HRP980316A2 - 9-oxime erythromycin derivatives - Google Patents

9-oxime erythromycin derivatives

Info

Publication number: HRP980316A2
Authority: HR; Croatia
Prior art keywords: carbamate; deoxy; hydrazo; desosaminyl; methyl
Prior art date: 1997-06-11

Application number

HR60/049,349A

Other languages

English (en)

Croatian (hr)

Inventor

Wu Yong-Jin

Original Assignee

Wu Yong-Jin

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

1998-06-11

Publication date

1999-04-30

1998-06-11 Application filed by Wu Yong-Jin filed Critical Wu Yong-Jin

1999-04-30 Publication of HRP980316A2 publication Critical patent/HRP980316A2/hr

Links

150000001875 compounds Chemical class 0.000 claims description 157
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 114
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 34
238000000034 method Methods 0.000 claims description 31
125000000623 heterocyclic group Chemical group 0.000 claims description 28
-1 -NR7R8 Chemical group 0.000 claims description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 18
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000002252 acyl group Chemical group 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 12
208000035143 Bacterial infection Diseases 0.000 claims description 12
208000010362 Protozoan Infections Diseases 0.000 claims description 12
208000022362 bacterial infectious disease Diseases 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
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241000124008 Mammalia Species 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
241000271566 Aves Species 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 88
239000000243 solution Substances 0.000 description 52
238000005160 1H NMR spectroscopy Methods 0.000 description 43
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
208000015181 infectious disease Diseases 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000007787 solid Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
239000012267 brine Substances 0.000 description 18
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
239000012043 crude product Substances 0.000 description 17
239000010410 layer Substances 0.000 description 17
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235000019341 magnesium sulphate Nutrition 0.000 description 17
239000012044 organic layer Substances 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
238000005481 NMR spectroscopy Methods 0.000 description 13
239000003120 macrolide antibiotic agent Substances 0.000 description 13
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238000002474 experimental method Methods 0.000 description 11
239000002585 base Substances 0.000 description 10
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238000012746 preparative thin layer chromatography Methods 0.000 description 10
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
230000001580 bacterial effect Effects 0.000 description 7
125000001589 carboacyl group Chemical group 0.000 description 7
229960002626 clarithromycin Drugs 0.000 description 7
230000000694 effects Effects 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
229910004373 HOAc Inorganic materials 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
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238000002360 preparation method Methods 0.000 description 5
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
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231100000252 nontoxic Toxicity 0.000 description 4
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000003752 polymerase chain reaction Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
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AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
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229910017912 NH2OH Inorganic materials 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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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 description 3
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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)
Genetics & Genomics (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Tropical Medicine & Parasitology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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HR60/049,349A 1997-06-11 1998-06-11 9-oxime erythromycin derivatives HRP980316A2 (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
HRP980316A2 true HRP980316A2 (en)	1999-04-30

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ID=21959341

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR60/049,349A HRP980316A2 (en)	1997-06-11	1998-06-11	9-oxime erythromycin derivatives

Country Status (31)

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

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1998
- 1998-05-15 JP JP11501928A patent/JP2000513026A/ja active Pending
- 1998-05-15 CN CN98805848A patent/CN1259135A/zh active Pending
- 1998-05-15 ID IDW991570A patent/ID24529A/id unknown
- 1998-05-15 EA EA199901016A patent/EA199901016A1/ru unknown
- 1998-05-15 WO PCT/IB1998/000741 patent/WO1998056800A1/en not_active Application Discontinuation
- 1998-05-15 CZ CZ19994388A patent/CZ9904388A3/cs unknown
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- 1998-05-15 TR TR1999/02995T patent/TR199902995T2/xx unknown
- 1998-05-15 BR BR9810021-1A patent/BR9810021A/pt not_active IP Right Cessation
- 1998-05-15 AU AU72267/98A patent/AU7226798A/en not_active Abandoned
- 1998-05-15 IL IL13276798A patent/IL132767A0/xx unknown
- 1998-05-15 KR KR1019997011672A patent/KR20010013660A/ko not_active Ceased
- 1998-05-15 CA CA002293335A patent/CA2293335A1/en not_active Abandoned
- 1998-05-15 HU HU0002252A patent/HUP0002252A3/hu unknown
- 1998-05-15 EP EP98919394A patent/EP0988308A1/en not_active Withdrawn
- 1998-05-19 HN HN1998000073A patent/HN1998000073A/es unknown
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- 1998-06-08 TW TW087109086A patent/TW448174B/zh active
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- 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
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Also Published As

Publication number	Publication date
KR20010013660A (ko)	2001-02-26
CO4940506A1 (es)	2000-07-24
NO996108D0 (no)	1999-12-10
BR9810021A (pt)	2000-09-19
PL337606A1 (en)	2000-08-28
CA2293335A1 (en)	1998-12-17
BG103947A (en)	2000-07-31
AR012244A1 (es)	2000-09-27
AU7226798A (en)	1998-12-30
EP0988308A1 (en)	2000-03-29
IL132767A0 (en)	2001-03-19
GT199800074A (es)	1999-11-27
WO1998056800A1 (en)	1998-12-17
HUP0002252A3 (en)	2002-01-28
IS5251A (is)	1999-11-16
PA8451801A1 (es)	2000-05-24
NO996108L (no)	2000-02-10
MA26505A1 (fr)	2004-12-20
TW448174B (en)	2001-08-01
JP2000513026A (ja)	2000-10-03
PE79899A1 (es)	1999-08-25
CN1259135A (zh)	2000-07-05
EA199901016A1 (ru)	2000-06-26
TNSN98083A1 (fr)	2005-03-15
HUP0002252A2 (hu)	2000-12-28
ZA985018B (en)	1999-12-10
AP9801253A0 (en)	1999-12-04
ID24529A (id)	2000-07-20
OA11225A (en)	2003-07-17
TR199902995T2 (xx)	2000-02-21
CZ9904388A3 (cs)	2002-10-16
HN1998000073A (es)	1999-01-08

Publication	Publication Date	Title
HRP980316A2 (en)	1999-04-30	9-oxime erythromycin derivatives
EP0988310B9 (en)	2006-03-08	4"-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives
US6833444B2 (en)	2004-12-21	Ketolide antibiotics
HRP980571A2 (en)	1999-08-31	9-amino-3-keto erythromycin derivatives
US6329345B1 (en)	2001-12-11	13-membered azalides and their use as antibiotic agents
EP0895999A1 (en)	1999-02-10	C-4" substituted macrolide antibiotics
EP1132392B1 (en)	2004-03-03	Ketolide antibiotics
EP1167376B1 (en)	2004-07-14	Macrolide antibiotics
US20030100742A1 (en)	2003-05-29	Erythromycin a derivatives
US6162794A (en)	2000-12-19	Erythromycin derivatives
US6248719B1 (en)	2001-06-19	Tricyclic 3-keto derivatives of 6-O-methylerthromycin
US20020025937A1 (en)	2002-02-28	9-oxime erythromycin derivatives
US6482801B2 (en)	2002-11-19	9a, 11b-dehydro derivatives of 9-oxime-3-keto-6-O- methylerythromycin
MXPA99011494A (en)	2000-07-01	9-oxime erythromycin derivatives
MXPA01005055A (en)	2001-12-04	13-membered azalides and their use as antibiotic agents
MXPA01002355A (en)	2002-06-05	Ketolide antibiotics
MXPA01007584A (en)	2002-05-09	Ketolide antibiotics

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Date	Code	Title	Description
1998-06-11	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
1999-04-30	A1OB	Publication of a patent application
2000-06-11	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20000611 Year of fee payment: 3
2008-02-06	ODBI	Application refused