HUP0402424A2 - Imidazoquinoline derivatives, process for their preparation and pharmaceutical compositions containing the same - Google Patents
Imidazoquinoline derivatives, process for their preparation and pharmaceutical compositions containing the sameInfo
- Publication number
- HUP0402424A2 HUP0402424A2 HU0402424A HUP0402424A HUP0402424A2 HU P0402424 A2 HUP0402424 A2 HU P0402424A2 HU 0402424 A HU0402424 A HU 0402424A HU P0402424 A HUP0402424 A HU P0402424A HU P0402424 A2 HUP0402424 A2 HU P0402424A2
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- halo
- alkoxy
- branched
- straight
- Prior art date
Links
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 14
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- -1 cyano, aminocarbonyl Chemical group 0.000 abstract 5
- 125000005843 halogen group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 239000003112 inhibitor Substances 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000012453 solvate Substances 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 229940124669 imidazoquinoline Drugs 0.000 abstract 2
- 125000004430 oxygen atom Chemical group 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
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- 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 abstract 1
- 102000008161 Adenosine A3 Receptor Human genes 0.000 abstract 1
- 108010060261 Adenosine A3 Receptor Proteins 0.000 abstract 1
- 229940123786 Adenosine A3 receptor antagonist Drugs 0.000 abstract 1
- 206010006482 Bronchospasm Diseases 0.000 abstract 1
- 206010015866 Extravasation Diseases 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000002580 adenosine A3 receptor antagonist Substances 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 230000002456 anti-arthritic effect Effects 0.000 abstract 1
- 230000001088 anti-asthma Effects 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 230000003178 anti-diabetic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000000648 anti-parkinson Effects 0.000 abstract 1
- 230000002682 anti-psoriatic effect Effects 0.000 abstract 1
- 230000003356 anti-rheumatic effect Effects 0.000 abstract 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- 239000000924 antiasthmatic agent Substances 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000003472 antidiabetic agent Substances 0.000 abstract 1
- 239000000939 antiparkinson agent Substances 0.000 abstract 1
- 239000003435 antirheumatic agent Substances 0.000 abstract 1
- 230000007885 bronchoconstriction Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 abstract 1
- 230000012292 cell migration Effects 0.000 abstract 1
- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000016396 cytokine production Effects 0.000 abstract 1
- 239000000824 cytostatic agent Substances 0.000 abstract 1
- 230000001085 cytostatic effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 210000003979 eosinophil Anatomy 0.000 abstract 1
- 230000036251 extravasation Effects 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 210000002865 immune cell Anatomy 0.000 abstract 1
- 230000001506 immunosuppresive effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 210000000440 neutrophil Anatomy 0.000 abstract 1
- 230000001777 nootropic effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 230000000241 respiratory effect Effects 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Imidazoquinoline derivatives (I), their salts, solvates and optically active isomers and salts or solvates, are new. Imidazoquinoline derivatives of formula (I), their salts, solvates and optically active isomers and salts or solvates, are new. [Image] R 1>, R 2>H or 1-4C alkyl; R 3>1-4C alkyl, 3-6C cycloalkyl, phenyl, thienyl, furyl (optionally substituted by at least one 1-4C alkyl, 1-4C alkoxy or halo), H, 5 - 6 membered heteroaromatic ring containing 1 - 3 N atoms or 5-membered heteroaromatic ring (containing one nitrogen atom and one oxygen atom or one nitrogen atom and one sulfur atom and optionally substituted by at least one 1-4C alkyl, 1-4C alkoxy or halo); R 4> - R 7>H, 1-4C alkyl, 1-4C alkoxy, OH or halo; or R 5>+R 6>methylenedioxy; R 8>H, cyano, aminocarbonyl, 1-4C alkoxycarbonyl or carboxy; R 9>, R 1> 0>T 1> or (CH 2) p-NR 1> 2>R 1> 3>; T 1>phenyl, phenyl-(1-4C)alkyl, thienyl-(1-4C)alkyl, furyl-(1-4C)alkyl (optionally substituted by methylenedioxy or at least one straight or branched 1-4C alkyl, straight or branched 1-4C alkoxy, OH, trifluoromethyl, cyano or halo), H, straight or branched 1-4C alkyl, 3-6C cycloalkyl, -(CH 2) m-OH, 5 - 6 membered heteroaromatic ring containing 1 - 3 N atoms or 5-membered heteroaromatic ring (containing one nitrogen atom and one oxygen atom or one nitrogen atom and one sulfur atom and optionally substituted by at least one straight or branched 1-4C alkyl, 1-4C alkoxy or halo); R 1> 2>, R 1> 3>T 1>; or NR 9>R 1> 0>, NR 1> 2>R 1> 3>3 - 7-membered heterocyclic group (optionally substituted by straight or branched 1-4C alkyl; X : -CH 2-, -NH-, -NR 1> 1>-, S, O, sulfo or sulfoxy; R 1> 1>1-4C alkyl or 3-6C cycloalkyl; n : 0 - 2; m : 1 - 4; p : 0 - 4; and provided that R 5>+R 6> is only methylenedioxy when R 4> and R 7> are H. Independent claims are also included for the following: (a) preparation of (I); and (b) new intermediates, imidazoquinoline acid compound of formula (II) and imidazoquinoline ester compound of formula (III). [Image] [Image] R 1> 4>1-4C alkyl. ACTIVITY : Cardiant; Nephrotropic; CNS Gen.; Respiratory Gen.; Antiallergic; Antiinflammatory; Dermatological; Antipsoriatic; Hypotensive; Ophthalmological; Antidiabetic; Antiasthmatic; Immunosuppressive; Antirheumatic; Cytostatic; Vasotropic; Antiarrhythmic; Antiparkinsonian; Antiarthritic; Antidepressant; Nootropic. MECHANISM OF ACTION : Adenosine A 3 Receptor Antagonist; Cytokine Production Inhibitor; TNF-alpha Release Inhibitor; Eosinophil, Neutrophil and Immune Cell Migration Inhibitor; Bronchoconstriction and Plasma Extravasation Inhibitor. The compounds were tested for adenosine A 3 receptor antagonistic activity using HEK293 cells. The general compound (I) showed a K i of 1.6 and 0.38 nM. No results for specific compounds given.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0402424A HUP0402424A3 (en) | 2001-12-21 | 2002-12-17 | Imidazoquinoline derivatives, process for their preparation and pharmaceutical compositions containing the same |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0105406A HUP0105406A3 (en) | 2001-12-21 | 2001-12-21 | Imidazo[1,2-a]quinolin derivatives, process for their preparation, pharmaceutical compositions thereof and intermediates |
| PCT/HU2002/000144 WO2003053969A1 (en) | 2001-12-21 | 2002-12-17 | Imidazoquinoline derivatives |
| HU0402424A HUP0402424A3 (en) | 2001-12-21 | 2002-12-17 | Imidazoquinoline derivatives, process for their preparation and pharmaceutical compositions containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP0402424A2 true HUP0402424A2 (en) | 2005-04-28 |
| HUP0402424A3 HUP0402424A3 (en) | 2012-10-29 |
Family
ID=89985623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0402424A HUP0402424A3 (en) | 2001-12-21 | 2002-12-17 | Imidazoquinoline derivatives, process for their preparation and pharmaceutical compositions containing the same |
Country Status (1)
| Country | Link |
|---|---|
| HU (1) | HUP0402424A3 (en) |
-
2002
- 2002-12-17 HU HU0402424A patent/HUP0402424A3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0402424A3 (en) | 2012-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD9A | Lapse of provisional protection due to non-payment of fees |