SE457084B - N-metyl-11-aza-10-deoxo-10-dihydroerytromycin a och derivat samt foerfarande foer framstaellning daerav - Google Patents

N-metyl-11-aza-10-deoxo-10-dihydroerytromycin a och derivat samt foerfarande foer framstaellning daerav

Info

Publication number: SE457084B
Authority: SE; Sweden
Prior art keywords: aza; methyl; deoxo; dihydroerythromycin; hydrogen
Prior art date: 1981-03-06

Application number

SE8201311A

Other languages

English (en)

Swedish (sv)

Other versions

SE8201311L (sv

Inventor

G Kobrehel

Original Assignee

Pliva Pharm & Chem Works

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.)

1981-03-06

Filing date

1982-03-03

Publication date

1988-11-28

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25550598&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SE457084(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1982-03-03 Application filed by Pliva Pharm & Chem Works filed Critical Pliva Pharm & Chem Works

1982-09-07 Publication of SE8201311L publication Critical patent/SE8201311L/

1988-11-28 Publication of SE457084B publication Critical patent/SE457084B/sv

Links

238000000034 method Methods 0.000 title claims description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 48
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 23
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[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 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
239000003513 alkali Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 7
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
229960003276 erythromycin Drugs 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class 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 20
239000000243 solution Substances 0.000 description 18
239000000047 product Substances 0.000 description 15
150000001875 compounds Chemical class 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
229930006677 Erythromycin A Natural products 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
150000002148 esters Chemical class 0.000 description 7
150000002596 lactones Chemical class 0.000 description 7
239000007858 starting material Substances 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000000605 extraction Methods 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
241001478240 Coccus Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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229940125904 compound 1 Drugs 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
150000008064 anhydrides Chemical class 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000194106 Bacillus mycoides Species 0.000 description 2
244000063299 Bacillus subtilis Species 0.000 description 2
235000014469 Bacillus subtilis Nutrition 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
241000588914 Enterobacter Species 0.000 description 2
241000194032 Enterococcus faecalis Species 0.000 description 2
241000588748 Klebsiella Species 0.000 description 2
241000515012 Micrococcus flavus Species 0.000 description 2
241000191938 Micrococcus luteus Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
241000751182 Staphylococcus epidermidis ATCC 12228 Species 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
244000005700 microbiome Species 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000035807 sensation Effects 0.000 description 2
241001148471 unidentified anaerobic bacterium Species 0.000 description 2
KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec 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)(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 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 description 1
OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-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
241000606125 Bacteroides Species 0.000 description 1
238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
241000192132 Leuconostoc Species 0.000 description 1
241000219470 Mirabilis Species 0.000 description 1
241000580463 Nicrophorus Species 0.000 description 1
206010058667 Oral toxicity Diseases 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000008272 agar Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical class OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
231100000418 oral toxicity Toxicity 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 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
- 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)

SE8201311A 1981-03-06 1982-03-03 N-metyl-11-aza-10-deoxo-10-dihydroerytromycin a och derivat samt foerfarande foer framstaellning daerav SE457084B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
YU592/81A YU43006B (en)	1981-03-06	1981-03-06	Process for preparing n-methyl-11-aza-10-deoxo-10-dihydro erythromycin and derivatives thereof

Publications (2)

Publication Number	Publication Date
SE8201311L SE8201311L (sv)	1982-09-07
SE457084B true SE457084B (sv)	1988-11-28

Family

ID=25550598

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8201311A SE457084B (sv)	1981-03-06	1982-03-03	N-metyl-11-aza-10-deoxo-10-dihydroerytromycin a och derivat samt foerfarande foer framstaellning daerav

Country Status (19)

Country	Link
US (1)	US4517359A (de)
JP (1)	JPS5858357B2 (de)
AT (1)	AT375945B (de)
BE (1)	BE892357A (de)
CA (1)	CA1191843A (de)
CH (1)	CH655728A5 (de)
CZ (1)	CZ418991A3 (de)
DD (1)	DD202437A5 (de)
DE (1)	DE3140449C2 (de)
FR (1)	FR2501212B1 (de)
GB (1)	GB2094293B (de)
HU (1)	HU186845B (de)
IT (1)	IT1200960B (de)
PL (2)	PL131784B1 (de)
SE (1)	SE457084B (de)
SI (1)	SI8110592A8 (de)
SK (1)	SK418991A3 (de)
SU (1)	SU1287755A3 (de)
YU (1)	YU43006B (de)

Families Citing this family (153)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4474768A (en) *	1982-07-19	1984-10-02	Pfizer Inc.	N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor
ZA835204B (en) *	1982-07-19	1985-02-27	Pfizer	N-methyl 11-aza-10-deoxo-10-dihydroerythromycin a,intermediates therefor and processes for their preparation
PH19293A (en) *	1982-11-15	1986-03-04	Pfizer	Epimeric azahomoerythromycin,pharmaceutical composition containing the same and method of use thereof
US4526889A (en) *	1982-11-15	1985-07-02	Pfizer Inc.	Epimeric azahomoerythromycin A derivative, intermediates and method of use
US4492688A (en) *	1983-11-25	1985-01-08	Pfizer Inc.	Antibacterial cyclic ethers of 9-deoxo-9a-aza-9a-homoerythromycin A and intermediates therefor
JPS59225198A (ja) *	1983-05-23	1984-12-18	フアイザ−・インコ−ポレ−テツド	抗菌性を有する９―デオキソ―９ａ―アザ―９ａ―ホモエリスロマイシンＡ，その製造方法および組成物
DE3461803D1 (en) *	1983-05-23	1987-02-05	Pfizer	Antibacterial cyclic ethers of 9-deoxo-9a-aza-9a-homoerythromycin a and intermediates therefor
US4464527A (en) *	1983-06-30	1984-08-07	Pfizer Inc.	Antibacterial 9-deoxo-9a-alkyl-9a-aza-9a-homoerythromycin A derivatives and intermediates therefore
DE3475073D1 (en) *	1983-09-06	1988-12-15	Pfizer	Azahomoerythromycin b derivatives and intermediates thereof
US4465674A (en) *	1983-09-06	1984-08-14	Pfizer Inc.	Azahomoerythromycin D derivative and intermediates therefor
US4518590A (en) *	1984-04-13	1985-05-21	Pfizer Inc.	9α-Aza-9α-homoerythromycin compounds, pharmaceutical compositions and therapeutic method
US4512982A (en) *	1984-04-13	1985-04-23	Pfizer Inc.	9α-Aza-9α-homoerythromycin compounds, pharmaceutical composition and therapeutic method
US4921947A (en) *	1986-03-31	1990-05-01	Eli Lilly And Company	Process for preparing macrolide derivatives
RO107257B1 (ro)	1987-07-09	1993-10-30	Pfizer	Procedeu de obtinere a unui dihidrat de azitromicina, cristalin
WO1989002271A1 (en) *	1987-09-10	1989-03-23	Pfizer	Azithromycin and derivatives as antiprotozoal agents
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1982
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- 1982-03-04 FR FR8203601A patent/FR2501212B1/fr not_active Expired
- 1982-03-05 HU HU82683A patent/HU186845B/hu unknown
- 1982-03-05 IT IT67263/82A patent/IT1200960B/it active Protection Beyond IP Right Term
- 1982-03-05 SU SU823402600A patent/SU1287755A3/ru active
- 1982-03-05 PL PL1982235329A patent/PL131784B1/pl unknown
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1991
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Publication number	Publication date
BE892357A (fr)	1982-07-01
SU1287755A3 (ru)	1987-01-30
FR2501212A1 (fr)	1982-09-10
IT1200960B (it)	1989-01-27
PL133764B1 (en)	1985-06-29
HU186845B (en)	1985-09-30
DE3140449A1 (de)	1983-10-13
SE8201311L (sv)	1982-09-07
JPS57158798A (en)	1982-09-30
YU59281A (en)	1983-06-30
DE3140449C2 (de)	1984-06-20
AT375945B (de)	1984-09-25
PL235329A1 (de)	1982-09-27
PL131784B1 (en)	1985-01-31
CA1191843A (en)	1985-08-13
GB2094293A (en)	1982-09-15
JPS5858357B2 (ja)	1983-12-24
US4517359A (en)	1985-05-14
SK418991A3 (en)	1995-07-11
YU43006B (en)	1989-02-28
ATA440081A (de)	1984-02-15
CH655728A5 (de)	1986-05-15
IT8267263A0 (it)	1982-03-05
GB2094293B (en)	1985-12-18
FR2501212B1 (fr)	1985-08-09
SI8110592A8 (en)	1996-06-30
CZ418991A3 (en)	1993-01-13
DD202437A5 (de)	1983-09-14

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Publication	Publication Date	Title
SE457084B (sv)	1988-11-28	N-metyl-11-aza-10-deoxo-10-dihydroerytromycin a och derivat samt foerfarande foer framstaellning daerav
US4331803A (en)	1982-05-25	Novel erythromycin compounds
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DE69305987T2 (de)	1997-03-06	5-0-desosaminylerythronolide a derivate
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JPS58159499A (ja)	1983-09-21	抗菌剤として有用な４″−エピエリスロマイシンａおよびその誘導体
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Morimoto et al.	1990	Chemical modification of erythromycins VI. Structure and antibacterial activity of acid degradation products of 6-O-methylerythromycins A
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KR0158692B1 (ko)	1998-11-16	항생물질 ll-e19020 알파 및 베타의 화학적 유도체
EP0394907A1 (de)	1990-10-31	Verfahren zur Herstellung von Etoposiden
DE2462053C3 (de)	1977-09-22	Isopurpuromycin, Pentaacetylisopurpuromycin, Verfahren zur Herstellung von Pentaacetylisopurpuromycin und diese Verbindung enthaltende Arzneimittel
US5268462A (en)	1993-12-07	Oleandomycin oximes
US4603212A (en)	1986-07-29	Analogs of the antibiotic spectinomycin
CH658660A5 (de)	1986-11-28	3-0-acyl-4''-deoxydesmycosin-derivate und verfahren zu ihrer herstellung.
DE69118126T2 (de)	1996-10-31	Derivate von 10,11,12,13-tetra-hydrodesmycosin, Verfahren zu ihrer Herstellung, und ihre Verwendung zur Herstellung von Arzneimitteln