CA2540196C - Pyridine derivatives and use thereof as urotensin ii antagonists - Google Patents

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Publication number

CA2540196C

CA2540196C CA2540196A CA2540196A CA2540196C CA 2540196 C CA2540196 C CA 2540196C CA 2540196 A CA2540196 A CA 2540196A CA 2540196 A CA2540196 A CA 2540196A CA 2540196 C CA2540196 C CA 2540196C

Authority

CA

Canada

Prior art keywords

ethyl

pyridin

piperidin

ureido

dimethyl

Prior art date

2003-09-26

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 239000005557 antagonist Substances 0.000 title claims abstract description 9
• HFNHAPQMXICKCF-USJMABIRSA-N urotensin-ii Chemical compound N([C@@H](CC(O)=O)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@@H](C(C)C)C(O)=O)C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](N)CCC(O)=O)[C@@H](C)O HFNHAPQMXICKCF-USJMABIRSA-N 0.000 title abstract description 30
• 150000003222 pyridines Chemical class 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 182
• 238000002360 preparation method Methods 0.000 claims abstract description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• -1 C1-7-alkyl-O- Chemical group 0.000 claims description 203
• 125000003118 aryl group Chemical group 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 28
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
• 210000004027 cell Anatomy 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 125000002837 carbocyclic group Chemical group 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 238000011282 treatment Methods 0.000 claims description 14
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 12
• 206010012601 diabetes mellitus Diseases 0.000 claims description 12
• 206010019280 Heart failures Diseases 0.000 claims description 11
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 206010012289 Dementia Diseases 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• 206010020772 Hypertension Diseases 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 206010016654 Fibrosis Diseases 0.000 claims description 6
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• 201000011510 cancer Diseases 0.000 claims description 6
• 230000007882 cirrhosis Effects 0.000 claims description 6
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• 238000002054 transplantation Methods 0.000 claims description 6
• 230000002792 vascular Effects 0.000 claims description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
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• 206010006458 Bronchitis chronic Diseases 0.000 claims description 5
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
• 206010008120 Cerebral ischaemia Diseases 0.000 claims description 5
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
• 206010010904 Convulsion Diseases 0.000 claims description 5
• PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 5
• 229930105110 Cyclosporin A Natural products 0.000 claims description 5
• 108010036949 Cyclosporine Proteins 0.000 claims description 5
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• 208000035202 High altitude pulmonary edema Diseases 0.000 claims description 5
• 208000019695 Migraine disease Diseases 0.000 claims description 5
• 208000002193 Pain Diseases 0.000 claims description 5
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 5
• 206010037423 Pulmonary oedema Diseases 0.000 claims description 5
• 208000003782 Raynaud disease Diseases 0.000 claims description 5
• 208000012322 Raynaud phenomenon Diseases 0.000 claims description 5
• 208000001647 Renal Insufficiency Diseases 0.000 claims description 5
• 206010038419 Renal colic Diseases 0.000 claims description 5
• 206010063897 Renal ischaemia Diseases 0.000 claims description 5
• 206010040047 Sepsis Diseases 0.000 claims description 5
• 208000006011 Stroke Diseases 0.000 claims description 5
• 206010051895 acute chest syndrome Diseases 0.000 claims description 5
• 206010001902 amaurosis Diseases 0.000 claims description 5
• 238000002399 angioplasty Methods 0.000 claims description 5
• 230000036506 anxiety Effects 0.000 claims description 5
• 206010003119 arrhythmia Diseases 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• 206010006451 bronchitis Diseases 0.000 claims description 5
• 238000007675 cardiac surgery Methods 0.000 claims description 5
• 206010008118 cerebral infarction Diseases 0.000 claims description 5
• 208000007451 chronic bronchitis Diseases 0.000 claims description 5
• 208000020832 chronic kidney disease Diseases 0.000 claims description 5
• 229960001265 ciclosporin Drugs 0.000 claims description 5
• 208000018631 connective tissue disease Diseases 0.000 claims description 5
• 229930182912 cyclosporin Natural products 0.000 claims description 5
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 5
• 230000010370 hearing loss Effects 0.000 claims description 5
• 231100000888 hearing loss Toxicity 0.000 claims description 5
• 208000016354 hearing loss disease Diseases 0.000 claims description 5
• 201000001881 impotence Diseases 0.000 claims description 5
• 208000001286 intracranial vasospasm Diseases 0.000 claims description 5
• 201000006370 kidney failure Diseases 0.000 claims description 5
• 239000000463 material Substances 0.000 claims description 5
• 206010027599 migraine Diseases 0.000 claims description 5
• 208000031225 myocardial ischemia Diseases 0.000 claims description 5
• 230000004770 neurodegeneration Effects 0.000 claims description 5
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
• 208000018360 neuromuscular disease Diseases 0.000 claims description 5
• 210000000056 organ Anatomy 0.000 claims description 5
• 238000011321 prophylaxis Methods 0.000 claims description 5
• 201000004240 prostatic hypertrophy Diseases 0.000 claims description 5
• 208000005333 pulmonary edema Diseases 0.000 claims description 5
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 5
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 5
• 102000005962 receptors Human genes 0.000 claims description 5
• 108020003175 receptors Proteins 0.000 claims description 5
• 208000037803 restenosis Diseases 0.000 claims description 5
• 201000000980 schizophrenia Diseases 0.000 claims description 5
• 208000013223 septicemia Diseases 0.000 claims description 5
• 230000035939 shock Effects 0.000 claims description 5
• 208000007056 sickle cell anemia Diseases 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 230000006016 thyroid dysfunction Effects 0.000 claims description 5
• 238000007631 vascular surgery Methods 0.000 claims description 5
• JDVGXDKBBVIBMO-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[ethyl-(2-fluorophenyl)sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=CC=C(F)C=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 JDVGXDKBBVIBMO-UHFFFAOYSA-N 0.000 claims description 4
• GBDWYYKYTDAMCC-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[ethyl-(2-methoxyphenyl)sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=CC=C(OC)C=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 GBDWYYKYTDAMCC-UHFFFAOYSA-N 0.000 claims description 4
• IQAFVYRKOXYDGL-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[ethyl-(2-methylphenyl)sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=CC=C(C)C=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 IQAFVYRKOXYDGL-UHFFFAOYSA-N 0.000 claims description 4
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
• KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 3
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• HZELKNSFZAVHMR-UHFFFAOYSA-N 1-(2,6-diethylpyridin-4-yl)-3-[2-[4-[ethyl-(4-fluorophenyl)sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(CC)=NC(CC)=C1 HZELKNSFZAVHMR-UHFFFAOYSA-N 0.000 claims description 2
• JKDDBJBEOWBQTQ-UHFFFAOYSA-N 1-(2,6-diethylpyridin-4-yl)-3-[2-[4-[ethyl-(4-methoxyphenyl)sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(CC)=NC(CC)=C1 JKDDBJBEOWBQTQ-UHFFFAOYSA-N 0.000 claims description 2
• PLSKNELYIIFMGO-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[(3-fluorophenyl)sulfonyl-methylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=CC(F)=CC=1S(=O)(=O)N(C)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 PLSKNELYIIFMGO-UHFFFAOYSA-N 0.000 claims description 2
• IGKPJRRYCSGXRA-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[(4-ethylphenyl)sulfonyl-methylamino]piperidin-1-yl]ethyl]urea Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)N(C)C1CCN(CCNC(=O)NC=2C=C(C)N=C(C)C=2)CC1 IGKPJRRYCSGXRA-UHFFFAOYSA-N 0.000 claims description 2
• JGDGUNSEKOPXOU-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[(4-fluorophenyl)sulfonyl-propylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)N(CCC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 JGDGUNSEKOPXOU-UHFFFAOYSA-N 0.000 claims description 2
• JFDOKVYWBWGADE-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[(4-methoxyphenyl)sulfonyl-methylamino]piperidin-1-yl]ethyl]urea Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C)C1CCN(CCNC(=O)NC=2C=C(C)N=C(C)C=2)CC1 JFDOKVYWBWGADE-UHFFFAOYSA-N 0.000 claims description 2
• KAHOIQBQHJKIDM-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[(4-methoxyphenyl)sulfonyl-propylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)N(CCC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 KAHOIQBQHJKIDM-UHFFFAOYSA-N 0.000 claims description 2
• LADRCNFDDBKAMC-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[ethyl(thiophen-2-ylsulfonyl)amino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=CSC=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 LADRCNFDDBKAMC-UHFFFAOYSA-N 0.000 claims description 2
• VHJQAIAVQFTDIL-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[ethyl-(4-ethylphenyl)sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=C(CC)C=CC=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 VHJQAIAVQFTDIL-UHFFFAOYSA-N 0.000 claims description 2
• STBVPDRVTORRHF-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[ethyl-(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound CC=1C=C(OC)C(C)=C(C)C=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 STBVPDRVTORRHF-UHFFFAOYSA-N 0.000 claims description 2
• DYLDNIREWJZHME-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[methyl-(2-methylphenyl)sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=CC=C(C)C=1S(=O)(=O)N(C)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 DYLDNIREWJZHME-UHFFFAOYSA-N 0.000 claims description 2
• XUGOACVIBOHSAP-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[methyl-(4-methylphenyl)sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(C)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 XUGOACVIBOHSAP-UHFFFAOYSA-N 0.000 claims description 2
• ULNJPPWZHNAHOG-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[methyl-(4-propan-2-yloxyphenyl)sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound C1=CC(OC(C)C)=CC=C1S(=O)(=O)N(C)C1CCN(CCNC(=O)NC=2C=C(C)N=C(C)C=2)CC1 ULNJPPWZHNAHOG-UHFFFAOYSA-N 0.000 claims description 2
• XSFHNEMWFKRGDS-UHFFFAOYSA-N 1-[2-[4-[(2,4-difluorophenyl)sulfonyl-ethylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound C=1C=C(F)C=C(F)C=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 XSFHNEMWFKRGDS-UHFFFAOYSA-N 0.000 claims description 2
• QMVZXPOLUYWLHM-UHFFFAOYSA-N 1-[2-[4-[(2,4-difluorophenyl)sulfonyl-methylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound C=1C=C(F)C=C(F)C=1S(=O)(=O)N(C)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 QMVZXPOLUYWLHM-UHFFFAOYSA-N 0.000 claims description 2
• KXHHTKCDRFFXKF-UHFFFAOYSA-N 1-[2-[4-[(2,5-dichlorothiophen-3-yl)sulfonyl-ethylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound C1=C(Cl)SC(Cl)=C1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 KXHHTKCDRFFXKF-UHFFFAOYSA-N 0.000 claims description 2
• GBDCYEMRIVDQFP-UHFFFAOYSA-N 1-[2-[4-[(2,6-difluorophenyl)sulfonyl-ethylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound FC=1C=CC=C(F)C=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 GBDCYEMRIVDQFP-UHFFFAOYSA-N 0.000 claims description 2
• CSQPNDSFSILJAY-UHFFFAOYSA-N 1-[2-[4-[(2,6-difluorophenyl)sulfonyl-methylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound FC=1C=CC=C(F)C=1S(=O)(=O)N(C)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 CSQPNDSFSILJAY-UHFFFAOYSA-N 0.000 claims description 2
• NFBVMUAEWZXGQB-UHFFFAOYSA-N 1-[2-[4-[(2-chlorophenyl)sulfonyl-cyclopropylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound CC1=NC(C)=CC(NC(=O)NCCN2CCC(CC2)N(C2CC2)S(=O)(=O)C=2C(=CC=CC=2)Cl)=C1 NFBVMUAEWZXGQB-UHFFFAOYSA-N 0.000 claims description 2
• NWEIUZSIJVOAOP-UHFFFAOYSA-N 1-[2-[4-[(2-chlorophenyl)sulfonyl-ethylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 NWEIUZSIJVOAOP-UHFFFAOYSA-N 0.000 claims description 2
• WZBZEEBTVPLCOO-UHFFFAOYSA-N 1-[2-[4-[(2-chlorophenyl)sulfonyl-methylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound C=1C=CC=C(Cl)C=1S(=O)(=O)N(C)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 WZBZEEBTVPLCOO-UHFFFAOYSA-N 0.000 claims description 2
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