JP2008526946A5 - - Google Patents
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- Publication number
- JP2008526946A5 JP2008526946A5 JP2007550875A JP2007550875A JP2008526946A5 JP 2008526946 A5 JP2008526946 A5 JP 2008526946A5 JP 2007550875 A JP2007550875 A JP 2007550875A JP 2007550875 A JP2007550875 A JP 2007550875A JP 2008526946 A5 JP2008526946 A5 JP 2008526946A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- decrazinosyl
- formula
- compound
- methyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- -1 hydroxy, methoxy Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 208000027866 inflammatory disease Diseases 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 11
- 238000004519 manufacturing process Methods 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 230000002757 inflammatory effect Effects 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 229960003276 erythromycin Drugs 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 230000004054 inflammatory process Effects 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 230000035755 proliferation Effects 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 3
- 108010002350 Interleukin-2 Proteins 0.000 claims 3
- 108010002616 Interleukin-5 Proteins 0.000 claims 3
- 229960004099 azithromycin Drugs 0.000 claims 3
- 229960002626 clarithromycin Drugs 0.000 claims 3
- 230000016396 cytokine production Effects 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 210000000265 leukocyte Anatomy 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims 2
- 108010002352 Interleukin-1 Proteins 0.000 claims 2
- 108090001005 Interleukin-6 Proteins 0.000 claims 2
- 108090001007 Interleukin-8 Proteins 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 206010062952 diffuse panbronchiolitis Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000028993 immune response Effects 0.000 claims 2
- 210000004698 lymphocyte Anatomy 0.000 claims 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 2
- 150000002926 oxygen Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 2
- 230000028327 secretion Effects 0.000 claims 2
- 210000003491 skin Anatomy 0.000 claims 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 206010006448 Bronchiolitis Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000032170 Congenital Abnormalities Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 206010061619 Deformity Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010014824 Endotoxic shock Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000000592 Nasal Polyps Diseases 0.000 claims 1
- 206010031252 Osteomyelitis Diseases 0.000 claims 1
- 206010036774 Proctitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 230000006052 T cell proliferation Effects 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 230000002052 anaphylactic effect Effects 0.000 claims 1
- 239000000427 antigen Substances 0.000 claims 1
- 102000036639 antigens Human genes 0.000 claims 1
- 108091007433 antigens Proteins 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 201000009267 bronchiectasis Diseases 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 230000006020 chronic inflammation Effects 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 210000001508 eye Anatomy 0.000 claims 1
- 210000002216 heart Anatomy 0.000 claims 1
- 230000008595 infiltration Effects 0.000 claims 1
- 238000001764 infiltration Methods 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 210000000936 intestine Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000016366 nasal cavity polyp Diseases 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 210000002460 smooth muscle Anatomy 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 0 CC[C@]([C@@](C)(*)[C@](*)[C@@](C)**[C@](C)C[C@](C)([C@@]([C@](C)[C@@]([C@]1C)OC(*(C)(C)C)=O)O[C@@]([C@@]2O)O[C@](C)C[C@@]2N(C)*)O*)OC1=O Chemical compound CC[C@]([C@@](C)(*)[C@](*)[C@@](C)**[C@](C)C[C@](C)([C@@]([C@](C)[C@@]([C@]1C)OC(*(C)(C)C)=O)O[C@@]([C@@]2O)O[C@](C)C[C@@]2N(C)*)O*)OC1=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64384005P | 2005-01-13 | 2005-01-13 | |
| US60/643,840 | 2005-01-13 | ||
| PCT/IB2006/001097 WO2006077501A2 (en) | 2005-01-13 | 2006-01-13 | Decladinosyl-macrolides with anti-inflammatory activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008526946A JP2008526946A (ja) | 2008-07-24 |
| JP2008526946A5 true JP2008526946A5 (https=) | 2009-02-26 |
| JP5036557B2 JP5036557B2 (ja) | 2012-09-26 |
Family
ID=36692605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007550875A Expired - Fee Related JP5036557B2 (ja) | 2005-01-13 | 2006-01-13 | 抗炎症活性デクラジノシル−マクロライド |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7910559B2 (https=) |
| EP (1) | EP1841776B1 (https=) |
| JP (1) | JP5036557B2 (https=) |
| AT (1) | ATE419261T1 (https=) |
| DE (1) | DE602006004555D1 (https=) |
| ES (1) | ES2317527T3 (https=) |
| WO (1) | WO2006077501A2 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1851236E (pt) | 2005-01-13 | 2010-10-25 | Glaxosmithkline Zagreb | Macrólidos com actividade anti-inflamatória |
| US20090075916A1 (en) * | 2005-11-23 | 2009-03-19 | Upadhyay Dilip J | Use of Macrolide Derivatives for Treating Acne |
| EP2526959B1 (en) | 2006-08-11 | 2017-08-02 | CSL Limited | Treatment of pulmonary disease conditions |
| TW201038277A (en) * | 2009-01-30 | 2010-11-01 | Glaxosmithkline Zagreb | Anti-inflammatory macrolide |
| AU2014252462A1 (en) * | 2013-04-10 | 2015-10-01 | Probiotic Pharmaceuticals Aps | Azithromycin antimicrobial derivatives with non-antibiotic pharmaceutical effect |
| GB201520419D0 (en) * | 2015-11-19 | 2016-01-06 | Epi Endo Pharmaceuticals Ehf | Compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL114589A (en) * | 1990-11-21 | 1999-12-22 | Roussel Uclaf | Intermediates for the preparation of erythromycin derivatives |
| US5523399A (en) * | 1991-12-27 | 1996-06-04 | Taisho Pharmaceutical Co., Ltd. | 5-O-desosaminylerythronolide derivatives |
| KR970704456A (ko) | 1994-08-12 | 1997-09-06 | 우에하라 아끼라 | 인터류킨 5 생성 억제제(Interleukin 5 Production Inhibitor) |
| EP0771564A4 (en) | 1994-08-12 | 1998-05-06 | Taisho Pharmaceutical Co Ltd | Interleukin-5 production inhibitor |
| US20020115621A1 (en) | 2000-08-07 | 2002-08-22 | Wei-Gu Su | Macrolide antibiotics |
| ITMI20021726A1 (it) * | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| ITMI20022292A1 (it) | 2002-10-29 | 2004-04-30 | Zambon Spa | 9a-azalidi ad attivita' antiinfiammatoria. |
-
2006
- 2006-01-13 EP EP06727561A patent/EP1841776B1/en not_active Expired - Lifetime
- 2006-01-13 US US11/813,876 patent/US7910559B2/en not_active Expired - Fee Related
- 2006-01-13 JP JP2007550875A patent/JP5036557B2/ja not_active Expired - Fee Related
- 2006-01-13 AT AT06727561T patent/ATE419261T1/de not_active IP Right Cessation
- 2006-01-13 WO PCT/IB2006/001097 patent/WO2006077501A2/en not_active Ceased
- 2006-01-13 ES ES06727561T patent/ES2317527T3/es not_active Expired - Lifetime
- 2006-01-13 DE DE602006004555T patent/DE602006004555D1/de not_active Expired - Lifetime
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