OA10557A - Nouveaux dérivés de la tylosine leur procédé de préparation et les compositions pharmaceutiques qui les contiennent - Google Patents

Nouveaux dérivés de la tylosine leur procédé de préparation et les compositions pharmaceutiques qui les contiennent Download PDF

Info

Publication number: OA10557A
Authority: OA; OAPI
Prior art keywords: formula; derivative; same meaning; group; carbonate
Prior art date: 1988-10-27

Application number

OA59672A

Other languages

English (en)

French (fr)

Inventor

Gabor Lukacs

Catherine Ruggeri-Duchatelle

Aimee Dessinges

Alain Olesker

Maria Laborde

Li Ming

Original Assignee

Adir

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.)

1988-10-27

Filing date

1989-10-27

Publication date

2002-05-30

1989-10-27 Application filed by Adir filed Critical Adir

2002-05-30 Publication of OA10557A publication Critical patent/OA10557A/fr

Links

WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical class O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 title claims description 38
238000002360 preparation method Methods 0.000 title claims description 9
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
238000000034 method Methods 0.000 title claims description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 54
-1 benzyloxyimino Chemical group 0.000 claims description 50
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
239000003960 organic solvent Substances 0.000 claims description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
239000000377 silicon dioxide Substances 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 13
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
238000004587 chromatography analysis Methods 0.000 claims description 12
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
239000002585 base Substances 0.000 claims description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
125000004430 oxygen atom Chemical group O* 0.000 claims description 9
238000000605 extraction Methods 0.000 claims description 8
229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
238000005406 washing Methods 0.000 claims description 8
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 7
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 7
238000004440 column chromatography Methods 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
230000021962 pH elevation Effects 0.000 claims description 7
229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
239000001632 sodium acetate Substances 0.000 claims description 7
235000017281 sodium acetate Nutrition 0.000 claims description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 7
235000017557 sodium bicarbonate Nutrition 0.000 claims description 7
235000017550 sodium carbonate Nutrition 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
UZFFXSFICBBZEA-UHFFFAOYSA-N n-benzylmethanimine oxide Chemical compound [O-][N+](=C)CC1=CC=CC=C1 UZFFXSFICBBZEA-UHFFFAOYSA-N 0.000 claims description 6
235000015497 potassium bicarbonate Nutrition 0.000 claims description 6
235000011181 potassium carbonates Nutrition 0.000 claims description 6
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
229910000019 calcium carbonate Inorganic materials 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
230000003115 biocidal effect Effects 0.000 claims description 4
235000010216 calcium carbonate Nutrition 0.000 claims description 4
ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 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
239000011736 potassium bicarbonate Substances 0.000 claims description 4
229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
229940086066 potassium hydrogencarbonate Drugs 0.000 claims description 4
238000000746 purification Methods 0.000 claims description 4
239000011877 solvent mixture Substances 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
238000007796 conventional method Methods 0.000 claims description 3
238000001640 fractional crystallisation Methods 0.000 claims description 3
150000002923 oximes Chemical class 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000004615 ingredient Substances 0.000 claims description 2
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
229960003975 potassium Drugs 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
CDGBOELIEDXBBR-UHFFFAOYSA-N OP(=O)OC#N Chemical compound OP(=O)OC#N CDGBOELIEDXBBR-UHFFFAOYSA-N 0.000 claims 1
XLUXHEZIGIDTCC-UHFFFAOYSA-N acetonitrile;ethyl acetate Chemical compound CC#N.CCOC(C)=O XLUXHEZIGIDTCC-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
239000004182 Tylosin Substances 0.000 description 23
229960004059 tylosin Drugs 0.000 description 23
229930194936 Tylosin Natural products 0.000 description 20
235000019375 tylosin Nutrition 0.000 description 20
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
230000003595 spectral effect Effects 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
238000003756 stirring Methods 0.000 description 9
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical class N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 8
239000003480 eluent Substances 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
ZVOOGERIHVAODX-QWWGUZMMSA-N 2-[(4r,5s,6s,7r,9r,11e,13e,15r,16r)-6-[(2r,3r,4r,5r,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-(hydroxymethyl)-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-d Chemical compound O=CC[C@H]1C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@H](CO)[C@@H](CC)OC(=O)C[C@@H](O)[C@H](C)[C@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1 ZVOOGERIHVAODX-QWWGUZMMSA-N 0.000 description 5
ZVOOGERIHVAODX-UHFFFAOYSA-N O-demycinosyltylosin Natural products O=CCC1CC(C)C(=O)C=CC(C)=CC(CO)C(CC)OC(=O)CC(O)C(C)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(O)C(C)(O)C2)C(C)O1 ZVOOGERIHVAODX-UHFFFAOYSA-N 0.000 description 5
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 5
HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
201000010099 disease Diseases 0.000 description 3
LKCAFSOYOMFQSL-UHFFFAOYSA-N hydron;o-[(4-nitrophenyl)methyl]hydroxylamine;chloride Chemical compound Cl.NOCC1=CC=C([N+]([O-])=O)C=C1 LKCAFSOYOMFQSL-UHFFFAOYSA-N 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
241000304886 Bacilli Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
241000588652 Neisseria gonorrhoeae Species 0.000 description 2
241000295644 Staphylococcaceae Species 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
239000002609 medium Substances 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
239000003826 tablet Substances 0.000 description 2
LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical class CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
BVJLPHPIQOZHNQ-JOOIDHKUSA-N 2-[(11e,13e)-6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[(5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl)oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde Chemical compound O=CCC1CC(C)C(=O)\C=C\C(\C)=C\C(COC2C(C(OC)C(O)C(C)O2)OC)C(CC)OC(=O)CC(O)C(C)C1OC1OC(C)CC(N(C)C)C1O BVJLPHPIQOZHNQ-JOOIDHKUSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241001480043 Arthrodermataceae Species 0.000 description 1
241000193738 Bacillus anthracis Species 0.000 description 1
241000588807 Bordetella Species 0.000 description 1
201000004813 Bronchopneumonia Diseases 0.000 description 1
241000589562 Brucella Species 0.000 description 1
206010006500 Brucellosis Diseases 0.000 description 1
229920002261 Corn starch Polymers 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
206010059024 Gastrointestinal toxicity Diseases 0.000 description 1
206010018612 Gonorrhoea Diseases 0.000 description 1
241000606790 Haemophilus Species 0.000 description 1
241000606768 Haemophilus influenzae Species 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 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
108010002352 Interleukin-1 Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241001430197 Mollicutes Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
208000005141 Otitis Diseases 0.000 description 1
208000035109 Pneumococcal Infections Diseases 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
208000006311 Pyoderma Diseases 0.000 description 1
241000606701 Rickettsia Species 0.000 description 1
101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
206010039587 Scarlet Fever Diseases 0.000 description 1
241000589970 Spirochaetales Species 0.000 description 1
206010056430 Staphylococcal sepsis Diseases 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
206010001093 acute tonsillitis Diseases 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
125000005466 alkylenyl group Chemical group 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006161 blood agar Substances 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000037304 dermatophytes Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
206010013023 diphtheria Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
208000019258 ear infection Diseases 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LTZZYVWUGIPISL-UHFFFAOYSA-N ethyl(hydroxy)azanium;chloride Chemical compound [Cl-].CC[NH2+]O LTZZYVWUGIPISL-UHFFFAOYSA-N 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
239000000499 gel Substances 0.000 description 1
208000001786 gonorrhea Diseases 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
XIQUJVRFXPBMHS-UHFFFAOYSA-N hydron;o-prop-2-enylhydroxylamine;chloride Chemical compound Cl.NOCC=C XIQUJVRFXPBMHS-UHFFFAOYSA-N 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
YSNXOQGDHGUKCZ-UHFFFAOYSA-N n-benzylhydroxylamine;hydron;chloride Chemical compound Cl.ONCC1=CC=CC=C1 YSNXOQGDHGUKCZ-UHFFFAOYSA-N 0.000 description 1
239000007923 nasal drop Substances 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
101150035983 str1 gene Proteins 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- 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)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

OA59672A 1988-10-27 1989-10-27 Nouveaux dérivés de la tylosine leur procédé de préparation et les compositions pharmaceutiques qui les contiennent OA10557A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8814004A FR2638458A1 (fr)	1988-10-27	1988-10-27	Nouveaux derives de la tylosine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Publications (1)

Publication Number	Publication Date
OA10557A true OA10557A (fr)	2002-05-30

Family

ID=9371300

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA59672A OA10557A (fr)	1988-10-27	1989-10-27	Nouveaux dérivés de la tylosine leur procédé de préparation et les compositions pharmaceutiques qui les contiennent

Country Status (11)

Country	Link
US (1)	US5032581A (de)
EP (1)	EP0366560A1 (de)
JP (1)	JPH03169889A (de)
AU (1)	AU616316B2 (de)
CA (1)	CA2001571A1 (de)
DK (1)	DK538089A (de)
FR (1)	FR2638458A1 (de)
NZ (1)	NZ231155A (de)
OA (1)	OA10557A (de)
PT (1)	PT92112A (de)
ZA (1)	ZA898179B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW226373B (de) *	1992-07-15	1994-07-11	Pfizer
CA2127578A1 (en) *	1993-07-08	1995-01-09	Keiichi Ajito	16-membered macrolide derivatives and process for producing the same
US5716939A (en) *	1993-07-15	1998-02-10	Pfizer Inc.	Amide derivatives of 16-membered ring antibiotic macrolides
EP0778283A3 (de) *	1995-12-05	1998-01-28	Pfizer Inc.	Antibiotische Makrolide
US6576615B2 (en) *	2001-11-08	2003-06-10	Enanta Pharmaceuticals, Inc.	4′-O-substituted tylosin analogs

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS53132584A (en) *	1977-04-26	1978-11-18	Toyo Jozo Co Ltd	18-cyano-18-substituted amino-18-deoxy-macrolide anibiotic substance derivative
JPS58146595A (ja) *	1982-02-25	1983-09-01	Satoshi Omura	マクロライド系抗生物質
JPS61191692A (ja) *	1985-02-20	1986-08-26	Toyo Jozo Co Ltd	Ｃ−１９−修飾デホルミルデスマイコシン誘導体
JPS62221695A (ja) *	1986-03-24	1987-09-29	Microbial Chem Res Found	タイロシンオキシム誘導体およびその製造法
US4921947A (en) *	1986-03-31	1990-05-01	Eli Lilly And Company	Process for preparing macrolide derivatives
YU45033B (en) *	1987-04-14	1991-06-30	Pliva Zagreb	Process for preparing 10,11,12,13-tetrahydro derivative
PT87417B (pt) *	1987-05-06	1992-08-31	Adir	Processo para a preparacao de novos compostos macrolidos

1988
- 1988-10-27 FR FR8814004A patent/FR2638458A1/fr active Pending
1989
- 1989-10-11 US US07/419,826 patent/US5032581A/en not_active Expired - Fee Related
- 1989-10-26 NZ NZ231155A patent/NZ231155A/en unknown
- 1989-10-26 JP JP1279628A patent/JPH03169889A/ja active Pending
- 1989-10-26 AU AU43733/89A patent/AU616316B2/en not_active Ceased
- 1989-10-26 CA CA002001571A patent/CA2001571A1/fr not_active Abandoned
- 1989-10-26 PT PT92112A patent/PT92112A/pt not_active Application Discontinuation
- 1989-10-27 DK DK538089A patent/DK538089A/da not_active Application Discontinuation
- 1989-10-27 EP EP19890402969 patent/EP0366560A1/de not_active Withdrawn
- 1989-10-27 ZA ZA898179A patent/ZA898179B/xx unknown
- 1989-10-27 OA OA59672A patent/OA10557A/fr unknown

Also Published As

Publication number	Publication date
CA2001571A1 (fr)	1990-04-27
AU616316B2 (en)	1991-10-24
EP0366560A1 (de)	1990-05-02
FR2638458A1 (fr)	1990-05-04
NZ231155A (en)	1991-06-25
PT92112A (pt)	1990-04-30
DK538089D0 (da)	1989-10-27
DK538089A (da)	1990-04-28
US5032581A (en)	1991-07-16
ZA898179B (en)	1991-01-30
AU4373389A (en)	1990-05-03
JPH03169889A (ja)	1991-07-23

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