JP2007519685A5 - - Google Patents
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- Publication number
- JP2007519685A5 JP2007519685A5 JP2006550180A JP2006550180A JP2007519685A5 JP 2007519685 A5 JP2007519685 A5 JP 2007519685A5 JP 2006550180 A JP2006550180 A JP 2006550180A JP 2006550180 A JP2006550180 A JP 2006550180A JP 2007519685 A5 JP2007519685 A5 JP 2007519685A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl group
- hydrogen atom
- alkyl
- phenyl
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 16
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 16
- 229930192474 thiophene Natural products 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- -1 thiophene-yl-methyl group Chemical group 0.000 claims description 9
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 2
- YHVUVJYEERGYNU-UHFFFAOYSA-N 4',8-Di-Me ether-5,7,8-Trihydroxy-3-(4-hydroxybenzyl)-4-chromanone Natural products COC1(C)CC(O)OC(C)C1O YHVUVJYEERGYNU-UHFFFAOYSA-N 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 238000007112 amidation reaction Methods 0.000 claims 1
- AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical compound O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 claims 1
- 230000017858 demethylation Effects 0.000 claims 1
- 238000010520 demethylation reaction Methods 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 0 CC[C@@](*C([C@](C)[C@]([C@](C)[C@]([C@](C)(*)C[C@@](C)C(*)(*)[C@](C)C[C@]1*)OC2O[C@@](C)CC(*(C)C)[C@]2O)OC(C2)O[C@@](C)[C@](*)[C@]2(C)O)=O)[C@@]1(C)O Chemical compound CC[C@@](*C([C@](C)[C@]([C@](C)[C@]([C@](C)(*)C[C@@](C)C(*)(*)[C@](C)C[C@]1*)OC2O[C@@](C)CC(*(C)C)[C@]2O)OC(C2)O[C@@](C)[C@](*)[C@]2(C)O)=O)[C@@]1(C)O 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2004A000124 | 2004-01-29 | ||
| IT000124A ITMI20040124A1 (it) | 2004-01-29 | 2004-01-29 | Macrolidi ad attivita' antiinfiammatoria |
| PCT/EP2005/050312 WO2005075494A1 (en) | 2004-01-29 | 2005-01-25 | Macrolides with antiinflammatory activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007519685A JP2007519685A (ja) | 2007-07-19 |
| JP2007519685A5 true JP2007519685A5 (enExample) | 2011-04-07 |
| JP4709774B2 JP4709774B2 (ja) | 2011-06-22 |
Family
ID=34835570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006550180A Expired - Fee Related JP4709774B2 (ja) | 2004-01-29 | 2005-01-25 | 抗炎症活性を有するマクロライド |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7507721B2 (enExample) |
| EP (1) | EP1713818A1 (enExample) |
| JP (1) | JP4709774B2 (enExample) |
| CN (1) | CN1956993B (enExample) |
| AU (1) | AU2005210032B9 (enExample) |
| CA (1) | CA2554070C (enExample) |
| EA (1) | EA010906B1 (enExample) |
| IL (1) | IL176846A (enExample) |
| IT (1) | ITMI20040124A1 (enExample) |
| WO (1) | WO2005075494A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR043050A1 (es) | 2002-09-26 | 2005-07-13 | Rib X Pharmaceuticals Inc | Compuestos heterociclicos bifuncionales y metodos para preparar y usar los mismos |
| EP1723159B1 (en) | 2004-02-27 | 2019-06-12 | Melinta Therapeutics, Inc. | Macrocyclic compounds and methods of making and using the same |
| US20080249034A1 (en) * | 2005-03-21 | 2008-10-09 | Zambon S.P.A. | Use of Macrolides for Treating Intestinal Inflammation |
| WO2007129646A1 (ja) | 2006-05-01 | 2007-11-15 | Taisho Pharmaceutical Co., Ltd. | マクロライド誘導体 |
| ES2391653T3 (es) * | 2006-12-12 | 2012-11-28 | Zambon S.P.A. | Compuestos macrólidos dotados de actividad antiinflamatoria |
| EP4118091B1 (en) | 2020-03-12 | 2025-06-18 | Zoetis Services LLC | Immunomodulating urea azalides |
| CA3231535A1 (en) * | 2021-09-07 | 2023-03-16 | Zoetis Services Llc | Immunomodulating azalides |
| CN121038797A (zh) * | 2023-03-22 | 2025-11-28 | 艾比恩多制药有限责任公司 | 用于治疗嗜酸性粒细胞相关疾病的阿奇霉素衍生物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5215980A (en) * | 1992-01-17 | 1993-06-01 | Merck & Co., Inc. | 10-AZA-9-deoxo-11-deoxy-erythromycin A and derivatives thereof |
| IT1306205B1 (it) | 1999-01-15 | 2001-05-30 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| ITMI20021726A1 (it) * | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
-
2004
- 2004-01-29 IT IT000124A patent/ITMI20040124A1/it unknown
-
2005
- 2005-01-25 WO PCT/EP2005/050312 patent/WO2005075494A1/en not_active Ceased
- 2005-01-25 US US10/587,623 patent/US7507721B2/en not_active Expired - Fee Related
- 2005-01-25 EA EA200601368A patent/EA010906B1/ru not_active IP Right Cessation
- 2005-01-25 JP JP2006550180A patent/JP4709774B2/ja not_active Expired - Fee Related
- 2005-01-25 AU AU2005210032A patent/AU2005210032B9/en not_active Ceased
- 2005-01-25 CA CA2554070A patent/CA2554070C/en not_active Expired - Fee Related
- 2005-01-25 CN CN2005800035758A patent/CN1956993B/zh not_active Expired - Fee Related
- 2005-01-25 EP EP05701607A patent/EP1713818A1/en not_active Withdrawn
-
2006
- 2006-07-13 IL IL176846A patent/IL176846A/en not_active IP Right Cessation
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