MXPA05002839A

MXPA05002839A - Derivados de 1-piridin-4-il-urea.

Derivados de 1-piridin-4-il-urea.

Info

Publication number: MXPA05002839A
Authority: MX; Mexico
Prior art keywords: pyrrolidin; urea; methyl; quinolin; diphenyl
Prior art date: 2002-09-17

Application number

MXPA05002839A

Other languages

English (en)

Spanish (es)

Inventor

Jorg Velker

Original Assignee

Actelion Pharmaceuticals Ltd

Priority date

2002-09-17

Filing date

2003-09-12

Publication date

2005-05-27

2003-09-12 Application filed by Actelion Pharmaceuticals Ltd filed Critical Actelion Pharmaceuticals Ltd

2005-05-27 Publication of MXPA05002839A publication Critical patent/MXPA05002839A/es

Links

ICJVRPQWEPOSOL-UHFFFAOYSA-N pyridin-4-ylurea Chemical class NC(=O)NC1=CC=NC=C1 ICJVRPQWEPOSOL-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 161
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
239000005557 antagonist Substances 0.000 claims abstract description 6
-1 di-substituted quinolin-4-yl Chemical group 0.000 claims description 87
125000000217 alkyl group Chemical group 0.000 claims description 84
239000000203 mixture Substances 0.000 claims description 59
229910052757 nitrogen Inorganic materials 0.000 claims description 47
229910052739 hydrogen Inorganic materials 0.000 claims description 44
239000001257 hydrogen Substances 0.000 claims description 43
108010018369 Urotensin II Proteins 0.000 claims description 38
102000050488 Urotensin II Human genes 0.000 claims description 38
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 claims description 38
125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
125000006413 ring segment Chemical group 0.000 claims description 28
125000003118 aryl group Chemical group 0.000 claims description 27
150000002431 hydrogen Chemical group 0.000 claims description 26
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 21
239000004202 carbamide Substances 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
108050002984 Urotensin II receptors Proteins 0.000 claims description 11
102000012327 Urotensin II receptors Human genes 0.000 claims description 11
239000002904 solvent Chemical class 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
239000002464 receptor antagonist Substances 0.000 claims description 9
229940044551 receptor antagonist Drugs 0.000 claims description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
206010012601 diabetes mellitus Diseases 0.000 claims description 8
206010019280 Heart failures Diseases 0.000 claims description 7
208000035475 disorder Diseases 0.000 claims description 7
YAMBRNOLFOVLAX-UHFFFAOYSA-N 1-(2-methylquinolin-4-yl)-3-pyrrolidin-3-ylurea Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=O)NC1CCNC1 YAMBRNOLFOVLAX-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
208000006011 Stroke Diseases 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
102000005962 receptors Human genes 0.000 claims description 6
108020003175 receptors Proteins 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
HVEANDTZNLHJIQ-QFIPXVFZSA-N 1-[(3s)-1-(2,2-diphenylethyl)pyrrolidin-3-yl]-3-[2-(methylamino)pyridin-4-yl]urea Chemical compound C1=NC(NC)=CC(NC(=O)N[C@@H]2CN(CC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 HVEANDTZNLHJIQ-QFIPXVFZSA-N 0.000 claims description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
206010012289 Dementia Diseases 0.000 claims description 5
206010020772 Hypertension Diseases 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
230000002792 vascular Effects 0.000 claims description 5
UQOCWXTYTANLFQ-UHFFFAOYSA-N 1-[1-(3,3-diphenylpropyl)pyrrolidin-3-yl]-3-(2-methylquinolin-4-yl)urea Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=O)NC(C1)CCN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 UQOCWXTYTANLFQ-UHFFFAOYSA-N 0.000 claims description 4
206010016654 Fibrosis Diseases 0.000 claims description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
206010037423 Pulmonary oedema Diseases 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
230000007882 cirrhosis Effects 0.000 claims description 4
208000019425 cirrhosis of liver Diseases 0.000 claims description 4
210000000056 organ Anatomy 0.000 claims description 4
208000007232 portal hypertension Diseases 0.000 claims description 4
208000005333 pulmonary edema Diseases 0.000 claims description 4
CSJXSJKKACKVQN-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-3-yl)-3-(2-methylquinolin-4-yl)urea Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=O)NC(C1)CCN1CC1=CC=CC=C1 CSJXSJKKACKVQN-UHFFFAOYSA-N 0.000 claims description 3
VMIZAIMXAFAAJC-QHCPKHFHSA-N 1-(2-methylquinolin-4-yl)-3-[(3s)-1-[(2-phenylphenyl)methyl]pyrrolidin-3-yl]urea Chemical compound C([C@@H](C1)NC(=O)NC=2C=C(N=C3C=CC=CC3=2)C)CN1CC1=CC=CC=C1C1=CC=CC=C1 VMIZAIMXAFAAJC-QHCPKHFHSA-N 0.000 claims description 3
LZZUZEUKHIXPFM-UHFFFAOYSA-N 1-(2-methylquinolin-4-yl)-3-[1-[(3-phenylphenyl)methyl]pyrrolidin-3-yl]urea Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=O)NC(C1)CCN1CC(C=1)=CC=CC=1C1=CC=CC=C1 LZZUZEUKHIXPFM-UHFFFAOYSA-N 0.000 claims description 3
XKPYPTHZQZGEOJ-NSAACQBQSA-N 1-[(3s)-1-(3,3-diphenylpropyl)pyrrolidin-3-yl]-3-[2-methyl-6-[(e)-2-phenylethenyl]pyridin-4-yl]urea Chemical compound C([C@@H](C1)NC(=O)NC=2C=C(N=C(\C=C\C=3C=CC=CC=3)C=2)C)CN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 XKPYPTHZQZGEOJ-NSAACQBQSA-N 0.000 claims description 3
CRTFHNZNUSVPFV-UHFFFAOYSA-N 1-[1-(2,2-diphenylethyl)pyrrolidin-3-yl]-3-(2-methylquinolin-4-yl)urea Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=O)NC(C1)CCN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 CRTFHNZNUSVPFV-UHFFFAOYSA-N 0.000 claims description 3
GKIPRRXILIPLFF-LJAQVGFWSA-N 1-[2-[benzyl(methyl)amino]pyridin-4-yl]-3-[(3s)-1-(2,2-diphenylethyl)pyrrolidin-3-yl]urea Chemical compound C=1C(NC(=O)N[C@@H]2CN(CC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=CC=NC=1N(C)CC1=CC=CC=C1 GKIPRRXILIPLFF-LJAQVGFWSA-N 0.000 claims description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
206010002383 Angina Pectoris Diseases 0.000 claims description 3
208000019901 Anxiety disease Diseases 0.000 claims description 3
200000000007 Arterial disease Diseases 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 3
201000004569 Blindness Diseases 0.000 claims description 3
201000006474 Brain Ischemia Diseases 0.000 claims description 3
206010006458 Bronchitis chronic Diseases 0.000 claims description 3
206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
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 3
108010036949 Cyclosporine Proteins 0.000 claims description 3
206010011878 Deafness Diseases 0.000 claims description 3
206010012335 Dependence Diseases 0.000 claims description 3
208000002249 Diabetes Complications Diseases 0.000 claims description 3
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
206010012655 Diabetic complications Diseases 0.000 claims description 3
208000010412 Glaucoma Diseases 0.000 claims description 3
206010018364 Glomerulonephritis Diseases 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 3
208000002193 Pain Diseases 0.000 claims description 3
208000003782 Raynaud disease Diseases 0.000 claims description 3
208000012322 Raynaud phenomenon Diseases 0.000 claims description 3
208000001647 Renal Insufficiency Diseases 0.000 claims description 3
206010038419 Renal colic Diseases 0.000 claims description 3
206010063897 Renal ischaemia Diseases 0.000 claims description 3
208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims description 3
206010001902 amaurosis Diseases 0.000 claims description 3
238000002399 angioplasty Methods 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
206010003119 arrhythmia Diseases 0.000 claims description 3
206010006451 bronchitis Diseases 0.000 claims description 3
238000007675 cardiac surgery Methods 0.000 claims description 3
206010008118 cerebral infarction Diseases 0.000 claims description 3
208000007451 chronic bronchitis Diseases 0.000 claims description 3
208000020832 chronic kidney disease Diseases 0.000 claims description 3
229960001265 ciclosporin Drugs 0.000 claims description 3
208000018631 connective tissue disease Diseases 0.000 claims description 3
208000033679 diabetic kidney disease Diseases 0.000 claims description 3
230000010370 hearing loss Effects 0.000 claims description 3
231100000888 hearing loss Toxicity 0.000 claims description 3
208000016354 hearing loss disease Diseases 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000003112 inhibitor Substances 0.000 claims description 3
208000001286 intracranial vasospasm Diseases 0.000 claims description 3
201000006370 kidney failure Diseases 0.000 claims description 3
206010027599 migraine Diseases 0.000 claims description 3
230000000877 morphologic effect Effects 0.000 claims description 3
208000031225 myocardial ischemia Diseases 0.000 claims description 3
238000011321 prophylaxis Methods 0.000 claims description 3
208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
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208000037803 restenosis Diseases 0.000 claims description 3
201000000980 schizophrenia Diseases 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 3
230000006016 thyroid dysfunction Effects 0.000 claims description 3
238000002054 transplantation Methods 0.000 claims description 3
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DAWSENUBSHJCQD-HSZRJFAPSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[(3r)-1-(2-hydroxy-2,2-diphenylethyl)pyrrolidin-3-yl]urea Chemical compound CC1=NC(C)=CC(NC(=O)N[C@H]2CN(CC(O)(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 DAWSENUBSHJCQD-HSZRJFAPSA-N 0.000 claims description 2
ZTLMHQHOFUJVPJ-XMMPIXPASA-N 1-(2,6-dimethylpyridin-4-yl)-3-[(3r)-1-(3,3-diphenylpropyl)pyrrolidin-3-yl]urea Chemical compound CC1=NC(C)=CC(NC(=O)N[C@H]2CN(CCC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 ZTLMHQHOFUJVPJ-XMMPIXPASA-N 0.000 claims description 2
AVXTWBHRXGTMNK-DEOSSOPVSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[(3s)-1-(1,3-diphenylpropan-2-yl)pyrrolidin-3-yl]urea Chemical compound CC1=NC(C)=CC(NC(=O)N[C@@H]2CN(CC2)C(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 AVXTWBHRXGTMNK-DEOSSOPVSA-N 0.000 claims description 2
DAWSENUBSHJCQD-QHCPKHFHSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[(3s)-1-(2-hydroxy-2,2-diphenylethyl)pyrrolidin-3-yl]urea Chemical compound CC1=NC(C)=CC(NC(=O)N[C@@H]2CN(CC(O)(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 DAWSENUBSHJCQD-QHCPKHFHSA-N 0.000 claims description 2
ZTLMHQHOFUJVPJ-DEOSSOPVSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[(3s)-1-(3,3-diphenylpropyl)pyrrolidin-3-yl]urea Chemical compound CC1=NC(C)=CC(NC(=O)N[C@@H]2CN(CCC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 ZTLMHQHOFUJVPJ-DEOSSOPVSA-N 0.000 claims description 2
DPDDVTVONRJHBM-UHFFFAOYSA-N 1-(2-methylquinolin-4-yl)-3-[1-(1-phenylethyl)pyrrolidin-3-yl]urea Chemical compound C1CC(NC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)CN1C(C)C1=CC=CC=C1 DPDDVTVONRJHBM-UHFFFAOYSA-N 0.000 claims description 2
OBNSKGHLBBYGFD-UHFFFAOYSA-N 1-(2-methylquinolin-4-yl)-3-[1-(3-phenylpropyl)pyrrolidin-3-yl]urea Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=O)NC(C1)CCN1CCCC1=CC=CC=C1 OBNSKGHLBBYGFD-UHFFFAOYSA-N 0.000 claims description 2
UEXAKODCCRGVKK-UHFFFAOYSA-N 1-(2-methylquinolin-4-yl)-3-[1-(4-phenylcyclohexyl)pyrrolidin-3-yl]urea Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=O)NC(C1)CCN1C(CC1)CCC1C1=CC=CC=C1 UEXAKODCCRGVKK-UHFFFAOYSA-N 0.000 claims description 2
NSSFGHRLJFJRDV-UHFFFAOYSA-N 1-(2-methylquinolin-4-yl)-3-[1-(naphthalen-1-ylmethyl)pyrrolidin-3-yl]urea Chemical compound C1=CC=CC2=NC(C)=CC(NC(=O)NC3CN(CC=4C5=CC=CC=C5C=CC=4)CC3)=C21 NSSFGHRLJFJRDV-UHFFFAOYSA-N 0.000 claims description 2
XISUXQPUSTXGNA-UHFFFAOYSA-N 1-(2-methylquinolin-4-yl)-3-[1-(naphthalen-2-ylmethyl)pyrrolidin-3-yl]urea Chemical compound C1=CC=CC2=NC(C)=CC(NC(=O)NC3CN(CC=4C=C5C=CC=CC5=CC=4)CC3)=C21 XISUXQPUSTXGNA-UHFFFAOYSA-N 0.000 claims description 2
NQNGYSXJFKNLEU-UHFFFAOYSA-N 1-(2-methylquinolin-4-yl)-3-[1-[(4-phenylphenyl)methyl]pyrrolidin-3-yl]urea Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=O)NC(C1)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 NQNGYSXJFKNLEU-UHFFFAOYSA-N 0.000 claims description 2
HQKNRZGCWMSVKG-NRWPOFLRSA-N 1-[(3r)-1-(1,1-diphenylpropan-2-yl)pyrrolidin-3-yl]-3-(2-methylquinolin-4-yl)urea Chemical compound C([C@@H](CC1)NC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)N1C(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 HQKNRZGCWMSVKG-NRWPOFLRSA-N 0.000 claims description 2
ALXDTSKWSQIQBV-RUZDIDTESA-N 1-[(3r)-1-(1,3-diphenylpropan-2-yl)pyrrolidin-3-yl]-3-(2-methylquinolin-4-yl)urea Chemical compound C([C@H](C1)NC(=O)NC=2C=C(N=C3C=CC=CC3=2)C)CN1C(CC=1C=CC=CC=1)CC1=CC=CC=C1 ALXDTSKWSQIQBV-RUZDIDTESA-N 0.000 claims description 2
SIEDSGWYFKYBTE-XMMPIXPASA-N 1-[(3r)-1-(2-hydroxy-2,2-diphenylethyl)pyrrolidin-3-yl]-3-(2-methylquinolin-4-yl)urea Chemical compound C([C@H](C1)NC(=O)NC=2C=C(N=C3C=CC=CC3=2)C)CN1CC(O)(C=1C=CC=CC=1)C1=CC=CC=C1 SIEDSGWYFKYBTE-XMMPIXPASA-N 0.000 claims description 2
UQOCWXTYTANLFQ-RUZDIDTESA-N 1-[(3r)-1-(3,3-diphenylpropyl)pyrrolidin-3-yl]-3-(2-methylquinolin-4-yl)urea Chemical compound C([C@H](C1)NC(=O)NC=2C=C(N=C3C=CC=CC3=2)C)CN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 UQOCWXTYTANLFQ-RUZDIDTESA-N 0.000 claims description 2
LYSDRQQEDWTEPV-AREMUKBSSA-N 1-[(3r)-1-(3-cyano-3,3-diphenylpropyl)pyrrolidin-3-yl]-3-(2-methylquinolin-4-yl)urea Chemical compound C([C@H](C1)NC(=O)NC=2C=C(N=C3C=CC=CC3=2)C)CN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 LYSDRQQEDWTEPV-AREMUKBSSA-N 0.000 claims description 2
CSJXSJKKACKVQN-GOSISDBHSA-N 1-[(3r)-1-benzylpyrrolidin-3-yl]-3-(2-methylquinolin-4-yl)urea Chemical compound C([C@H](C1)NC(=O)NC=2C=C(N=C3C=CC=CC3=2)C)CN1CC1=CC=CC=C1 CSJXSJKKACKVQN-GOSISDBHSA-N 0.000 claims description 2
HQKNRZGCWMSVKG-TUXUZCGSSA-N 1-[(3s)-1-(1,1-diphenylpropan-2-yl)pyrrolidin-3-yl]-3-(2-methylquinolin-4-yl)urea Chemical compound C([C@H](CC1)NC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)N1C(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 HQKNRZGCWMSVKG-TUXUZCGSSA-N 0.000 claims description 2
VASZNWWWMQOFBM-VWLOTQADSA-N 1-[(3s)-1-(1,3-diphenylpropan-2-yl)pyrrolidin-3-yl]-3-(2-ethyl-6-methylpyridin-4-yl)urea Chemical compound CC1=NC(CC)=CC(NC(=O)N[C@@H]2CN(CC2)C(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 VASZNWWWMQOFBM-VWLOTQADSA-N 0.000 claims description 2
DHDWSFLSMAUIST-SANMLTNESA-N 1-[(3s)-1-(1,3-diphenylpropan-2-yl)pyrrolidin-3-yl]-3-(2-methyl-6-propylpyridin-4-yl)urea Chemical compound CC1=NC(CCC)=CC(NC(=O)N[C@@H]2CN(CC2)C(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 DHDWSFLSMAUIST-SANMLTNESA-N 0.000 claims description 2
CYWRXQDEQUAXFP-DEOSSOPVSA-N 1-[(3s)-1-(2,2-diphenylethyl)pyrrolidin-3-yl]-3-(2-ethyl-6-methylpyridin-4-yl)urea Chemical compound CC1=NC(CC)=CC(NC(=O)N[C@@H]2CN(CC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 CYWRXQDEQUAXFP-DEOSSOPVSA-N 0.000 claims description 2
VUTISFXPLPGWAS-PMERELPUSA-N 1-[(3s)-1-(2,2-diphenylethyl)pyrrolidin-3-yl]-3-[2-methyl-6-(2-phenylethyl)pyridin-4-yl]urea Chemical compound C([C@@H](C1)NC(=O)NC=2C=C(N=C(CCC=3C=CC=CC=3)C=2)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 VUTISFXPLPGWAS-PMERELPUSA-N 0.000 claims description 2
DBMMTKKCTNZCIH-VWLOTQADSA-N 1-[(3s)-1-(3,3-diphenylpropyl)pyrrolidin-3-yl]-3-(2-ethyl-6-methylpyridin-4-yl)urea Chemical compound CC1=NC(CC)=CC(NC(=O)N[C@@H]2CN(CCC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 DBMMTKKCTNZCIH-VWLOTQADSA-N 0.000 claims description 2
WDIFRXXJMMXIHN-SANMLTNESA-N 1-[(3s)-1-(3,3-diphenylpropyl)pyrrolidin-3-yl]-3-(2-methyl-6-propylpyridin-4-yl)urea Chemical compound CC1=NC(CCC)=CC(NC(=O)N[C@@H]2CN(CCC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 WDIFRXXJMMXIHN-SANMLTNESA-N 0.000 claims description 2
MKBMVELFWQNGRT-HKBQPEDESA-N 1-[(3s)-1-(3,3-diphenylpropyl)pyrrolidin-3-yl]-3-[2-methyl-6-(2-phenylethyl)pyridin-4-yl]urea Chemical compound C([C@@H](C1)NC(=O)NC=2C=C(N=C(CCC=3C=CC=CC=3)C=2)C)CN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 MKBMVELFWQNGRT-HKBQPEDESA-N 0.000 claims description 2
CSJXSJKKACKVQN-SFHVURJKSA-N 1-[(3s)-1-benzylpyrrolidin-3-yl]-3-(2-methylquinolin-4-yl)urea Chemical compound C([C@@H](C1)NC(=O)NC=2C=C(N=C3C=CC=CC3=2)C)CN1CC1=CC=CC=C1 CSJXSJKKACKVQN-SFHVURJKSA-N 0.000 claims description 2
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