TW448174B - 9-oxime erythromycin derivatives, the preparation process thereof and pharmaceutical composition for treating bacterial infection or protozoa infection - Google Patents

9-oxime erythromycin derivatives, the preparation process thereof and pharmaceutical composition for treating bacterial infection or protozoa infection Download PDF

Info

Publication number: TW448174B
Authority: TW; Taiwan
Prior art keywords: deoxy; methyl; hydrazine; carbamate; oxolactide
Prior art date: 1997-06-11

Application number

TW087109086A

Other languages

English (en)

Chinese (zh)

Inventor

Yong-Jin Wu

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.)

1997-06-11

Filing date

1998-06-08

Publication date

2001-08-01

1998-06-08 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2001-08-01 Application granted granted Critical

2001-08-01 Publication of TW448174B publication Critical patent/TW448174B/zh

Links

208000015181 infectious disease Diseases 0.000 title claims abstract description 39
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
208000035143 Bacterial infection Diseases 0.000 title claims description 18
208000022362 bacterial infectious disease Diseases 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 13
150000001875 compounds Chemical class 0.000 claims abstract description 156
150000003839 salts Chemical class 0.000 claims abstract description 45
238000000034 method Methods 0.000 claims abstract description 39
230000001580 bacterial effect Effects 0.000 claims abstract description 12
238000011282 treatment Methods 0.000 claims abstract description 8
-1 imidyl Chemical group 0.000 claims description 94
238000011049 filling Methods 0.000 claims description 77
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 74
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 24
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 22
230000002079 cooperative effect Effects 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 19
239000003120 macrolide antibiotic agent Substances 0.000 claims description 18
125000000623 heterocyclic group Chemical group 0.000 claims description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
241000251468 Actinopterygii Species 0.000 claims description 8
206010037075 Protozoal infections Diseases 0.000 claims description 8
239000003242 anti bacterial agent Substances 0.000 claims description 8
229940088710 antibiotic agent Drugs 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
JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical class CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
241000271566 Aves Species 0.000 claims description 6
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 claims description 6
241000124008 Mammalia Species 0.000 claims description 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
241000894006 Bacteria Species 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229960003276 erythromycin Drugs 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 claims description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
150000007857 hydrazones Chemical class 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
NNRXCKZMQLFUPL-WBMZRJHASA-N (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;(2r,3 Chemical compound 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.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 NNRXCKZMQLFUPL-WBMZRJHASA-N 0.000 claims description 2
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
RMZBTNCACRJLHK-UHFFFAOYSA-N 4-phenylbutylhydrazine Chemical compound NNCCCCC1=CC=CC=C1 RMZBTNCACRJLHK-UHFFFAOYSA-N 0.000 claims description 2
XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 claims description 2
AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 claims description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 2
239000012964 benzotriazole Substances 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical class C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
206010061592 cardiac fibrillation Diseases 0.000 claims description 2
229940098008 erythrocin Drugs 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
230000002600 fibrillogenic effect Effects 0.000 claims description 2
239000000178 monomer Substances 0.000 claims description 2
HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
239000000047 product Substances 0.000 claims description 2
239000007921 spray Substances 0.000 claims description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 4
PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 2
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
- 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
- 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

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

TW087109086A 1997-06-11 1998-06-08 9-oxime erythromycin derivatives, the preparation process thereof and pharmaceutical composition for treating bacterial infection or protozoa infection TW448174B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4934997P	1997-06-11	1997-06-11

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Publication Number	Publication Date
TW448174B true TW448174B (en)	2001-08-01

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TW087109086A TW448174B (en)	1997-06-11	1998-06-08	9-oxime erythromycin derivatives, the preparation process thereof and pharmaceutical composition for treating bacterial infection or protozoa infection

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EP (1)	EP0988308A1 (id)
JP (1)	JP2000513026A (id)
KR (1)	KR20010013660A (id)
CN (1)	CN1259135A (id)
AP (1)	AP9801253A0 (id)
AR (1)	AR012244A1 (id)
AU (1)	AU7226798A (id)
BG (1)	BG103947A (id)
BR (1)	BR9810021A (id)
CA (1)	CA2293335A1 (id)
CO (1)	CO4940506A1 (id)
CZ (1)	CZ9904388A3 (id)
EA (1)	EA199901016A1 (id)
GT (1)	GT199800074A (id)
HN (1)	HN1998000073A (id)
HR (1)	HRP980316A2 (id)
HU (1)	HUP0002252A3 (id)
ID (1)	ID24529A (id)
IL (1)	IL132767A0 (id)
IS (1)	IS5251A (id)
MA (1)	MA26505A1 (id)
NO (1)	NO996108L (id)
OA (1)	OA11225A (id)
PA (1)	PA8451801A1 (id)
PE (1)	PE79899A1 (id)
PL (1)	PL337606A1 (id)
TN (1)	TNSN98083A1 (id)
TR (1)	TR199902995T2 (id)
TW (1)	TW448174B (id)
WO (1)	WO1998056800A1 (id)
ZA (1)	ZA985018B (id)

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HN1998000159A (es) *	1997-10-29	1999-02-09	Monsanto Co	Derivados de 9- amino - 3 ceto eritromicina
WO2000017218A1 (en) *	1998-09-22	2000-03-30	Pfizer Products Inc.	Carbamate and carbazate ketolide antibiotics
FR2786188B1 (fr) *	1998-11-24	2002-10-31	Hoechst Marion Roussel Inc	Nouveaux derives de l'erythromycine, leur procede de preparation et leur applicaion comme medicaments
US6258785B1 (en)	1998-12-02	2001-07-10	Pfizer Inc.	Crystalline 9-E-(O-methyl)oxime of 11, 12-dideoxy-3-de(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribohexopyranosyloxy)-6-O-methyl-12,11-(iminocarbonyl-(2-(3-(4-(3-pyridinyl)1H-imadazol-1-yl)propyl)hydrazono))-3-oxoerythromycin
EP1298138B1 (en) *	1998-12-10	2006-11-02	Pfizer Products Inc.	Carbamate and Carbazate Ketolide Antibiotics
US6284732B1 (en) *	1998-12-18	2001-09-04	Bio-Rad Laboratories, Inc.	Peptides and peptide analogues designed from HFE protein and their uses in the treatment of iron overload diseases
AU775637B2 (en) *	1999-04-16	2004-08-12	Kosan Biosciences, Inc.	Macrolide antiinfective agents
EE200100613A (et)	1999-05-24	2003-02-17	Pfizer Products Inc.	13-metüülerütromütsiini derivaadid
ATE250076T1 (de) *	1999-06-07	2003-10-15	Abbott Lab	6-o-carbamat ketolide derivate
ID27331A (id) *	1999-09-29	2001-03-29	Pfizer Prod Inc	Pembuatan antibiotik-antibiotik ketolida karbamat
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1998
- 1998-05-15 KR KR1019997011672A patent/KR20010013660A/ko not_active Ceased
- 1998-05-15 PL PL98337606A patent/PL337606A1/xx unknown
- 1998-05-15 HU HU0002252A patent/HUP0002252A3/hu unknown
- 1998-05-15 WO PCT/IB1998/000741 patent/WO1998056800A1/en not_active Ceased
- 1998-05-15 CZ CZ19994388A patent/CZ9904388A3/cs unknown
- 1998-05-15 EA EA199901016A patent/EA199901016A1/ru unknown
- 1998-05-15 TR TR1999/02995T patent/TR199902995T2/xx unknown
- 1998-05-15 AU AU72267/98A patent/AU7226798A/en not_active Abandoned
- 1998-05-15 BR BR9810021-1A patent/BR9810021A/pt not_active IP Right Cessation
- 1998-05-15 CA CA002293335A patent/CA2293335A1/en not_active Abandoned
- 1998-05-15 EP EP98919394A patent/EP0988308A1/en not_active Withdrawn
- 1998-05-15 JP JP11501928A patent/JP2000513026A/ja active Pending
- 1998-05-15 IL IL13276798A patent/IL132767A0/xx unknown
- 1998-05-15 ID IDW991570A patent/ID24529A/id unknown
- 1998-05-15 CN CN98805848A patent/CN1259135A/zh active Pending
- 1998-05-19 HN HN1998000073A patent/HN1998000073A/es unknown
- 1998-05-21 PA PA19988451801A patent/PA8451801A1/es unknown
- 1998-06-04 AP APAP/P/1998/001253A patent/AP9801253A0/en unknown
- 1998-06-05 GT GT199800074A patent/GT199800074A/es unknown
- 1998-06-08 PE PE1998000470A patent/PE79899A1/es not_active Application Discontinuation
- 1998-06-08 TW TW087109086A patent/TW448174B/zh active
- 1998-06-09 AR ARP980102703A patent/AR012244A1/es unknown
- 1998-06-10 ZA ZA9805018A patent/ZA985018B/xx unknown
- 1998-06-10 MA MA25105A patent/MA26505A1/fr unknown
- 1998-06-10 TN TNTNSN98083A patent/TNSN98083A1/fr unknown
- 1998-06-11 HR HR60/049,349A patent/HRP980316A2/hr not_active Application Discontinuation
- 1998-06-11 CO CO98033538A patent/CO4940506A1/es unknown
1999
- 1999-11-16 IS IS5251A patent/IS5251A/is unknown
- 1999-12-03 BG BG103947A patent/BG103947A/xx unknown
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Also Published As

Publication number	Publication date
HUP0002252A2 (hu)	2000-12-28
AP9801253A0 (en)	1999-12-04
CO4940506A1 (es)	2000-07-24
BR9810021A (pt)	2000-09-19
JP2000513026A (ja)	2000-10-03
GT199800074A (es)	1999-11-27
HUP0002252A3 (en)	2002-01-28
HRP980316A2 (en)	1999-04-30
HN1998000073A (es)	1999-01-08
CZ9904388A3 (cs)	2002-10-16
KR20010013660A (ko)	2001-02-26
NO996108L (no)	2000-02-10
EA199901016A1 (ru)	2000-06-26
OA11225A (en)	2003-07-17
WO1998056800A1 (en)	1998-12-17
IL132767A0 (en)	2001-03-19
CN1259135A (zh)	2000-07-05
MA26505A1 (fr)	2004-12-20
AU7226798A (en)	1998-12-30
AR012244A1 (es)	2000-09-27
CA2293335A1 (en)	1998-12-17
ZA985018B (en)	1999-12-10
TR199902995T2 (xx)	2000-02-21
PE79899A1 (es)	1999-08-25
NO996108D0 (no)	1999-12-10
TNSN98083A1 (fr)	2005-03-15
ID24529A (id)	2000-07-20
PA8451801A1 (es)	2000-05-24
BG103947A (en)	2000-07-31
IS5251A (is)	1999-11-16
PL337606A1 (en)	2000-08-28
EP0988308A1 (en)	2000-03-29

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HK1127924A (en)	2009-10-09	13-membered azalides and their use as antibiotic agents