NO780445L - Everninomicinderivater og fremstilling av disse - Google Patents

Everninomicinderivater og fremstilling av disse

Info

Publication number: NO780445L
Authority: NO; Norway
Prior art keywords: aminoeverninomicin; pharmaceutically acceptable; compound according; starting material; group
Prior art date: 1977-02-14

Application number

NO780445A

Other languages

English (en)

Norwegian (no)

Inventor

Viyyoor Moopil Girijavallabhan

Ashit Kumar Ganguly

Hans Reimann

Olga Sarre

Original Assignee

Scherico 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.)

1977-02-14

Filing date

1978-02-09

Publication date

1978-08-15

1978-02-09 Application filed by Scherico Ltd filed Critical Scherico Ltd

1978-08-15 Publication of NO780445L publication Critical patent/NO780445L/no

Links

UPADRKHAIMTUCC-OWALTSPQSA-N [(2r,3r,4r,6s)-6-[(2r,2'r,3's,3ar,4r,4'r,6s,7s,7ar)-6-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4s,5s,6s)-6-[(3ar,3'as,4r,6's,7r,7'r,7as,7'as)-7-(2,4-dihydroxy-6-methylbenzoyl)oxy-7'-hydroxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,2'-4,6,7,7a-tetrahydro-3a Chemical class O([C@@H]1CO[C@]2([C@@H]3OCO[C@H]31)O[C@H]1CO[C@H]([C@@H]([C@@H]1O2)O)O[C@@H]1O[C@@H]([C@H]([C@H](O)[C@@H]1OC)O[C@H]1[C@@H]([C@@H](O[C@H]2[C@H]([C@@]3(C)O[C@]4(O[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@@H](OC(=O)C=6C(=C(Cl)C(O)=C(Cl)C=6C)OC)[C@H](O[C@@H]6O[C@@H](C)[C@H](OC)[C@](C)(C6)[N+]([O-])=O)C5)[C@H](O)C4)O[C@@H]3[C@@H](C)O2)O)[C@@H](OC)[C@@H](C)O1)O)COC)C(=O)C1=C(C)C=C(O)C=C1O UPADRKHAIMTUCC-OWALTSPQSA-N 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims description 6
238000000034 method Methods 0.000 claims description 88
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
150000001875 compounds Chemical class 0.000 claims description 42
150000003839 salts Chemical class 0.000 claims description 34
239000007858 starting material Substances 0.000 claims description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
230000008569 process Effects 0.000 claims description 23
239000000047 product Substances 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
238000006722 reduction reaction Methods 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
239000011541 reaction mixture Substances 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 15
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 14
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 14
-1 hydroxylamino group Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 11
229930188253 Everninomicin Natural products 0.000 claims description 10
230000002829 reductive effect Effects 0.000 claims description 10
229910000761 Aluminium amalgam Inorganic materials 0.000 claims description 9
238000005984 hydrogenation reaction Methods 0.000 claims description 9
239000000725 suspension Substances 0.000 claims description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 8
150000008064 anhydrides Chemical class 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
230000006181 N-acylation Effects 0.000 claims description 7
150000008065 acid anhydrides Chemical class 0.000 claims description 7
230000010933 acylation Effects 0.000 claims description 7
238000005917 acylation reaction Methods 0.000 claims description 7
230000000844 anti-bacterial effect Effects 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 7
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 5
239000007868 Raney catalyst Substances 0.000 claims description 5
229910000564 Raney nickel Inorganic materials 0.000 claims description 5
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
150000001413 amino acids Chemical class 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 5
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
229910052782 aluminium Inorganic materials 0.000 claims description 4
235000019270 ammonium chloride Nutrition 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
150000001844 chromium Chemical class 0.000 claims description 4
WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical group [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
239000003182 parenteral nutrition solution Substances 0.000 claims description 4
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 4
208000035143 Bacterial infection Diseases 0.000 claims description 3
238000007126 N-alkylation reaction Methods 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
208000022362 bacterial infectious disease Diseases 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
230000007935 neutral effect Effects 0.000 claims description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 3
229910003446 platinum oxide Inorganic materials 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
238000005932 reductive alkylation reaction Methods 0.000 claims description 3
229910052725 zinc Inorganic materials 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000000842 isoxazolyl group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
239000004411 aluminium Substances 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 1
235000011114 ammonium hydroxide Nutrition 0.000 claims 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
229950002947 evernimicin Drugs 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
239000000243 solution Substances 0.000 description 25
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229910052796 boron Inorganic materials 0.000 description 9
239000012141 concentrate Substances 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
239000008363 phosphate buffer Substances 0.000 description 5
239000002002 slurry Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
235000001014 amino acid Nutrition 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
238000011946 reduction process Methods 0.000 description 4
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 4
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
238000005755 formation reaction Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical group O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 2
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-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
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
UPADRKHAIMTUCC-JBNGTWNESA-N Everninomycin Chemical class O([C@@H]1CO[C@]2([C@@H]3OCO[C@H]31)O[C@H]1CO[C@H]([C@@H]([C@@H]1O2)O)O[C@@H]1O[C@@H](C([C@H](O)C1OC)O[C@H]1[C@@H]([C@H](O[C@H]2[C@H]([C@@]3(C)OC4(O[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@@H](OC(=O)C=6C(=C(Cl)C(O)=C(Cl)C=6C)OC)[C@H](O[C@H]6O[C@@H](C)[C@H](OC)[C@](C)(C6)[N+]([O-])=O)C5)[C@H](O)C4)O[C@@H]3[C@@H](C)O2)O)[C@@H](OC)[C@@H](C)O1)O)COC)C(=O)C1=C(C)C=C(O)C=C1O UPADRKHAIMTUCC-JBNGTWNESA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
HZLMUDOBOCVXQT-YOQBUGDQSA-N [(2r,3r,4r,6s)-6-[(2r,2'r,3's,3ar,4r,4'r,6s,7ar)-6-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4s,5s,6s)-6-[(2r,3as,3'ar,6s,7r,7'r,7ar,7'ar)-7'-hydroxy-7-methoxy-7'-[(1s)-1-methoxyethyl]spiro[4,6,7,7a-tetrahydro-3ah-[1,3]dioxolo[4,5-c]pyran-2,4'-6,7a-dihydro-3ah-[1,3]dio Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1OC(=O)C=1C(=C(Cl)C(O)=C(Cl)C=1C)OC)O[C@H]1[C@H](O)C[C@@]2(O[C@]3(C)C[C@@H](O[C@H](C)[C@H]3O2)O[C@H]2[C@@H](OC)[C@@H](C)O[C@H]([C@@H]2O)O[C@H]2[C@H](O)[C@H](OC)[C@H](O[C@H]3[C@@H]([C@@H]4O[C@]5(O[C@H]4CO3)[C@@H]3OCO[C@H]3[C@](O)([C@H](C)OC)CO5)OC)O[C@@H]2COC)O[C@@H]1C)[C@H]1C[C@](C)([N+]([O-])=O)[C@@H](OC)[C@H](C)O1 HZLMUDOBOCVXQT-YOQBUGDQSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229940117916 cinnamic aldehyde Drugs 0.000 description 2
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 2
150000001924 cycloalkanes Chemical class 0.000 description 2
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
229960002216 methylparaben Drugs 0.000 description 2
244000005700 microbiome Species 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
229960003415 propylparaben Drugs 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
238000006894 reductive elimination reaction Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
241000894007 species Species 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
229940005605 valeric acid Drugs 0.000 description 2
238000005406 washing Methods 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
LDXUQIQQIPCVEE-UHFFFAOYSA-N 2-(n-phenylmethoxycarbonylanilino)acetic acid Chemical compound C=1C=CC=CC=1N(CC(=O)O)C(=O)OCC1=CC=CC=C1 LDXUQIQQIPCVEE-UHFFFAOYSA-N 0.000 description 1
RLDJWBVOZVJJOS-UHFFFAOYSA-N 2-phenyl-2-(phenylmethoxycarbonylamino)acetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NC(=O)OCC1=CC=CC=C1 RLDJWBVOZVJJOS-UHFFFAOYSA-N 0.000 description 1
SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical compound OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
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 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical class [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
241000218955 Micromonospora carbonacea Species 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
241000786363 Rhampholeon spectrum 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
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
239000004473 Threonine Substances 0.000 description 1
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
241000857212 Varanus nebulosus Species 0.000 description 1
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 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
238000004821 distillation Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000008570 general process Effects 0.000 description 1
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
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 description 1
150000002431 hydrogen Chemical group 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000007788 liquid Substances 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
229960002510 mandelic acid Drugs 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229960002523 mercuric chloride Drugs 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
150000002832 nitroso derivatives Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
239000004474 valine Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

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

NO780445A 1977-02-14 1978-02-09 Everninomicinderivater og fremstilling av disse NO780445L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US76812477A	1977-02-14	1977-02-14

Publications (1)

Publication Number	Publication Date
NO780445L true NO780445L (no)	1978-08-15

Family

ID=25081594

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO780445A NO780445L (no)	1977-02-14	1978-02-09	Everninomicinderivater og fremstilling av disse

Country Status (15)

Country	Link
US (1)	US4129720A (fr)
JP (1)	JPS53103495A (fr)
AT (1)	ATA90478A (fr)
AU (1)	AU3313978A (fr)
BE (1)	BE863802A (fr)
DE (1)	DE2805408A1 (fr)
DK (1)	DK61778A (fr)
FI (1)	FI780420A7 (fr)
FR (1)	FR2384791A1 (fr)
GB (1)	GB1589954A (fr)
IL (1)	IL54013A0 (fr)
NL (1)	NL7801522A (fr)
NO (1)	NO780445L (fr)
PT (1)	PT67635B (fr)
ZA (1)	ZA78808B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4767748A (en) *	1985-10-15	1988-07-30	Schering Corporation	Substituted oligosaccharide antibodies
US5150906A (en) *	1989-03-10	1992-09-29	Lisco, Inc.	Multi-piece golf balls and methods of manufacture
NZ244735A (en) *	1991-10-16	1995-12-21	Schering Corp	Pharmaceutical compositions containing a lipophilic oligosaccharide antibiotic salt
US5763600A (en) *	1997-04-18	1998-06-09	Schering Corporation	Oligosaccharide antibiotics and process for preparation thereof
JP5862787B2 (ja) *	2012-02-24	2016-02-16	ダイキン工業株式会社	フッ素ゴム組成物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3920629A (en) *	1973-09-19	1975-11-18	Schering Corp	Desevernitrose everninomicins and method for their manufacture
US4006225A (en) *	1973-10-31	1977-02-01	Schering Corporation	Method of using reduction products of everninomicins as antibacterial agents and pharmaceutical compositions useful therefor
US3901973A (en) *	1973-11-05	1975-08-26	Schering Corp	Antibiotic everninomicin 1
US3998708A (en) *	1976-01-19	1976-12-21	Schering Corporation	Electrochemical process for preparing hydroxylaminoeverninomicins

1977
- 1977-09-16 US US05/833,838 patent/US4129720A/en not_active Expired - Lifetime
1978
- 1978-02-09 PT PT67635A patent/PT67635B/pt unknown
- 1978-02-09 AT AT90478A patent/ATA90478A/de not_active IP Right Cessation
- 1978-02-09 AU AU33139/78A patent/AU3313978A/en active Pending
- 1978-02-09 DE DE19782805408 patent/DE2805408A1/de not_active Withdrawn
- 1978-02-09 IL IL54013A patent/IL54013A0/xx unknown
- 1978-02-09 FR FR7803662A patent/FR2384791A1/fr not_active Withdrawn
- 1978-02-09 GB GB5286/78A patent/GB1589954A/en not_active Expired
- 1978-02-09 BE BE185032A patent/BE863802A/fr unknown
- 1978-02-09 NO NO780445A patent/NO780445L/no unknown
- 1978-02-09 NL NL7801522A patent/NL7801522A/xx not_active Application Discontinuation
- 1978-02-09 FI FI780420A patent/FI780420A7/fi not_active Application Discontinuation
- 1978-02-10 JP JP1487178A patent/JPS53103495A/ja active Pending
- 1978-02-10 ZA ZA00780808A patent/ZA78808B/xx unknown
- 1978-02-10 DK DK61778A patent/DK61778A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
FR2384791A1 (fr)	1978-10-20
BE863802A (fr)	1978-08-09
IL54013A0 (en)	1978-04-30
GB1589954A (en)	1981-05-20
AU3313978A (en)	1979-08-16
US4129720A (en)	1978-12-12
PT67635B (en)	1979-07-18
DK61778A (da)	1978-08-15
DE2805408A1 (de)	1978-08-17
ATA90478A (de)	1980-10-15
NL7801522A (nl)	1978-08-16
JPS53103495A (en)	1978-09-08
PT67635A (en)	1978-03-01
FI780420A7 (fi)	1978-08-15
ZA78808B (en)	1979-01-31

Publication	Publication Date	Title
JP5490384B2 (ja)	2014-05-14	キラル化合物の調製方法
AU618483B2 (en)	1991-12-19	Dioxothiazolidine derivatives
JP4237224B2 (ja)	2009-03-11	ノイラミニダーゼ阻害剤ｒ６を調製するためのアジドを含まない方法
WO1998004543A1 (fr)	1998-02-05	Procede ameliore de synthese d'esters proteges de l'acide (s)-3,4-dihydroxybutyrique
JP2002526467A (ja)	2002-08-20	新規のＨＭＧ−ＣｏＡレダクターゼインヒビターの塩
Maehr et al.	1980	The chemistry of aurodox and related antibiotics
JP3298644B2 (ja)	2002-07-02	Ｎ‐アセチルノイラミン酸誘導体の製造法
NO780445L (no)	1978-08-15	Everninomicinderivater og fremstilling av disse
Ganguly et al.	1982	Chemical modification of everninomicins
BG64701B1 (bg)	2005-12-30	Метод за получаване на 2-азадихидроксибицикло[2.2.1]хептаново съединение и сол на съединението и l-винена киселина
JPH0331259A (ja)	1991-02-12	新規フコシダーゼ阻害剤
FR2801054A1 (fr)	2001-05-18	Nouveaux derives de 12,13-(pyranosyl)-indolo[2,3-a]pyrrolo [3,4-c]carbazole et 12,13-(pyranosyl)-furo[3,4-c]indolo [2,3-a]carbazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP0241541A1 (fr)	1987-10-21	Nouveaux derives du complexe 13-384 antibiotique oligosaccharide, leur preparation et compositions pharmaceutiques les contenant
EP0040764B1 (fr)	1983-07-20	Aminoglycosides et leur emploi antibiotique
US4290972A (en)	1981-09-22	Process for the production of 4-aminobutyric acid or its derivatives
FR2566410A1 (fr)	1985-12-27	Nouveaux derives de l'acide diaminopimelique, leur procede de preparation et leur application en therapeutique
RU2807924C1 (ru)	2023-11-21	N-ЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ 6α-ПИПЕРАЗИНОМЕТИЛАНДРОСТ-4-ЕН-3,17-ДИОНА, ОБЛАДАЮЩИЕ АНТИМИКРОБНОЙ АКТИВНОСТЬЮ, И СПОСОБ ИХ ПОЛУЧЕНИЯ
US3681398A (en)	1972-08-01	5-acetamide-6-methyltetrahydropyran-2-one and method for its production
KR20070087258A (ko)	2007-08-27	아릴 융합된 폴리시클릭 락탐의 제조 방법
JPS60204750A (ja)	1985-10-16	ＤＬ‐β‐アリールアミノ酸の調製方法
JPH07508046A (ja)	1995-09-07	オルニチンデカルボキシラーゼを阻害する枝分れアミノオキシアミノアルカン誘導体
HU191813B (en)	1987-04-28	Process for preparing carnitine amide chloride
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SU1190988A3 (ru)	1985-11-07	Способ получени 1- @ -(-)- @ -амино- @ -оксибутирил @ канамицина @
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