CA1128057A - Derives de la fortimicine b et procede de preparation - Google Patents

Derives de la fortimicine b et procede de preparation

Info

Publication number: CA1128057A
Authority: CA; Canada
Prior art keywords: group; compound; carbon atoms; amino; fortimicin
Prior art date: 1977-12-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA318,372A

Other languages

English (en)

Inventor

Shigeo Yoshiie

Moriyuki Sato

Kenichi Mochida

Yasuki Mori

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Abbott Laboratories

Original Assignee

Abbott Laboratories

Priority date (The priority date 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 date listed.)

1977-12-21

Filing date

1978-12-21

Publication date

1982-07-20

1978-12-21 Application filed by Abbott Laboratories filed Critical Abbott Laboratories

1982-07-20 Application granted granted Critical

1982-07-20 Publication of CA1128057A publication Critical patent/CA1128057A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
BIDUPMYXGFNAEJ-APGVDKLISA-N astromicin Chemical class O[C@@H]1[C@H](N(C)C(=O)CN)[C@@H](OC)[C@@H](O)[C@H](N)[C@H]1O[C@@H]1[C@H](N)CC[C@@H]([C@H](C)N)O1 BIDUPMYXGFNAEJ-APGVDKLISA-N 0.000 title description 17
WFMQYKIRAVMXSU-LCVFDZPESA-N Fortimicin B Chemical class N[C@H]1[C@H](O)[C@H](OC)[C@@H](NC)[C@@H](O)[C@@H]1O[C@@H]1[C@H](N)CC[C@@H]([C@H](C)N)O1 WFMQYKIRAVMXSU-LCVFDZPESA-N 0.000 claims abstract description 50
WFMQYKIRAVMXSU-UHFFFAOYSA-N Fortimicin AE Natural products NC1C(O)C(OC)C(NC)C(O)C1OC1C(N)CCC(C(C)N)O1 WFMQYKIRAVMXSU-UHFFFAOYSA-N 0.000 claims abstract description 42
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
239000002253 acid Substances 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 11
125000003277 amino group Chemical group 0.000 claims abstract description 9
125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 7
231100000252 nontoxic Toxicity 0.000 claims abstract description 7
230000003000 nontoxic effect Effects 0.000 claims abstract description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
238000000034 method Methods 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 6
230000003197 catalytic effect Effects 0.000 claims description 3
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
230000000844 anti-bacterial effect Effects 0.000 abstract description 9
150000001875 compounds Chemical class 0.000 description 186
239000000243 solution Substances 0.000 description 114
239000002904 solvent Substances 0.000 description 113
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 73
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 58
239000000047 product Substances 0.000 description 56
239000007787 solid Substances 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 38
229960001701 chloroform Drugs 0.000 description 37
238000002360 preparation method Methods 0.000 description 31
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 29
238000010828 elution Methods 0.000 description 25
239000011541 reaction mixture Substances 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 21
238000001816 cooling Methods 0.000 description 19
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 16
238000001228 spectrum Methods 0.000 description 16
-1 sulfuric acid Chemical class 0.000 description 16
229930195503 Fortimicin Natural products 0.000 description 15
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 13
238000001914 filtration Methods 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000003153 chemical reaction reagent Substances 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 9
238000004809 thin layer chromatography Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 8
239000011259 mixed solution Substances 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
239000003638 chemical reducing agent Substances 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
229920001429 chelating resin Polymers 0.000 description 6
229940093499 ethyl acetate Drugs 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 6
239000003456 ion exchange resin Substances 0.000 description 6
229920003303 ion-exchange polymer Polymers 0.000 description 6
238000001819 mass spectrum Methods 0.000 description 6
239000000843 powder Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000007858 starting material Substances 0.000 description 6
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 5
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
DLVFJQXRKNWSCB-CPLRHSGFSA-N Fortimicin C Natural products CO[C@H]1[C@@H](O)[C@H](N)[C@H](O[C@H]2O[C@@H](CN)CC[C@@H]2N)[C@@H](O)[C@H]1N(C)C(=O)CNC(=O)N DLVFJQXRKNWSCB-CPLRHSGFSA-N 0.000 description 5
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 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
150000001735 carboxylic acids Chemical class 0.000 description 5
238000002955 isolation Methods 0.000 description 5
VKGIGFQBOYWLHV-APGVDKLISA-N n-[(1s,2r,3r,4s,5s,6r)-4-amino-3-[(2r,3r,6s)-3-amino-6-[(1s)-1-aminoethyl]oxan-2-yl]oxy-2,5-dihydroxy-6-methoxycyclohexyl]-2-(carbamoylamino)-n-methylacetamide Chemical compound O[C@@H]1[C@H](N(C)C(=O)CNC(N)=O)[C@@H](OC)[C@@H](O)[C@H](N)[C@H]1O[C@@H]1[C@H](N)CC[C@@H]([C@H](C)N)O1 VKGIGFQBOYWLHV-APGVDKLISA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
BIDUPMYXGFNAEJ-UHFFFAOYSA-N Fortimicin A Natural products OC1C(N(C)C(=O)CN)C(OC)C(O)C(N)C1OC1C(N)CCC(C(C)N)O1 BIDUPMYXGFNAEJ-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
ATCZFEUVYCQLLE-UHFFFAOYSA-N azane;chloroform Chemical compound N.ClC(Cl)Cl ATCZFEUVYCQLLE-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
ULKOBRDRCYROKY-JTQLQIEISA-N (2s)-2-hydroxy-4-(phenylmethoxycarbonylamino)butanoic acid Chemical compound OC(=O)[C@@H](O)CCNC(=O)OCC1=CC=CC=C1 ULKOBRDRCYROKY-JTQLQIEISA-N 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
MJSHDCCLFGOEIK-UHFFFAOYSA-N benzyl (2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)OCC1=CC=CC=C1 MJSHDCCLFGOEIK-UHFFFAOYSA-N 0.000 description 2
229960004132 diethyl ether Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 2
QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
230000000704 physical 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
238000010898 silica gel chromatography Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229960002317 succinimide Drugs 0.000 description 2
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
IXYBWKXLAGQSJE-UHFFFAOYSA-N 2-hydroxy-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CCC(O)(C(O)=O)NC(=O)OCC1=CC=CC=C1 IXYBWKXLAGQSJE-UHFFFAOYSA-N 0.000 description 1
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-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
FYWDUQCSMYWUHV-UHFFFAOYSA-N 3-chloro-5-hydroxypentan-2-one Chemical compound CC(=O)C(Cl)CCO FYWDUQCSMYWUHV-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
241001072332 Monia Species 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 1
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
229950004074 astromicin Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
VPYJBEIOKFRWQZ-UHFFFAOYSA-N benzyl 2-hydroxyacetate Chemical compound OCC(=O)OCC1=CC=CC=C1 VPYJBEIOKFRWQZ-UHFFFAOYSA-N 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940126142 compound 16 Drugs 0.000 description 1
229940126086 compound 21 Drugs 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
229910052805 deuterium Inorganic materials 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012632 extractable Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
244000005700 microbiome Species 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
238000005192 partition Methods 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 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
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/224—Cyclohexane rings substituted by at least two nitrogen atoms with only one saccharide radical directly attached to the cyclohexyl radical, e.g. destomycin, fortimicin, neamine
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA318,372A 1977-12-21 1978-12-21 Derives de la fortimicine b et procede de preparation Expired CA1128057A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP15300277A JPS5488242A (en)	1977-12-21	1977-12-21	Novel derivative of fortimicin b and its preparation
JP153002/77		1977-12-21

Publications (1)

Publication Number	Publication Date
CA1128057A true CA1128057A (fr)	1982-07-20

Family

ID=15552790

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA318,372A Expired CA1128057A (fr)	1977-12-21	1978-12-21	Derives de la fortimicine b et procede de preparation

Country Status (9)

Country	Link
JP (1)	JPS5488242A (fr)
AU (1)	AU528071B2 (fr)
BE (1)	BE873630A (fr)
CA (1)	CA1128057A (fr)
DE (1)	DE2855350A1 (fr)
FR (1)	FR2412561A1 (fr)
GB (1)	GB2011894A (fr)
GR (1)	GR65332B (fr)
PH (1)	PH14722A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4214076A (en) *	1977-12-21	1980-07-22	Abbott Laboratories	2'-N-Substituted fortimicin B and derivatives
JPS5488240A (en) *	1977-12-21	1979-07-13	Kyowa Hakko Kogyo Co Ltd	Novel fortimicin a derivative
JPS5488241A (en) *	1977-12-21	1979-07-13	Kyowa Hakko Kogyo Co Ltd	Novel fortimicin a derivative
JPS58213774A (ja) *	1982-06-04	1983-12-12	Kowa Co	新規アミノ配糖体
JPS6116850U (ja) *	1985-06-20	1986-01-31	三谷電子工業株式会社	カラー表示装置
JPH06266596A (ja)	1993-03-11	1994-09-22	Hitachi Ltd	フラッシュメモリファイル記憶装置および情報処理装置
WO2012173736A1 (fr) *	2011-06-16	2012-12-20	Dow Global Technologies Llc	Dendrimères et leurs procédés de préparation

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4214076A (en) *	1977-12-21	1980-07-22	Abbott Laboratories	2'-N-Substituted fortimicin B and derivatives
JPS5488240A (en) *	1977-12-21	1979-07-13	Kyowa Hakko Kogyo Co Ltd	Novel fortimicin a derivative
JPS5488241A (en) *	1977-12-21	1979-07-13	Kyowa Hakko Kogyo Co Ltd	Novel fortimicin a derivative

1977
- 1977-12-21 JP JP15300277A patent/JPS5488242A/ja active Pending
1978
- 1978-12-13 PH PH21941A patent/PH14722A/en unknown
- 1978-12-20 GR GR57946A patent/GR65332B/el unknown
- 1978-12-21 GB GB7849712A patent/GB2011894A/en not_active Withdrawn
- 1978-12-21 FR FR7835880A patent/FR2412561A1/fr not_active Withdrawn
- 1978-12-21 DE DE19782855350 patent/DE2855350A1/de not_active Withdrawn
- 1978-12-21 CA CA318,372A patent/CA1128057A/fr not_active Expired
1979
- 1979-01-03 AU AU43076/79A patent/AU528071B2/en not_active Ceased
- 1979-01-22 BE BE0/193014A patent/BE873630A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU528071B2 (en)	1983-04-14
AU4307679A (en)	1979-06-28
PH14722A (en)	1981-11-13
JPS5488242A (en)	1979-07-13
GB2011894A (en)	1979-07-18
BE873630A (fr)	1979-07-23
FR2412561A1 (fr)	1979-07-20
GR65332B (en)	1980-08-13
DE2855350A1 (de)	1979-07-05

Legal Events

Date	Code	Title	Description
1999-07-20	MKEX	Expiry

Publication	Publication Date	Title
CA1114809A (fr)	1981-12-22	Derives de la 4-n-acylfortimicine b et conversion chimique de la fortimicine b en fortimicine a
GB1598704A (en)	1981-09-23	3-de-o-methylfortimicins
US4117221A (en)	1978-09-26	Aminoacyl derivatives of aminoglycoside antibiotics
US3860574A (en)	1975-01-14	Derivatives of neomycin b and neomycin c
US4055715A (en)	1977-10-25	Method of producing 1-N-[L-(-)-α-hydroxy-γ-aminobutyryl]XK-62-2
CA1128057A (fr)	1982-07-20	Derives de la fortimicine b et procede de preparation
US3808198A (en)	1974-04-30	Lividomycin b derivatives
US4237272A (en)	1980-12-02	Derivatives of fortimicin A
US3896106A (en)	1975-07-22	Antibiotic derivatives
RANE et al.	1976	Selective N-acylation of gentamicin antibiotics-Synthesis of 1-N-acyl derivatives
EP0096392B1 (fr)	1985-10-09	Aminoglycosides, leur procédé de préparation et leur emploi
US4169942A (en)	1979-10-02	Fortimicin derivatives and method for production thereof
CA1044229A (fr)	1978-12-12	Derives antibiotiques du xk-62-2 et methode de production
US3939143A (en)	1976-02-17	1-N-isoserylkanamycins and the production thereof
US4547492A (en)	1985-10-15	1-N-(ω-Amino-α-hydroxyalkanoyl-2',3'-dideoxykanamycin A and pharmaceutical composition containing same
US4226980A (en)	1980-10-07	Novel derivatives of fortimicin B and process for preparing same
US4283528A (en)	1981-08-11	1-N-aminohydroxyacyl derivatives of gentamicin B
EP0040764B1 (fr)	1983-07-20	Aminoglycosides et leur emploi antibiotique
CA1046513A (fr)	1979-01-16	Derives d'antibiotiques
US4237269A (en)	1980-12-02	Derivatives of fortimicin A
US4132846A (en)	1979-01-02	1-N-(α-Hydroxy-β-aminopropionyl) XK-62-2 and method of production thereof
CA2325082A1 (fr)	1990-12-22	2-formylmercaptobenzothiazole
HK1000153B (en)	1998-01-02	N-protected-(s)-isoserine compounds
US4268664A (en)	1981-05-19	Process for the preparation of 1-N-isoseryl- or 1-N-(L-4-amino-2-hydroxybutyryl)-3',4'-dideoxykanamycin B and intermediates thereof
CA1083174A (fr)	1980-08-05	SYNTHESE DE DERIVES DE LA NEGAMYCINE SUBSTITUEE EN .alpha.