MX2013006900A

MX2013006900A - Nuevos derivados n-(4-(azetidina-1-carbonil)fenil)-(hetero-)arilsu lfonamida como moduladores piruvato quinasa m2 (pmk2).

Nuevos derivados n-(4-(azetidina-1-carbonil)fenil)-(hetero-)arilsu lfonamida como moduladores piruvato quinasa m2 (pmk2).

Info

Publication number: MX2013006900A
Authority: MX; Mexico
Prior art keywords: compound; optionally substituted; alkyl; compounds; mmol
Prior art date: 2010-12-17

Application number

MX2013006900A

Other languages

English (en)

Spanish (es)

Inventor

Francesco G Salituro

Shunqi Yan

Jeffrey O Saunders

Original Assignee

Agios Pharmaceuticals Inc

Priority date

2010-12-17

Filing date

2011-12-16

Publication date

2013-10-17

2011-12-16 Application filed by Agios Pharmaceuticals Inc filed Critical Agios Pharmaceuticals Inc

2013-10-17 Publication of MX2013006900A publication Critical patent/MX2013006900A/es

Links

-1 4- (azetidine - 1 - carbonyl) phenyl Chemical group 0.000 title claims description 66
102000013009 Pyruvate Kinase Human genes 0.000 title abstract description 13
108020005115 Pyruvate Kinase Proteins 0.000 title abstract description 13
125000005842 heteroatom Chemical group 0.000 title description 14
101100083745 Caenorhabditis elegans pmk-2 gene Proteins 0.000 title description 2
125000004421 aryl sulphonamide group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 196
238000000034 method Methods 0.000 claims abstract description 70
206010028980 Neoplasm Diseases 0.000 claims abstract description 46
201000011510 cancer Diseases 0.000 claims abstract description 28
102100034911 Pyruvate kinase PKM Human genes 0.000 claims description 61
101001091538 Homo sapiens Pyruvate kinase PKM Proteins 0.000 claims description 58
125000000217 alkyl group Chemical group 0.000 claims description 51
230000000694 effects Effects 0.000 claims description 30
125000003118 aryl group Chemical group 0.000 claims description 28
125000001072 heteroaryl group Chemical group 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 25
239000008194 pharmaceutical composition Substances 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
125000003710 aryl alkyl group Chemical group 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000000623 heterocyclic group Chemical group 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000004452 carbocyclyl group Chemical group 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 6
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101710204616 Pyruvate kinase 2 Proteins 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 39
238000011282 treatment Methods 0.000 abstract description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 10
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RNBGYGVWRKECFJ-UHFFFAOYSA-N fructose-1,6-phosphate Natural products OC1C(O)C(O)(COP(O)(O)=O)OC1COP(O)(O)=O RNBGYGVWRKECFJ-UHFFFAOYSA-N 0.000 description 8
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102000004190 Enzymes Human genes 0.000 description 7
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238000009169 immunotherapy Methods 0.000 description 7
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 7
BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 7
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125000001424 substituent group Chemical group 0.000 description 7
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YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 5
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