CA1105458A - Spectinomycin derivatives and processes for their preparation - Google Patents

Spectinomycin derivatives and processes for their preparation

Info

Publication number: CA1105458A
Authority: CA; Canada
Prior art keywords: carbonyl; group; bis; process according; carbon atoms
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

CA318,316A

Other languages

English (en)

French (fr)

Inventor

Roland Maier

Eberhard Woitun

Wolfgang Reuter

Bernd Wetzel

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.)

Boehringer Ingelheim Pharma GmbH and Co KG

Original Assignee

Individual

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

1978-12-20

Publication date

1981-07-21

1978-12-20 Application filed by Individual filed Critical Individual

1981-07-21 Application granted granted Critical

1981-07-21 Publication of CA1105458A publication Critical patent/CA1105458A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 46
230000008569 process Effects 0.000 title claims description 42
UNFWWIHTNXNPBV-WXKVUWSESA-N spectinomycin Chemical class O([C@@H]1[C@@H](NC)[C@@H](O)[C@H]([C@@H]([C@H]1O1)O)NC)[C@]2(O)[C@H]1O[C@H](C)CC2=O UNFWWIHTNXNPBV-WXKVUWSESA-N 0.000 title claims description 33
238000002360 preparation method Methods 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 26
239000002253 acid Substances 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 8
125000006239 protecting group Chemical group 0.000 claims abstract description 3
-1 2-(p-tolylsulfonyl)-ethoxy carbonyl Chemical group 0.000 claims description 94
229960000268 spectinomycin Drugs 0.000 claims description 45
125000004432 carbon atom Chemical group C* 0.000 claims description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
239000000126 substance Substances 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 10
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
150000007522 mineralic acids Chemical class 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
125000000962 organic group Chemical group 0.000 claims description 3
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
229910052697 platinum Inorganic materials 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
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 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
UJQDRPLHEPIIAC-FDYZEBBJSA-N 2-[(z)-[(3z)-3-(diaminomethylidenehydrazinylidene)cyclopenta[b]naphthalen-1-ylidene]amino]guanidine Chemical compound C1=CC=C2C=C3C(=N/N=C(N)N)\C\C(=N\N=C(N)N)C3=CC2=C1 UJQDRPLHEPIIAC-FDYZEBBJSA-N 0.000 claims 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 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
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
YXJYBPXSEKMEEJ-UHFFFAOYSA-N phosphoric acid;sulfuric acid Chemical compound OP(O)(O)=O.OS(O)(=O)=O YXJYBPXSEKMEEJ-UHFFFAOYSA-N 0.000 claims 1
230000000845 anti-microbial effect Effects 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
239000000741 silica gel Substances 0.000 description 26
229910002027 silica gel Inorganic materials 0.000 description 26
229960001701 chloroform Drugs 0.000 description 24
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000001913 cellulose Substances 0.000 description 8
229920002678 cellulose Polymers 0.000 description 8
239000000047 product Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000001819 mass spectrum Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
241000194017 Streptococcus Species 0.000 description 3
YQKFJYBRZVNXKQ-UHFFFAOYSA-N [Na].BC#N Chemical compound [Na].BC#N YQKFJYBRZVNXKQ-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
BOVISBAPSYSQPI-UHFFFAOYSA-N (4-methoxyphenyl)methyl carbonochloridate Chemical compound COC1=CC=C(COC(Cl)=O)C=C1 BOVISBAPSYSQPI-UHFFFAOYSA-N 0.000 description 2
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000588747 Klebsiella pneumoniae Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
241000588770 Proteus mirabilis Species 0.000 description 2
241000589517 Pseudomonas aeruginosa Species 0.000 description 2
241000607715 Serratia marcescens Species 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
244000052616 bacterial pathogen Species 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
229940045505 klebsiella pneumoniae Drugs 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000000843 powder Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 1
LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000901842 Escherichia coli W Species 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
OAYGUTJTMLRJHU-UHFFFAOYSA-N anisole;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.COC1=CC=CC=C1 OAYGUTJTMLRJHU-UHFFFAOYSA-N 0.000 description 1
WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
229910001626 barium chloride Inorganic materials 0.000 description 1
WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229940098362 serratia marcescens Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VYGSFTVYZHNGBU-UHFFFAOYSA-N trichloromethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)Cl VYGSFTVYZHNGBU-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
- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CA318,316A 1977-12-21 1978-12-20 Spectinomycin derivatives and processes for their preparation Expired CA1105458A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19772756913 DE2756913A1 (de)	1977-12-21	1977-12-21	Spectinomycinderivate und verfahren zu ihrer herstellung
DEP2756913.7		1977-12-21

Publications (1)

Publication Number	Publication Date
CA1105458A true CA1105458A (en)	1981-07-21

Family

ID=6026672

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA318,316A Expired CA1105458A (en)	1977-12-21	1978-12-20	Spectinomycin derivatives and processes for their preparation

Country Status (9)

Country	Link
AT (2)	AT362063B (pt)
CA (1)	CA1105458A (pt)
DE (1)	DE2756913A1 (pt)
DK (1)	DK572778A (pt)
ES (1)	ES476163A1 (pt)
FI (1)	FI783899A7 (pt)
GR (1)	GR65311B (pt)
NO (1)	NO784298L (pt)
PT (1)	PT68953A (pt)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4465848A (en) *	1981-10-23	1984-08-14	The Upjohn Company	Spectinomycin compounds
US4523022A (en) *	1983-07-07	1985-06-11	The Upjohn Company	Analogs of the antibiotic spectinomycin
US4603212A (en) *	1983-10-18	1986-07-29	The Upjohn Company	Analogs of the antibiotic spectinomycin

1977
- 1977-12-21 DE DE19772756913 patent/DE2756913A1/de not_active Withdrawn
1978
- 1978-12-04 AT AT862978A patent/AT362063B/de not_active IP Right Cessation
- 1978-12-14 GR GR57884A patent/GR65311B/el unknown
- 1978-12-19 FI FI783899A patent/FI783899A7/fi unknown
- 1978-12-20 ES ES476163A patent/ES476163A1/es not_active Expired
- 1978-12-20 NO NO784298A patent/NO784298L/no unknown
- 1978-12-20 DK DK572778A patent/DK572778A/da not_active Application Discontinuation
- 1978-12-20 PT PT68953A patent/PT68953A/pt unknown
- 1978-12-20 CA CA318,316A patent/CA1105458A/en not_active Expired
- 1978-12-21 AT AT912478A patent/AT362066B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
NO784298L (no)	1979-06-22
GR65311B (en)	1980-08-02
ES476163A1 (es)	1979-05-01
DE2756913A1 (de)	1979-07-05
ATA862978A (de)	1980-09-15
ATA912478A (de)	1980-09-15
AT362066B (de)	1981-04-27
PT68953A (de)	1979-01-01
DK572778A (da)	1979-06-22
AT362063B (de)	1981-04-27
FI783899A7 (fi)	1979-06-22

Legal Events

Date	Code	Title	Description
1998-07-21	MKEX	Expiry

Publication	Publication Date	Title
US3579579A (en)	1971-05-18	Substituted 7- and/or 9-amino-6-demethyl-6-deoxytetracyclines
US3518306A (en)	1970-06-30	7- and/or 9-(n-nitrosoalkylamino)-6-demethyl-6-deoxytetracyclines
GB2042523A (en)	1980-09-24	Geldanamycin derivatives and anti-tumor drug
EP0253340B1 (en)	1993-09-29	Alkyl-substituted benzoxazinorifamycin derivative, process for preparing the same and antibacterial agent containing the same
US4173647A (en)	1979-11-06	4-Spectinomycylamine and salts thereof
EP0087905B1 (en)	1985-08-21	4"-epi erythromycin a and derivatives thereof as useful antibacterial agents
EP0080818A1 (en)	1983-06-08	Erythromycin B derivatives
CA1129852A (en)	1982-08-17	Aminoglycoside derivatives
EP0132944A1 (en)	1985-02-13	Antibacterial homoerythromycin A derivatives and intermediates therefor
US4382086A (en)	1983-05-03	9-Dihydro-11,12-ketal derivatives of erythromycin A and epi-erythromycin A
US4273923A (en)	1981-06-16	Process for preparing aminoglycoside derivatives
US3769273A (en)	1973-10-30	Bis-urea adducts of macrolide antibiotics
SU1054352A1 (ru)	1983-11-15	N-гликозиловые производные даунорубицина,про вл ющие антибиотическую активность
JPH0633310B2 (ja)	1994-05-02	１１−アザ−１０−デオキソ−１０−ジヒドロエリスロマイシンａ又はそのｎ−メチル誘導体の金属錯塩及びそれらの製造法
US3306821A (en)	1967-02-28	Porfiromycin derivatives and method of making same
Snyder Jr et al.	1977	Imidazo [4, 5‐f] quinolines III: Antibacterial 7‐methyl‐9‐(substituted arylamino) imidazo [4, 5‐f] quinolines
IE52912B1 (en)	1988-04-13	4"-modified methylene oleandomycins
US3915956A (en)	1975-10-28	Reduction products of everninomicins and methods for their manufacture
EP0189281A2 (en)	1986-07-30	Antibacterial derivatives of a neutral macrolide
KR810001504B1 (ko)	1981-10-25	스펙티노 마이신 유도체의 제조방법
DE2820637A1 (de)	1978-11-16	Fortimicin-derivate und ihre salze, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung bakterieller infektionen
US4281107A (en)	1981-07-28	Neamine derivatives and process for preparing the same
NO139562B (no)	1978-12-27	Analogifremgangsmaate til fremstilling av derivater av antibiotikum xk-62-2
CA1109466A (en)	1981-09-22	Spectinomycin derivatives, their salts with acids and processes for their preparation
KR820001126B1 (ko)	1982-06-26	4-스펙티노마이실아민의 제조방법