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Pyrrolopyridazine compounds with antiviral properties

A compound, alkyl technology, applied in the field of HIV treatment, HIV replication inhibitor, integrase allosteric inhibitor, can solve crystal form stability, solubility lipophilicity, CYP inhibition liver microsome stability and plasma stability sexual insufficiency

Inactive Publication Date: 2013-09-11
世方科技(杭州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

More specifically, these problems with existing drugs may include deficiencies in crystal form stability, solubility, lipophilicity, CYP inhibition, hepatic microsomal stability, and plasma stability

Method used

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  • Pyrrolopyridazine compounds with antiviral properties
  • Pyrrolopyridazine compounds with antiviral properties
  • Pyrrolopyridazine compounds with antiviral properties

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0183] Example 1: Synthesis using pyrrolo[1,2-b]pyridazine derivatives.

[0184]

[0185] A compound of formula (I), wherein R 3 Yes - O(C 1 -C 6 )alkyl. More specifically, -O tert-butyl, R 2 , R 4 A is a compound of formula (I) as defined herein and can be prepared according to Scheme 1.

[0186] Scheme 1 discloses a method for synthesizing compounds of formula (I).

[0187] A general method for the synthesis of pyrrolo[1,2-b]pyridazine derivatives, starting with a 1-aminopyrrole derivative, eg 1a. The original method for the synthesis of pyrrolo[1,2-b]pyridazines from 1-aminopyrrole and β-dicarbonyl compounds, see Flitsch and Kramer (Flitsch, W.; Kramer, U. Tetrahedron Lett. 1968, 1479 and Flitsch, W .; Kramer, U. Liebigs Ann. Chem. 1970, 735, 35).

[0188] Condensation of 1-aminopyrrole (1a) and diethyl (ethoxymethylene)malonate (1b) in a suitable solvent, optionally heated and catalyzed with acids such as toluenesulfonic acid, will form pyrrolo[1,2 -b] pyridazi...

Embodiment 2

[0195] Example 2 Another synthetic method of pyrrolopyridazine derivatives.

[0196]

[0197] Scheme 2 discloses an alternative method for the synthesis of compounds of formula (I). A Condensation of 1-aminopyrrole derivative (2a) with β-dicarbonyl compound 2b in a suitable solvent, optionally acid catalyzed or heated, to obtain 2c.

[0198] Compound 2c and 4-acetamidobenzenesulfonyl azide in anhydrous acetonitrile were treated with DBU and stirred to give azide 2d (conditions were similar to those described in Hahn et al. J. Organometallic Chem. 2004, 689, 2662).

[0199] Heating, or optionally microwave treatment of 2d with rhodium(II) acetate dimer and isopropanol yields 2e.

[0200] Carry out saponification with lithium hydroxide or sodium hydroxide of 2e, generate the compound of structural formula (I).

[0201] Those skilled in the art will recognize that compounds of formula (I) have a chiral center. Those skilled in the art will recognize that there are many enan...

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Abstract

The invention discloses pyrrolopyridazine compounds used for treating or preventing HIV (human immunodeficiency virus) infection or other virus infections. The compounds can be used for as inhibitors for inhibiting HIV replication and can be used with other treatment drugs (particularly other antiviral drugs). Specifically, the invention discloses compounds for inhibiting HIV replication, a drug containing the compounds and a method for treating retrovirus infection through the compounds, for example, HIV infection. More specifically, the invention discloses an integrase allosteric inhibitor.

Description

technical field [0001] The present invention discloses compounds useful for treating human immunodeficiency virus (HIV) infection. The invention particularly discloses inhibitors for inhibiting HIV replication, medicines containing the compounds and methods for treating HIV with these compounds. More specifically, the present invention discloses integrase allosteric inhibitors. Background technique [0002] Acquired immunodeficiency syndrome (AIDS) is caused by a retrovirus, the human immunodeficiency virus (HIV). There are two types of HIV virus, HIV-1 and HIV-2, HIV-2 causes less severe disease than HIV-1. The genetic material of retroviruses is RNA (ribonucleic acid), which consists of two separate strands of RNA. Along with the RNA is reverse transcriptase (polymerase and ribonuclease activity), integrase, a protease, and several other proteins. [0003] Compounds that inhibit HIV replication are effective agents for the treatment of HIV and similar diseases. Drugs ...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/5025A61K31/538A61P31/18
Inventor 吴劲梓古德木德森·克里斯金
Owner 世方科技(杭州)有限公司
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