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Showing metabocard for 1,3-Dihydro-(2H)-indol-2-one (HMDB0061918)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:57:18 UTC
Update Date2023-02-21 17:30:34 UTC
HMDB IDHMDB0061918
Secondary Accession Numbers
  • HMDB61918
Metabolite Identification
Common Name1,3-Dihydro-(2H)-indol-2-one
Description1,3-Dihydro-(2H)-indol-2-one, also known as 2-oxindole or 2-indolinone, belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. 1,3-Dihydro-(2H)-indol-2-one is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on 1,3-Dihydro-(2H)-indol-2-one.
Structure
Data?1677000634
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061918 (1,3-Dihydro-(2H)-indol-2-one)


  Mrv1652305272020352D          

 10 11  0  0  0  0            999 V2000
   -2.9015    1.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6160    2.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3305    1.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3306    0.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6161    0.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015    0.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1170    0.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320    1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1168    2.0289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070    1.3614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  7  8  1  0  0  0  0
  6  7  1  0  0  0  0
  8 10  2  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
M  END
Download

3D MOL for HMDB0061918 (1,3-Dihydro-(2H)-indol-2-one)

HMDB0240739
     RDKit          3D
Oxindole
 17 18  0  0  0  0  0  0  0  0999 V2000
   -3.5482   -1.0096    0.0522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3024   -0.6753    0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7535    0.6801   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2986    0.5267   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105    1.5032   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0380    1.1494   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356   -0.1901    0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3515   -1.1479    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039   -0.7996    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021   -1.5534    0.1514 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139    1.0454   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350    1.3835    0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4354    2.5578   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8399    1.8718   -0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3702   -0.5348    0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5454   -2.2065    0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2687   -2.6006    0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  2  1  0
  9  4  1  0
  3 11  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
 10 17  1  0
M  END
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3D SDF for HMDB0061918 (1,3-Dihydro-(2H)-indol-2-one)


  Mrv1652305272020352D          

 10 11  0  0  0  0            999 V2000
   -2.9015    1.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6160    2.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3305    1.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3306    0.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6161    0.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015    0.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1170    0.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320    1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1168    2.0289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070    1.3614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  7  8  1  0  0  0  0
  6  7  1  0  0  0  0
  8 10  2  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061918

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1CC2=CC=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10)

> <INCHI_KEY>
JYGFTBXVXVMTGB-UHFFFAOYSA-N

> <FORMULA>
C8H7NO

> <MOLECULAR_WEIGHT>
133.1473

> <EXACT_MASS>
133.052763851

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.698561232357015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydro-1H-indol-2-one

> <JCHEM_LOGP>
1.0720501869999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.284746640939577

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.136061880454271

> <JCHEM_PKA_STRONGEST_BASIC>
-5.488596497373129

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
39.5849

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
oxindole

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0061918 (1,3-Dihydro-(2H)-indol-2-one)

HMDB0240739
     RDKit          3D
Oxindole
 17 18  0  0  0  0  0  0  0  0999 V2000
   -3.5482   -1.0096    0.0522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3024   -0.6753    0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7535    0.6801   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2986    0.5267   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105    1.5032   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0380    1.1494   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356   -0.1901    0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3515   -1.1479    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039   -0.7996    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021   -1.5534    0.1514 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139    1.0454   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350    1.3835    0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4354    2.5578   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8399    1.8718   -0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3702   -0.5348    0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5454   -2.2065    0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2687   -2.6006    0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  2  1  0
  9  4  1  0
  3 11  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
 10 17  1  0
M  END
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PDB for HMDB0061918 (1,3-Dihydro-(2H)-indol-2-one)

HEADER    PROTEIN                                 27-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-20         0                                  
HETATM    1  C   UNK     0      -5.416   3.312   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.750   4.082   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.084   3.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.084   1.772   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.750   1.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.416   1.772   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.952   1.296   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.046   2.541   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -3.951   3.787   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -1.506   2.541   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    8    6                                                       
CONECT    8    7   10    9                                                  
CONECT    9    8    1                                                       
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0061918 (1,3-Dihydro-(2H)-indol-2-one)

COMPND    HMDB0240739
HETATM    1  O1  UNL     1      -3.548  -1.010   0.052  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.302  -0.675   0.038  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.754   0.680  -0.097  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.299   0.527  -0.055  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.710   1.503  -0.142  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.038   1.149  -0.081  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.336  -0.190   0.067  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.352  -1.148   0.153  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.004  -0.800   0.092  1.00  0.00           C  
HETATM   10  N1  UNL     1      -1.202  -1.553   0.151  1.00  0.00           N  
HETATM   11  H1  UNL     1      -2.114   1.045  -1.101  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.135   1.384   0.675  1.00  0.00           H  
HETATM   13  H3  UNL     1       0.435   2.558  -0.260  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.840   1.872  -0.145  1.00  0.00           H  
HETATM   15  H5  UNL     1       3.370  -0.535   0.122  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.545  -2.206   0.269  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.269  -2.601   0.262  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   11   12
CONECT    4    5    5    9
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   10
CONECT   10   17
END
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SMILES for HMDB0061918 (1,3-Dihydro-(2H)-indol-2-one)

O=C1CC2=CC=CC=C2N1
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INCHI for HMDB0061918 (1,3-Dihydro-(2H)-indol-2-one)

InChI=1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,3-Dihydroindol-2-oneChEBI
2-IndolinoneChEBI
2-OxindoleChEBI
OxindoleChEBI
1,3-Dihydro-2H-indol-2-oneHMDB
2,3-Dihydro-1H-indol-2-oneHMDB
2-IndoloneHMDB
2-oxo-2,3-DihydroindoleHMDB
2-OxoindoleHMDB
2-OxoindolineHMDB
indol-2(3H)-OneHMDB
Indoline-2-oneHMDB
OxindolHMDB
Chemical FormulaC8H7NO
Average Molecular Weight133.1473
Monoisotopic Molecular Weight133.052763851
IUPAC Name2,3-dihydro-1H-indol-2-one
Traditional Nameoxindole
CAS Registry Number59-48-3
SMILES
O=C1CC2=CC=CC=C2N1
InChI Identifier
InChI=1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10)
InChI KeyJYGFTBXVXVMTGB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolines
Direct ParentIndolines
Alternative Parents
Substituents
  • Dihydroindole
  • Benzenoid
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.07 g/LALOGPS
logP1.07ChemAxon
pKa (Strongest Acidic)12.14ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.58 m³·mol⁻¹ChemAxon
Polarizability13.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+126.76531661259
DarkChem[M-H]-122.9931661259
DeepCCS[M+H]+123.26930932474
DeepCCS[M-H]-119.63130932474
DeepCCS[M-2H]-156.91130932474
DeepCCS[M+Na]+131.96330932474
AllCCS[M+H]+126.832859911
AllCCS[M+H-H2O]+121.932859911
AllCCS[M+NH4]+131.332859911
AllCCS[M+Na]+132.732859911
AllCCS[M-H]-125.232859911
AllCCS[M+Na-2H]-126.432859911
AllCCS[M+HCOO]-127.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.3.56 minutes32390414
Predicted by Siyang on May 30, 20229.9698 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.4 minutes32390414

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,3-Dihydro-(2H)-indol-2-oneO=C1CC2=CC=CC=C2N12562.4Standard polar33892256
1,3-Dihydro-(2H)-indol-2-oneO=C1CC2=CC=CC=C2N11434.7Standard non polar33892256
1,3-Dihydro-(2H)-indol-2-oneO=C1CC2=CC=CC=C2N11484.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,3-Dihydro-(2H)-indol-2-one,1TMS,isomer #1C[Si](C)(C)N1C(=O)CC2=CC=CC=C211514.8Semi standard non polar33892256
1,3-Dihydro-(2H)-indol-2-one,1TMS,isomer #1C[Si](C)(C)N1C(=O)CC2=CC=CC=C211459.2Standard non polar33892256
1,3-Dihydro-(2H)-indol-2-one,1TMS,isomer #1C[Si](C)(C)N1C(=O)CC2=CC=CC=C211810.8Standard polar33892256
1,3-Dihydro-(2H)-indol-2-one,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CC2=CC=CC=C211746.9Semi standard non polar33892256
1,3-Dihydro-(2H)-indol-2-one,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CC2=CC=CC=C211708.0Standard non polar33892256
1,3-Dihydro-(2H)-indol-2-one,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CC2=CC=CC=C211955.3Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID284794
KEGG Compound IDC12312
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound321710
PDB IDNot Available
ChEBI ID31697
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Haun M, Pereira MF, Hoffmann ME, Joyas A, Campos V, Filardi LD, de Castro SL, Duran N: Bacterial chemistry. VI. Biological activities and cytotoxicity of 1,3-dihydro-2H-indol-2-one derivatives. Biol Res. 1992;25(1):21-5. [PubMed:1341576 ]
  2. Claudine Serradeil-Le-Gal, 'Novel 1,3-dihydro-2h-indol-2-one, preparation method and pharmaceutical compositions containing same.' U.S. Patent US20030109545, issued June 12, 2003. [Link]
  3. Venkatasubramanian Tarur, Dhananjay Sathe, Harish Mondkar, Rajesh Bhopalkar, Samadhan Patil, 'Process for the preparation of 4-(2-dipropylaminoethyl)-1,3-dihydro-2H-indol-2-one hydrochloride.' U.S. Patent US20050159605, issued July 21, 2005. [Link]
  4. Toshihito Kumagai, Takeshi Kuwada, Tsuyoshi Shibata, Masato Hayashi, Yuri Fujisawa, Yoshinori Sekiguchi, '1,3-Dihydro-2h-indol-2-one derivative.' U.S. Patent US20060276449, issued December 07, 2006. [Link]
  5. Jozsef Neu, Jozsef Torley, Sandor Garadnay, 'NOVEL PROCESS FOR PRODUCTION OF 5--6-CHLORO-1,3-DIHYDRO-2H-INDOL-2-ONE (ZIPRASIDONE).' U.S. Patent US20090111988, issued April 30, 2009. [Link]
  6. Loic FOULON, Laurent GOULLIEUX, Brigitte POUZET, Claudine SERRADEIL-LE GAL, Gerard VALETTE, 'NOVEL 3-AMINOALKYL-1,3-DIHYDRO-2H-INDOL-2-ONE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF.' U.S. Patent US20110059955, issued March 10, 2011. [Link]
  7. Richard Roux, Claudine Serradeil-Le Gal, Jean Wagnon, '1,3-dihydro-2H-indol-2-one derivatives, method for preparing same and pharmaceutical compositions containing them.' U.S. Patent US06864277, issued March 08, 2005. [Link]
  8. Venkatasubramanian Radhakrishna Tarur, Dhananjay Govind Sathe, Harish Kashinath Mondkar, Rajesh Ganpat Bhopalkar, Samadhan Daulat Patil, U.S. Patent US07378439, issued May 27, 2008. [Link]
  9. Richard Roux, Claudine Serradeil-le Gal, Jean Wagnon, '1,3-dihydro-2H-indol-2-one derivatives, process for preparing them and pharmaceutical compositions containing them.' U.S. Patent US07425566, issued September 16, 2008. [Link]
  10. Toshihito Kumagai, Takeshi Kuwada, Tsuyoshi Shibata, Masato Hayashi, Yuri Fujisawa, Yoshinori Sekiguchi, '1,3-dihydro-2H-indol-2-one derivative.' U.S. Patent US07528124, issued May 05, 2009. [Link]