FI62100C - Foerfarande foer framstaellning av 1-n-substituerade derivat av 4,6-di-(aminoglykosyl)-1,3-diaminocyklitolerna gentamicin b gentamicin c1 gentamicin c1a sisomicin verdamicin antibiotikum ji-20b antibiotikum g-52 mutamicin 2 och mutamicin 6 - Google Patents
Foerfarande foer framstaellning av 1-n-substituerade derivat av 4,6-di-(aminoglykosyl)-1,3-diaminocyklitolerna gentamicin b gentamicin c1 gentamicin c1a sisomicin verdamicin antibiotikum ji-20b antibiotikum g-52 mutamicin 2 och mutamicin 6 Download PDFInfo
- Publication number
- FI62100C FI62100C FI2304/74A FI230474A FI62100C FI 62100 C FI62100 C FI 62100C FI 2304/74 A FI2304/74 A FI 2304/74A FI 230474 A FI230474 A FI 230474A FI 62100 C FI62100 C FI 62100C
- Authority
- FI
- Finland
- Prior art keywords
- gentamicin
- aminoglycosyl
- amino
- antibiotic
- solution
- Prior art date
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- 229960005456 sisomicin Drugs 0.000 title claims description 37
- 229960002518 gentamicin Drugs 0.000 title claims description 33
- URWAJWIAIPFPJE-UHFFFAOYSA-N Rickamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N URWAJWIAIPFPJE-UHFFFAOYSA-N 0.000 title claims description 28
- 229930192786 Sisomicin Natural products 0.000 title claims description 28
- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 title claims description 28
- 229930182566 Gentamicin Natural products 0.000 title claims description 26
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 title claims description 24
- VEGXETMJINRLTH-BOZYPMBZSA-N gentamycin C1a Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N VEGXETMJINRLTH-BOZYPMBZSA-N 0.000 title claims description 19
- XUSXOPRDIDWMFO-CTMSJIKGSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[[(2s,3r)-3-amino-6-[(1s)-1-aminoethyl]-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(O2)[C@H](C)N)N)[C@@H](N)C[C@H]1N XUSXOPRDIDWMFO-CTMSJIKGSA-N 0.000 title claims description 14
- XUSXOPRDIDWMFO-UHFFFAOYSA-N Verdamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(O2)C(C)N)N)C(N)CC1N XUSXOPRDIDWMFO-UHFFFAOYSA-N 0.000 title claims description 14
- 230000003115 biocidal effect Effects 0.000 title claims description 13
- 229930076781 gentamycin C1 Natural products 0.000 title description 2
- CEAZRRDELHUEMR-CAMVTXANSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-[(1r)-1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1[C@H]([C@@H](C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-CAMVTXANSA-N 0.000 title 1
- DNYGXMICFMACRA-UHFFFAOYSA-N gentamicin C1A Natural products O1C(CNC)CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N DNYGXMICFMACRA-UHFFFAOYSA-N 0.000 title 1
- -1 cyclic imide Chemical class 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 34
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- 150000003839 salts Chemical class 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 125000006239 protecting group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- VIAXDDBFFSKHGA-UHFFFAOYSA-N Antibiotic G52 Natural products CNC1CC(N)C(OC2OCC(C)(O)C(NC)C2O)C(O)C1OC3OC(=CCC3N)CN VIAXDDBFFSKHGA-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 150000004678 hydrides Chemical class 0.000 claims description 13
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- 239000000376 reactant Substances 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- ARCVBMPERJRMKB-UHFFFAOYSA-N antibiotic g-52 Chemical compound O1C(CNC)=CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N ARCVBMPERJRMKB-UHFFFAOYSA-N 0.000 claims description 10
- URWAJWIAIPFPJE-VHLNBGGKSA-N (2r,3r,4r,5r)-2-[(1s,2r,3r,4s,6r)-4,6-diamino-3-[[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-VHLNBGGKSA-N 0.000 claims description 9
- ZWWVMGQAOAIIQO-UHFFFAOYSA-N Mutamicin 2 Natural products CNC1C(O)C(OC2CC(OC3OC(=CCC3N)CN)C(N)CC2N)OCC1(C)O ZWWVMGQAOAIIQO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- WYJSPPYVEJPMJA-DJWUNRQOSA-N Antibiotic JI-20B Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H]([C@@H](C)N)O2)N)[C@@H](N)C[C@H]1N WYJSPPYVEJPMJA-DJWUNRQOSA-N 0.000 claims description 8
- RHRAMPXHWHSKQB-GGEUKFTFSA-N betamicin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)O)[C@@H](N)C[C@H]1N RHRAMPXHWHSKQB-GGEUKFTFSA-N 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- RHRAMPXHWHSKQB-UHFFFAOYSA-N gentamicin B Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(C(O)C(O)C(CN)O2)O)C(N)CC1N RHRAMPXHWHSKQB-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
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- 239000000243 solution Substances 0.000 description 81
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- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 230000000398 anti-amebic effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 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 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- CDSGJHCARATGKG-UHFFFAOYSA-N bis(3-methylbutyl)borane Chemical compound CC(C)CCBCCC(C)C CDSGJHCARATGKG-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000003999 cyclitols Chemical class 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- HUQOFZLCQISTTJ-UHFFFAOYSA-N diethylaminoboron Chemical compound CCN([B])CC HUQOFZLCQISTTJ-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YPTUAQWMBNZZRN-UHFFFAOYSA-N dimethylaminoboron Chemical compound [B]N(C)C YPTUAQWMBNZZRN-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- CEAZRRDELHUEMR-UHFFFAOYSA-N gentamicin Chemical class O1C(C(C)NC)CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N CEAZRRDELHUEMR-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- ANAFTYVSHCSQPP-UHFFFAOYSA-N lithium;trimethoxyalumane Chemical compound [Li].CO[Al](OC)OC ANAFTYVSHCSQPP-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- KEWWQVKVKJMZLL-UHFFFAOYSA-N methyl 2-acetamido-3-hydroxyoctanoate Chemical compound CCCCCC(O)C(NC(C)=O)C(=O)OC KEWWQVKVKJMZLL-UHFFFAOYSA-N 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 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
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940045681 other alkylating agent in atc Drugs 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical class CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229960001435 sisomicin sulfate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- ACWQBUSCFPJUPN-HWKANZROSA-N trans-2-methyl-2-butenal Chemical compound C\C=C(/C)C=O ACWQBUSCFPJUPN-HWKANZROSA-N 0.000 description 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 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
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
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
-
- 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
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
- C07H15/236—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
-
- 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
- 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)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI802746A FI62843C (fi) | 1973-08-06 | 1980-09-01 | Foerfarande foer framstaellning av ett syraadditionssalt av 1--etylsisomicin |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38575173A | 1973-08-06 | 1973-08-06 | |
| US38575173 | 1973-08-06 | ||
| US45260074A | 1974-03-19 | 1974-03-19 | |
| US45260074 | 1974-03-19 | ||
| US05/452,586 US4029882A (en) | 1974-03-19 | 1974-03-19 | Selective acylation of the C-1 amino group of aminoglycoside antibiotics |
| US45258674 | 1974-03-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI230474A7 FI230474A7 (en)) | 1975-02-07 |
| FI62100B FI62100B (fi) | 1982-07-30 |
| FI62100C true FI62100C (fi) | 1982-11-10 |
Family
ID=27409729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2304/74A FI62100C (fi) | 1973-08-06 | 1974-08-01 | Foerfarande foer framstaellning av 1-n-substituerade derivat av 4,6-di-(aminoglykosyl)-1,3-diaminocyklitolerna gentamicin b gentamicin c1 gentamicin c1a sisomicin verdamicin antibiotikum ji-20b antibiotikum g-52 mutamicin 2 och mutamicin 6 |
Country Status (20)
| Country | Link |
|---|---|
| AR (1) | AR215834A1 (en)) |
| BE (1) | BE818431A (en)) |
| BG (1) | BG25804A3 (en)) |
| CH (1) | CH606076A5 (en)) |
| CY (1) | CY1018A (en)) |
| DD (1) | DD119037A5 (en)) |
| DE (2) | DE2437160C3 (en)) |
| DK (1) | DK146298C (en)) |
| FI (1) | FI62100C (en)) |
| FR (1) | FR2240015B1 (en)) |
| GB (1) | GB1473733A (en)) |
| HK (1) | HK55179A (en)) |
| IE (1) | IE40437B1 (en)) |
| IL (1) | IL45385A (en)) |
| KE (1) | KE2981A (en)) |
| LU (1) | LU70661A1 (en)) |
| MY (1) | MY8000090A (en)) |
| NL (1) | NL171587C (en)) |
| NO (1) | NO139483C (en)) |
| SE (1) | SE424994B (en)) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1464401A (en) * | 1974-10-26 | 1977-02-16 | Pfizer Ltd | Aminoglycosides |
| US4217446A (en) | 1974-10-26 | 1980-08-12 | Pfizer Inc. | ωAmino-2-hydroxyalkyl derivatives of aminoglycoside antibiotics |
| FR2405266A1 (fr) * | 1975-09-08 | 1979-05-04 | Scherico Ltd | Nouveaux pseudotrisaccharides, et applications pharmaceutiques de ceux-ci |
| US4190722A (en) * | 1977-06-10 | 1980-02-26 | Bayer Aktiengesellschaft | 4,6-Di-O-(aminoglycosyl)-1,3-diaminocyclitols, process for their production and their use |
| US4282350A (en) * | 1977-08-05 | 1981-08-04 | Schering Corporation | Selective 3"-N-acylation of 1,3"-di-N-unprotected-poly-N-protected-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols |
| JPS5492951A (en) * | 1977-12-29 | 1979-07-23 | Shionogi & Co Ltd | Novel aminoglycoside derivative |
| JPS5538345A (en) * | 1978-09-11 | 1980-03-17 | Shionogi & Co Ltd | Novel aminoglycoside derivative |
| DE2840907A1 (de) * | 1978-09-20 | 1980-04-03 | Bayer Ag | Selektiv geschuetzte 4,6-di-o-(aminoglykosyl)-1,3-diaminocyclitole |
| DE2928183A1 (de) * | 1979-07-12 | 1981-01-29 | Bayer Ag | 1-n-alkylsisomicin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| CN1040177C (zh) * | 1993-04-23 | 1998-10-14 | 江苏省微生物研究所 | 一种含1-N-乙基庆大霉素C1a或其盐的药用制剂及制备方法 |
| MX2010005632A (es) | 2007-11-21 | 2010-09-10 | Achaogen Inc | Analogos de aminoglucosidos antibacterianos. |
| WO2010132765A2 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010132760A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of tobramycin |
| WO2010132757A2 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010132768A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of sisomicin |
| WO2010132759A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of dibekacin |
| CN101575311B (zh) * | 2009-06-19 | 2011-05-04 | 无锡好芳德药业有限公司 | 一种制备褪黑素的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1235311B (de) * | 1963-03-25 | 1967-03-02 | Roussel Uclaf | Verfahren zur Herstellung von N-Monophenylaethylneomycin B bzw. seinen therapeutisch vertraeglichen Salzen |
-
1974
- 1974-07-31 CH CH1060274A patent/CH606076A5/xx not_active IP Right Cessation
- 1974-08-01 AR AR255007A patent/AR215834A1/es active
- 1974-08-01 FI FI2304/74A patent/FI62100C/sv active
- 1974-08-01 DK DK412474A patent/DK146298C/da not_active IP Right Cessation
- 1974-08-01 DE DE2437160A patent/DE2437160C3/de not_active Expired
- 1974-08-01 GB GB3396874A patent/GB1473733A/en not_active Expired
- 1974-08-01 IE IE1638/74A patent/IE40437B1/en not_active IP Right Cessation
- 1974-08-01 CY CY1018A patent/CY1018A/xx unknown
- 1974-08-01 SE SE7409946A patent/SE424994B/xx not_active IP Right Cessation
- 1974-08-01 DE DE2462485A patent/DE2462485C2/de not_active Expired
- 1974-08-01 NL NLAANVRAGE7410363,A patent/NL171587C/xx not_active IP Right Cessation
- 1974-08-01 NO NO742787A patent/NO139483C/no unknown
- 1974-08-01 FR FR7426815A patent/FR2240015B1/fr not_active Expired
- 1974-08-02 LU LU70661A patent/LU70661A1/xx unknown
- 1974-08-02 BE BE147234A patent/BE818431A/xx not_active IP Right Cessation
- 1974-08-02 IL IL45385A patent/IL45385A/xx unknown
- 1974-08-05 DD DD180344A patent/DD119037A5/xx unknown
- 1974-08-06 BG BG027440A patent/BG25804A3/xx unknown
-
1979
- 1979-07-09 KE KE2981A patent/KE2981A/xx unknown
- 1979-08-09 HK HK551/79A patent/HK55179A/xx unknown
-
1980
- 1980-12-30 MY MY90/80A patent/MY8000090A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK146298C (da) | 1984-02-06 |
| HK55179A (en) | 1979-08-17 |
| NO742787L (en)) | 1975-03-03 |
| NO139483B (no) | 1978-12-11 |
| MY8000090A (en) | 1980-12-31 |
| AU7194274A (en) | 1976-02-05 |
| DE2437160C3 (de) | 1979-08-30 |
| DE2437160B2 (de) | 1979-01-04 |
| IE40437L (en) | 1975-02-06 |
| CY1018A (en) | 1979-11-23 |
| IE40437B1 (en) | 1979-06-06 |
| LU70661A1 (en)) | 1975-05-21 |
| DE2462485C2 (de) | 1987-04-09 |
| DE2437160A1 (de) | 1975-02-20 |
| NL171587C (nl) | 1983-04-18 |
| IL45385A (en) | 1978-10-31 |
| IL45385A0 (en) | 1974-11-29 |
| DD119037A5 (en)) | 1976-04-05 |
| DE2462485A1 (de) | 1977-04-21 |
| BG25804A3 (bg) | 1978-12-12 |
| DK412474A (en)) | 1975-04-01 |
| FI230474A7 (en)) | 1975-02-07 |
| SE424994B (sv) | 1982-08-23 |
| KE2981A (en) | 1979-07-20 |
| BE818431A (fr) | 1975-02-03 |
| FR2240015B1 (en)) | 1978-08-18 |
| AR215834A1 (es) | 1979-11-15 |
| FI62100B (fi) | 1982-07-30 |
| NL7410363A (nl) | 1975-02-10 |
| CH606076A5 (en)) | 1978-10-13 |
| FR2240015A1 (en)) | 1975-03-07 |
| NL171587B (nl) | 1982-11-16 |
| NO139483C (no) | 1979-03-21 |
| SE7409946L (en)) | 1975-02-07 |
| GB1473733A (en) | 1977-05-18 |
| DK146298B (da) | 1983-08-29 |
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