JPS6331478B2 - - Google Patents

Info

Publication number: JPS6331478B2
Authority: JP; Japan
Prior art keywords: amino; alkanoylamino; hydroxy; formula; acylamino
Prior art date: 1982-10-25
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

JP19972883A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5998097A (ja

Inventor

Takao Takatani

Nobusachi Yasuda

Hideo Tsutsumi

Keiji Matsuda

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.)

Fujisawa Pharmaceutical Co Ltd

Original Assignee

Fujisawa Pharmaceutical Co Ltd

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.)

1982-10-25

Filing date

1983-10-25

Publication date

1988-06-23

1983-10-25 Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd

1984-06-06 Publication of JPS5998097A publication Critical patent/JPS5998097A/ja

1988-06-23 Publication of JPS6331478B2 publication Critical patent/JPS6331478B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 124
-1 hydroxy, amino Chemical group 0.000 claims description 117
238000004519 manufacturing process Methods 0.000 claims description 113
150000003839 salts Chemical class 0.000 claims description 104
125000005236 alkanoylamino group Chemical group 0.000 claims description 88
125000004442 acylamino group Chemical group 0.000 claims description 87
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 66
125000003545 alkoxy group Chemical group 0.000 claims description 54
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 43
125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 41
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 37
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 33
125000001424 substituent group Chemical group 0.000 claims description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
125000003277 amino group Chemical group 0.000 claims description 31
238000005947 deacylation reaction Methods 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
229940126575 aminoglycoside Drugs 0.000 claims description 20
238000005917 acylation reaction Methods 0.000 claims description 17
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 16
125000001589 carboacyl group Chemical group 0.000 claims description 14
125000004423 acyloxy group Chemical group 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
238000003379 elimination reaction Methods 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
229940124597 therapeutic agent Drugs 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 11
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 4
208000035473 Communicable disease Diseases 0.000 claims 1
125000005239 aroylamino group Chemical group 0.000 claims 1
230000002265 prevention Effects 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 154
239000000203 mixture Substances 0.000 description 123
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 123
238000006243 chemical reaction Methods 0.000 description 119
238000002844 melting Methods 0.000 description 118
230000008018 melting Effects 0.000 description 118
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 106
238000000354 decomposition reaction Methods 0.000 description 105
239000000243 solution Substances 0.000 description 96
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 79
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 74
230000002829 reductive effect Effects 0.000 description 72
238000003756 stirring Methods 0.000 description 61
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 55
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 55
229960000318 kanamycin Drugs 0.000 description 41
229930182823 kanamycin A Natural products 0.000 description 41
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
239000012141 concentrate Substances 0.000 description 38
235000008504 concentrate Nutrition 0.000 description 38
SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 35
239000011541 reaction mixture Substances 0.000 description 34
239000002253 acid Substances 0.000 description 32
238000000034 method Methods 0.000 description 32
239000002244 precipitate Substances 0.000 description 31
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
239000007788 liquid Substances 0.000 description 27
239000003795 chemical substances by application Substances 0.000 description 25
239000007787 solid Substances 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
238000001816 cooling Methods 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 16
239000000725 suspension Substances 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 14
125000004432 carbon atom Chemical group C* 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
238000005406 washing Methods 0.000 description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
239000012298 atmosphere Substances 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
229910052783 alkali metal Inorganic materials 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000005457 ice water Substances 0.000 description 8
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
125000002252 acyl group Chemical group 0.000 description 7
229910052784 alkaline earth metal Inorganic materials 0.000 description 7
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
229920001450 Alpha-Cyclodextrin Polymers 0.000 description 5
229940043377 alpha-cyclodextrin Drugs 0.000 description 5
239000002585 base Substances 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
238000004113 cell culture Methods 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
238000012360 testing method Methods 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
150000001342 alkaline earth metals Chemical class 0.000 description 4
230000000840 anti-viral effect Effects 0.000 description 4
125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 4
238000001035 drying Methods 0.000 description 4
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000004703 alkoxides Chemical class 0.000 description 3
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
229960001192 bekanamycin Drugs 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
XEKAUTDWPYQNFU-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl XEKAUTDWPYQNFU-UHFFFAOYSA-N 0.000 description 3
230000003013 cytotoxicity Effects 0.000 description 3
231100000135 cytotoxicity Toxicity 0.000 description 3
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229930182824 kanamycin B Natural products 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
GKJHGOAZEUCGOD-UHFFFAOYSA-N 3-acetyloxytetradecanoic acid Chemical compound CCCCCCCCCCCC(CC(O)=O)OC(C)=O GKJHGOAZEUCGOD-UHFFFAOYSA-N 0.000 description 2
JLIJUQBAUMUMJK-UHFFFAOYSA-N 3-ethoxy-3-methylpentane Chemical compound CCOC(C)(CC)CC JLIJUQBAUMUMJK-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
108091003079 Bovine Serum Albumin Proteins 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241001042386 Canama Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
229920000858 Cyclodextrin Polymers 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920000388 Polyphosphate Polymers 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
230000002411 adverse Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
230000020176 deacylation Effects 0.000 description 2
GBMDVOWEEQVZKZ-JMLOAXHOSA-N deuterated water trideuterio(deuteriooxy)methane Chemical compound [2H]O[2H].[2H]OC([2H])([2H])[2H] GBMDVOWEEQVZKZ-JMLOAXHOSA-N 0.000 description 2
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150000003852 triazoles Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
GRVDJDISBSALJP-FIBGUPNXSA-N trideuterio($l^{1}-oxidanyl)methane Chemical compound [2H]C([2H])([2H])[O] GRVDJDISBSALJP-FIBGUPNXSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZRQJSWOPZOITNN-UHFFFAOYSA-N urea;dihydrochloride Chemical compound Cl.Cl.NC(N)=O ZRQJSWOPZOITNN-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP19972883A 1982-10-25 1983-10-25 新規アミノグリコシド誘導体 Granted JPS5998097A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB8230421		1982-10-25
GB8230421		1982-10-25
GB8310436		1983-04-18

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP29281687A Division JPS63146894A (ja)	1982-10-25	1987-11-19	アミノグリコシド誘導体

Publications (2)

Publication Number	Publication Date
JPS5998097A JPS5998097A (ja)	1984-06-06
JPS6331478B2 true JPS6331478B2 (da)	1988-06-23

Family

ID=10533824

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP19972883A Granted JPS5998097A (ja)	1982-10-25	1983-10-25	新規アミノグリコシド誘導体
JP29281687A Granted JPS63146894A (ja)	1982-10-25	1987-11-19	アミノグリコシド誘導体

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP29281687A Granted JPS63146894A (ja)	1982-10-25	1987-11-19	アミノグリコシド誘導体

Country Status (2)

Country	Link
JP (2)	JPS5998097A (da)
ZA (1)	ZA837252B (da)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH03171280A (ja) *	1989-08-23	1991-07-24	Fuji Electric Co Ltd	硬貨選別装置
JPH11219421A (ja) *	1998-01-30	1999-08-10	Toshiba Corp	画像認識装置及び画像認識装置方法

1983
- 1983-09-28 ZA ZA837252A patent/ZA837252B/xx unknown
- 1983-10-25 JP JP19972883A patent/JPS5998097A/ja active Granted
1987
- 1987-11-19 JP JP29281687A patent/JPS63146894A/ja active Granted

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH03171280A (ja) *	1989-08-23	1991-07-24	Fuji Electric Co Ltd	硬貨選別装置
JPH11219421A (ja) *	1998-01-30	1999-08-10	Toshiba Corp	画像認識装置及び画像認識装置方法

Also Published As

Publication number	Publication date
JPH0149720B2 (da)	1989-10-25
JPS63146894A (ja)	1988-06-18
JPS5998097A (ja)	1984-06-06
ZA837252B (en)	1984-05-30

Publication	Publication Date	Title
DE2810922C2 (de)	1985-08-29	Syn-Isomere von 3-Cephem-4-carbonsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung bakterieller Infektionen
DE69005286T2 (de)	1994-04-21	Peptide mit tachykininantagonistischer Aktivität, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate.
DE60315178T3 (de)	2015-06-18	Cephemverbindungen
KR930007418B1 (ko)	1993-08-10	세팔로스포린 화합물, 그의 제조방법
WO1996016981A2 (en)	1996-06-06	Peptide compounds for prevention and/or treatment of no-mediated diseases
JPH06104673B2 (ja)	1994-12-21	７―アシルアミノ―３―置換セファロスポラン酸誘導体
JPS5896092A (ja)	1983-06-07	７−アシルアミノ−３−置換セフアロスポラン酸誘導体およびその製造法
US4493831A (en)	1985-01-15	Aminoglycoside derivatives
AU728892B2 (en)	2001-01-18	Nucleosides analogues, such as antivirals including inhibitors of retroviral reverse transcriptase and the DNA polymerase of hepatitis B virus (HBV)
GB1572683A (en)	1980-07-30	Oxime derivatives of 7-aminothiazolyl-acet-amido-cephalosporanic acid processes for preparing them and pharmaceutical compositions containing them
US4477447A (en)	1984-10-16	7-Acylaminocephalosporanic acid derivatives
JPS6331478B2 (da)	1988-06-23
FR2533926A1 (fr)	1984-04-06	Procede de production de composes de 3-vinyl-3-cephem 7-substitues et nouveaux produits ainsi obtenus
CH645116A5 (de)	1984-09-14	Cephem-verbindungen, verfahren zu ihrer herstellung und sie enthaltende antibakterielle pharmazeutische mittel.
US4656160A (en)	1987-04-07	Aminoglycoside derivatives
KR900006212B1 (ko)	1990-08-25	신규 1,4-디아미노사이클리톨 유도체의 제조방법
NO862910L (no)	1987-02-06	Fremgangsmaate for fremstilling av 3,7-disubstituerte-3-cefemforbindelser.
NL8201820A (nl)	1982-12-01	2-methoxyfenylesters van n-gesubstitueerde aminozuren, een werkwijze voor hun bereiding en farmaceutica die deze verbindingen bevatten.
JPS611696A (ja)	1986-01-07	新規アミノグリコシド誘導体
JPS615089A (ja)	1986-01-10	新規アミノグリコシド誘導体
HUP0105115A2 (hu)	2002-04-29	Éter típusú lipid A1-karbonsav-analógok, valamint ezeket tartalmazó gyógyszerkészítmények
AT371471B (de)	1983-06-27	Verfahren zur herstellung von neuen cephemverbindungen
KR820000927B1 (ko)	1982-05-26	신규의 세펨 및 세팜화합물의 제조방법
JPH027316B2 (da)	1990-02-16
WO1992020665A1 (en)	1992-11-26	Thiazolidine derivatives and their use in therapy

JPS6331478B2 - - Google Patents

Info

Links

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Applications Claiming Priority (3)

Related Child Applications (1)

Publications (2)

Family

ID=10533824

Family Applications (2)

Family Applications After (1)

Country Status (2)

Cited By (2)

Cited By (2)

Also Published As

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