OA11507A - 2"-Deoxy hygromycin derivatives. - Google Patents

2"-Deoxy hygromycin derivatives. Download PDF

Info

Publication number: OA11507A
Authority: OA; OAPI
Prior art keywords: methyl; deoxy; oxo; methylene; neo
Prior art date: 1998-05-04

Application number

OA1200000298A

Other languages

English (en)

Inventor

Linde Robert Gerald Ii

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.)

1998-05-04

Filing date

2000-10-27

Publication date

2004-05-13

2000-10-27 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2004-05-13 Publication of OA11507A publication Critical patent/OA11507A/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 34
150000001875 compounds Chemical class 0.000 claims abstract description 117
208000015181 infectious disease Diseases 0.000 claims abstract description 36
238000000034 method Methods 0.000 claims abstract description 34
150000003839 salts Chemical class 0.000 claims abstract description 27
239000000651 prodrug Substances 0.000 claims abstract description 16
229940002612 prodrug Drugs 0.000 claims abstract description 16
208000035143 Bacterial infection Diseases 0.000 claims abstract description 15
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 272
150000002923 oximes Chemical class 0.000 claims description 271
-1 trifluorbmethyl Chemical group 0.000 claims description 201
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 182
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
125000003118 aryl group Chemical group 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 40
125000000623 heterocyclic group Chemical group 0.000 claims description 36
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 33
125000005843 halogen group Chemical group 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 21
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical group [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 14
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 13
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
125000004434 sulfur atom Chemical group 0.000 claims description 11
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
241000251468 Actinopterygii Species 0.000 claims description 9
238000010511 deprotection reaction Methods 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004122 cyclic group Chemical group 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 7
GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims description 7
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
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125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
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125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
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125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 4
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125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
125000004494 ethyl ester group Chemical group 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
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
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
235000015320 potassium carbonate Nutrition 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 4
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims 2
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125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
229910000029 sodium carbonate Inorganic materials 0.000 claims 1
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208000035475 disorder Diseases 0.000 abstract description 10
206010037075 Protozoal infections Diseases 0.000 abstract description 9
230000001580 bacterial effect Effects 0.000 abstract description 6
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239000003904 antiprotozoal agent Substances 0.000 abstract description 2
239000012453 solvate Substances 0.000 abstract 1
YQYJSBFKSSDGFO-FWAVGLHBSA-N hygromycin A Chemical compound 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 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
239000000872 buffer Substances 0.000 description 16
239000002585 base Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
230000000694 effects Effects 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
150000002576 ketones Chemical class 0.000 description 14
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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241000193996 Streptococcus pyogenes Species 0.000 description 6
150000001732 carboxylic acid derivatives Chemical group 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
150000002148 esters Chemical group 0.000 description 6
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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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239000000829 suppository Substances 0.000 description 1
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125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000003354 tissue distribution assay Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
206010044008 tonsillitis Diseases 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003053 toxin Substances 0.000 description 1
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125000001425 triazolyl group Chemical group 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
208000000143 urethritis Diseases 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

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
- 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
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- 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
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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

OA1200000298A 1998-05-04 2000-10-27 2"-Deoxy hygromycin derivatives. OA11507A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US8405898P	1998-05-04	1998-05-04

Publications (1)

Publication Number	Publication Date
OA11507A true OA11507A (en)	2004-05-13

Family

ID=22182624

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200000298A OA11507A (en)	1998-05-04	2000-10-27	2"-Deoxy hygromycin derivatives.

Country Status (38)

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US (1)	US6342497B1 (sh)
EP (1)	EP1077984B1 (sh)
JP (1)	JP2002513798A (sh)
KR (1)	KR100396099B1 (sh)
CN (1)	CN1299367A (sh)
AP (1)	AP1069A (sh)
AR (1)	AR015776A1 (sh)
AT (1)	ATE243218T1 (sh)
AU (1)	AU762302B2 (sh)
BG (1)	BG104995A (sh)
BR (1)	BR9910232A (sh)
CA (1)	CA2331261C (sh)
DE (1)	DE69908936T2 (sh)
DK (1)	DK1077984T3 (sh)
DZ (1)	DZ2779A1 (sh)
EA (1)	EA004374B1 (sh)
ES (1)	ES2199559T3 (sh)
GT (1)	GT199900058A (sh)
HN (1)	HN1999000064A (sh)
HR (1)	HRP20000748A2 (sh)
HU (1)	HUP0102412A3 (sh)
ID (1)	ID26368A (sh)
IL (1)	IL139020A0 (sh)
IS (1)	IS5680A (sh)
MA (1)	MA26626A1 (sh)
NO (1)	NO20005551L (sh)
NZ (1)	NZ507450A (sh)
OA (1)	OA11507A (sh)
PA (1)	PA8471901A1 (sh)
PE (1)	PE20000440A1 (sh)
PL (1)	PL344085A1 (sh)
PT (1)	PT1077984E (sh)
SK (1)	SK16442000A3 (sh)
TN (1)	TNSN99084A1 (sh)
TR (1)	TR200003249T2 (sh)
WO (1)	WO1999057127A1 (sh)
YU (1)	YU64300A (sh)
ZA (1)	ZA993063B (sh)

Families Citing this family (5)

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Publication number	Priority date	Publication date	Assignee	Title
CZ20011904A3 (cs) *	1998-12-02	2001-10-17	Pfizer Products Inc.	Deriváty hygromycinu jako antibakteriální činidla
GB9923078D0 (en) *	1999-09-29	1999-12-01	Phytopharm Plc	Sapogenin derivatives and their use
EE200200671A (et)	2000-06-02	2004-08-16	Pfizer Products Inc.	Hügromütsiin A derivaadid bakteriaalsete ja algloomadest põhjustatud infektsioonide ravimiseks
CN102168034B (zh) *	2010-11-29	2012-12-05	中国科学院南海海洋研究所	一种海洋链霉菌以及利用该菌制备替达霉素a和b的方法
EP3840743A4 (en) *	2018-08-20	2022-08-17	Northeastern University	Hygromycin a compounds and methods of treating spirochete diseases

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* Cited by examiner, † Cited by third party
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JP2832356B2 (ja) *	1988-03-31	1998-12-09	武田薬品工業株式会社	ハイグロマイシン類の合成中間体および製造法

1999
- 1999-04-08 IL IL13902099A patent/IL139020A0/xx unknown
- 1999-04-08 AU AU28508/99A patent/AU762302B2/en not_active Ceased
- 1999-04-08 BR BR9910232-3A patent/BR9910232A/pt not_active IP Right Cessation
- 1999-04-08 TR TR2000/03249T patent/TR200003249T2/xx unknown
- 1999-04-08 PL PL99344085A patent/PL344085A1/xx unknown
- 1999-04-08 ES ES99909164T patent/ES2199559T3/es not_active Expired - Lifetime
- 1999-04-08 DK DK99909164T patent/DK1077984T3/da active
- 1999-04-08 PT PT99909164T patent/PT1077984E/pt unknown
- 1999-04-08 ID IDW20002256A patent/ID26368A/id unknown
- 1999-04-08 HU HU0102412A patent/HUP0102412A3/hu unknown
- 1999-04-08 DE DE69908936T patent/DE69908936T2/de not_active Expired - Fee Related
- 1999-04-08 US US09/380,718 patent/US6342497B1/en not_active Expired - Fee Related
- 1999-04-08 CN CN99805810A patent/CN1299367A/zh active Pending
- 1999-04-08 EA EA200001028A patent/EA004374B1/ru not_active IP Right Cessation
- 1999-04-08 NZ NZ507450A patent/NZ507450A/en unknown
- 1999-04-08 CA CA002331261A patent/CA2331261C/en not_active Expired - Fee Related
- 1999-04-08 JP JP2000547096A patent/JP2002513798A/ja active Pending
- 1999-04-08 WO PCT/IB1999/000611 patent/WO1999057127A1/en active IP Right Grant
- 1999-04-08 YU YU64300A patent/YU64300A/sh unknown
- 1999-04-08 KR KR10-2000-7012222A patent/KR100396099B1/ko not_active IP Right Cessation
- 1999-04-08 AT AT99909164T patent/ATE243218T1/de not_active IP Right Cessation
- 1999-04-08 SK SK1644-2000A patent/SK16442000A3/sk unknown
- 1999-04-08 EP EP99909164A patent/EP1077984B1/en not_active Expired - Lifetime
- 1999-04-16 GT GT199900058A patent/GT199900058A/es unknown
- 1999-04-29 PE PE1999000355A patent/PE20000440A1/es not_active Application Discontinuation
- 1999-04-29 AP APAP/P/1999/001525A patent/AP1069A/en active
- 1999-04-30 AR ARP990102023A patent/AR015776A1/es not_active Application Discontinuation
- 1999-05-03 DZ DZ990079A patent/DZ2779A1/xx active
- 1999-05-03 TN TNTNSN99084A patent/TNSN99084A1/fr unknown
- 1999-05-03 MA MA25566A patent/MA26626A1/fr unknown
- 1999-05-03 HN HN1999000064A patent/HN1999000064A/es unknown
- 1999-05-03 ZA ZA9903063A patent/ZA993063B/xx unknown
- 1999-05-04 PA PA19998471901A patent/PA8471901A1/es unknown
2000
- 2000-10-24 IS IS5680A patent/IS5680A/is unknown
- 2000-10-27 OA OA1200000298A patent/OA11507A/en unknown
- 2000-11-03 HR HR20000748A patent/HRP20000748A2/hr not_active Application Discontinuation
- 2000-11-03 NO NO20005551A patent/NO20005551L/no not_active Application Discontinuation
- 2000-11-28 BG BG104995A patent/BG104995A/bg unknown

Also Published As

Publication number	Publication date
BG104995A (bg)	2001-07-31
AU762302B2 (en)	2003-06-19
JP2002513798A (ja)	2002-05-14
TNSN99084A1 (fr)	2005-11-10
CA2331261C (en)	2004-07-27
SK16442000A3 (sk)	2001-07-10
MA26626A1 (fr)	2004-12-20
BR9910232A (pt)	2001-01-09
DK1077984T3 (da)	2003-09-15
HN1999000064A (es)	2000-01-12
EA200001028A1 (ru)	2001-04-23
ID26368A (id)	2000-12-14
AR015776A1 (es)	2001-05-16
US6342497B1 (en)	2002-01-29
PA8471901A1 (es)	2000-09-29
IS5680A (is)	2000-10-24
GT199900058A (es)	2000-10-07
AU2850899A (en)	1999-11-23
YU64300A (sh)	2003-07-07
NO20005551D0 (no)	2000-11-03
EA004374B1 (ru)	2004-04-29
ATE243218T1 (de)	2003-07-15
KR100396099B1 (ko)	2003-08-27
IL139020A0 (en)	2001-11-25
NZ507450A (en)	2003-08-29
HUP0102412A2 (hu)	2001-11-28
EP1077984B1 (en)	2003-06-18
EP1077984A1 (en)	2001-02-28
CA2331261A1 (en)	1999-11-11
PE20000440A1 (es)	2000-05-26
AP9901525A0 (en)	1999-06-30
AP1069A (en)	2002-05-14
NO20005551L (no)	2001-01-02
ES2199559T3 (es)	2004-02-16
DE69908936T2 (de)	2004-05-19
PL344085A1 (en)	2001-09-24
DZ2779A1 (fr)	2005-04-23
WO1999057127A1 (en)	1999-11-11
HRP20000748A2 (en)	2001-06-30
KR20010043267A (ko)	2001-05-25
PT1077984E (pt)	2003-09-30
CN1299367A (zh)	2001-06-13
HUP0102412A3 (en)	2003-07-28
TR200003249T2 (tr)	2001-03-21
DE69908936D1 (en)	2003-07-24
ZA993063B (en)	2000-11-03

Publication	Publication Date	Title
EP1075483B1 (en)	2003-12-03	Hygromycin a derivatives
CA2331261C (en)	2004-07-27	2"-deoxy hygromycin derivatives
US6245745B1 (en)	2001-06-12	Hygromycin A derivatives
US6867230B2 (en)	2005-03-15	Hygromycin A derivatives
EP1369490B1 (en)	2006-02-08	Method of preparing a composition containing hygromycin A and epi-hygromycin
MXPA00010822A (es)	2001-07-31	Derivados de 2"-desoxi higromicina
CZ20004075A3 (cs)	2001-05-16	Deriváty 2"-deoxy-hygromycinu
NZ523779A (en)	2003-09-26	Hygromycin A derivatives
AU2004201309A1 (en)	2004-04-29	Hygromycin A Derivatives as Antibacterial Agents
MXPA00010821A (en)	2001-07-31	Hygromycin a derivatives