CS199736B2 - Method of preparing antibiotic bm 123 gama - Google Patents
Method of preparing antibiotic bm 123 gama Download PDFInfo
- Publication number
- CS199736B2 CS199736B2 CS784640A CS464078A CS199736B2 CS 199736 B2 CS199736 B2 CS 199736B2 CS 784640 A CS784640 A CS 784640A CS 464078 A CS464078 A CS 464078A CS 199736 B2 CS199736 B2 CS 199736B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- trans
- succinimide
- carbon atoms
- formula
- give
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 230000003115 biocidal effect Effects 0.000 title description 6
- ZSPJOQBEUKQIIA-KWUZUVEWSA-N (e)-3-[4-[(2r,3r,4s,5s,6r)-5-[[(2s,3r,4r,5r)-5-[[(3as,6s,7r,7ar)-7-(carbamoylamino)-2-oxo-1,3a,4,6,7,7a-hexahydropyrano[4,3-d][1,3]oxazol-6-yl]oxy]-3-(carbamoylamino)-4-hydroxyoxan-2-yl]carbamoylamino]-3-(diaminomethylideneamino)-4-hydroxy-6-methyloxan-2- Chemical compound Cl.O([C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1N=C(N)N)NC(=O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O[C@H]2[C@@H]([C@H]3NC(=O)O[C@@H]3CO2)NC(N)=O)CO1)NC(N)=O)C)C1=CC=C(\C=C\C(=O)NCCCNCCCCN)C=C1 ZSPJOQBEUKQIIA-KWUZUVEWSA-N 0.000 claims abstract description 7
- -1 8-bromo-1-naphthyl Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 abstract description 5
- 230000010933 acylation Effects 0.000 abstract description 4
- 238000005917 acylation reaction Methods 0.000 abstract description 4
- 230000003389 potentiating effect Effects 0.000 abstract 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- 229960002317 succinimide Drugs 0.000 description 17
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ZHCGDUYHEXICCS-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) decanoate Chemical compound CCCCCCCCCC(=O)ON1C(=O)CCC1=O ZHCGDUYHEXICCS-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CFDZREOMQOUPSR-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2,2,2-trichloroacetate Chemical compound ClC(Cl)(Cl)C(=O)ON1C(=O)CCC1=O CFDZREOMQOUPSR-UHFFFAOYSA-N 0.000 description 1
- RKVYTNXYOBDNEH-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2,4-dichlorobenzoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)ON1C(=O)CCC1=O RKVYTNXYOBDNEH-UHFFFAOYSA-N 0.000 description 1
- ZPEHKHLHBKPABR-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2,5-dibromobenzoate Chemical compound BrC1=CC=C(Br)C(C(=O)ON2C(CCC2=O)=O)=C1 ZPEHKHLHBKPABR-UHFFFAOYSA-N 0.000 description 1
- DPNMWIJRTFFJCZ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2,6-dimethoxybenzoate Chemical compound COC1=CC=CC(OC)=C1C(=O)ON1C(=O)CCC1=O DPNMWIJRTFFJCZ-UHFFFAOYSA-N 0.000 description 1
- SVLOWSQZBNSVQV-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-acetyloxybenzoate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)ON1C(=O)CCC1=O SVLOWSQZBNSVQV-UHFFFAOYSA-N 0.000 description 1
- NYKHVFOHSFQWCJ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-fluorobenzoate Chemical compound FC1=CC=CC=C1C(=O)ON1C(=O)CCC1=O NYKHVFOHSFQWCJ-UHFFFAOYSA-N 0.000 description 1
- AWZUHVDJTBEXNW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)ON1C(=O)CCC1=O AWZUHVDJTBEXNW-UHFFFAOYSA-N 0.000 description 1
- KDVRYSGGAUUSIE-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-methoxyacetate Chemical compound COCC(=O)ON1C(=O)CCC1=O KDVRYSGGAUUSIE-UHFFFAOYSA-N 0.000 description 1
- FHNMAOLQZHUPIJ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-methylpropanoate Chemical compound CC(C)C(=O)ON1C(=O)CCC1=O FHNMAOLQZHUPIJ-UHFFFAOYSA-N 0.000 description 1
- CUSRGDOKYSVDPX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-naphthalen-2-yloxyacetate Chemical compound C=1C=C2C=CC=CC2=CC=1OCC(=O)ON1C(=O)CCC1=O CUSRGDOKYSVDPX-UHFFFAOYSA-N 0.000 description 1
- SMBVSRKAVRAVKU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-phenoxyacetate Chemical compound O=C1CCC(=O)N1OC(=O)COC1=CC=CC=C1 SMBVSRKAVRAVKU-UHFFFAOYSA-N 0.000 description 1
- CUTMPCNIMNVGIP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-phenoxypropanoate Chemical compound O=C1CCC(=O)N1OC(=O)C(C)OC1=CC=CC=C1 CUTMPCNIMNVGIP-UHFFFAOYSA-N 0.000 description 1
- QXMQCYFMIDJWAC-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-phenylbenzoate Chemical compound C=1(C(=CC=CC1)C(=O)ON1C(CCC1=O)=O)C1=CC=CC=C1 QXMQCYFMIDJWAC-UHFFFAOYSA-N 0.000 description 1
- PGHGEHFJLUAJRG-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-sulfanylbenzoate Chemical compound SC1=CC=CC=C1C(=O)ON1C(=O)CCC1=O PGHGEHFJLUAJRG-UHFFFAOYSA-N 0.000 description 1
- FKVDOCZMBDDTLH-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3,4,5-trimethoxybenzoate Chemical compound COC1=C(OC)C(OC)=CC(C(=O)ON2C(CCC2=O)=O)=C1 FKVDOCZMBDDTLH-UHFFFAOYSA-N 0.000 description 1
- NZOOCRIQABWYKN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3,5-dichlorobenzoate Chemical compound ClC1=CC(Cl)=CC(C(=O)ON2C(CCC2=O)=O)=C1 NZOOCRIQABWYKN-UHFFFAOYSA-N 0.000 description 1
- WMWZKPQQSXKNEW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-fluorobenzoate Chemical compound FC1=CC=CC(C(=O)ON2C(CCC2=O)=O)=C1 WMWZKPQQSXKNEW-UHFFFAOYSA-N 0.000 description 1
- CYUNDFVNNBMIEE-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-methylbenzoate Chemical compound CC1=CC=CC(C(=O)ON2C(CCC2=O)=O)=C1 CYUNDFVNNBMIEE-UHFFFAOYSA-N 0.000 description 1
- HWJDKYQDNRUICL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)ON1C(=O)CCC1=O HWJDKYQDNRUICL-UHFFFAOYSA-N 0.000 description 1
- KZGLLPWMYMOTRJ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-sulfanylbenzoate Chemical compound SC1=CC=CC(C(=O)ON2C(CCC2=O)=O)=C1 KZGLLPWMYMOTRJ-UHFFFAOYSA-N 0.000 description 1
- BOBFZKXGHXWZAM-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-(4-chlorophenyl)sulfonylbenzoate Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(C(=O)ON2C(CCC2=O)=O)C=C1 BOBFZKXGHXWZAM-UHFFFAOYSA-N 0.000 description 1
- FNGFZOAQGYOQTG-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-(dimethylamino)benzoate Chemical compound C1=CC(N(C)C)=CC=C1C(=O)ON1C(=O)CCC1=O FNGFZOAQGYOQTG-UHFFFAOYSA-N 0.000 description 1
- NWCJAIZMANMQOO-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-chlorobenzoate Chemical compound C1=CC(Cl)=CC=C1C(=O)ON1C(=O)CCC1=O NWCJAIZMANMQOO-UHFFFAOYSA-N 0.000 description 1
- BFETYBITNBCEGC-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-ethyl-2,3-dioxopiperazine-1-carboxylate Chemical compound O=C1C(=O)N(CC)CCN1C(=O)ON1C(=O)CCC1=O BFETYBITNBCEGC-UHFFFAOYSA-N 0.000 description 1
- NACXFYUMWSYYRU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-nitrobenzoate Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)ON1C(=O)CCC1=O NACXFYUMWSYYRU-UHFFFAOYSA-N 0.000 description 1
- WDHGSBZURLICCZ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-tert-butylbenzoate Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)ON1C(=O)CCC1=O WDHGSBZURLICCZ-UHFFFAOYSA-N 0.000 description 1
- KXYXPZAUKDAELN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 8-bromonaphthalene-1-carboxylate Chemical compound C=12C(Br)=CC=CC2=CC=CC=1C(=O)ON1C(=O)CCC1=O KXYXPZAUKDAELN-UHFFFAOYSA-N 0.000 description 1
- BVUOEDOMUOJKOY-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) benzoate Chemical compound C=1C=CC=CC=1C(=O)ON1C(=O)CCC1=O BVUOEDOMUOJKOY-UHFFFAOYSA-N 0.000 description 1
- GIXFBSIJEBFUBL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) naphthalene-1-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)ON1C(=O)CCC1=O GIXFBSIJEBFUBL-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- SCCCIUGOOQLDGW-UHFFFAOYSA-N 1,1-dicyclohexylurea Chemical compound C1CCCCC1N(C(=O)N)C1CCCCC1 SCCCIUGOOQLDGW-UHFFFAOYSA-N 0.000 description 1
- FGBUALIUQAADKR-UHFFFAOYSA-N 1-(4-ethoxybenzoyl)pyrrolidine-2,5-dione Chemical compound C1=CC(OCC)=CC=C1C(=O)N1C(=O)CCC1=O FGBUALIUQAADKR-UHFFFAOYSA-N 0.000 description 1
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IPOLXHGYHTXPEZ-UHFFFAOYSA-N 2-o-(2,5-dioxopyrrolidin-1-yl) 1-o-ethyl oxalate Chemical compound CCOC(=O)C(=O)ON1C(=O)CCC1=O IPOLXHGYHTXPEZ-UHFFFAOYSA-N 0.000 description 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- NPJJAKJQFJQZNH-UHFFFAOYSA-N 4-O-(2,5-dioxopyrrolidin-1-yl) 1-O-ethyl 2,6-dimethoxybenzene-1,4-dicarboxylate Chemical compound C1=C(OC)C(C(=O)OCC)=C(OC)C=C1C(=O)ON1C(=O)CCC1=O NPJJAKJQFJQZNH-UHFFFAOYSA-N 0.000 description 1
- XLWQUESMILVIPR-UHFFFAOYSA-N 4-ethoxybenzoyl chloride Chemical compound CCOC1=CC=C(C(Cl)=O)C=C1 XLWQUESMILVIPR-UHFFFAOYSA-N 0.000 description 1
- SXVBQOZRZIUHKU-UHFFFAOYSA-N 4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride Chemical compound CCN1CCN(C(Cl)=O)C(=O)C1=O SXVBQOZRZIUHKU-UHFFFAOYSA-N 0.000 description 1
- YIPHYCQSJTXLFM-UHFFFAOYSA-N 4-hydroxybenzoyl chloride Chemical compound OC1=CC=C(C(Cl)=O)C=C1 YIPHYCQSJTXLFM-UHFFFAOYSA-N 0.000 description 1
- SFDYRZUJXKXXRU-UHFFFAOYSA-N 8-bromonaphthalene-1-carbonyl chloride Chemical compound C1=CC(Br)=C2C(C(=O)Cl)=CC=CC2=C1 SFDYRZUJXKXXRU-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- LBZVHZYRUJPCLQ-UHFFFAOYSA-N CC(C)(C)C(=O)OC1CC(=O)NC1=O Chemical compound CC(C)(C)C(=O)OC1CC(=O)NC1=O LBZVHZYRUJPCLQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229940053198 antiepileptics succinimide derivative Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009640 blood culture Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- GCPLXOULOLVENT-UHFFFAOYSA-N pyrrolidine-2,5-dione;2,2,2-trichloroethyl hydrogen carbonate Chemical compound O=C1CCC(=O)N1.OC(=O)OCC(Cl)(Cl)Cl GCPLXOULOLVENT-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 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
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/815,340 US4112219A (en) | 1977-07-13 | 1977-07-13 | Acyl derivatives of antibiotic BM123γ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199736B2 true CS199736B2 (en) | 1980-07-31 |
Family
ID=25217505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS784640A CS199736B2 (en) | 1977-07-13 | 1978-07-11 | Method of preparing antibiotic bm 123 gama |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4112219A (ro) |
| JP (1) | JPS5436260A (ro) |
| AR (1) | AR220715A1 (ro) |
| AT (1) | AT359192B (ro) |
| AU (1) | AU520453B2 (ro) |
| BE (1) | BE868724A (ro) |
| CA (1) | CA1113931A (ro) |
| CS (1) | CS199736B2 (ro) |
| DD (1) | DD137529A5 (ro) |
| DE (1) | DE2827962A1 (ro) |
| DK (1) | DK314178A (ro) |
| ES (1) | ES471692A1 (ro) |
| FI (1) | FI782027A7 (ro) |
| FR (1) | FR2397424A1 (ro) |
| GB (1) | GB2002345A (ro) |
| GR (1) | GR68418B (ro) |
| IL (1) | IL54927A (ro) |
| NL (1) | NL7806859A (ro) |
| NZ (1) | NZ187630A (ro) |
| PH (1) | PH14227A (ro) |
| PL (1) | PL117126B1 (ro) |
| RO (1) | RO76164A (ro) |
| SE (1) | SE7807776L (ro) |
| ZA (1) | ZA783361B (ro) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5650270A (en) * | 1982-02-01 | 1997-07-22 | Northeastern University | Molecular analytical release tags and their use in chemical analysis |
| WO1990004599A1 (en) * | 1988-10-21 | 1990-05-03 | Abbott Laboratories | Coumamidine compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL48476A (en) * | 1974-12-05 | 1980-12-31 | American Cyanamid Co | Alkylated derivatives of antibiotic bm123 and process for preparing them |
| US4048431A (en) * | 1975-09-12 | 1977-09-13 | American Cyanamid Company | Alkylated derivatives of antibiotic BM123γ |
| US4018972A (en) * | 1976-03-08 | 1977-04-19 | American Cyanamid Company | Antibacterial agents cis-BM123γ1 and cis-BM123γ2 |
-
1977
- 1977-07-13 US US05/815,340 patent/US4112219A/en not_active Expired - Lifetime
-
1978
- 1978-06-12 ZA ZA783361A patent/ZA783361B/xx unknown
- 1978-06-13 AU AU37065/78A patent/AU520453B2/en not_active Expired
- 1978-06-15 IL IL54927A patent/IL54927A/xx unknown
- 1978-06-16 GB GB7827171A patent/GB2002345A/en not_active Withdrawn
- 1978-06-20 NZ NZ187630A patent/NZ187630A/xx unknown
- 1978-06-26 CA CA306,218A patent/CA1113931A/en not_active Expired
- 1978-06-26 DE DE19782827962 patent/DE2827962A1/de not_active Withdrawn
- 1978-06-26 FI FI782027A patent/FI782027A7/fi not_active Application Discontinuation
- 1978-06-26 NL NL7806859A patent/NL7806859A/xx not_active Application Discontinuation
- 1978-06-27 GR GR56613A patent/GR68418B/el unknown
- 1978-06-29 AR AR272757A patent/AR220715A1/es active
- 1978-07-04 BE BE189064A patent/BE868724A/xx unknown
- 1978-07-07 PH PH21344A patent/PH14227A/en unknown
- 1978-07-10 RO RO7894632A patent/RO76164A/ro unknown
- 1978-07-11 CS CS784640A patent/CS199736B2/cs unknown
- 1978-07-12 PL PL1978208342A patent/PL117126B1/pl unknown
- 1978-07-12 SE SE7807776A patent/SE7807776L/xx unknown
- 1978-07-12 AT AT503878A patent/AT359192B/de not_active IP Right Cessation
- 1978-07-12 DK DK783141A patent/DK314178A/da not_active Application Discontinuation
- 1978-07-13 FR FR7820990A patent/FR2397424A1/fr not_active Withdrawn
- 1978-07-13 ES ES471692A patent/ES471692A1/es not_active Expired
- 1978-07-13 DD DD78206705A patent/DD137529A5/xx unknown
- 1978-07-13 JP JP8566078A patent/JPS5436260A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI782027A7 (fi) | 1979-01-14 |
| DE2827962A1 (de) | 1979-02-01 |
| PL208342A1 (pl) | 1979-09-10 |
| NZ187630A (en) | 1981-03-16 |
| AU3706578A (en) | 1979-12-20 |
| ZA783361B (en) | 1980-02-27 |
| NL7806859A (nl) | 1979-01-16 |
| FR2397424A1 (fr) | 1979-02-09 |
| PH14227A (en) | 1981-04-09 |
| AU520453B2 (en) | 1982-02-04 |
| BE868724A (fr) | 1979-01-04 |
| SE7807776L (sv) | 1979-01-14 |
| RO76164A (ro) | 1981-08-17 |
| AT359192B (de) | 1980-10-27 |
| DD137529A5 (de) | 1979-09-12 |
| CA1113931A (en) | 1981-12-08 |
| PL117126B1 (en) | 1981-07-31 |
| ATA503878A (de) | 1980-03-15 |
| IL54927A (en) | 1981-09-13 |
| DK314178A (da) | 1979-01-14 |
| US4112219A (en) | 1978-09-05 |
| JPS5436260A (en) | 1979-03-16 |
| GB2002345A (en) | 1979-02-21 |
| ES471692A1 (es) | 1979-10-01 |
| AR220715A1 (es) | 1980-11-28 |
| GR68418B (ro) | 1981-12-29 |
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