ZA200104434B - Hygromycin a derivatives as antibacterial agents. - Google Patents

Hygromycin a derivatives as antibacterial agents. Download PDF

Info

Publication number: ZA200104434B
Authority: ZA; South Africa
Prior art keywords: methyl; hydroxy; furan; tetrahydro; dioxol
Prior art date: 1998-12-02

Application number

ZA200104434A

Other languages

English (en)

Inventor

Hayward Matthew Merrill

Original Assignee

Pfizer Prod Inc

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.)

1998-12-02

Filing date

2001-05-30

Publication date

2002-05-30

2001-05-30 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2002-05-30 Publication of ZA200104434B publication Critical patent/ZA200104434B/en

Links

YQYJSBFKSSDGFO-UHFFFAOYSA-N Epihygromycin Natural products OC1C(O)C(C(=O)C)OC1OC(C(=C1)O)=CC=C1C=C(C)C(=O)NC1C(O)C(O)C2OCOC2C1O YQYJSBFKSSDGFO-UHFFFAOYSA-N 0.000 title description 77
239000003242 anti bacterial agent Substances 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims description 93
125000003118 aryl group Chemical group 0.000 claims description 77
125000000217 alkyl group Chemical group 0.000 claims description 45
238000000034 method Methods 0.000 claims description 40
125000000623 heterocyclic group Chemical group 0.000 claims description 39
150000003839 salts Chemical class 0.000 claims description 34
-1 triflucromethoxy Chemical group 0.000 claims description 33
125000005843 halogen group Chemical group 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 15
208000035143 Bacterial infection Diseases 0.000 claims description 14
208000022362 bacterial infectious disease Diseases 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000004430 oxygen atom Chemical group O* 0.000 claims description 12
125000004434 sulfur atom Chemical group 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
229920002554 vinyl polymer Polymers 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 11
150000002148 esters Chemical class 0.000 claims description 11
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
241000251468 Actinopterygii Species 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
239000005711 Benzoic acid Substances 0.000 claims description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
229910052792 caesium Inorganic materials 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
208000028172 protozoa infectious disease Diseases 0.000 claims description 7
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
238000010511 deprotection reaction Methods 0.000 claims description 4
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
235000010233 benzoic acid Nutrition 0.000 claims description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 3
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
RRIWSQXXBIFKQM-UHFFFAOYSA-N monomeric N-benzylcarbamic acid Natural products OC(=O)NCC1=CC=CC=C1 RRIWSQXXBIFKQM-UHFFFAOYSA-N 0.000 claims description 2
WPWXYQIMXTUMJB-UHFFFAOYSA-N tert-butyl 3-(aminomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(CN)C1 WPWXYQIMXTUMJB-UHFFFAOYSA-N 0.000 claims description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
239000000651 prodrug Substances 0.000 claims 1
229940002612 prodrug Drugs 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 130
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
239000000243 solution Substances 0.000 description 58
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
YQYJSBFKSSDGFO-FWAVGLHBSA-N hygromycin A Chemical class O[C@H]1[C@H](O)[C@H](C(=O)C)O[C@@H]1Oc1ccc(\C=C(/C)C(=O)N[C@@H]2[C@@H]([C@H]3OCO[C@H]3[C@@H](O)[C@@H]2O)O)cc1O YQYJSBFKSSDGFO-FWAVGLHBSA-N 0.000 description 46
235000019439 ethyl acetate Nutrition 0.000 description 44
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
208000015181 infectious disease Diseases 0.000 description 41
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 32
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 18
239000000872 buffer Substances 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
229910052943 magnesium sulfate Inorganic materials 0.000 description 16
235000019341 magnesium sulphate Nutrition 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 15
230000000694 effects Effects 0.000 description 15
238000002360 preparation method Methods 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000012043 crude product Substances 0.000 description 12
238000000855 fermentation Methods 0.000 description 12
230000004151 fermentation Effects 0.000 description 12
239000000203 mixture Substances 0.000 description 12
238000010898 silica gel chromatography Methods 0.000 description 12
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
239000002253 acid Substances 0.000 description 11
239000007787 solid Substances 0.000 description 11
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 10
239000002054 inoculum Substances 0.000 description 10
239000002609 medium Substances 0.000 description 10
208000035475 disorder Diseases 0.000 description 9
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
241000283690 Bos taurus Species 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
125000004122 cyclic group Chemical group 0.000 description 7
125000004494 ethyl ester group Chemical group 0.000 description 7
150000002576 ketones Chemical class 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000003527 Peterson olefination reaction Methods 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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239000003153 chemical reaction reagent Substances 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
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LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical class [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 5
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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 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
- 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
- A61P31/02—Local antiseptics
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Oncology (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

ZA200104434A 1998-12-02 2001-05-30 Hygromycin a derivatives as antibacterial agents. ZA200104434B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US11061898P	1998-12-02	1998-12-02

Publications (1)

Publication Number	Publication Date
ZA200104434B true ZA200104434B (en)	2002-05-30

Family

ID=22334003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200104434A ZA200104434B (en)	1998-12-02	2001-05-30	Hygromycin a derivatives as antibacterial agents.

Country Status (38)

Country	Link
US (1)	US6245745B1 (xx)
EP (1)	EP1135400A1 (xx)
JP (1)	JP3393189B2 (xx)
KR (1)	KR100418167B1 (xx)
CN (1)	CN1329617A (xx)
AP (1)	AP2001002154A0 (xx)
AR (1)	AR019784A1 (xx)
AU (1)	AU6362799A (xx)
BG (1)	BG105645A (xx)
BR (1)	BR9915813A (xx)
CA (1)	CA2352332C (xx)
CO (1)	CO5150171A1 (xx)
CZ (1)	CZ20011904A3 (xx)
DZ (1)	DZ2932A1 (xx)
EA (1)	EA004303B1 (xx)
EE (1)	EE200100301A (xx)
GE (1)	GEP20033144B (xx)
GT (1)	GT199900205A (xx)
HN (1)	HN1999000202A (xx)
HR (1)	HRP20010413A2 (xx)
HU (1)	HUP0104949A3 (xx)
ID (1)	ID28848A (xx)
IL (1)	IL142882A0 (xx)
IS (1)	IS5930A (xx)
MA (1)	MA26705A1 (xx)
NO (1)	NO20012687L (xx)
NZ (1)	NZ511424A (xx)
OA (1)	OA11721A (xx)
PA (1)	PA8486101A1 (xx)
PE (1)	PE20001429A1 (xx)
PL (1)	PL348063A1 (xx)
SK (1)	SK7302001A3 (xx)
TN (1)	TNSN99211A1 (xx)
TR (1)	TR200101540T2 (xx)
UY (1)	UY25827A1 (xx)
WO (1)	WO2000032616A1 (xx)
YU (1)	YU32601A (xx)
ZA (1)	ZA200104434B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR0015153A (pt) *	1999-10-29	2002-07-16	Pfizer Prod Inc	Derivados de higromicina
BR0015156A (pt) *	1999-10-29	2002-07-16	Pfizer Prod Inc	Pró-drogas de higromicina a
IL152984A0 (en) *	2000-06-02	2003-06-24	Pfizer Prod Inc	Hygromycin a derivatives for the treatment of bacterial and protozoal infections
EP1643901A4 (en) *	2003-06-19	2008-10-29	Compumed Inc	METHOD AND SYSTEM FOR ANALYZING BONE CONDITIONS USING A RADIOGRAPHIC IMAGE OF COMPATIBLE DICOM OS

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MA24852A1 (fr) *	1998-05-04	1999-12-31	Pfizer Prod Inc	Derives d'hygromycine a et leur procede de preparation
AU762302B2 (en) *	1998-05-04	2003-06-19	Pfizer Products Inc.	2"-deoxy hygromycin derivatives

1999
- 1999-11-09 YU YU32601A patent/YU32601A/sh unknown
- 1999-11-09 SK SK730-2001A patent/SK7302001A3/sk unknown
- 1999-11-09 ID IDW00200101182A patent/ID28848A/id unknown
- 1999-11-09 GE GEAP19995922A patent/GEP20033144B/en unknown
- 1999-11-09 EE EEP200100301A patent/EE200100301A/xx unknown
- 1999-11-09 CZ CZ20011904A patent/CZ20011904A3/cs unknown
- 1999-11-09 OA OA1200100135A patent/OA11721A/en unknown
- 1999-11-09 KR KR10-2001-7006849A patent/KR100418167B1/ko not_active IP Right Cessation
- 1999-11-09 BR BR9915813-2A patent/BR9915813A/pt not_active IP Right Cessation
- 1999-11-09 IL IL14288299A patent/IL142882A0/xx unknown
- 1999-11-09 AU AU63627/99A patent/AU6362799A/en not_active Abandoned
- 1999-11-09 JP JP2000585257A patent/JP3393189B2/ja not_active Expired - Fee Related
- 1999-11-09 NZ NZ511424A patent/NZ511424A/en unknown
- 1999-11-09 HU HU0104949A patent/HUP0104949A3/hu unknown
- 1999-11-09 EA EA200100444A patent/EA004303B1/ru not_active IP Right Cessation
- 1999-11-09 EP EP99951055A patent/EP1135400A1/en not_active Withdrawn
- 1999-11-09 AP APAP/P/2001/002154A patent/AP2001002154A0/en unknown
- 1999-11-09 CA CA002352332A patent/CA2352332C/en not_active Expired - Fee Related
- 1999-11-09 TR TR2001/01540T patent/TR200101540T2/xx unknown
- 1999-11-09 WO PCT/IB1999/001798 patent/WO2000032616A1/en not_active Application Discontinuation
- 1999-11-09 CN CN99813939A patent/CN1329617A/zh active Pending
- 1999-11-09 PL PL99348063A patent/PL348063A1/xx not_active Application Discontinuation
- 1999-11-10 MA MA25843A patent/MA26705A1/fr unknown
- 1999-11-10 TN TNTNSN99211A patent/TNSN99211A1/fr unknown
- 1999-11-10 DZ DZ990232A patent/DZ2932A1/xx active
- 1999-11-15 AR ARP990105799A patent/AR019784A1/es not_active Application Discontinuation
- 1999-11-18 HN HN1999000202A patent/HN1999000202A/es unknown
- 1999-11-25 CO CO99074411A patent/CO5150171A1/es unknown
- 1999-11-29 PE PE1999001195A patent/PE20001429A1/es not_active Application Discontinuation
- 1999-11-30 PA PA19998486101A patent/PA8486101A1/es unknown
- 1999-11-30 UY UY25827A patent/UY25827A1/es unknown
- 1999-12-01 GT GT199900205A patent/GT199900205A/es unknown
- 1999-12-02 US US09/453,429 patent/US6245745B1/en not_active Expired - Fee Related
2001
- 2001-04-27 IS IS5930A patent/IS5930A/is unknown
- 2001-05-29 HR HR20010413A patent/HRP20010413A2/hr not_active Application Discontinuation
- 2001-05-30 ZA ZA200104434A patent/ZA200104434B/en unknown
- 2001-05-31 NO NO20012687A patent/NO20012687L/no not_active Application Discontinuation
- 2001-06-25 BG BG105645A patent/BG105645A/bg unknown

Also Published As

Publication number	Publication date
OA11721A (en)	2005-01-25
HN1999000202A (es)	2000-06-13
SK7302001A3 (en)	2001-12-03
JP2002531463A (ja)	2002-09-24
IL142882A0 (en)	2002-03-10
CN1329617A (zh)	2002-01-02
EA200100444A1 (ru)	2001-10-22
NO20012687D0 (no)	2001-05-31
ID28848A (id)	2001-07-05
KR20010093136A (ko)	2001-10-27
TR200101540T2 (tr)	2001-10-22
CO5150171A1 (es)	2002-04-29
MA26705A1 (fr)	2004-12-20
CA2352332C (en)	2004-12-07
BR9915813A (pt)	2001-08-21
DZ2932A1 (fr)	2004-03-15
GEP20033144B (en)	2003-12-25
TNSN99211A1 (fr)	2005-11-10
AU6362799A (en)	2000-06-19
HUP0104949A3 (en)	2003-12-29
GT199900205A (es)	2001-05-24
HUP0104949A2 (hu)	2002-04-29
JP3393189B2 (ja)	2003-04-07
YU32601A (sh)	2004-05-12
HRP20010413A2 (en)	2002-06-30
EE200100301A (et)	2002-08-15
AP2001002154A0 (en)	2001-05-09
EP1135400A1 (en)	2001-09-26
PA8486101A1 (es)	2000-09-29
IS5930A (is)	2001-04-27
AR019784A1 (es)	2002-03-13
NO20012687L (no)	2001-05-31
KR100418167B1 (ko)	2004-02-11
CA2352332A1 (en)	2000-06-08
NZ511424A (en)	2003-08-29
PL348063A1 (en)	2002-05-06
PE20001429A1 (es)	2000-12-18
WO2000032616A1 (en)	2000-06-08
BG105645A (bg)	2002-02-28
US6245745B1 (en)	2001-06-12
UY25827A1 (es)	2001-08-27
EA004303B1 (ru)	2004-02-26
CZ20011904A3 (cs)	2001-10-17

Publication	Publication Date	Title
EP1075483B1 (en)	2003-12-03	Hygromycin a derivatives
ZA200104434B (en)	2002-05-30	Hygromycin a derivatives as antibacterial agents.
EP1077984B1 (en)	2003-06-18	2"-deoxy hygromycin derivatives
US6562792B1 (en)	2003-05-13	Hygromycin derivatives
US6867230B2 (en)	2005-03-15	Hygromycin A derivatives
AU2004201309A1 (en)	2004-04-29	Hygromycin A Derivatives as Antibacterial Agents
EP1369490B1 (en)	2006-02-08	Method of preparing a composition containing hygromycin A and epi-hygromycin
MXPA01005554A (en)	2001-12-04	Hygromycin a derivatives as antibacterial agents
MXPA00010822A (es)	2001-07-31	Derivados de 2"-desoxi higromicina