AU2001270947A1 - 1,4-dihydropyridines as bradykinin antagonists - Google Patents

Info

Publication number

AU2001270947A1

AU2001270947A1 AU2001270947A AU7094701A AU2001270947A1 AU 2001270947 A1 AU2001270947 A1 AU 2001270947A1 AU 2001270947 A AU2001270947 A AU 2001270947A AU 7094701 A AU7094701 A AU 7094701A AU 2001270947 A1 AU2001270947 A1 AU 2001270947A1

Authority

AU

Australia

Prior art keywords

alkoxy

alkylamino

amino

alkyl

methyl

Prior art date

2000-08-10

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title description 19
• 239000003152 bradykinin antagonist Substances 0.000 title description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 384
• 150000001875 compounds Chemical class 0.000 claims description 304
• -1 hydroxy, amino Chemical group 0.000 claims description 284
• 125000003282 alkyl amino group Chemical group 0.000 claims description 201
• 238000000034 method Methods 0.000 claims description 140
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 131
• 125000004442 acylamino group Chemical group 0.000 claims description 123
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 121
• 125000001424 substituent group Chemical group 0.000 claims description 110
• 125000004414 alkyl thio group Chemical group 0.000 claims description 97
• 125000000217 alkyl group Chemical group 0.000 claims description 92
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 85
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 58
• 125000004043 oxo group Chemical group O=* 0.000 claims description 57
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 56
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 56
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
• 125000004193 piperazinyl group Chemical group 0.000 claims description 51
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 47
• 125000004423 acyloxy group Chemical group 0.000 claims description 46
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 36
• 125000005843 halogen group Chemical group 0.000 claims description 33
• 208000006673 asthma Diseases 0.000 claims description 32
• 208000006752 brain edema Diseases 0.000 claims description 30
• 238000011282 treatment Methods 0.000 claims description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
• 239000002253 acid Substances 0.000 claims description 27
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 27
• 206010048962 Brain oedema Diseases 0.000 claims description 24
• 206010019196 Head injury Diseases 0.000 claims description 18
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
• 206010061218 Inflammation Diseases 0.000 claims description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 230000004054 inflammatory process Effects 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 14
• 125000002252 acyl group Chemical group 0.000 claims description 14
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 14
• 101800004538 Bradykinin Proteins 0.000 claims description 13
• QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 208000002193 Pain Diseases 0.000 claims description 13
• 206010033645 Pancreatitis Diseases 0.000 claims description 13
• QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 claims description 13
• 239000003054 catalyst Substances 0.000 claims description 13
• 230000036407 pain Effects 0.000 claims description 13
• 208000010412 Glaucoma Diseases 0.000 claims description 12
• 208000003251 Pruritus Diseases 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 208000006011 Stroke Diseases 0.000 claims description 11
• 125000005035 acylthio group Chemical group 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 11
• 208000030159 metabolic disease Diseases 0.000 claims description 11
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 10
• 206010020751 Hypersensitivity Diseases 0.000 claims description 10
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
• 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 claims description 10
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 9
• 230000007815 allergy Effects 0.000 claims description 9
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 8
• 206010012601 diabetes mellitus Diseases 0.000 claims description 8
• 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 201000009240 nasopharyngitis Diseases 0.000 claims description 8
• 201000008482 osteoarthritis Diseases 0.000 claims description 8
• 206010039083 rhinitis Diseases 0.000 claims description 8
• 230000009385 viral infection Effects 0.000 claims description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 208000023105 Huntington disease Diseases 0.000 claims description 7
• 206010027476 Metastases Diseases 0.000 claims description 7
• 208000019695 Migraine disease Diseases 0.000 claims description 7
• 208000004221 Multiple Trauma Diseases 0.000 claims description 7
• 208000018737 Parkinson disease Diseases 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 7
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 7
• 201000003146 cystitis Diseases 0.000 claims description 7
• 208000014674 injury Diseases 0.000 claims description 7
• 230000000302 ischemic effect Effects 0.000 claims description 7
• 230000001404 mediated effect Effects 0.000 claims description 7
• 230000009401 metastasis Effects 0.000 claims description 7
• 206010027599 migraine Diseases 0.000 claims description 7
• 201000006417 multiple sclerosis Diseases 0.000 claims description 7
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 7
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 208000023504 respiratory system disease Diseases 0.000 claims description 7
• 208000034577 Benign intracranial hypertension Diseases 0.000 claims description 6
• 206010019845 Hepatorenal failure Diseases 0.000 claims description 6
• 208000018127 Idiopathic intracranial hypertension Diseases 0.000 claims description 6
• 208000004880 Polyuria Diseases 0.000 claims description 6
• 206010040047 Sepsis Diseases 0.000 claims description 6
• 206010063036 Spinal cord oedema Diseases 0.000 claims description 6
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 230000035619 diuresis Effects 0.000 claims description 6
• 208000003906 hydrocephalus Diseases 0.000 claims description 6
• 230000007803 itching Effects 0.000 claims description 6
• 208000004296 neuralgia Diseases 0.000 claims description 6
• 230000004770 neurodegeneration Effects 0.000 claims description 6
• 208000021722 neuropathic pain Diseases 0.000 claims description 6
• 230000012495 positive regulation of renal sodium excretion Effects 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 208000001381 pseudotumor cerebri Diseases 0.000 claims description 6
• 210000000278 spinal cord Anatomy 0.000 claims description 6
• 230000008733 trauma Effects 0.000 claims description 6
• JFZHPXPIBBBLAK-UHFFFAOYSA-N 4-(2,6-dichlorophenyl)-2-[2-[2-[2-(diethylamino)ethoxymethyl]phenyl]ethyl]-6-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound CCN(CC)CCOCC1=CC=CC=C1CCC(N1)=C(C(O)=O)C(C=2C(=CC=CC=2Cl)Cl)C(C(O)=O)=C1CC(=O)N1CCN(C2CC3CCC(N3C)C2)CC1 JFZHPXPIBBBLAK-UHFFFAOYSA-N 0.000 claims description 5
• 208000028185 Angioedema Diseases 0.000 claims description 5
• 208000006069 Corneal Opacity Diseases 0.000 claims description 5
• 206010015958 Eye pain Diseases 0.000 claims description 5
• 206010029113 Neovascularisation Diseases 0.000 claims description 5
• 206010030043 Ocular hypertension Diseases 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• LUAVSTHCMSKEPP-UHFFFAOYSA-N dimethyl 2-[2-[2-(2-aminoethoxymethyl)phenyl]ethyl]-4-(2,6-dichlorophenyl)-6-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1COCCN LUAVSTHCMSKEPP-UHFFFAOYSA-N 0.000 claims description 5
• YGKGLBYPJXQPKB-UHFFFAOYSA-N dimethyl 4-(2,6-dichlorophenyl)-2-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-6-[2-[2-(piperazine-1-carbonyl)phenyl]ethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1C(=O)N1CCNCC1 YGKGLBYPJXQPKB-UHFFFAOYSA-N 0.000 claims description 5
• VCBXVMCLKCISIE-UHFFFAOYSA-N dimethyl 4-(2,6-dichlorophenyl)-2-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-6-[2-[2-[2-(2-oxopyrrolidin-1-yl)ethoxy]phenyl]ethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1OCCN1CCCC1=O VCBXVMCLKCISIE-UHFFFAOYSA-N 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 229910052751 metal Inorganic materials 0.000 claims description 5
• 239000002184 metal Substances 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• XHBHLQKQFLCOEZ-UHFFFAOYSA-N dimethyl 4-(2,6-dichlorophenyl)-2-[2-(2-hydroxyphenyl)ethyl]-6-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1O XHBHLQKQFLCOEZ-UHFFFAOYSA-N 0.000 claims description 4
• YDQXZLHXCHFOAX-UHFFFAOYSA-N dimethyl 4-(2,6-dichlorophenyl)-2-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-6-[2-[2-(phenylsulfanylmethyl)phenyl]ethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1CSC1=CC=CC=C1 YDQXZLHXCHFOAX-UHFFFAOYSA-N 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 229910052700 potassium Inorganic materials 0.000 claims description 4
• 229910052708 sodium Inorganic materials 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• HKZOTGKPRFXEIU-UHFFFAOYSA-N dimethyl 2-[2-[2-(2-aminoethoxy)phenyl]ethyl]-4-(2,6-dichlorophenyl)-6-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1OCCN HKZOTGKPRFXEIU-UHFFFAOYSA-N 0.000 claims description 3
• LBZLFLWAYATJJQ-UHFFFAOYSA-N dimethyl 2-[2-[2-(3-aminopropoxy)phenyl]ethyl]-4-(2,6-dichlorophenyl)-6-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1OCCCN LBZLFLWAYATJJQ-UHFFFAOYSA-N 0.000 claims description 3
• ODOIYUVANTUHOK-UHFFFAOYSA-N dimethyl 4-(2,6-dichlorophenyl)-2-[2-[2-(diethylaminomethyl)phenyl]ethyl]-6-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCN(CC)CC1=CC=CC=C1CCC(N1)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CC(=O)N1CCN(C2CC3CCC(N3C)C2)CC1 ODOIYUVANTUHOK-UHFFFAOYSA-N 0.000 claims description 3
• RNZBWLITTBDESM-UHFFFAOYSA-N dimethyl 4-(2,6-dichlorophenyl)-2-[2-[2-(methanesulfonamido)phenyl]ethyl]-6-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1NS(C)(=O)=O RNZBWLITTBDESM-UHFFFAOYSA-N 0.000 claims description 3
• XDKMPADWQKGKRF-UHFFFAOYSA-N dimethyl 4-(2,6-dichlorophenyl)-2-[2-[2-[2-(diethylamino)ethoxymethyl]phenyl]ethyl]-6-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCN(CC)CCOCC1=CC=CC=C1CCC(N1)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CC(=O)N1CCN(C2CC3CCC(N3C)C2)CC1 XDKMPADWQKGKRF-UHFFFAOYSA-N 0.000 claims description 3
• WQPLSTXYNQUNPP-UHFFFAOYSA-N dimethyl 4-(2,6-dichlorophenyl)-2-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-6-[2-[2-(2-morpholin-4-ylethoxymethyl)phenyl]ethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1COCCN1CCOCC1 WQPLSTXYNQUNPP-UHFFFAOYSA-N 0.000 claims description 3
• AFORYBKHEBBSDB-UHFFFAOYSA-N dimethyl 4-(2,6-dichlorophenyl)-2-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-6-[2-[2-(morpholin-4-ylmethyl)phenyl]ethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1CN1CCOCC1 AFORYBKHEBBSDB-UHFFFAOYSA-N 0.000 claims description 3
• 229910052744 lithium Inorganic materials 0.000 claims description 3
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
• FTBXNYMYWGMIPG-UHFFFAOYSA-N dimethyl 4-(2,6-dichlorophenyl)-2-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-6-[2-[2-(2,2,2-trifluoroethylamino)phenyl]ethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1NCC(F)(F)F FTBXNYMYWGMIPG-UHFFFAOYSA-N 0.000 claims description 2
• 230000003301 hydrolyzing effect Effects 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 102100035792 Kininogen-1 Human genes 0.000 claims 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
• MKNLIURDDFOFLC-UHFFFAOYSA-N dimethyl 2-[2-[2-(3-aminopropoxymethyl)phenyl]ethyl]-4-(2,6-dichlorophenyl)-6-[2-[4-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)piperazin-1-yl]-2-oxoethyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(CC(=O)N2CCN(CC2)C2CC3CCC(N3C)C2)=C(C(=O)OC)C(C=2C(=CC=CC=2Cl)Cl)C(C(=O)OC)=C1CCC1=CC=CC=C1COCCCN MKNLIURDDFOFLC-UHFFFAOYSA-N 0.000 claims 1
• 239000002831 pharmacologic agent Substances 0.000 claims 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 107
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
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• 239000000203 mixture Substances 0.000 description 85
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
• 238000006243 chemical reaction Methods 0.000 description 79
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 61
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
• 229910001868 water Inorganic materials 0.000 description 49
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 47
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• 239000003921 oil Substances 0.000 description 42
• 235000019198 oils Nutrition 0.000 description 42
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 40
• 235000019439 ethyl acetate Nutrition 0.000 description 35
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
• 239000012267 brine Substances 0.000 description 30
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 29
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 28
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• 239000007787 solid Substances 0.000 description 22
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