PATENT CLAIM ANALYSIS

Application Number: 15991222
Application Type: Utility
Filing Date: 2018-05
Publication Date: 2018-09
Patent Classification: ["544", "408000"]

Abstract:
The present invention relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted heterocyclic derivative compounds and pharmaceutical compositions comprising said compounds as exemplified as follows, The subject compounds and compositions are useful for inhibition of lysine specific demethylase-1. Furthermore, the subject compounds and compositions are useful for the treatment of cancer, such as prostate cancer, breast cancer, bladder cancer, lung cancer and/or melanoma and the like.

Claim (Index 19):
A compound, or a pharmaceutically acceptable salt thereof, selected from:\n 4-[6-(4-aminopiperidin-1-yl)-4-benzyl-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-4-[(4-methylphenyl)methyl]-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-4-[(2-fluorophenyl)methyl]-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-4-(3-chloro-benzyl)-5-oxo-4,5-dihydro-pyrazin-2-yl]-benzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 4-[6-(4-Amino-piperidin-1-yl)-4-ethyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-cyclopropylmethyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 4-[6-(4-aminopiperidin-1-yl)-4-[(3-fluorophenyl)methyl]-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-4-[(4-fluorophenyl)methyl]-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-4-[(3-methoxyphenyl)methyl]-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-4-[(4-methoxyphenyl)methyl]-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-5-oxo-4-[(1R)-1-phenylethyl]-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-5-oxo-4-[(1S)-1-phenylethyl]-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-amino-piperidin-1-yl)-5-oxo-4-(tetrahydro-furan-3-ylmethyl)-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 4-[6-(4-amino-piperidin-1-yl)-5-oxo-4-(tetrahydro-pyran-4-ylmethyl)-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 4-[6-(4-aminopiperidin-1-yl)-4-methyl-3-(4-methylphenyl)-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[4-methyl-3-(4-methylphenyl)-5-oxo-6-{[(3S)-pyrrolidin-3-ylmethyl]amino}-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[4-methyl-3-(4-methylphenyl)-5-oxo-6-{[(3R)-pyrrolidin-3-ylmethyl]amino}-4,5-dihydropyrazin-2-yl]benzonitrile; 5-[6-(4-aminopiperidin-1-yl)-4-methyl-3-(4-methylphenyl)-5-oxo-4,5-dihydropyrazin-2-yl]pyridine-2-carbonitrile; 4-{4-methyl-6-[4-(methylamino)piperidin-1-yl]-3-(4-methylphenyl)-5-oxo-4,5-dihydropyrazin-2-yl}benzonitrile; 4-[6-(4-amino-4-methylpiperidin-1-yl)-4-methyl-3-(4-methylphenyl)-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(3-aminopiperidin-1-yl)-4-methyl-3-(4-methylphenyl)-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[4-methyl-3-(4-methylphenyl)-6-{octahydro-1H-pyrrolo[3,4-c]pyridin-5-yl}-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-(6-{2,8-diazaspiro[4.5]decan-8-yl}-4-methyl-3-(4-methylphenyl)-5-oxo-4,5-dihydropyrazin-2-yl)benzonitrile; 4-(6-{decahydropyrrolo[3,4-d]azepin-6-yl}-4-methyl-3-(4-methylphenyl)-5-oxo-4,5-dihydropyrazin-2-yl)benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-4-ethyl-3-(4-methylphenyl)-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-3-(4-ethylphenyl)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[3-(4-ethylphenyl)-4-methyl-5-oxo-6-{[(3S)-pyrrolidin-3-ylmethyl]amino}-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[3-(4-ethylphenyl)-4-methyl-5-oxo-6-{[(3R)-pyrrolidin-3-ylmethyl]amino}-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-3-(4-methoxyphenyl)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[3-(4-methoxyphenyl)-4-methyl-5-oxo-6-{[(3 S)-pyrrolidin-3-ylmethyl]amino}-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[3-(4-methoxyphenyl)-4-methyl-5-oxo-6-{[(3R)-pyrrolidin-3-ylmethyl]amino}-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-aminopiperidin-1-yl)-3-(4-cyclopropylphenyl)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[3-(4-cyclopropylphenyl)-4-methyl-5-oxo-6-{[(3S)-pyrrolidin-3-ylmethyl]amino}-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[3-(4-cyclopropylphenyl)-4-methyl-5-oxo-6-{[(3R)-pyrrolidin-3-ylmethyl]amino}-4,5-dihydropyrazin-2-yl]benzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-(2-methoxy-ethyl)-5-oxo-3-p-tolyl-4,5-dihydro-pyrazin-2-yl]-benzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-(2-hydroxy-ethyl)-5-oxo-3-p-tolyl-4,5-dihydro-pyrazin-2-yl]-benzonitrile; 4-[6-(4-amino-piperidin-1-yl)-3-(4-cyclopropyl-phenyl)-4-(2-hydroxy-ethyl)-5-oxo-4,5-dihydro-pyrazin-2-yl]-benzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-(3-methoxy-propyl)-5-oxo-3-p-tolyl-4,5-dihydro-pyrazin-2-yl]-benzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-(3-hydroxy-propyl)-5-oxo-3-p-tolyl-4,5-dihydro-pyrazin-2-yl]-benzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-(2-methoxy-ethyl)-5-oxo-3-p-tolyl-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-(2-hydroxy-ethyl)-5-oxo-3-p-tolyl-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 4-(6-{[((3 S)-pyrrolidin-3-yl)methyl]amino}-4-(2-methoxyethyl)-3-(4-methylphenyl)-5-oxo(4-hydropyrazin-2-yl))-2-fluorobenzenecarbonitrile; 4-(6-{[((3S)-pyrrolidin-3-yl)methyl]amino}-4-(2-hydroxyethyl)-3-(4-methylphenyl)-5-oxo(4-hydropyrazin-2-yl))-2-fluorobenzenecarbonitrile; 4-[6-(4-aminopiperidyl)-4-(3-methoxypropyl)-3-(4-methylphenyl)-5-oxo(4-hydropyrazin-2-yl)]-2-fluorobenzenecarbonitrile; 4-[6-(4-aminopiperidyl)-4-(3-hydroxypropyl)-3-(4-methylphenyl)-5-oxo(4-hydropyrazin-2-yl)]-2-fluorobenzenecarbonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-methyl-5-oxo-3-p-tolyl-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-methyl-5-oxo-3-p-tolyl-4,5-dihydro-pyrazin-2-yl]-3-fluorobenzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-methyl-3-(6-methyl-pyridin-3-yl)-5-oxo-4,5-dihydro-pyrazin-2-yl]-benzonitrile; 4-[6-(4-amino-piperidin-1-yl)-3-(4-cyclopropyl-phenyl)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 5-[6-(4-amino-piperidin-1-yl)-3-(4-methoxy-phenyl)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-pyridine-2-carbonitrile; 4-[6-(4-amino-piperidin-1l-yl)-3-(4-methoxy-phenyl)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 5-[6-(4-amino-piperidin-1-yl)-3-(4-cyclopropyl-phenyl)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-pyridine-2-carbonitrile; 5-{3-(4-methoxy-phenyl)-4-methyl-5-oxo-6-[((35 S)-pyrrolidin-3-ylmethyl)-amino]-4,5-dihydro-pyrazin-2-yl}-pyridine-2-carbonitrile; 2-fluoro-4-{3-(4-methoxy-phenyl)-4-methyl-5-oxo-6-[((3 S)-pyrrolidin-3-ylmethyl)-amino]-4,5-dihydro-pyrazin-2-yl}-benzonitrile; 5-{3-(4-ethyl-phenyl)-4-methyl-5-oxo-6-[((3S)-pyrrolidin-3-ylmethyl)-amino]-4,5-dihydro-pyrazin-2-yl}-pyridine-2-carbonitrile; 4-{3-(4-ethyl-phenyl)-4-methyl-5-oxo-6-[((3S)-pyrrolidin-3-ylmethyl)-amino]-4,5-dihydro-pyrazin-2-yl}-2-fluorobenzonitrile; 5-{3-(4-cyclopropyl-phenyl)-4-methyl-5-oxo-6-[((3 S)-pyrrolidin-3-ylmethyl)-amino]-4,5-dihydro-pyrazin-2-yl}-pyridine-2-carbonitrile; 4-{3-(4-cyclopropyl-phenyl)-4-methyl-5-oxo-6-[((3 S)-pyrrolidin-3-ylmethyl)-amino]-4,5-dihydro-pyrazin-2-yl}-2-fluorobenzonitrile; 4-[6-(4-amino-piperidin-1-yl)-4-methyl-3-(1-methyl-1H-benzoimidazol-5-yl)-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 4-{3-(4-cyclopropylmethoxy-phenyl)-4-methyl-5-oxo-6-[((3 S)-pyrrolidin-3-ylmethyl)-amino]-4,5-dihydro-pyrazin-2-yl}-2-fluorobenzonitrile; 4-{3-(4-ethoxy-phenyl)-4-methyl-5-oxo-6-[((3 S)-pyrrolidin-3-ylmethyl)-amino]-4,5-dihydro-pyrazin-2-yl}-2-fluorobenzonitrile; 2-fluoro-4-[4-methyl-5-oxo-6-[((3S)-pyrrolidin-3-ylmethyl)-amino]-3-(4-trifluoromethoxy-phenyl)-4,5-dihydro-pyrazin-2-yl]-benzonitrile; 2-Fluoro-4-[4-(3-hydroxy-propyl)-6-(4-methylamino-piperidin-1-yl)-5-oxo-3-p-tolyl-4,5-dihydro-pyrazin-2-yl]-benzonitrile; 2-Fluoro-4-[4-(2-hydroxy-ethyl)-6-(4-methylamino-piperidin-1-yl)-5-oxo-3-p-tolyl-4,5-dihydro-pyrazin-2-yl]-benzonitrile; 4-[6-(4-Amino-piperidin-1-yl)-4-methyl-3-(6-methyl-pyridin-3-yl)-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-fluorobenzonitrile; 4-(5-(4-aminopiperidin-1-yl)-2-(4-methoxyphenyl)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorobenzonitrile; 5-(5-(4-aminopiperidin-1-yl)-2-(4-methoxyphenyl)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)picolinonitrile; (S)-5-(2-(4-methoxyphenyl)-1-methyl-6-oxo-5-(pyrrolidin-3-ylmethylamino)-1,6-dihydropyridin-3-yl)picolinonitrile; (S)-2-fluoro-4-(2-(4-methoxyphenyl)-1-methyl-6-oxo-5-(pyrrolidin-3-ylmethylamino)-1,6-dihydropyridin-3-yl)benzonitrile; (S)-5-(2-(4-ethylphenyl)-1-methyl-6-oxo-5-(pyrrolidin-3-ylmethylamino)-1,6-dihydropyridin-3-yl)picolinonitrile; (S)-4-(2-(4-ethylphenyl)-1-methyl-6-oxo-5-(pyrrolidin-3-ylmethylamino)-1,6-dihydropyridin-3-yl)-2-fluorobenzonitrile; (S)-5-(2-(4-cyclopropylphenyl)-1-methyl-6-oxo-5-(pyrrolidin-3-ylmethylamino)-1,6-dihydropyridin-3-yl)picolinonitrile; (S)-4-(2-(4-cyclopropylphenyl)-1-methyl-6-oxo-5-(pyrrolidin-3-ylmethylamino)-1,6-dihydropyridin-3-yl)-2-fluorobenzonitrile; 4-[5-(4-aminopiperidin-1-yl)-1-methyl-2-(4-methylphenyl)-6-oxopyridin-3-yl]benzonitrile; 4-[5-(4-aminopiperidin-1-yl)-1-methyl-2-(4-methylphenyl)-6-oxopyridin-3-yl]-2-fluorobenzonitrile; 4-[5-(4-aminopiperidin-1-yl)-2-(4-methoxyphenyl)-1-methyl-6-oxopyridin-3-yl]benzonitrile; 4-{2-(4-methoxyphenyl)-1-methyl-5-[4-(methylamino)piperidyl]-6-oxo-3-hydropyridyl}benzenecarbonitrile; 2-fluoro-4-{2-(4-methoxyphenyl)-1-methyl-5-[4-(methylamino)piperidyl]-6-oxo(3-hydropyridyl)}benzenecarbonitrile; 4-{1-methyl-5-[4-(methylamino)piperidyl]-2-(4-methylphenyl)-6-oxo-3-hydropyridyl}benzenecarbonitrile; 4-[5-(4-aminopiperidin-1-yl)-1-(cyclopropylmethyl)-2-(4-methoxyphenyl)-6-oxopyridin-3-yl]benzonitrile; 4-[5-(4-aminopiperidin-1-yl)-1-ethyl-2-(4-methoxyphenyl)-6-oxopyridin-3-yl]benzonitrile; 4-[5-(4-aminopiperidin-1-yl)-2-(3-fluoro-4-methoxyphenyl)-1-methyl-6-oxopyridin-3-yl]benzonitrile; 4-[5-(4-aminopiperidin-1-yl)-2-(3-fluoro-4-methoxyphenyl)-1-methyl-6-oxopyridin-3-yl]-2-fluorobenzonitrile; 4-[5-(4-aminopiperidin-1-yl)-1-(cyclopropylmethyl)-2-(4-methoxyphenyl)-6-oxopyridin-3-yl]-2-fluorobenzonitrile; 2-fluoro-4-[2-(3-fluoro-4-methoxyphenyl)-1-methyl-5-[4-(methylamino)piperidin-1-yl]-6-oxopyridin-3-yl]benzonitrile; 4-[5-(4-aminopiperidin-1-yl)-1-ethyl-2-(4-methoxyphenyl)-6-oxopyridin-3-yl]-2-fluorobenzonitrile; 2-[3-(4-aminopiperidyl)-5-(4-cyano-3-fluorophenyl)-6-(4-methoxyphenyl)-2-oxohydropyrazinyl]acetamide; 3-[3-(4-aminopiperidyl)-5-(4-cyano-3-fluorophenyl)-6-(4-methoxyphenyl)-2-oxohydropyrazinyl]propenamide; 4-[3-(4-aminopiperidyl)-5-(4-cyano-3-fluorophenyl)-6-(4-methoxyphenyl)-2-oxohydropyrazinyl]butanamide; 4-{5-(4-aminopiperidyl)-2-[6-(dimethylamino)(3-pyridyl)]-1-methyl-6-oxo(3-hydropyridyl)}-2-fluorobenzenecarbonitrile; or 4-{2-[6-(dimethylamino)(3-pyridyl)]-1-methyl-5-[4-(methylamino)piperidyl]-6-oxo-3-hydropyridyl}benzenecarbonitrile.

Metadata:
- Claim Count in Document: 18.0
- Percentile: 93.0
- Lexical Diversity: 1.74468
- Patent Class: 544.0
- Transitional Phrase Type: none
- Component Type: 0
- Foreign Priority: False
- Related Applications: ['10918317', '11247046', '13991603', '15900737', '13701039']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.8383199109423567
- 35 USC 102 Novelty (BERT): 0.5077189164357719
- Combined Prediction Score: 0.8052598114916982
- Mean Citation Score: 299.586328
- Max Citation Score: 317.8995700000001
- Similarity Product: 270.0983564177925

Labels:
- Claim Label 101: 1
- Claim Label 102: 1
- Claim Label 103: 1
- Claim Label 112: 1
- Combined Label: 1
- Label 101 Adjusted: 1

Dataset: test