HRP950449A2 - Derivatives of 12, 13-epoxy-tylosin and processes of manufacture thereof - Google Patents

Derivatives of 12, 13-epoxy-tylosin and processes of manufacture thereof Download PDF

Info

Publication number: HRP950449A2
Authority: HR; Croatia
Prior art keywords: epoxy; compound; mycarosyl; dihydro; formula
Prior art date: 1995-08-14

Application number

HR950449A

Other languages

English (en)

Croatian (hr)

Inventor

Nevenka Lopotar

Original Assignee

Nevenka Lopotar

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.)

1995-08-14

Filing date

1995-08-14

Publication date

1997-12-31

1995-08-14 Application filed by Nevenka Lopotar filed Critical Nevenka Lopotar

1995-08-14 Priority to HR950449A priority Critical patent/HRP950449A2/hr

1996-07-25 Priority to BA960113A priority patent/BA96113A/bs

1996-07-29 Priority to HU9602080A priority patent/HUP9602080A3/hu

1996-07-29 Priority to EP96112219A priority patent/EP0792885A3/en

1996-08-01 Priority to CZ962290A priority patent/CZ229096A3/cs

1996-08-09 Priority to CA002183049A priority patent/CA2183049A1/en

1996-08-09 Priority to SK1047-96A priority patent/SK282511B6/sk

1996-08-12 Priority to BG100779A priority patent/BG63309B1/bg

1996-08-13 Priority to PL96315675A priority patent/PL182429B1/pl

1996-08-13 Priority to US08/696,178 priority patent/US5688924A/en

1996-08-13 Priority to SI9600250A priority patent/SI9600250A/sl

1996-08-13 Priority to RO96-01642A priority patent/RO115526B1/ro

1996-08-14 Priority to JP8232518A priority patent/JPH09183790A/ja

1996-08-14 Priority to CN96109447A priority patent/CN1062867C/zh

1997-12-31 Publication of HRP950449A2 publication Critical patent/HRP950449A2/hr

Links

239000004182 Tylosin Substances 0.000 title claims description 9
238000000034 method Methods 0.000 title claims description 9
229960004059 tylosin Drugs 0.000 title claims description 9
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 35
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000000741 silica gel Substances 0.000 claims description 7
229910002027 silica gel Inorganic materials 0.000 claims description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000004036 acetal group Chemical group 0.000 claims description 4
238000006146 oximation reaction Methods 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
235000017550 sodium carbonate Nutrition 0.000 claims description 3
229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
238000004587 chromatography analysis Methods 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
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 2
239000007864 aqueous solution Substances 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 56
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
239000004593 Epoxy Substances 0.000 description 7
150000002923 oximes Chemical class 0.000 description 7
229960001866 silicon dioxide Drugs 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000000605 extraction Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
238000002955 isolation Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229930184158 Maridomycin Natural products 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
229930194936 Tylosin Natural products 0.000 description 2
FFXJTOKFQATYBI-RUTGJBPVSA-N [(1s,3r,7r,8s,9s,10r,12r,13r,14e,16s)-9-[(2s,3r,4r,5s,6r)-4-(dimethylamino)-3-hydroxy-5-[(2s,4r,5s,6s)-4-hydroxy-4,6-dimethyl-5-propanoyloxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-13-hydroxy-8-methoxy-3,12-dimethyl-5-oxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1 Chemical compound C1[C@](O)(C)[C@@H](OC(=O)CC)[C@H](C)O[C@H]1O[C@H]1[C@H](N(C)C)[C@@H](O)[C@H](O[C@@H]2[C@H]([C@H](OC(=O)CC)CC(=O)O[C@H](C)C[C@@H]3O[C@H]3/C=C/[C@H](O)[C@H](C)C[C@@H]2CC=O)OC)O[C@@H]1C FFXJTOKFQATYBI-RUTGJBPVSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
150000001993 dienes Chemical group 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000003120 macrolide antibiotic agent Substances 0.000 description 2
229940041033 macrolides Drugs 0.000 description 2
229950002784 maridomycin Drugs 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
IUPCWCLVECYZRV-ZRDIBKRKSA-N rosamicin Chemical compound O=CCC1CC(C)C(=O)\C=C\C2(C)OC2C(C)C(CC)OC(=O)CC(O)C(C)C1OC1OC(C)CC(N(C)C)C1O IUPCWCLVECYZRV-ZRDIBKRKSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
235000019375 tylosin Nutrition 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 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
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000003245 coal Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 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
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
-1 their oximes Chemical class 0.000 description 1
150000003573 thiols Chemical class 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
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Genetics & Genomics (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Epoxy Compounds (AREA)

HR950449A 1995-08-14 1995-08-14 Derivatives of 12, 13-epoxy-tylosin and processes of manufacture thereof HRP950449A2 (en)

Priority Applications (14)

Application Number	Priority Date	Filing Date	Title
HR950449A HRP950449A2 (en)	1995-08-14	1995-08-14	Derivatives of 12, 13-epoxy-tylosin and processes of manufacture thereof
BA960113A BA96113A (bs)	1995-08-14	1996-07-25	Derivati 12,11113-epoksi-tilozina i postupci za njihovo dobivanje
HU9602080A HUP9602080A3 (en)	1995-08-14	1996-07-29	12,13-epoxi-tylosin derivatives and process for producing them
EP96112219A EP0792885A3 (en)	1995-08-14	1996-07-29	Derivatives of 12,13-epoxy-tylosin and processes of manufacture thereof
CZ962290A CZ229096A3 (en)	1995-08-14	1996-08-01	Derivatives of 12,13-epoxy-tylosin and process for preparing thereof
CA002183049A CA2183049A1 (en)	1995-08-14	1996-08-09	Derivatives of 12, 13-epoxy-tylosin and processes of manufacture thereof
SK1047-96A SK282511B6 (sk)	1995-08-14	1996-08-09	Deriváty 12,13-epoxy-tylozínu a spôsob ich výroby
BG100779A BG63309B1 (bg)	1995-08-14	1996-08-12	Производни на 12,13-епокситилозин и методи за получаването им
PL96315675A PL182429B1 (pl)	1995-08-14	1996-08-13	Pochodne 12,13-epoksy-tylozyny i sposób ich wytwarzania
US08/696,178 US5688924A (en)	1995-08-14	1996-08-13	Derivatives of 12,13-Epoxy-tylosin and processes of manufacture thereof
SI9600250A SI9600250A (en)	1995-08-14	1996-08-13	12,13-epoxy-tylosin derivatives and processes for their preparation
RO96-01642A RO115526B1 (ro)	1995-08-14	1996-08-13	Derivati de 12, 13-epoxi-tilozina si procedeu de obtinere a acestora
JP8232518A JPH09183790A (ja)	1995-08-14	1996-08-14	１２，１３ −エポキシチロシン誘導体及びその製造方法
CN96109447A CN1062867C (zh)	1995-08-14	1996-08-14	12,13－环氧－泰乐菌素的衍生物及其制备方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HR950449A HRP950449A2 (en)	1995-08-14	1995-08-14	Derivatives of 12, 13-epoxy-tylosin and processes of manufacture thereof

Publications (1)

Publication Number	Publication Date
HRP950449A2 true HRP950449A2 (en)	1997-12-31

Family

ID=10946293

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR950449A HRP950449A2 (en)	1995-08-14	1995-08-14	Derivatives of 12, 13-epoxy-tylosin and processes of manufacture thereof

Country Status (14)

Country	Link
US (1)	US5688924A (cs)
EP (1)	EP0792885A3 (cs)
JP (1)	JPH09183790A (cs)
CN (1)	CN1062867C (cs)
BA (1)	BA96113A (cs)
BG (1)	BG63309B1 (cs)
CA (1)	CA2183049A1 (cs)
CZ (1)	CZ229096A3 (cs)
HR (1)	HRP950449A2 (cs)
HU (1)	HUP9602080A3 (cs)
PL (1)	PL182429B1 (cs)
RO (1)	RO115526B1 (cs)
SI (1)	SI9600250A (cs)
SK (1)	SK282511B6 (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HRP960509A2 (en) *	1996-10-30	1998-06-30	Pliva Pharm & Chem Works	Novel polyhydro tylosin derivatives and a process for the preparation thereof
HRP980496B1 (en) *	1998-09-10	2007-03-31	GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o.	New thilozine hydroxy derivatives and a process for the preparation thereof
US7247617B2 (en) *	2004-07-13	2007-07-24	Kosan Biosciences Incorporated	Sixteen-member macrolide antiinfective agents

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4056616A (en) *	1976-03-05	1977-11-01	Schering Corporation	Rosamicin derivatives and method of using same
AU551142B2 (en) *	1981-07-09	1986-04-17	Zaidan Hojin Biseibutsu Kagaku Kenkyukai	Tylosin derivatives
US4808575A (en) *	1986-06-23	1989-02-28	Schering Corporation	12,13-oxoderivatives of macrolides
IT1217839B (it) *	1988-06-17	1990-03-30	Ausimont Spa	Microemulsioni del tipo olio in acqua elettricamente conduttrici,a base di composti perfluorurati,usate come catolita in processi elettrochimici
CN1022981C (zh) *	1989-09-09	1993-12-08	中国科学院广州化学所	二醋酸纤维素微孔滤膜的制造方法
JPH04164093A (ja) *	1990-10-25	1992-06-09	Mercian Corp	新タイロシン誘導体

1995
- 1995-08-14 HR HR950449A patent/HRP950449A2/hr not_active Application Discontinuation
1996
- 1996-07-25 BA BA960113A patent/BA96113A/bs unknown
- 1996-07-29 EP EP96112219A patent/EP0792885A3/en not_active Withdrawn
- 1996-07-29 HU HU9602080A patent/HUP9602080A3/hu unknown
- 1996-08-01 CZ CZ962290A patent/CZ229096A3/cs unknown
- 1996-08-09 SK SK1047-96A patent/SK282511B6/sk unknown
- 1996-08-09 CA CA002183049A patent/CA2183049A1/en not_active Abandoned
- 1996-08-12 BG BG100779A patent/BG63309B1/bg unknown
- 1996-08-13 RO RO96-01642A patent/RO115526B1/ro unknown
- 1996-08-13 PL PL96315675A patent/PL182429B1/pl unknown
- 1996-08-13 SI SI9600250A patent/SI9600250A/sl unknown
- 1996-08-13 US US08/696,178 patent/US5688924A/en not_active Expired - Fee Related
- 1996-08-14 JP JP8232518A patent/JPH09183790A/ja active Pending
- 1996-08-14 CN CN96109447A patent/CN1062867C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
BG100779A (en)	1997-09-30
PL182429B1 (pl)	2002-01-31
EP0792885A3 (en)	1998-01-14
BG63309B1 (bg)	2001-09-28
CN1148047A (zh)	1997-04-23
CN1062867C (zh)	2001-03-07
BA96113A (bs)	2000-05-02
SI9600250A (en)	1997-04-30
HUP9602080A3 (en)	1998-04-28
HUP9602080A2 (en)	1997-05-28
HU9602080D0 (en)	1996-09-30
CZ229096A3 (en)	1997-03-12
SK104796A3 (en)	1997-04-09
US5688924A (en)	1997-11-18
JPH09183790A (ja)	1997-07-15
SK282511B6 (sk)	2002-10-08
EP0792885A2 (en)	1997-09-03
RO115526B1 (ro)	2000-03-30
PL315675A1 (en)	1997-02-17
CA2183049A1 (en)	1997-02-15

Legal Events

Date	Code	Title
1997-12-31	A1OB	Publication of a patent application
1998-02-09	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2004-09-30	ODBC	Application rejected

Publication	Publication Date	Title
HRP920491A2 (en)	1994-08-31	O-methyl derivatives of azitromycin a, methods and intermediates for obtaining them; methods for the preparation and use thereof as pharmaceutical preparations
HU201089B (en)	1990-09-28	Process for producing tylosin and 10,11,12,13-tetrahydro-tylosin derivatives
EP0410433A2 (en)	1991-01-30	Tylosin derivatives
HRP950449A2 (en)	1997-12-31	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
RU2173689C2 (ru)	2001-09-20	Производные 12,13-эпокситилозина и способы их получения
Narandja et al.	1994	Structure-activity relationship among polyhydro derivatives of tylosin
EP0985679B1 (en)	2003-04-23	New hydroxy derivatives of tylosin and process for their preparation
NO322424B1 (no)	2006-10-02	Derivater av 4'-demykarosyl-8a-aza-8a-homotylosin
EA004059B1 (ru)	2003-12-25	Производные 3-деоксидесмикозина
HRP940257A2 (en)	1997-06-30	Preparation and properties of certain tylosin derivatives