JP2005531603A - ３−デスクラジノシル−６−ｏ−カルバモイルおよび６−ｏ−カルボノイルマクロライド抗菌剤 - Google Patents
３−デスクラジノシル−６−ｏ−カルバモイルおよび６−ｏ−カルボノイルマクロライド抗菌剤 Download PDFInfo
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- JP2005531603A JP2005531603A JP2004509701A JP2004509701A JP2005531603A JP 2005531603 A JP2005531603 A JP 2005531603A JP 2004509701 A JP2004509701 A JP 2004509701A JP 2004509701 A JP2004509701 A JP 2004509701A JP 2005531603 A JP2005531603 A JP 2005531603A
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- 239000003242 anti bacterial agent Substances 0.000 title abstract description 10
- 239000003120 macrolide antibiotic agent Substances 0.000 title abstract description 6
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 184
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- 238000000034 method Methods 0.000 claims description 48
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- 125000000217 alkyl group Chemical group 0.000 claims description 31
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- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
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- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 206010005940 Bone and joint infections Diseases 0.000 claims description 3
- 206010024971 Lower respiratory tract infections Diseases 0.000 claims description 3
- 201000009906 Meningitis Diseases 0.000 claims description 3
- 206010035664 Pneumonia Diseases 0.000 claims description 3
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- 206010062255 Soft tissue infection Diseases 0.000 claims description 3
- 206010046306 Upper respiratory tract infection Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
- 241000606768 Haemophilus influenzae Species 0.000 claims description 2
- 241000588655 Moraxella catarrhalis Species 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 230000002685 pulmonary effect Effects 0.000 claims description 2
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- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 241000194033 Enterococcus Species 0.000 claims 1
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- 208000024891 symptom Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 783
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- 239000000243 solution Substances 0.000 description 218
- 229920006395 saturated elastomer Polymers 0.000 description 199
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 174
- 238000006243 chemical reaction Methods 0.000 description 158
- 238000004587 chromatography analysis Methods 0.000 description 147
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 145
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- 239000012267 brine Substances 0.000 description 133
- 238000000746 purification Methods 0.000 description 133
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 133
- 235000019439 ethyl acetate Nutrition 0.000 description 131
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 93
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 88
- 230000003197 catalytic effect Effects 0.000 description 83
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 64
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- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 54
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 49
- 239000012043 crude product Substances 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 239000002904 solvent Substances 0.000 description 31
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 29
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 28
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 27
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 15
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- 239000012264 purified product Substances 0.000 description 15
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 13
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 235000011181 potassium carbonates Nutrition 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 11
- 239000012442 inert solvent Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 10
- 230000000844 anti-bacterial effect Effects 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 0 CC[C@]([C@](C)(C([C@@](C)C([C@](*)C[C@](C)([C@@]([C@](C)[C@@]([C@]1C)OC(N*)O)O[C@@]([C@]2O)O[C@](C)C[C@@]2N(C)C)OC(CNC*)=O)=O)=N2)OC2=O)OC1=O Chemical compound CC[C@]([C@](C)(C([C@@](C)C([C@](*)C[C@](C)([C@@]([C@](C)[C@@]([C@]1C)OC(N*)O)O[C@@]([C@]2O)O[C@](C)C[C@@]2N(C)C)OC(CNC*)=O)=O)=N2)OC2=O)OC1=O 0.000 description 9
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- VHGYZPVCPDXGIG-UHFFFAOYSA-N 12,15-dioxa-17-azabicyclo[12.3.0]heptadeca-1,4,6,8,13-pentaene-3,11,16-trione Chemical compound O1C(=O)CC=CC=CC=CC(=O)C=C2NC(=O)OC2=C1 VHGYZPVCPDXGIG-UHFFFAOYSA-N 0.000 description 8
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 6
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38448302P | 2002-05-31 | 2002-05-31 | |
| PCT/US2003/016617 WO2003102010A1 (en) | 2002-05-31 | 2003-05-28 | 3-descladinosyl-6-o-carbamoyl and 6-o-carbonoyl macrolide antibacterial agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005531603A true JP2005531603A (ja) | 2005-10-20 |
| JP2005531603A5 JP2005531603A5 (https=) | 2006-06-29 |
Family
ID=29712041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004509701A Pending JP2005531603A (ja) | 2002-05-31 | 2003-05-28 | ３−デスクラジノシル−６−ｏ−カルバモイルおよび６−ｏ−カルボノイルマクロライド抗菌剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6825172B2 (https=) |
| EP (1) | EP1513856A1 (https=) |
| JP (1) | JP2005531603A (https=) |
| CN (1) | CN1671726A (https=) |
| AU (1) | AU2003234650A1 (https=) |
| CA (1) | CA2487918A1 (https=) |
| WO (1) | WO2003102010A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014007362A1 (ja) * | 2012-07-06 | 2014-01-09 | 合同酒精株式会社 | 環状マクロライド系化合物の分離方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100695322B1 (ko) | 2005-02-23 | 2007-03-15 | (주)에스.앤.디 | 메밀등겨로부터 수용성섬유소 및 파고피리톨의 저온 및 연속추출 방법 |
| US20090075916A1 (en) * | 2005-11-23 | 2009-03-19 | Upadhyay Dilip J | Use of Macrolide Derivatives for Treating Acne |
| US8796474B1 (en) | 2010-08-23 | 2014-08-05 | Rutgers, The State University Of New Jersey | Macrolide compounds and methods and intermediates useful for their preparation |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997017356A1 (en) * | 1995-11-08 | 1997-05-15 | Abbott Laboratories | Tricyclic erythromycin derivatives |
| WO1998030574A1 (en) * | 1997-01-07 | 1998-07-16 | Abbott Laboratories | Tricyclic erythromycin derivatives |
| WO1999021869A1 (en) * | 1997-10-29 | 1999-05-06 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a, 11,12-carbamate derivatives |
| WO1999021870A1 (en) * | 1997-10-29 | 1999-05-06 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a 11, 12-carbamate derivatives |
| WO2000075156A1 (en) * | 1999-06-07 | 2000-12-14 | Abbott Laboratories | 6-o-carbamate ketolide derivatives |
| JP2001500855A (ja) * | 1996-09-04 | 2001-01-23 | アボツト・ラボラトリーズ | 抗菌活性を有する６―ｏ―置換ケトリド |
| JP2001515844A (ja) * | 1997-09-02 | 2001-09-25 | アボット・ラボラトリーズ | ３−デスクラジノース６−ｏ−置換エリスロマイシン誘導体 |
| JP2001348397A (ja) * | 2000-04-10 | 2001-12-18 | Pfizer Prod Inc | エリスロマイシンａ誘導体 |
| WO2002012260A1 (en) * | 2000-08-07 | 2002-02-14 | Pfizer Products Inc. | Macrolide antibiotics |
| WO2002046204A1 (en) * | 2000-12-06 | 2002-06-13 | Ortho-Mcneil Pharmaceutical, Inc. | 6-0-carbamoyl ketolide derivatives of erythromycin useful as antibacterials |
| WO2003050132A1 (en) * | 2001-12-05 | 2003-06-19 | Ortho-Mcneil Pharmaceutical, Inc. | 6-o-acyl ketolide derivatives of erythromycine useful as antibacterials |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8521402D0 (en) | 1985-08-28 | 1985-10-02 | Beecham Group Plc | Chemical compounds |
| IL114589A (en) | 1990-11-21 | 1999-12-22 | Roussel Uclaf | Intermediates for the preparation of erythromycin derivatives |
| UA51730C2 (uk) | 1996-09-04 | 2002-12-16 | Ебботт Лабораторіз | 6-o-заміщені кетоліди з антибактеріальною активністю, спосіб їх одержання (варіанти), фармацевтична композиція та спосіб регулювання бактеріальної інфекції у ссавців |
| AU720921B2 (en) | 1996-11-27 | 2000-06-15 | Taisho Pharmaceutical Co., Ltd. | Erythromycin A derivatives |
| US6037137A (en) * | 1997-02-20 | 2000-03-14 | Oncoimmunin, Inc. | Fluorogenic peptides for the detection of protease activity |
| US6169168B1 (en) | 1997-10-29 | 2001-01-02 | Taisho Pharmaceuticals Co., Ltd. | Erythromycin A derivatives |
| AP1060A (en) | 1998-01-02 | 2002-04-23 | Pfizer Prod Inc | Novel erythromycin derivatives. |
| US6020521A (en) | 1998-08-26 | 2000-02-01 | Abbott Laboratories | Macrolide LHRH antagonists |
| ID30547A (id) | 1999-04-16 | 2001-12-20 | Kosan Biosciences Inc | Zat anti-infeksi makrolida |
| IL145976A0 (en) | 1999-04-16 | 2002-07-25 | Ortho Mcneil Pharm Inc | Ketolide antibacterials |
| GB9910079D0 (en) | 1999-05-01 | 1999-06-30 | Smithkline Beecham Plc | Novel compounds |
| US6420535B1 (en) * | 1999-06-07 | 2002-07-16 | Abbott Laboratories | 6-O-carbamate ketolide derivatives |
| WO2001010880A1 (fr) | 1999-08-06 | 2001-02-15 | Taisho Pharmaceutical Co., Ltd. | Derives d'erythromycine a |
| WO2001010878A1 (fr) | 1999-08-06 | 2001-02-15 | Taisho Pharmaceutical Co., Ltd. | Derives d'erythromycine a |
| US6498146B1 (en) * | 1999-10-28 | 2002-12-24 | Pfizer Inc | Erythromycin derivatives |
| JP2002173498A (ja) | 2000-09-27 | 2002-06-21 | Hokuriku Seiyaku Co Ltd | エリスロマイシン誘導体 |
-
2003
- 2003-05-28 US US10/447,058 patent/US6825172B2/en not_active Expired - Lifetime
- 2003-05-28 CN CNA038177595A patent/CN1671726A/zh active Pending
- 2003-05-28 CA CA002487918A patent/CA2487918A1/en not_active Abandoned
- 2003-05-28 AU AU2003234650A patent/AU2003234650A1/en not_active Abandoned
- 2003-05-28 EP EP03729151A patent/EP1513856A1/en not_active Withdrawn
- 2003-05-28 WO PCT/US2003/016617 patent/WO2003102010A1/en not_active Ceased
- 2003-05-28 JP JP2004509701A patent/JP2005531603A/ja active Pending
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997017356A1 (en) * | 1995-11-08 | 1997-05-15 | Abbott Laboratories | Tricyclic erythromycin derivatives |
| JP2001500855A (ja) * | 1996-09-04 | 2001-01-23 | アボツト・ラボラトリーズ | 抗菌活性を有する６―ｏ―置換ケトリド |
| WO1998030574A1 (en) * | 1997-01-07 | 1998-07-16 | Abbott Laboratories | Tricyclic erythromycin derivatives |
| JP2001515844A (ja) * | 1997-09-02 | 2001-09-25 | アボット・ラボラトリーズ | ３−デスクラジノース６−ｏ−置換エリスロマイシン誘導体 |
| WO1999021869A1 (en) * | 1997-10-29 | 1999-05-06 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a, 11,12-carbamate derivatives |
| WO1999021870A1 (en) * | 1997-10-29 | 1999-05-06 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a 11, 12-carbamate derivatives |
| WO2000075156A1 (en) * | 1999-06-07 | 2000-12-14 | Abbott Laboratories | 6-o-carbamate ketolide derivatives |
| JP2001348397A (ja) * | 2000-04-10 | 2001-12-18 | Pfizer Prod Inc | エリスロマイシンａ誘導体 |
| WO2002012260A1 (en) * | 2000-08-07 | 2002-02-14 | Pfizer Products Inc. | Macrolide antibiotics |
| WO2002046204A1 (en) * | 2000-12-06 | 2002-06-13 | Ortho-Mcneil Pharmaceutical, Inc. | 6-0-carbamoyl ketolide derivatives of erythromycin useful as antibacterials |
| WO2003050132A1 (en) * | 2001-12-05 | 2003-06-19 | Ortho-Mcneil Pharmaceutical, Inc. | 6-o-acyl ketolide derivatives of erythromycine useful as antibacterials |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014007362A1 (ja) * | 2012-07-06 | 2014-01-09 | 合同酒精株式会社 | 環状マクロライド系化合物の分離方法 |
| JPWO2014007362A1 (ja) * | 2012-07-06 | 2016-06-02 | 合同酒精株式会社 | 環状マクロライド系化合物の分離方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1671726A (zh) | 2005-09-21 |
| AU2003234650A1 (en) | 2003-12-19 |
| WO2003102010A1 (en) | 2003-12-11 |
| EP1513856A1 (en) | 2005-03-16 |
| CA2487918A1 (en) | 2003-12-11 |
| US20040018994A1 (en) | 2004-01-29 |
| US6825172B2 (en) | 2004-11-30 |
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