CA2572119A1

CA2572119A1 - Combination therapies utilizing benzamide inhibitors of the p2x7 receptor

Combination therapies utilizing benzamide inhibitors of the p2x7 receptor Download PDF

Info

Publication number: CA2572119A1
Authority: CA; Canada
Prior art keywords: hydroxy; alkyl; chloro; dioxo; dihydro
Prior art date: 2004-06-29
Legal status : Abandoned

Application number

CA002572119A

Other languages

English (en)

French (fr)

Inventor

James B. Chung

Christopher A. Gabel

Gail L. Jungbluth

Current Assignee

Warner Lambert Co LLC

Original Assignee

Individual

Priority date

2004-06-29

Filing date

2005-06-16

Publication date

2006-01-12

2005-06-16 Application filed by Individual filed Critical Individual

2006-01-12 Publication of CA2572119A1 publication Critical patent/CA2572119A1/en

Status Abandoned legal-status Critical Current

Links

239000003112 inhibitor Substances 0.000 title claims abstract description 26
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title abstract description 63
102100037602 P2X purinoceptor 7 Human genes 0.000 title abstract description 36
101710189965 P2X purinoceptor 7 Proteins 0.000 title abstract description 36
238000002648 combination therapy Methods 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 69
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 claims abstract description 19
UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 claims abstract description 18
239000003795 chemical substances by application Substances 0.000 claims abstract description 18
229960001940 sulfasalazine Drugs 0.000 claims abstract description 18
NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 claims abstract description 18
102000051628 Interleukin-1 receptor antagonist Human genes 0.000 claims abstract description 17
108700021006 Interleukin-1 receptor antagonist Proteins 0.000 claims abstract description 17
102000000589 Interleukin-1 Human genes 0.000 claims abstract description 16
108010002352 Interleukin-1 Proteins 0.000 claims abstract description 16
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 15
HMLGSIZOMSVISS-ONJSNURVSA-N (7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2,2-dimethylpropanoyloxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(C=C)CSC21)C(O)=O)=O)C(=O)\C(=N/OCOC(=O)C(C)(C)C)C1=CSC(N)=N1 HMLGSIZOMSVISS-ONJSNURVSA-N 0.000 claims abstract description 11
229960004238 anakinra Drugs 0.000 claims abstract description 11
201000010099 disease Diseases 0.000 claims abstract description 11
239000008177 pharmaceutical agent Substances 0.000 claims abstract description 11
229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims abstract description 10
239000003862 glucocorticoid Substances 0.000 claims abstract description 10
230000001404 mediated effect Effects 0.000 claims abstract description 10
229940124292 CD20 monoclonal antibody Drugs 0.000 claims abstract description 9
108010019421 Janus Kinase 3 Proteins 0.000 claims abstract description 9
102000006500 Janus Kinase 3 Human genes 0.000 claims abstract description 9
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 8
201000008482 osteoarthritis Diseases 0.000 claims abstract description 8
108010046938 Macrophage Colony-Stimulating Factor Proteins 0.000 claims abstract 2
102100028123 Macrophage colony-stimulating factor 1 Human genes 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 174
-1 hydroxy, amino Chemical group 0.000 claims description 93
229910052736 halogen Inorganic materials 0.000 claims description 67
150000002367 halogens Chemical class 0.000 claims description 67
125000000623 heterocyclic group Chemical group 0.000 claims description 59
229910052757 nitrogen Inorganic materials 0.000 claims description 52
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 47
125000004093 cyano group Chemical group *C#N 0.000 claims description 43
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 37
125000001424 substituent group Chemical group 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
239000008194 pharmaceutical composition Substances 0.000 claims description 19
241000124008 Mammalia Species 0.000 claims description 18
229940002612 prodrug Drugs 0.000 claims description 18
239000000651 prodrug Substances 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
FUCKCIVGBCBZNP-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-3-methoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(O)COC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 FUCKCIVGBCBZNP-UHFFFAOYSA-N 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 10
102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 10
239000012453 solvate Substances 0.000 claims description 10
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 7
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 7
229960005370 atorvastatin Drugs 0.000 claims description 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
201000001320 Atherosclerosis Diseases 0.000 claims description 6
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 6
201000004681 Psoriasis Diseases 0.000 claims description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
RGFRMICGIFODJR-UHFFFAOYSA-N 5-[4-(2,3-dihydroxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[(1-hydroxycycloheptyl)methyl]-2-methylbenzamide Chemical compound CC1=CC=C(N2C(N(CC(O)CO)C(=O)C=N2)=O)C=C1C(=O)NCC1(O)CCCCCC1 RGFRMICGIFODJR-UHFFFAOYSA-N 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 5
208000011231 Crohn disease Diseases 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
OAEZUGNBLUMOLY-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-2-phenylethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound C=1C=CC=CC=1C(O)CN(C1=O)C(=O)C=NN1C(C=1)=CC=C(Cl)C=1C(=O)NCC1(O)CCCCCC1 OAEZUGNBLUMOLY-UHFFFAOYSA-N 0.000 claims description 4
NAVAMNWMBLWSNC-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycyclooctyl)methyl]-5-[4-(2-hydroxy-3-methoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(O)COC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCCC2)=C1 NAVAMNWMBLWSNC-UHFFFAOYSA-N 0.000 claims description 4
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
201000001263 Psoriatic Arthritis Diseases 0.000 claims description 4
208000036824 Psoriatic arthropathy Diseases 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
KJPZROKEPKPKNY-UHFFFAOYSA-N 2-chloro-5-[3,5-dioxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-1,2,4-triazin-2-yl]-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound O=C1N(CC(O)C(F)(F)F)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 KJPZROKEPKPKNY-UHFFFAOYSA-N 0.000 claims description 3
JMVYKXHUTCCANK-UHFFFAOYSA-N 2-chloro-5-[4-(2,3-dihydroxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound O=C1N(CC(O)CO)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 JMVYKXHUTCCANK-UHFFFAOYSA-N 0.000 claims description 3
LMVZQBQXTHCTDI-UHFFFAOYSA-N 2-chloro-5-[4-(2,3-dihydroxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[(1-hydroxycyclohexyl)methyl]benzamide Chemical compound O=C1N(CC(O)CO)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCC2)=C1 LMVZQBQXTHCTDI-UHFFFAOYSA-N 0.000 claims description 3
JBSOMXMDEHIYEI-UHFFFAOYSA-N 2-chloro-5-[4-(2-cyanoethyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound C=1C(N2C(N(CCC#N)C(=O)C=N2)=O)=CC=C(Cl)C=1C(=O)NCC1(O)CCCCCC1 JBSOMXMDEHIYEI-UHFFFAOYSA-N 0.000 claims description 3
SKHOFKQIJDWTCL-UHFFFAOYSA-N 2-chloro-5-[4-(2-hydroxy-3-methoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-(2-hydroxy-2-phenylethyl)benzamide Chemical compound O=C1N(CC(O)COC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC(O)C=2C=CC=CC=2)=C1 SKHOFKQIJDWTCL-UHFFFAOYSA-N 0.000 claims description 3
GELUSLDHFNHTJQ-UHFFFAOYSA-N 2-chloro-5-[4-(2-hydroxy-3-methoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[[1-(hydroxymethyl)cycloheptyl]methyl]benzamide Chemical compound O=C1N(CC(O)COC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(CO)CCCCCC2)=C1 GELUSLDHFNHTJQ-UHFFFAOYSA-N 0.000 claims description 3
IUPMKDQZZPUSLS-UHFFFAOYSA-N 2-chloro-5-[4-(cyanomethyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound C=1C(N2C(N(CC#N)C(=O)C=N2)=O)=CC=C(Cl)C=1C(=O)NCC1(O)CCCCCC1 IUPMKDQZZPUSLS-UHFFFAOYSA-N 0.000 claims description 3
KMQUFVMVCXCGKB-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxyethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CCO)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 KMQUFVMVCXCGKB-UHFFFAOYSA-N 0.000 claims description 3
RBAADOGLQCDEJX-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-methoxyethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CCOC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 RBAADOGLQCDEJX-UHFFFAOYSA-N 0.000 claims description 3
YHXISHVHTWUPKM-UHFFFAOYSA-N 5-[4-(2-amino-2-oxoethyl)-3,5-dioxo-1,2,4-triazin-2-yl]-2-chloro-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound O=C1N(CC(=O)N)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 YHXISHVHTWUPKM-UHFFFAOYSA-N 0.000 claims description 3
BSTQMIPJWUKIBV-UHFFFAOYSA-N 5-[4-(3-amino-2-hydroxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-2-chloro-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound O=C1N(CC(O)CN)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 BSTQMIPJWUKIBV-UHFFFAOYSA-N 0.000 claims description 3
208000003456 Juvenile Arthritis Diseases 0.000 claims description 3
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MDTBAOKMFWFWIA-UHFFFAOYSA-N n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxyethyl)-3,5-dioxo-1,2,4-triazin-2-yl]-2-methylbenzamide Chemical compound CC1=CC=C(N2C(N(CCO)C(=O)C=N2)=O)C=C1C(=O)NCC1(O)CCCCCC1 MDTBAOKMFWFWIA-UHFFFAOYSA-N 0.000 claims description 3
150000002829 nitrogen Chemical class 0.000 claims description 3
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
CMDPHTPJKKJNDM-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-2-methylpropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(C)(O)C)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 CMDPHTPJKKJNDM-UHFFFAOYSA-N 0.000 claims description 2
UTVQECIXWCMQOC-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycyclohexyl)methyl]-5-[4-(2-hydroxy-3-methoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(O)COC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCC2)=C1 UTVQECIXWCMQOC-UHFFFAOYSA-N 0.000 claims description 2
125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims 4
125000001475 halogen functional group Chemical group 0.000 claims 3
208000035475 disorder Diseases 0.000 abstract description 8
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 43
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
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125000006622 cycloheptylmethyl group Chemical group 0.000 description 28
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JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 17
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
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PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 6
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NCYPXHTVGLDGTJ-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-2-pyridin-4-ylethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound C=1C=NC=CC=1C(O)CN(C1=O)C(=O)C=NN1C(C=1)=CC=C(Cl)C=1C(=O)NCC1(O)CCCCCC1 NCYPXHTVGLDGTJ-UHFFFAOYSA-N 0.000 description 1
ZJEKSNCXSOPUMP-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-2-thiophen-2-ylethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound C=1C=CSC=1C(O)CN(C1=O)C(=O)C=NN1C(C=1)=CC=C(Cl)C=1C(=O)NCC1(O)CCCCCC1 ZJEKSNCXSOPUMP-UHFFFAOYSA-N 0.000 description 1
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NRCSWOIXGXIZML-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-3-phenylmethoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1C=NN(C=2C=C(C(Cl)=CC=2)C(=O)NCC2(O)CCCCCC2)C(=O)N1CC(O)COCC1=CC=CC=C1 NRCSWOIXGXIZML-UHFFFAOYSA-N 0.000 description 1
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SFCAUXWZZRXMOB-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(O)C)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 SFCAUXWZZRXMOB-UHFFFAOYSA-N 0.000 description 1
BPOOHYCEGLEHDF-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-morpholin-4-yl-2-oxoethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound C=1C(N2C(N(CC(=O)N3CCOCC3)C(=O)C=N2)=O)=CC=C(Cl)C=1C(=O)NCC1(O)CCCCCC1 BPOOHYCEGLEHDF-UHFFFAOYSA-N 0.000 description 1
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YPPDSNMOIGEKNS-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-[2-hydroxy-3-(trifluoromethoxy)propyl]-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(COC(F)(F)F)O)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 YPPDSNMOIGEKNS-UHFFFAOYSA-N 0.000 description 1
WKTCMXWIYOEFJC-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycyclohexyl)methyl]-5-[4-(2-hydroxy-2-methylpropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(C)(O)C)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCC2)=C1 WKTCMXWIYOEFJC-UHFFFAOYSA-N 0.000 description 1
YEQKVQDPTNVXMO-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycyclohexyl)methyl]-5-[4-(2-hydroxyethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CCO)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCC2)=C1 YEQKVQDPTNVXMO-UHFFFAOYSA-N 0.000 description 1
XPPRQOOOXRWHBH-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycyclooctyl)methyl]-5-[4-(2-hydroxy-2-methylpropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(C)(O)C)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCCC2)=C1 XPPRQOOOXRWHBH-UHFFFAOYSA-N 0.000 description 1
ZQQFBWCWDWXIJV-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycyclooctyl)methyl]-5-[4-(2-hydroxyethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CCO)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCCC2)=C1 ZQQFBWCWDWXIJV-UHFFFAOYSA-N 0.000 description 1
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DGZVFWMLQCIIBO-UHFFFAOYSA-N 2-chloro-n-[(2-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxyethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CCO)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2C(CCCCC2)O)=C1 DGZVFWMLQCIIBO-UHFFFAOYSA-N 0.000 description 1
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VXKARJXPUSNKFR-UHFFFAOYSA-N 2-chloro-n-[[1-(hydroxymethyl)cycloheptyl]methyl]-5-[4-(2-hydroxy-2-methylpropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(C)(O)C)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(CO)CCCCCC2)=C1 VXKARJXPUSNKFR-UHFFFAOYSA-N 0.000 description 1
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
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125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
UACOXBQBNWQWOK-UHFFFAOYSA-N 4-(2,5-difluorophenyl)-5-(3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-oxazole Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC(F)=CC=C1F UACOXBQBNWQWOK-UHFFFAOYSA-N 0.000 description 1
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DKWSSJZOBSFGSI-UHFFFAOYSA-N 5-[4-(2-amino-2-oxoethyl)-3,5-dioxo-1,2,4-triazin-2-yl]-2-chloro-n-[(1-hydroxycyclohexyl)methyl]benzamide Chemical compound O=C1N(CC(=O)N)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCC2)=C1 DKWSSJZOBSFGSI-UHFFFAOYSA-N 0.000 description 1
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