AP888A - Novel 5-0-deosaminyl 6-0-methyl erythronolide derivatives, preparation method therefor and use thereof for preparing biologically active materials. - Google Patents

Novel 5-0-deosaminyl 6-0-methyl erythronolide derivatives, preparation method therefor and use thereof for preparing biologically active materials. Download PDF

Info

Publication number: AP888A
Authority: AP; ARIPO
Prior art keywords: formula; compound; action; subjected; compounds
Prior art date: 1995-10-09

Application number

APAP/P/1998/001216A

Other languages

English (en)

Inventor

Alain Bonnet

Bernadette Chappert

Jacques Lagouardat

Original Assignee

Aventis Pharma Sa

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.)

1995-10-09

Filing date

1996-10-08

Publication date

2000-11-10

1996-10-08 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2000-11-10 Application granted granted Critical

2000-11-10 Publication of AP888A publication Critical patent/AP888A/en

Links

238000002360 preparation method Methods 0.000 title claims description 9
239000011149 active material Substances 0.000 title 1
229930193775 erythronolide Natural products 0.000 title 1
ZFBRGCCVTUPRFQ-UHFFFAOYSA-N erythronolide-B Natural products CCC1OC(=O)C(C)C(O)C(C)C(O)C(C)(O)CC(C)C(=O)C(C)C(O)C1C ZFBRGCCVTUPRFQ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 32
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 7
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 4
230000003213 activating effect Effects 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
229910017852 NH2NH2 Inorganic materials 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
125000002843 carboxylic acid group Chemical group 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
230000003115 biocidal effect Effects 0.000 abstract description 3
150000001732 carboxylic acid derivatives Chemical group 0.000 abstract description 3
239000000047 product Substances 0.000 description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
238000013019 agitation Methods 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 9
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
-1 isobutyryl Chemical group 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
MWBJRTBANFUBOX-SQYJNGITSA-N (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/O)/[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MWBJRTBANFUBOX-SQYJNGITSA-N 0.000 description 4
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
238000010908 decantation Methods 0.000 description 3
229960003276 erythromycin Drugs 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
238000000605 extraction Methods 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
125000005638 hydrazono group Chemical group 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000000034 method Methods 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
OKJFQNPFBIKFPM-UHFFFAOYSA-N 2-quinolin-4-ylpropanal Chemical compound C1=CC=C2C(C(C=O)C)=CC=NC2=C1 OKJFQNPFBIKFPM-UHFFFAOYSA-N 0.000 description 1
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
235000019980 sodium acid phosphate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

APAP/P/1998/001216A 1995-10-09 1996-10-08 Novel 5-0-deosaminyl 6-0-methyl erythronolide derivatives, preparation method therefor and use thereof for preparing biologically active materials. AP888A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9511861A FR2739620B1 (fr)	1995-10-09	1995-10-09	Nouveaux derives de la 5-0-desosaminyl 6-o-methyl erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs

Publications (1)

Publication Number	Publication Date
AP888A true AP888A (en)	2000-11-10

Family

ID=9483377

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1998/001216A AP888A (en)	1995-10-09	1996-10-08	Novel 5-0-deosaminyl 6-0-methyl erythronolide derivatives, preparation method therefor and use thereof for preparing biologically active materials.

Country Status (33)

Country	Link
US (1)	US6011142A (no)
EP (1)	EP0854879B1 (no)
JP (1)	JP4327248B2 (no)
KR (1)	KR100451063B1 (no)
CN (1)	CN1067401C (no)
AP (1)	AP888A (no)
AR (1)	AR004688A1 (no)
AT (1)	ATE212034T1 (no)
AU (1)	AU708351B2 (no)
BG (1)	BG63752B1 (no)
BR (1)	BR9610959A (no)
CA (1)	CA2231562C (no)
CZ (1)	CZ293430B6 (no)
DE (1)	DE69618607T2 (no)
DK (1)	DK0854879T3 (no)
EA (1)	EA000765B1 (no)
EE (1)	EE03878B1 (no)
ES (1)	ES2171722T3 (no)
FR (1)	FR2739620B1 (no)
GE (1)	GEP20032899B (no)
HU (1)	HUP9900136A3 (no)
IL (1)	IL123613A0 (no)
MX (1)	MX9802655A (no)
NO (1)	NO312592B1 (no)
PL (1)	PL183645B1 (no)
PT (1)	PT854879E (no)
RO (1)	RO118874B1 (no)
SI (1)	SI0854879T1 (no)
SK (1)	SK283619B6 (no)
TR (1)	TR199800624T1 (no)
UA (1)	UA52621C2 (no)
WO (1)	WO1997013774A2 (no)
ZA (1)	ZA966666B (no)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2777282B1 (fr) *	1998-04-08	2001-04-20	Hoechst Marion Roussel Inc	Nouveaux derives de la 2-fluoro 3-de((2,6-dideoxy 3-c-methyl 3-0-methyl-alpha-l-ribohexopyranosyl) oxyl) 6-o-methyl 3-oxo erythromycine, leur procede de preparation et leur application a la synthese de principes actifs de medicaments
US6590083B1 (en)	1999-04-16	2003-07-08	Ortho-Mcneil Pharmaceutical, Inc.	Ketolide antibacterials
KR20020007374A (ko) *	1999-04-16	2002-01-26	추후제출	매크롤라이드 항감염제
WO2000062783A2 (en)	1999-04-16	2000-10-26	Ortho-Mcneil Pharmaceutical, Inc.	Ketolide antibacterials
GB0031312D0 (en) *	2000-12-21	2001-02-07	Glaxo Group Ltd	Macrolides
EP2664331B1 (en)	2003-03-10	2015-09-16	Merck Sharp & Dohme Corp.	Novel Antibacterial Agents
EP2214484A4 (en) *	2007-10-25	2013-01-02	Cempra Pharmaceuticals Inc	PROCESS FOR PREPARING ANTIBACTERIAL MAKROLIDE AGENTS
JP5602748B2 (ja) *	2008-10-24	2014-10-08	センプラファーマシューティカルズ，インコーポレイテッド	トリアゾール含有マクロライドを用いた生体防御
US9937194B1 (en)	2009-06-12	2018-04-10	Cempra Pharmaceuticals, Inc.	Compounds and methods for treating inflammatory diseases
AU2010292010B2 (en)	2009-09-10	2016-01-07	Cempra Pharmaceuticals, Inc.	Methods for treating malaria, tuberculosis and MAC diseases
BR112012023950A2 (pt)	2010-03-22	2016-07-05	Cempra Pharmaceuticals Inc	formas cristalinas de um macrolídeo, e usos dos mesmos
WO2011146829A1 (en)	2010-05-20	2011-11-24	Cempra Pharmaceuticals, Inc.	Processes for preparing macrolides and ketolides and intermediates therefor
KR20130120458A (ko)	2010-09-10	2013-11-04	셈프라 파마슈티컬스, 인크.	질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드
KR20140139083A (ko)	2012-03-27	2014-12-04	셈프라 파마슈티컬스, 인크.	마크롤라이드계 항생제를 투여하기 위한 비경구 제제
JP6426696B2 (ja)	2013-03-14	2018-11-21	センプラファーマシューティカルズ，インコーポレイテッド	呼吸器疾患の治療のための方法および製剤
RU2015138797A (ru)	2013-03-15	2017-04-24	Семпра Фармасьютикалс, Инк.	Конвергентные способы получения макролидных антибактериальных агентов

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- 1995-10-09 FR FR9511861A patent/FR2739620B1/fr not_active Expired - Fee Related
1996
- 1996-08-06 ZA ZA9606666A patent/ZA966666B/xx unknown
- 1996-08-10 UA UA98041836A patent/UA52621C2/uk unknown
- 1996-10-07 AR ARP960104634A patent/AR004688A1/es not_active Application Discontinuation
- 1996-10-08 ES ES96933501T patent/ES2171722T3/es not_active Expired - Lifetime
- 1996-10-08 DE DE69618607T patent/DE69618607T2/de not_active Expired - Lifetime
- 1996-10-08 AP APAP/P/1998/001216A patent/AP888A/en active
- 1996-10-08 SK SK431-98A patent/SK283619B6/sk unknown
- 1996-10-08 DK DK96933501T patent/DK0854879T3/da active
- 1996-10-08 US US09/051,378 patent/US6011142A/en not_active Ceased
- 1996-10-08 AU AU72208/96A patent/AU708351B2/en not_active Expired
- 1996-10-08 KR KR10-1998-0702581A patent/KR100451063B1/ko not_active IP Right Cessation
- 1996-10-08 BR BR9610959A patent/BR9610959A/pt not_active Application Discontinuation
- 1996-10-08 SI SI9630452T patent/SI0854879T1/xx unknown
- 1996-10-08 EE EE9800109A patent/EE03878B1/xx not_active IP Right Cessation
- 1996-10-08 IL IL12361396A patent/IL123613A0/xx not_active IP Right Cessation
- 1996-10-08 CA CA002231562A patent/CA2231562C/fr not_active Expired - Lifetime
- 1996-10-08 EA EA199800280A patent/EA000765B1/ru not_active IP Right Cessation
- 1996-10-08 GE GEAP19964227A patent/GEP20032899B/en unknown
- 1996-10-08 WO PCT/FR1996/001567 patent/WO1997013774A2/fr not_active Application Discontinuation
- 1996-10-08 JP JP51476697A patent/JP4327248B2/ja not_active Expired - Lifetime
- 1996-10-08 EP EP96933501A patent/EP0854879B1/fr not_active Expired - Lifetime
- 1996-10-08 RO RO98-00826A patent/RO118874B1/ro unknown
- 1996-10-08 TR TR1998/00624T patent/TR199800624T1/xx unknown
- 1996-10-08 PL PL96326001A patent/PL183645B1/pl not_active IP Right Cessation
- 1996-10-08 AT AT96933501T patent/ATE212034T1/de active
- 1996-10-08 CZ CZ19981055A patent/CZ293430B6/cs not_active IP Right Cessation
- 1996-10-08 HU HU9900136A patent/HUP9900136A3/hu unknown
- 1996-10-08 CN CN96197514A patent/CN1067401C/zh not_active Expired - Lifetime
- 1996-10-08 PT PT96933501T patent/PT854879E/pt unknown
1998
- 1998-03-25 BG BG102350A patent/BG63752B1/bg unknown
- 1998-04-03 MX MX9802655A patent/MX9802655A/es unknown
- 1998-04-08 NO NO19981630A patent/NO312592B1/no not_active IP Right Cessation

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EP0638585A1 (en) *	1992-04-22	1995-02-15	Taisho Pharmaceutical Co. Ltd	5-o-desosaminylerythronolide a derivative
FR2692579A1 (fr) *	1992-06-19	1993-12-24	Roussel Uclaf	Nouveaux dérivés de la picromycine, leur procédé de préparation et leur application comme médicaments.

Also Published As

Publication number	Publication date
NO981630L (no)	1998-04-08
DE69618607D1 (de)	2002-02-21
SK43198A3 (en)	1998-11-04
KR19990064100A (ko)	1999-07-26
MX9802655A (es)	1998-11-30
AU708351B2 (en)	1999-08-05
CN1199403A (zh)	1998-11-18
NO312592B1 (no)	2002-06-03
ZA966666B (en)	1997-08-06
TR199800624T1 (xx)	1998-06-22
UA52621C2 (uk)	2003-01-15
AR004688A1 (es)	1999-03-10
WO1997013774A3 (fr)	1997-05-29
GEP20032899B (en)	2003-02-25
DK0854879T3 (da)	2002-05-06
CZ293430B6 (cs)	2004-04-14
PT854879E (pt)	2002-07-31
WO1997013774A2 (fr)	1997-04-17
EE03878B1 (et)	2002-10-15
PL326001A1 (en)	1998-08-17
AU7220896A (en)	1997-04-30
BG63752B1 (bg)	2002-11-29
PL183645B1 (pl)	2002-06-28
CZ105598A3 (cs)	1998-07-15
BG102350A (en)	1999-03-31
CA2231562A1 (fr)	1997-04-17
JP4327248B2 (ja)	2009-09-09
US6011142A (en)	2000-01-04
ATE212034T1 (de)	2002-02-15
SK283619B6 (sk)	2003-10-07
IL123613A0 (en)	1998-10-30
ES2171722T3 (es)	2002-09-16
RO118874B1 (ro)	2003-12-30
EE9800109A (et)	1998-10-15
CN1067401C (zh)	2001-06-20
HUP9900136A3 (en)	2000-04-28
NO981630D0 (no)	1998-04-08
EP0854879A2 (fr)	1998-07-29
EP0854879B1 (fr)	2002-01-16
DE69618607T2 (de)	2002-08-14
EA000765B1 (ru)	2000-04-24
EA199800280A1 (ru)	1998-10-29
HUP9900136A1 (hu)	1999-05-28
CA2231562C (fr)	2006-11-28
BR9610959A (pt)	1999-03-02
KR100451063B1 (ko)	2004-12-17
FR2739620A1 (fr)	1997-04-11
SI0854879T1 (en)	2002-08-31
FR2739620B1 (fr)	1997-12-19
JPH11513401A (ja)	1999-11-16

Publication	Publication Date	Title
AP888A (en)	2000-11-10	Novel 5-0-deosaminyl 6-0-methyl erythronolide derivatives, preparation method therefor and use thereof for preparing biologically active materials.
KR100633835B1 (ko)	2006-10-13	2-플루오로 3-데[(2,6-디데옥시 3-Ｃ-메틸 3-Ｏ-메틸-α-Ｌ-리보헥소피라노실) 옥시] 6-Ｏ-메틸 3-옥소 에리트로마이신의 신규유도체, 그의 제조 방법 및 약제의 활성 성분 합성을 위한 그의용도
RU2100367C1 (ru)	1997-12-27	Производные эритромицина, способ их получения и промежуточные соединения, фармацевтическая композиция, обладающая антибиотической активностью
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HRP980189A2 (en)	2000-12-31	Novel 15-membered lactams ketolides
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EP0245013B1 (en)	1991-02-06	Erythromycin derivatives
USRE38426E1 (en)	2004-02-10	5-O-deosaminyl 6-O-methyl erythronolide A derivatives, preparation method therefor and use thereof for preparing biologically active materials
EP1181298B1 (en)	2006-07-19	Novel 8a- and 9a-15-membered lactams
FI76098C (fi)	1988-09-09	N-metyl-11-aza-10-deoxi-10 -dihydroerytromycin-n-oxidderivat, foerfarande foer framstaellning av dessa, vid foerfarandet anvaend mellanprodukt samt deras anvaendning vid framstaellning av n-metylderivat av 11-aza-10-deoxi-10 -dihydroerytromycin-a.
NO322424B1 (no)	2006-10-02	Derivater av 4'-demykarosyl-8a-aza-8a-homotylosin
Lartey et al.	1995	Stereoselective deoxygenation of erythromycin A at C-12: Effect of structure and conformation on prokinetic activity
HRP980497A2 (en)	2000-12-31	NOVEL 3,6-HEMIKETALS FROM THE CLASS OF 9a-AZALIDES
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CS241099B2 (cs)	1986-03-13	Způsob přípravy 4“-epi-9-deoxo-9a-methyl-9a-aza- -9a-bomoerythromycinu A
CZ20001045A3 (cs)	2000-07-12	3-N-módilikováné 6-O-substituované ketolidové deriváty erytromycinu