JP2016528262A5 - - Google Patents

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Publication number

JP2016528262A5

JP2016528262A5 JP2016535311A JP2016535311A JP2016528262A5 JP 2016528262 A5 JP2016528262 A5 JP 2016528262A5 JP 2016535311 A JP2016535311 A JP 2016535311A JP 2016535311 A JP2016535311 A JP 2016535311A JP 2016528262 A5 JP2016528262 A5 JP 2016528262A5

Authority

JP

Japan

Prior art keywords

alkyl

coor

phenyl

iii

independently

Prior art date

2014-04-22

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.)

Granted

Links

• Espacenet
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• 150000002367 halogens Chemical class 0.000 claims description 29
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 11
• MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical class O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 claims 14
• 125000000217 alkyl group Chemical group 0.000 claims 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
• 108010059993 Vancomycin Proteins 0.000 claims 6
• 229960003165 vancomycin Drugs 0.000 claims 6
• MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims 6
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 5
• -1 monosubstituted phenyl Chemical group 0.000 claims 5
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 4
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
• 238000006722 reduction reaction Methods 0.000 claims 3
• 241000894006 Bacteria Species 0.000 claims 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
• NUAQIRUAZSJTAI-YRPZDAAMSA-N O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@H](N)CC(C)C)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@H](N)CC(C)C)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 NUAQIRUAZSJTAI-YRPZDAAMSA-N 0.000 claims 2
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
• 125000002009 alkene group Chemical group 0.000 claims 2
• 125000003342 alkenyl group Chemical group 0.000 claims 2
• 125000002355 alkine group Chemical group 0.000 claims 2
• 125000000304 alkynyl group Chemical group 0.000 claims 2
• 229910000085 borane Inorganic materials 0.000 claims 2
• 239000003638 chemical reducing agent Substances 0.000 claims 2
• 150000001875 compounds Chemical class 0.000 claims 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
• 238000004519 manufacturing process Methods 0.000 claims 2
• 108700014375 norvancomycin Proteins 0.000 claims 2
• 239000002798 polar solvent Substances 0.000 claims 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims 1
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
• 229910052783 alkali metal Inorganic materials 0.000 claims 1
• 150000001340 alkali metals Chemical class 0.000 claims 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
• 150000001342 alkaline earth metals Chemical class 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 claims 1
• 150000002431 hydrogen Chemical class 0.000 claims 1
• 230000007062 hydrolysis Effects 0.000 claims 1
• 238000006460 hydrolysis reaction Methods 0.000 claims 1
• 208000015181 infectious disease Diseases 0.000 claims 1
• 229960004592 isopropanol Drugs 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 229910052700 potassium Inorganic materials 0.000 claims 1
• 239000011591 potassium Substances 0.000 claims 1
• 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
• 239000012279 sodium borohydride Substances 0.000 claims 1
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 claims 1
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 9