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WO-2017211246, SHENZHEN TARGETRX, INC.
SUBSTITUTED FUSED IMIDAZOLE CYCLIC COMPOUND AND PHARMACEUTICAL COMPOSITION THEREOF
WANG, Yihan; (CN).
XING, Qingfeng; (CN)
Novel deuterated analogs of substituted fused imidazole cyclic compounds, particularly alcaftadine are histamine H1-receptor antagonists and mast cell stabilizers, useful for treating allergy and nasal congestion.
The present invention relates to a substituted fused imidazole cyclic compound and a composition containing said compound and application thereof. Specifically disclosed is the fused imidazole cyclic compound represented by formula (I), or a pharmaceutical composition of its crystalline form, pharmaceutically acceptable salt, prodrug, stereoisomer, hydrate, or solvate. The compound of the present invention may be used as a histamine H1-receptor antagonist and mast-cell stabilizer, and is capable of inhibiting mast-cell release of histamine and preventing histamine function, thereby reducing allergic reaction
Example 1 Preparation of 6,11-dihydro -11- (1- (d3- methyl) piperidin-4-ylidene) -5H- imidazo [2,1-b]  benzazepine – 3- aldehyde (compound 8)
N-benzyloxycarbonylpiperidine-4-carboxylic acid (2.63 g, 10 mmol) was dissolved in 20 mL of dichloromethane, 6 mL of oxalyl chloride and 1 drop of DMF were added and the mixture was reacted at room temperature for 2 hours under nitrogen. The reaction mixture was concentrated to dryness under reduced pressure, dissolved in 20 mL of acetonitrile, and added with triethylamine (4.1 mL, 30 mmol) in an ice bath and stirred for 3 minutes. A solution of 1-phenethyl-1H-imidazole (2.06 g, 12 mmol) in 5 mL of acetonitrile was slowly added dropwise and the reaction was allowed to warm to room temperature overnight after the addition was completed. The reaction was completed, concentrated to dryness, 30 mL of ethyl acetate and 20 mL of water were added and the mixture was stirred for 5 minutes. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and concentrated to give 3.34 g of a colorless oil, benzyl-4- (1-phenethyl-1H-imidazole-2-formyl) piperidine-1-carboxylate (Compound 3) was obtained in a yield of 80%. ESI-MS: 418 [M ++ 1].
It was approved by the U.S. Food and Drug Administration in 2010 under the trade name Lastacaft.
Drug Patent Expiration and Exclusivity
|Active Ingredient||Form||Dosage||Drug Type||Application||Product|
There are 1 patent(s) protecting ALLERGAN’s LASTACAFT.
The last patent expires on 2013-11-21.
|US5468743||Imidazo[2,1-b]benzazepine derivatives, compositions and method of use
The present invention is concerned with novel imidazo[2, 1-b]benzazepines of formula ##STR1## the pharmaceutically acceptable addition salts and stereochemically isomeric forms thereof, wherein each of the dotted lines independently represents an optional bond; R.sup.1 represents hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkyloxy; R.sup.2 represents hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkyloxy; R.sup.3 represents hydrogen, C.sub.1-4 alkyl, ethenyl substituted with hydroxycarbonyl or C.sub.1-4 alkyloxycarbonyl, C.sub.1-4 alkyl substituted with hydroxycarbonyl or C.sub.1-4 alkyloxycarbonyl, hydroxyC.sub.1-4 alkyl, formyl or hydroxycarbonyl; R.sup.4 represents hydrogen, C.sub.1-4 alkyl, hydroxyC.sub.1-4 alkyl, phenyl or halo; R.sup.5 represents hydrogen, C.sub.1-4 alkyl or halo; L represents hydrogen; C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted with one substituent selected from the group consisting of hydroxy, halo, C.sub.1-4 alkyloxy, hydroxycarbonyl, C.sub.1-4 alkyloxycarbonyl, C.sub.1-4 alkyloxycarbonyl-C.sub.1-4 alkyloxy, hydroxycarbonylC.sub.1-4 alkyloxy, C.sub.1-4 alkyloxycarbonylamino, C.sub.1-4 alkylaminocarbonyl, C.sub.1-4 alkylaminocarbonylamino, C.sub.1-4 alkylaminothiocarbonylamino, aryl, aryloxy and arylcarbonyl; C.sub.1-6 alkyl substituted with both hydroxy and aryloxy; C.sub.3-6 alkenyl; C.sub.3-6 alkenyl substituted with aryl; or, L represents a radical of formula –Alk–Y–Het.sup.1 (a-1),–Alk–NH–CO–Het.sup.2 (a-2)or –Alk–Het.sup.3 (a-3); provided that 6,11-dihydro-11-(4-piperidinylidene)-5H-imidazo[2,1-b]benzazepine is ecxluded, which are useful antiallergic compounds.Compositions comprising said compounds, methods of using and processes for preparing the same.
Exclusivity is marketing rights granted by the FDA to the ALLERGAN.
Exclusivity ends on 2015-07-28.