 (de) | 1998-08-27 | 1999-08-20 | Tan-1057 derivate |
| NZ510153A NZ510153A (en) | 1998-08-27 | 1999-08-20 | Tan-1057 derivatives with reduced toxicity and their use in medicaments for treating bacterial infections in humans and mammals |
| HU0103316A HUP0103316A3 (en) | 1998-08-27 | 1999-08-20 | 2-ureido-pyrimidone derivatives, method for producing them, pharmaceutical compositions containing them and their use |
| HK02103758.4A HK1041884A1 (zh) | 1998-08-27 | 1999-08-20 | Tan-1057衍生物 |
| CN99812643A CN1324348A (zh) | 1998-08-27 | 1999-08-20 | Tan－1057衍生物 |
| PL99346143A PL346143A1 (en) | 1998-08-27 | 1999-08-20 | Tan-1057 derivatives |
| IL14132599A IL141325A0 (en) | 1998-08-27 | 1999-08-20 | Tan-1057 derivatives |
| ZA200101038A ZA200101038B (en) | 1998-08-27 | 2001-02-07 | Tan-1057 derivatives. |
| BG105275A BG105275A (en) | 1998-08-27 | 2001-02-20 | Tan-1057 derivatives |
| NO20010940A NO20010940L (no) | 1998-08-27 | 2001-02-23 | TAN-1057 derivater |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19838998A DE19838998A1 (de) | 1998-08-27 | 1998-08-27 | Neue Naturstoffderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19838998A1 true DE19838998A1 (de) | 2000-03-09 |
Family
ID=7878913
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19838998A Ceased DE19838998A1 (de) | 1998-08-27 | 1998-08-27 | Neue Naturstoffderivate |
| DE59909607T Expired - Lifetime DE59909607D1 (de) | 1998-08-27 | 1999-08-20 | Tan-1057 derivate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59909607T Expired - Lifetime DE59909607D1 (de) | 1998-08-27 | 1999-08-20 | Tan-1057 derivate |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6617332B1 (https=) |
| EP (1) | EP1117652B1 (https=) |
| JP (1) | JP4533535B2 (https=) |
| KR (1) | KR20010099629A (https=) |
| CN (1) | CN1324348A (https=) |
| AT (1) | ATE267816T1 (https=) |
| AU (1) | AU759618B2 (https=) |
| BG (1) | BG105275A (https=) |
| BR (1) | BR9913337A (https=) |
| CA (1) | CA2342102C (https=) |
| DE (2) | DE19838998A1 (https=) |
| EE (1) | EE200100125A (https=) |
| ES (1) | ES2219105T3 (https=) |
| HK (1) | HK1041884A1 (https=) |
| HR (1) | HRP20010135A2 (https=) |
| HU (1) | HUP0103316A3 (https=) |
| ID (1) | ID28365A (https=) |
| IL (1) | IL141325A0 (https=) |
| NO (1) | NO20010940L (https=) |
| NZ (1) | NZ510153A (https=) |
| PL (1) | PL346143A1 (https=) |
| SK (1) | SK2622001A3 (https=) |
| TR (1) | TR200100637T2 (https=) |
| WO (1) | WO2000012484A1 (https=) |
| ZA (1) | ZA200101038B (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1113008A1 (en) * | 1999-12-29 | 2001-07-04 | Pfizer Products Inc. | 4-oxo-2-ureido-1,4,5,6-tetrahydro-pyrimidine derivatives useful as antibacterial and antiprotozoal agents |
| US20040204404A1 (en) * | 2002-09-30 | 2004-10-14 | Robert Zelle | Human N-type calcium channel blockers |
| EP2599781A1 (en) * | 2007-12-20 | 2013-06-05 | Dr. Reddy's Laboratories Ltd. | Processes for the preparation of sitagliptin and pharmaceutically acceptable salts thereof |
| WO2011046007A1 (ja) | 2009-10-15 | 2011-04-21 | 国立大学法人徳島大学 | ジエチレントリアミン五酢酸誘導体の製造方法およびジエチレントリアミン五酢酸誘導体 |
| CN108456211A (zh) * | 2009-10-16 | 2018-08-28 | 梅琳塔治疗公司 | 抗微生物化合物和其制备和使用方法 |
| NZ599290A (en) * | 2009-10-16 | 2014-10-31 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| EA201270566A1 (ru) | 2009-10-16 | 2012-11-30 | Риб-Экс Фармасьютикалз, Инк. | Противомикробные соединения и способы их получения и применения |
| MX2012004341A (es) | 2009-10-16 | 2012-10-05 | Rib X Pharmaceuticals Inc | Compuestos antimicrobianos y metodos para fabricar y utilizar los mismos. |
| MY173518A (en) | 2011-04-15 | 2020-01-30 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| RU2475479C1 (ru) * | 2011-12-23 | 2013-02-20 | Федеральное государственное бюджетное учреждение Министерства здравоохранения и социального развития Российской Федерации "Медицинский радиологический научный центр" (ФГБУ МРНЦ Минздравсоцразвития России) | Вазоконстрикторное средство |
| CA2923214A1 (en) | 2013-09-09 | 2015-03-12 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| EP3038623A4 (en) | 2013-09-09 | 2017-04-19 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| HK1249758A1 (zh) | 2015-03-11 | 2018-11-09 | Melinta Therapeutics, Inc. | 抗微生物化合物及其制备和使用方法 |
| US11098047B2 (en) | 2016-05-06 | 2021-08-24 | BioVersys AG | Antimicrobials and methods of making and using same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4971965A (en) * | 1988-04-29 | 1990-11-20 | Takeda Chemical Industries, Ltd. | Antibiotics TAN-1057 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6110925A (en) | 1997-08-07 | 2000-08-29 | Research Corporation Technologies, Inc. | Antibiotic for methicillin resistant bacteria |
-
1998
- 1998-08-27 DE DE19838998A patent/DE19838998A1/de not_active Ceased
-
1999
- 1999-08-20 HK HK02103758.4A patent/HK1041884A1/zh unknown
- 1999-08-20 ES ES99968234T patent/ES2219105T3/es not_active Expired - Lifetime
- 1999-08-20 ID IDW20010483A patent/ID28365A/id unknown
- 1999-08-20 WO PCT/EP1999/006124 patent/WO2000012484A1/de not_active Ceased
- 1999-08-20 BR BR9913337-7A patent/BR9913337A/pt not_active IP Right Cessation
- 1999-08-20 PL PL99346143A patent/PL346143A1/xx not_active Application Discontinuation
- 1999-08-20 CN CN99812643A patent/CN1324348A/zh active Pending
- 1999-08-20 AU AU10099/00A patent/AU759618B2/en not_active Ceased
- 1999-08-20 AT AT99968234T patent/ATE267816T1/de not_active IP Right Cessation
- 1999-08-20 EP EP99968234A patent/EP1117652B1/de not_active Expired - Lifetime
- 1999-08-20 IL IL14132599A patent/IL141325A0/xx unknown
- 1999-08-20 JP JP2000567514A patent/JP4533535B2/ja not_active Expired - Fee Related
- 1999-08-20 US US09/763,711 patent/US6617332B1/en not_active Expired - Fee Related
- 1999-08-20 NZ NZ510153A patent/NZ510153A/xx unknown
- 1999-08-20 EE EEP200100125A patent/EE200100125A/xx unknown
- 1999-08-20 KR KR1020017002417A patent/KR20010099629A/ko not_active Withdrawn
- 1999-08-20 TR TR2001/00637T patent/TR200100637T2/xx unknown
- 1999-08-20 CA CA002342102A patent/CA2342102C/en not_active Expired - Fee Related
- 1999-08-20 HR HR20010135A patent/HRP20010135A2/hr not_active Application Discontinuation
- 1999-08-20 DE DE59909607T patent/DE59909607D1/de not_active Expired - Lifetime
- 1999-08-20 HU HU0103316A patent/HUP0103316A3/hu unknown
- 1999-08-20 SK SK262-2001A patent/SK2622001A3/sk unknown
-
2001
- 2001-02-07 ZA ZA200101038A patent/ZA200101038B/en unknown
- 2001-02-20 BG BG105275A patent/BG105275A/xx unknown
- 2001-02-23 NO NO20010940A patent/NO20010940L/no unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4971965A (en) * | 1988-04-29 | 1990-11-20 | Takeda Chemical Industries, Ltd. | Antibiotics TAN-1057 |
Non-Patent Citations (1)
| Title |
|---|
| J.Antibiotics 51(1998), S. 189-201 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE267816T1 (de) | 2004-06-15 |
| NO20010940L (no) | 2001-04-23 |
| US6617332B1 (en) | 2003-09-09 |
| JP2002523496A (ja) | 2002-07-30 |
| NO20010940D0 (no) | 2001-02-23 |
| JP4533535B2 (ja) | 2010-09-01 |
| HUP0103316A2 (hu) | 2002-04-29 |
| DE59909607D1 (de) | 2004-07-01 |
| EP1117652B1 (de) | 2004-05-26 |
| NZ510153A (en) | 2002-12-20 |
| EE200100125A (et) | 2002-06-17 |
| HUP0103316A3 (en) | 2002-06-28 |
| CN1324348A (zh) | 2001-11-28 |
| PL346143A1 (en) | 2002-01-28 |
| WO2000012484A1 (de) | 2000-03-09 |
| ID28365A (id) | 2001-05-17 |
| BR9913337A (pt) | 2001-05-15 |
| HRP20010135A2 (en) | 2002-02-28 |
| CA2342102C (en) | 2008-10-28 |
| AU1009900A (en) | 2000-03-21 |
| HK1041884A1 (zh) | 2002-07-26 |
| KR20010099629A (ko) | 2001-11-09 |
| SK2622001A3 (en) | 2001-11-06 |
| EP1117652A1 (de) | 2001-07-25 |
| ZA200101038B (en) | 2002-02-07 |
| AU759618B2 (en) | 2003-04-17 |
| CA2342102A1 (en) | 2000-03-09 |
| TR200100637T2 (tr) | 2001-10-22 |
| ES2219105T3 (es) | 2004-11-16 |
| IL141325A0 (en) | 2002-03-10 |
| BG105275A (en) | 2001-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8131 | Rejection |