6-Chloro-N-((5-(1,3-dimethylpyrazol-4-y1)-4-methyl-2-pyridyl)methyl)-4-ethoxy-3H-imidazo(4,5-)lpyridin-2-amine

ID: ALA4868016

PubChem CID: 164625126

Max Phase: Preclinical

Molecular Formula: C20H22ClN7O

Molecular Weight: 411.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1nc(Cl)cc2nc(NCc3cc(C)c(-c4cn(C)nc4C)cn3)[nH]c12

Standard InChI:  InChI=1S/C20H22ClN7O/c1-5-29-19-18-16(7-17(21)25-19)24-20(26-18)23-8-13-6-11(2)14(9-22-13)15-10-28(4)27-12(15)3/h6-7,9-10H,5,8H2,1-4H3,(H2,23,24,26)

Standard InChI Key:  NMQDOCXFDSUOAL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    4.3858  -14.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847  -14.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0927  -15.3849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8024  -14.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7996  -14.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0909  -13.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885  -12.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6780  -13.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923  -12.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7930  -12.7663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3845  -13.4742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9315  -14.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718  -13.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1995  -12.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5107  -15.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2178  -14.9732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9262  -15.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0155  -16.1909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6748  -15.0448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2226  -15.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8140  -16.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2215  -17.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375  -17.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4443  -16.3513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0344  -15.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4477  -17.7693    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.4404  -14.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2576  -14.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6637  -14.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  1  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  8  2  0
 11 13  1  0
  9 14  1  0
  4 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 21  1  0
 20 19  1  0
 19 17  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4868016

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 411.90

Molecular Weight (Monoisotopic): 411.1574

AlogP: 4.03

#Rotatable Bonds: 6

Polar Surface Area: 93.54

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.59

CX Basic pKa: 5.22

CX LogP: 3.12

CX LogD: 3.12

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -1.47

References

1. Mammoliti O, Palisse A, Joannesse C, El Bkassiny S, Allart B, Jaunet A, Menet C, Coornaert B, Sonck K, Duys I, Clément-Lacroix P, Oste L, Borgonovi M, Wakselman E, Christophe T, Houvenaghel N, Jans M, Heckmann B, Sanière L, Brys R..  (2021)  Discovery of the S1P2 Antagonist GLPG2938 (1-[2-Ethoxy-6-(trifluoromethyl)-4-pyridyl]-3-[[5-methyl-6-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]pyridazin-3-yl]methyl]urea), a Preclinical Candidate for the Treatment of Idiopathic Pulmonary Fibrosis.,  64  (9.0): [PMID:33939425] [10.1021/acs.jmedchem.1c00138]

2. Osada, Makoto M, Yatomi, Yutaka Y, Ohmori, Tsukasa T, Ikeda, Hitoshi H and Ozaki, Yukio Y.  2002-12-06  Enhancement of sphingosine 1-phosphate-induced migration of vascular endothelial cells and smooth muscle cells by an EDG-5 antagonist.  [PMID:12445827]

3. Sanna, M Germana MG and 10 more authors.  2004-04-02  Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate.  [PMID:14732717]

4. Deng, Hongfeng H and 6 more authors.  2013-10-10  Discovery of Clinical Candidate GSK1842799 As a Selective S1P1 Receptor Agonist (Prodrug) for Multiple Sclerosis.  [PMID:24900589]

5. Demont, Emmanuel H EH and 22 more authors.  2016-02-11  Discovery of Tetrahydropyrazolopyridine as Sphingosine 1-Phosphate Receptor 3 (S1P3)-Sparing S1P1 Agonists Active at Low Oral Doses.  [PMID:26751273]

6. Scott, F L FL and 12 more authors.  2016-06  Ozanimod (RPC1063) is a potent sphingosine-1-phosphate receptor-1 (S1P1 ) and receptor-5 (S1P5 ) agonist with autoimmune disease-modifying activity.  [PMID:26990079]

Source

Source(1):

• Scientific Literature