HUP0500878A2 - Amide derivatives as ccr3 receptor ligands, process for producing them, pharmaceutical compositions containing them and their use and intermediates - Google Patents
Amide derivatives as ccr3 receptor ligands, process for producing them, pharmaceutical compositions containing them and their use and intermediatesInfo
- Publication number
- HUP0500878A2 HUP0500878A2 HU0500878A HUP0500878A HUP0500878A2 HU P0500878 A2 HUP0500878 A2 HU P0500878A2 HU 0500878 A HU0500878 A HU 0500878A HU P0500878 A HUP0500878 A HU P0500878A HU P0500878 A2 HUP0500878 A2 HU P0500878A2
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- straight
- atom
- branched
- optionally substituted
- Prior art date
Links
- 102000004499 CCR3 Receptors Human genes 0.000 title abstract 3
- 108010017316 CCR3 Receptors Proteins 0.000 title abstract 3
- 150000001408 amides Chemical class 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 8
- -1 Amino alkyl amide Chemical class 0.000 abstract 6
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000004429 atom Chemical group 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 4
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 125000004434 sulfur atom Chemical group 0.000 abstract 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 2
- 102100023688 Eotaxin Human genes 0.000 abstract 2
- 101710139422 Eotaxin Proteins 0.000 abstract 2
- 101000980744 Homo sapiens C-C chemokine receptor type 3 Proteins 0.000 abstract 2
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical group CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 102000043445 human CCR3 Human genes 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000002464 receptor antagonist Substances 0.000 abstract 2
- 229940044551 receptor antagonist Drugs 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000012453 solvate Substances 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- VQNDBXJTIJKJPV-UHFFFAOYSA-N 2h-triazolo[4,5-b]pyridine Chemical group C1=CC=NC2=NNN=C21 VQNDBXJTIJKJPV-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 101150004010 CXCR3 gene Proteins 0.000 abstract 1
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 230000001088 anti-asthma Effects 0.000 abstract 1
- 230000036436 anti-hiv Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000000767 anti-ulcer Effects 0.000 abstract 1
- 239000000924 antiasthmatic agent Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 230000000324 neuroprotective effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002285 radioactive effect Effects 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 239000012873 virucide Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Amino alkyl amide derivatives and their salts, solvates and their isomers are new. Amino alkyl amide derivatives of formula Ar 1-X-N(R 1)-Y-N(R 2)-C(=O)-Z'-Ar 2 and their salts, solvates and their isomers are new. Ar 1phenyl (optionally substituted by halogen); X,Y : straight 1-4C alkylene (optionally substituted by straight or branched 1-4C alkyl); Z' : straight 2-4C alkylene or alkenylene (both optionally substituted by straight or branched 1-4C alkyl) or valence bond; R 1,R 2hydrogen atom or straight or branched 1-4C alkyl; Ar 2phenyl-, thienyl- or furyl (all optionally substituted by straight or branched 1-4C alkyl or alkoxy, hydroxyl, amino (optionally mono- or di-substituted by straight or branched 1-4C alkyl), trifluoromethyl, cyano, 1-2C alkylenedioxy or halogen atom), 5- or 6-membered heterocyclic ring (containing 1 - 3 nitrogen atoms, or 2 nitrogen atoms and 1 oxygen atom, or 1 nitrogen atom and 1 oxygen atom, or 1 nitrogen atom and 1 sulfur atom and optionally substituted by straight or branched 1-4C alkyl or alkoxy, halogen atom, nitro, cyano, carboxyl, phenyl (optionally substituted by straight or branched 1-4C alkyl, halogen atom or benzyloxy), oxo, NR 1 0R 1 1, CONR 1 0R 1 1 or SO 2NR 1 0R 1 1), the benzologs of these 5- or 6-membered heterocycle (in which the benzene ring is optionally substituted by T 1, trifluoromethyl, nitro, 1-2C alkylenedioxy or sulfonyl) or 5- or 6-membered heterocyclic ring (containing 1 - 3 nitrogen atoms, or 1 nitrogen atom and 1 oxygen atom, or 1 nitrogen atom and 1 sulfur atom and condensed with 6-membered heteroaromatic rings (containing 1 or 2 nitrogen atoms) and optionally substituted by T 1); T 1halogen atom, straight or branched 1-4C alkyl or alkoxy, cyano, carboxyl, hydroxyl, NR 1 0R 1 1, CONR 1 0R 1 1 or SO 2NR 1 0R 1 1; R 1 0,R 1 1,R 1 4hydrogen atom, straight or branched 1-4C alkyl, 3-6C cycloalkyl or benzyl; NR 1 0+R 1 1a group of formula (i); R 1 2,R 1 3hydrogen atom or straight or branched 1-4C alkyl; A : methylene group, oxygen atom, sulfur atom or NR 1 4; q : 0 - 3; r : 1 or 2; o,s : 0 or 1. Independent claims are included for the following: (1) preparation of the amino-alkyl-amide derivatives (I); and (2) a pyridine compound of formula Ar' 2-Z 1-C(=O)-W' forming a narrower group of a ketone compound of formula Ar 2-Z'-C(=O)-W' (II). Ar' 21,2,4-triazolo[1,5-a]pyridine- or triazolo[5,4-b]pyridine group (both optionally substituted by straight or branched 1-4C alkyl or alkoxy, hydroxyl, NR 1 0R 1 1, CONR 1 0R 1 1 or SO 2NR 1 0R 1 1); Z 11,3-propylene group; W' : halogen atom, hydroxyl, O(1-4C alkyl) or OCO-Z'-Ar 2. ACTIVITY : Antiasthmatic; Dermatological; Antiinflammatory; Gastrointestinal-Gen.; Antiulcer; Antiallergic; Ophthalmological; Neuroprotective; Virucide; Anti-HIV. MECHANISM OF ACTION : CC chemokine receptor 3 (CCR3) receptor antagonist. The CCR3 receptor antagonist effect of the amino-alkyl-amide derivatives (I) was examined on eotaxin binding test on human CCR3 (hCCR3) receptor expressing recombinant K562 and RBL2H3 cells and using Eotaxin labeled with radioactive iodine ( 1> 2> 3>I). The compound (I) showed IC 5 0 value of 0.5 - 500 (preferably 0.5 - 15) nM. No results for specific compounds are given.
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0500878A HUP0500878A2 (en) | 2005-09-22 | 2005-09-22 | Amide derivatives as ccr3 receptor ligands, process for producing them, pharmaceutical compositions containing them and their use and intermediates |
| CA002623317A CA2623317A1 (en) | 2005-09-22 | 2006-09-19 | Amino-alkyl-amide derivatives as ccr3 receptor liquids |
| BRPI0616150-2A BRPI0616150A2 (en) | 2005-09-22 | 2006-09-19 | amino alkyl amide derivatives as ccr3 receptor liquids |
| AU2006293635A AU2006293635A1 (en) | 2005-09-22 | 2006-09-19 | Amino-alkyl-amide derivatives as CCR3 receptor liquids |
| JP2008531798A JP2009508929A (en) | 2005-09-22 | 2006-09-19 | Amino-alkyl-amide derivatives as CCR3 receptor ligands |
| KR1020087007021A KR20080046209A (en) | 2005-09-22 | 2006-09-19 | Amino-alkyl-amide derivatives as ccr3 receptor liquids |
| RU2008115499/04A RU2008115499A (en) | 2005-09-22 | 2006-09-19 | NEW AMINOKILAMIDE DERIVATIVES AS CCR3 RECEPTOR LIGAND ANTAGONISTS |
| PCT/HU2006/000078 WO2007034252A1 (en) | 2005-09-22 | 2006-09-19 | Amino-alkyl-amide derivatives as ccr3 receptor liquids |
| EP06795036A EP1931620A1 (en) | 2005-09-22 | 2006-09-19 | Amino-alkyl-amide derivatives as ccr3 receptor liquids |
| CNA2006800348579A CN101268038A (en) | 2005-09-22 | 2006-09-19 | Amino-alkyl-amide derivatives as CCR3 receptor ligands |
| IL190094A IL190094A0 (en) | 2005-09-22 | 2008-03-11 | Amino-alkyl-amide derivatives as ccr3 receptor liquids |
| US12/050,969 US20080287434A1 (en) | 2005-09-22 | 2008-03-19 | New amino-alkyl-amide derivatives as CCR3 receptor ligands |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0500878A HUP0500878A2 (en) | 2005-09-22 | 2005-09-22 | Amide derivatives as ccr3 receptor ligands, process for producing them, pharmaceutical compositions containing them and their use and intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU0500878D0 HU0500878D0 (en) | 2005-11-28 |
| HUP0500878A2 true HUP0500878A2 (en) | 2007-05-29 |
Family
ID=89986278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0500878A HUP0500878A2 (en) | 2005-09-22 | 2005-09-22 | Amide derivatives as ccr3 receptor ligands, process for producing them, pharmaceutical compositions containing them and their use and intermediates |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN101268038A (en) |
| HU (1) | HUP0500878A2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023143194A1 (en) * | 2022-01-25 | 2023-08-03 | 瑞石生物医药有限公司 | Ccr4 small molecule antagonist and use thereof |
-
2005
- 2005-09-22 HU HU0500878A patent/HUP0500878A2/en unknown
-
2006
- 2006-09-19 CN CNA2006800348579A patent/CN101268038A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HU0500878D0 (en) | 2005-11-28 |
| CN101268038A (en) | 2008-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA9A | Lapse of provisional patent protection due to relinquishment or protection considered relinquished |