NO320141B1 - 3-deoksy-desmykosinderivater og fremgangsmate for deres fremstilling - Google Patents

3-deoksy-desmykosinderivater og fremgangsmate for deres fremstilling Download PDF

Info

Publication number: NO320141B1
Authority: NO; Norway
Prior art keywords: line; formula; och3; represent; single bond
Prior art date: 1999-05-03

Application number

NO20015347A

Other languages

English (en)

Norwegian (no)

Other versions

NO20015347L (no

NO20015347D0 (no

Inventor

Nevenka Lopotar

Marko Djerek

Drazen Pavlovic

Amalija Narandja

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.)

1999-05-03

Filing date

2001-11-01

Publication date

2005-10-31

2001-11-01 Application filed by Pliva Pharm & Chem Works filed Critical Pliva Pharm & Chem Works

2001-11-01 Publication of NO20015347L publication Critical patent/NO20015347L/no

2001-11-01 Publication of NO20015347D0 publication Critical patent/NO20015347D0/no

2005-10-31 Publication of NO320141B1 publication Critical patent/NO320141B1/no

Links

238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 7
238000007254 oxidation reaction Methods 0.000 claims abstract description 12
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 64
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 60
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
238000006140 methanolysis reaction Methods 0.000 claims description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
235000011114 ammonium hydroxide Nutrition 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 6
239000000843 powder Substances 0.000 claims description 6
238000006722 reduction reaction Methods 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 3
238000003379 elimination reaction Methods 0.000 claims description 3
238000003328 mesylation reaction Methods 0.000 claims description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
150000001241 acetals Chemical class 0.000 claims description 2
230000008030 elimination Effects 0.000 claims description 2
230000002829 reductive effect Effects 0.000 abstract description 8
125000000466 oxiranyl group Chemical group 0.000 abstract description 3
238000005984 hydrogenation reaction Methods 0.000 abstract description 2
230000003647 oxidation Effects 0.000 abstract description 2
QRPHLEPFYLNRDA-NLGRAQRVSA-N 2-[(4r,5s,6s,7r,9r,11e,13e,15r,16r)-6-[(2r,3r,4s,5s,6r)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2r,3r,4r,5r,6r)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,1 Chemical compound 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]1O[C@H](C)[C@@H](O)[C@H](N(C)C)[C@H]1O QRPHLEPFYLNRDA-NLGRAQRVSA-N 0.000 abstract 3
238000006735 epoxidation reaction Methods 0.000 abstract 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 54
239000000243 solution Substances 0.000 description 32
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
239000000047 product Substances 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
239000000741 silica gel Substances 0.000 description 19
229910002027 silica gel Inorganic materials 0.000 description 19
239000002904 solvent Substances 0.000 description 19
238000004587 chromatography analysis Methods 0.000 description 18
125000000468 ketone group Chemical group 0.000 description 16
238000005160 1H NMR spectroscopy Methods 0.000 description 15
229930194542 Keto Natural products 0.000 description 14
150000002085 enols Chemical class 0.000 description 13
239000000284 extract Substances 0.000 description 11
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
239000012044 organic layer Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000002211 ultraviolet spectrum Methods 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 5
238000003756 stirring Methods 0.000 description 5
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 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000002955 isolation Methods 0.000 description 4
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
229940126214 compound 3 Drugs 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
229930194936 Tylosin Natural products 0.000 description 2
239000004182 Tylosin Substances 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229960004059 tylosin Drugs 0.000 description 2
235000019375 tylosin Nutrition 0.000 description 2
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
229940126657 Compound 17 Drugs 0.000 description 1
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Natural products 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 1
238000005481 NMR spectroscopy Methods 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940126142 compound 16 Drugs 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
125000002587 enol group Chemical group 0.000 description 1
229960003276 erythromycin Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
238000000870 ultraviolet spectroscopy 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
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Peptides Or Proteins (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Steroid Compounds (AREA)

NO20015347A 1999-05-03 2001-11-01 3-deoksy-desmykosinderivater og fremgangsmate for deres fremstilling NO320141B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HR990129A HRP990129B1 (en)	1999-05-03	1999-05-03	New compounds of 3-deoxy-desmycosin class and process for the preparation thereof
PCT/HR2000/000012 WO2000066602A1 (en)	1999-05-03	2000-05-02	3-deoxy-desmycosin derivatives and process for their preparation

Publications (3)

Publication Number	Publication Date
NO20015347L NO20015347L (no)	2001-11-01
NO20015347D0 NO20015347D0 (no)	2001-11-01
NO320141B1 true NO320141B1 (no)	2005-10-31

Family

ID=10946915

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20015347A NO320141B1 (no)	1999-05-03	2001-11-01	3-deoksy-desmykosinderivater og fremgangsmate for deres fremstilling

Country Status (31)

Country	Link
US (1)	US6504035B1 (de)
EP (1)	EP1175428B1 (de)
JP (1)	JP2002543212A (de)
KR (1)	KR100679903B1 (de)
CN (1)	CN1191263C (de)
AT (1)	ATE238332T1 (de)
AU (1)	AU767549B2 (de)
BG (1)	BG106172A (de)
BR (1)	BR0010250A (de)
CA (1)	CA2368249A1 (de)
CZ (1)	CZ296455B6 (de)
DE (1)	DE60002314T2 (de)
DK (1)	DK1175428T3 (de)
EA (1)	EA004059B1 (de)
EE (1)	EE04594B1 (de)
ES (1)	ES2198302T3 (de)
GE (1)	GEP20032927B (de)
HK (1)	HK1050010A1 (de)
HR (1)	HRP990129B1 (de)
HU (1)	HUP0201140A3 (de)
IL (1)	IL145989A0 (de)
IS (1)	IS6117A (de)
MX (1)	MXPA01011089A (de)
NO (1)	NO320141B1 (de)
NZ (1)	NZ515280A (de)
PL (1)	PL352027A1 (de)
SK (1)	SK283967B6 (de)
TR (1)	TR200103146T2 (de)
UA (1)	UA66927C2 (de)
WO (1)	WO2000066602A1 (de)
ZA (1)	ZA200108482B (de)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8405087D0 (en) *	1984-02-27	1984-04-04	Omura S	Antibiotic
GB2171991B (en) *	1985-03-06	1988-08-17	Satoshi Omura	Novel macrolide derivatives, process for preparing same, and antibacterial compositions thereof
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
SI8710674B (sl) *	1987-04-14	1998-06-30	Pliva	Postopek za pripravo 10,11,12,13-tetrahidro derivatov tilozina
JPH05230094A (ja) *	1992-02-26	1993-09-07	Asahi Chem Ind Co Ltd	マイシナマイシン誘導体

1999
- 1999-05-03 HR HR990129A patent/HRP990129B1/xx not_active IP Right Cessation
2000
- 2000-05-02 GE GEAP20006228A patent/GEP20032927B/en unknown
- 2000-05-02 DK DK00920939T patent/DK1175428T3/da active
- 2000-05-02 CA CA002368249A patent/CA2368249A1/en not_active Abandoned
- 2000-05-02 ES ES00920939T patent/ES2198302T3/es not_active Expired - Lifetime
- 2000-05-02 TR TR2001/03146T patent/TR200103146T2/xx unknown
- 2000-05-02 UA UA2001118220A patent/UA66927C2/uk unknown
- 2000-05-02 PL PL00352027A patent/PL352027A1/xx not_active IP Right Cessation
- 2000-05-02 EP EP00920939A patent/EP1175428B1/de not_active Expired - Lifetime
- 2000-05-02 IL IL14598900A patent/IL145989A0/xx unknown
- 2000-05-02 CZ CZ20013821A patent/CZ296455B6/cs not_active IP Right Cessation
- 2000-05-02 EA EA200101169A patent/EA004059B1/ru not_active IP Right Cessation
- 2000-05-02 KR KR1020017014045A patent/KR100679903B1/ko not_active Expired - Fee Related
- 2000-05-02 HU HU0201140A patent/HUP0201140A3/hu unknown
- 2000-05-02 SK SK1568-2001A patent/SK283967B6/sk not_active IP Right Cessation
- 2000-05-02 AT AT00920939T patent/ATE238332T1/de not_active IP Right Cessation
- 2000-05-02 CN CNB008071519A patent/CN1191263C/zh not_active Expired - Fee Related
- 2000-05-02 WO PCT/HR2000/000012 patent/WO2000066602A1/en not_active Ceased
- 2000-05-02 AU AU41349/00A patent/AU767549B2/en not_active Ceased
- 2000-05-02 BR BR0010250-4A patent/BR0010250A/pt not_active IP Right Cessation
- 2000-05-02 MX MXPA01011089A patent/MXPA01011089A/es active IP Right Grant
- 2000-05-02 NZ NZ515280A patent/NZ515280A/xx unknown
- 2000-05-02 EE EEP200100571A patent/EE04594B1/xx not_active IP Right Cessation
- 2000-05-02 DE DE60002314T patent/DE60002314T2/de not_active Expired - Lifetime
- 2000-05-02 US US09/959,692 patent/US6504035B1/en not_active Expired - Fee Related
- 2000-05-02 HK HK03100593.8A patent/HK1050010A1/zh unknown
- 2000-05-02 JP JP2000615631A patent/JP2002543212A/ja active Pending
2001
- 2001-10-16 ZA ZA200108482A patent/ZA200108482B/xx unknown
- 2001-10-19 IS IS6117A patent/IS6117A/is unknown
- 2001-11-01 NO NO20015347A patent/NO320141B1/no unknown
- 2001-12-03 BG BG106172A patent/BG106172A/bg unknown

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Publication number	Publication date
HRP990129A2 (en)	2001-12-31
DE60002314D1 (de)	2003-05-28
IS6117A (is)	2001-10-19
AU767549B2 (en)	2003-11-13
WO2000066602A9 (en)	2001-12-20
GEP20032927B (en)	2003-03-25
KR20020007396A (ko)	2002-01-26
EP1175428A1 (de)	2002-01-30
WO2000066602A1 (en)	2000-11-09
DE60002314T2 (de)	2004-03-04
CZ296455B6 (cs)	2006-03-15
EP1175428B1 (de)	2003-04-23
NO20015347L (no)	2001-11-01
TR200103146T2 (tr)	2002-05-21
HUP0201140A3 (en)	2003-03-28
ATE238332T1 (de)	2003-05-15
BG106172A (bg)	2002-07-31
NZ515280A (en)	2002-12-20
BR0010250A (pt)	2002-02-19
CN1362963A (zh)	2002-08-07
EA004059B1 (ru)	2003-12-25
IL145989A0 (en)	2002-07-25
ZA200108482B (en)	2002-12-24
MXPA01011089A (es)	2002-07-22
UA66927C2 (uk)	2004-06-15
CN1191263C (zh)	2005-03-02
SK15682001A3 (sk)	2002-06-04
US6504035B1 (en)	2003-01-07
HRP990129B1 (en)	2003-10-31
CA2368249A1 (en)	2000-11-09
ES2198302T3 (es)	2004-02-01
SK283967B6 (sk)	2004-06-08
PL352027A1 (en)	2003-07-28
KR100679903B1 (ko)	2007-02-28
AU4134900A (en)	2000-11-17
JP2002543212A (ja)	2002-12-17
DK1175428T3 (da)	2003-08-11
NO20015347D0 (no)	2001-11-01
EE200100571A (et)	2003-02-17
EA200101169A1 (ru)	2002-04-25
EE04594B1 (et)	2006-02-15
HUP0201140A2 (en)	2002-08-28
HK1050010A1 (zh)	2003-06-06
CZ20013821A3 (cs)	2002-03-13

Publication	Publication Date	Title
EP0287082A2 (de)	1988-10-19	Tylosin- und 10,11,12,13-Tetrahydrotylosin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung in pharmazeutischen Zusammensetzungen und bei deren Herstellung
EP0410433A2 (de)	1991-01-30	Tylosin-Derivate
EP1175428B1 (de)	2003-04-23	3-deoxy-desmycosin-derivate und verfahren zu ihrer herstellung
RU2234510C2 (ru)	2004-08-20	Производные класса олеандомицина и способ их получения
US6211348B1 (en)	2001-04-03	Hydroxy derivatives of tylosin and process for their preparation
US5688924A (en)	1997-11-18	Derivatives of 12,13-Epoxy-tylosin and processes of manufacture thereof
US5922684A (en)	1999-07-13	Polyhydro derivatives of tylosine and process for their preparation
NO322424B1 (no)	2006-10-02	Derivater av 4'-demykarosyl-8a-aza-8a-homotylosin
RU2173689C2 (ru)	2001-09-20	Производные 12,13-эпокситилозина и способы их получения
PL217775B1 (pl)	2014-08-29	Sposób syntezy i izolacji N-demetylo-azytromycyny
JPH04234896A (ja)	1992-08-24	オレアンドマイシン　オキシム、その製造方法及びそれを含む抗微生物剤
JPS6155920B2 (de)	1986-11-29
JPWO1993021200A1 (ja)	1994-05-12	５−０−デソサミニルエリスロノライドａ誘導体
MXPA99006221A (en)	2000-12-06	Improved process in a single step for the preparation of 7,16-dioxa-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihidroxi-6-etil-3,5,9,11, 13,15-hexametilbiciclo [11.2.1] hexadeca-1 (2) -en-8-ona, from erythromycin