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Peptidomimetic compounds as immunomodulators

A compound, selected technology, applied in the fields of peptides, organic chemistry, drug combination, etc., can solve the problem of peptidomimetic compounds without PD-1 immunomodulator

Inactive Publication Date: 2014-11-19
AURIGENE DISCOVERY TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, there are currently no peptidomimetic compounds available as PD-1 immunomodulators

Method used

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  • Peptidomimetic compounds as immunomodulators
  • Peptidomimetic compounds as immunomodulators
  • Peptidomimetic compounds as immunomodulators

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0195] Example 1: Synthesis of Compound 1

[0196]

[0197] step 1:

[0198]

[0199] Diazomethane (generated from 8g N-nitroso-N-methylurea in 50% aqueous KOH) in ether was added to compound 1a (6g, 23.0mmol) at 0°C under a nitrogen atmosphere. MeOH (60 mL) solution, and the reaction was stirred at room temperature for 30 min. The reaction was monitored by TLC. After the reaction was completed, the reaction mixture was concentrated under reduced pressure to produce 5.9 g of pure compound 1b (yield: 93%).

[0200] LCMS: 220.1[(M-O t Bu)+H]) + , 298.2(M+Na) + .

[0201] Step 2:

[0202]

[0203] 99% hydrazine hydrate (1 mL) was added to a solution of intermediate 1b (1.0 g, 3.6 mmol) in methanol (10 mL), and stirred at room temperature for 12 h. The completion of the reaction was confirmed by TLC analysis. The reaction mixture was evaporated under reduced pressure to produce 0.75 g of pure compound 1c (yield: 75.0%).

[0204] LCMS: 276.3 (M+H) + .

[0205] Step 3:

[0206]

[0207] The...

Embodiment 2

[0215] Example 2: Synthesis of Compound 2

[0216]

[0217] Method A:

[0218] Step 1a:

[0219]

[0220] The bonding of urea was performed at room temperature using the coupling of compound 1f (5 g, 7.9 mmol) and compound 2f (3.36 g, 9.5 mmol) in THF (25 mL). The coupling was initiated by adding TEA (1.6 g, 15.8 mmol) in THF (25 mL), and the resulting mixture was stirred at room temperature. After the completion of 20h, THF was evaporated from the reaction mass and partitioned between water and ethyl acetate. The organic layer was washed with water, brine, and passed through Na 2 SO 4 It was dried and evaporated under reduced pressure to produce compound 2a, and the residue was additionally washed with ether / hexane (7:3) to produce 3.0 g of compound 2a. LCMS: 923.8 (M+H) + .

[0221] Step 2a:

[0222]

[0223] Under an inert atmosphere, to a solution of intermediate 2a (0.5 g) in methanol (10.0 mL) was added 10% Pd-C (0.1 g), and the mixture was heated at room temperature in H 2 St...

Embodiment 3

[0252] Example 3: Synthesis of Compound 3

[0253]

[0254] To intermediate 2j (0.92g, 1.0mmol) in CH 2 Cl 2 The solution in (5mL) was added with trifluoroacetic acid (5mL) and a catalytic amount of triisopropylsilane, and stirred at room temperature for 3h to remove acid-sensitive protecting groups. The resulting solution was concentrated in vacuo to produce 0.3 g of compound 3 as a crude solid. LCMS: 469.1 (M+H) + .

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Abstract

The present invention relates to novel peptidomimetic compounds as therapeutic agents capable of inhibiting the programmed cell death 1 (PD1) signalling pathway. The invention also relates to derivatives of the therapeutic agents. The invention also encompasses the use of the said therapeutic agents and derivatives for treatment of disorders via immunopotentiation comprising inhibition of immunosuppressive signal induced due to PD-1, PD-L1, or PD-L2 and therapies using them.

Description

[0001] This application claims the benefits of Indian Provisional Application No. 854 / CHE / 2012 filed on March 7, 2012, which is incorporated herein by reference. Technical field [0002] The present invention relates to novel mimetic peptide compounds that can be used as immunomodulators in therapy. The present invention also relates to a pharmaceutical composition containing the novel peptidomimetic compound and its derivatives as therapeutic agents. Background of the invention [0003] In mammals, the immune system has the ability to control the homeostasis of lymphocytes between activation and inactivation through a variety of regulatory mechanisms during and after the immune response. Among these mechanisms, there are mechanisms that specifically regulate the immune response as needed and when needed. The mechanism via the PD-1 pathway involves almost every aspect of the immune response, including autoimmunity, tumor immunity, infection immunity, transplantation immunity, all...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/02
CPCC07C327/56C07D209/20C07D209/18C07K5/0217A61K31/405C07C335/08A61K45/06C07C243/34A61K31/197C07C275/16A61K31/16A61K31/222A61P35/00Y02A50/30
Inventor 波塔伊尔·戈文丹·奈尔·萨斯库马尔穆拉利达拉·拉马钱德拉苏达山·纳雷玛戴帕里西撒拉梅安塞提
Owner AURIGENE DISCOVERY TECH
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