MXPA05006272A

MXPA05006272A - Novedosos antagonistas de receptores de mch.

Novedosos antagonistas de receptores de mch.

Info

Publication number: MXPA05006272A
Authority: MX; Mexico
Prior art keywords: carboxylic acid; biphenyl; phenoxy; ethylsulfanylmethyl; amide
Prior art date: 2002-12-11

Application number

MXPA05006272A

Other languages

English (en)

Spanish (es)

Inventor

Michael Morin Junior John

Original Assignee

Lilly Co Eli

Priority date

2002-12-11

Filing date

2003-12-03

Publication date

2005-08-19

2003-12-03 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

2005-08-19 Publication of MXPA05006272A publication Critical patent/MXPA05006272A/es

Links

102000029828 Melanin-concentrating hormone receptor Human genes 0.000 title description 14
108010047068 Melanin-concentrating hormone receptor Proteins 0.000 title description 14
229940044551 receptor antagonist Drugs 0.000 title description 12
239000002464 receptor antagonist Substances 0.000 title description 12
150000001875 compounds Chemical class 0.000 claims abstract description 161
239000000203 mixture Substances 0.000 claims abstract description 67
101800002739 Melanin-concentrating hormone Proteins 0.000 claims abstract description 28
ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 claims abstract description 28
208000008589 Obesity Diseases 0.000 claims abstract description 25
235000020824 obesity Nutrition 0.000 claims abstract description 25
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 18
201000010099 disease Diseases 0.000 claims abstract description 17
238000011282 treatment Methods 0.000 claims abstract description 14
208000024891 symptom Diseases 0.000 claims abstract description 6
239000012453 solvate Substances 0.000 claims abstract description 5
102000047659 melanin-concentrating hormone Human genes 0.000 claims abstract 2
-1 CiCi Chemical group 0.000 claims description 193
238000000034 method Methods 0.000 claims description 66
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 65
125000003118 aryl group Chemical group 0.000 claims description 64
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 52
125000005843 halogen group Chemical group 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 29
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
125000000623 heterocyclic group Chemical group 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 25
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 24
125000001424 substituent group Chemical group 0.000 claims description 24
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 22
125000002877 alkyl aryl group Chemical group 0.000 claims description 22
229910052760 oxygen Inorganic materials 0.000 claims description 22
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
125000005647 linker group Chemical group 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 18
125000001188 haloalkyl group Chemical group 0.000 claims description 18
229910052717 sulfur Chemical group 0.000 claims description 18
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 13
150000003891 oxalate salts Chemical class 0.000 claims description 13
KLOFYERXNUPFDL-UHFFFAOYSA-N 2-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1CSCCOC1=CC=CC=C1 KLOFYERXNUPFDL-UHFFFAOYSA-N 0.000 claims description 11
HGDWKUJSXRDQMH-UHFFFAOYSA-N 2-[3-(2-phenoxyethylsulfanylmethyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC(CSCCOC=2C=CC=CC=2)=C1 HGDWKUJSXRDQMH-UHFFFAOYSA-N 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
DPNYSFCIQJEEGC-UHFFFAOYSA-N 3-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=CC=CC=2)CSCCOC=2C=CC=CC=2)=C1 DPNYSFCIQJEEGC-UHFFFAOYSA-N 0.000 claims description 9
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
239000001301 oxygen Chemical group 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000004043 oxo group Chemical group O=* 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
206010012601 diabetes mellitus Diseases 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000002950 monocyclic group Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
239000000651 prodrug Substances 0.000 claims description 5
229940002612 prodrug Drugs 0.000 claims description 5
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 4
201000001320 Atherosclerosis Diseases 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
208000035475 disorder Diseases 0.000 claims description 4
239000012634 fragment Substances 0.000 claims description 4
DLMBMQNMBCWDEE-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-[3-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C1=CC=CC(CSCCOC=2C=CC=CC=2)=C1 DLMBMQNMBCWDEE-UHFFFAOYSA-N 0.000 claims description 4
LYEWBZQIZVAEFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3-[4-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC(C=2C=CC(CSCCOC=3C=CC=CC=3)=CC=2)=C1 LYEWBZQIZVAEFS-UHFFFAOYSA-N 0.000 claims description 4
125000004193 piperazinyl group Chemical group 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 3
206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
125000002837 carbocyclic group Chemical group 0.000 claims description 3
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
201000001421 hyperglycemia Diseases 0.000 claims description 3
125000001620 monocyclic carbocycle group Chemical group 0.000 claims description 3
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 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
229930192474 thiophene Natural products 0.000 claims description 3
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
206010009900 Colitis ulcerative Diseases 0.000 claims description 2
206010011224 Cough Diseases 0.000 claims description 2
208000011231 Crohn disease Diseases 0.000 claims description 2
206010012735 Diarrhoea Diseases 0.000 claims description 2
208000007882 Gastritis Diseases 0.000 claims description 2
208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
208000010412 Glaucoma Diseases 0.000 claims description 2
208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
206010022714 Intestinal ulcer Diseases 0.000 claims description 2
208000007920 Neurogenic Inflammation Diseases 0.000 claims description 2
208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims description 2
206010029279 Neurogenic bladder Diseases 0.000 claims description 2
206010030216 Oesophagitis Diseases 0.000 claims description 2
208000008469 Peptic Ulcer Diseases 0.000 claims description 2
206010036774 Proctitis Diseases 0.000 claims description 2
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
208000025865 Ulcer Diseases 0.000 claims description 2
201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
210000001367 artery Anatomy 0.000 claims description 2
208000006673 asthma Diseases 0.000 claims description 2
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
150000001924 cycloalkanes Chemical class 0.000 claims description 2
230000003247 decreasing effect Effects 0.000 claims description 2
230000004064 dysfunction Effects 0.000 claims description 2
230000004406 elevated intraocular pressure Effects 0.000 claims description 2
208000006881 esophagitis Diseases 0.000 claims description 2
230000002496 gastric effect Effects 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical class OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
208000006575 hypertriglyceridemia Diseases 0.000 claims description 2
208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
GLNGDYFLXUBPNG-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-[3-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC=C1C1=CC=CC(CSCCOC=2C=CC=CC=2)=C1 GLNGDYFLXUBPNG-UHFFFAOYSA-N 0.000 claims description 2
JUSRMRJMSMPGEH-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound C1=CC(C(=O)NCCCN(C)C)=CC=C1C1=CC=CC=C1CSCCOC1=CC=CC=C1 JUSRMRJMSMPGEH-UHFFFAOYSA-N 0.000 claims description 2
JCIWUZSRYDHNJP-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]-4-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound C1=CC(C(=O)NCCCCN(C)C)=CC=C1C1=CC=CC=C1CSCCOC1=CC=CC=C1 JCIWUZSRYDHNJP-UHFFFAOYSA-N 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
208000011906 peptic ulcer disease Diseases 0.000 claims description 2
230000002093 peripheral effect Effects 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
208000017497 prostate disease Diseases 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
210000002345 respiratory system Anatomy 0.000 claims description 2
208000011580 syndromic disease Diseases 0.000 claims description 2
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
230000036269 ulceration Effects 0.000 claims description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 2
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 2
101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
125000002393 azetidinyl group Chemical group 0.000 claims 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims 1
230000002265 prevention Effects 0.000 abstract description 4
239000003667 hormone antagonist Substances 0.000 abstract description 3
239000003921 oil Substances 0.000 description 142
235000019198 oils Nutrition 0.000 description 142
238000006243 chemical reaction Methods 0.000 description 139
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 119
125000004494 ethyl ester group Chemical group 0.000 description 116
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 116
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 110
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 110
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 90
239000002904 solvent Substances 0.000 description 74
238000010168 coupling process Methods 0.000 description 64
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
239000000047 product Substances 0.000 description 62
235000019439 ethyl acetate Nutrition 0.000 description 59
238000005481 NMR spectroscopy Methods 0.000 description 53
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 46
238000003818 flash chromatography Methods 0.000 description 45
238000005859 coupling reaction Methods 0.000 description 44
239000000741 silica gel Substances 0.000 description 44
229910002027 silica gel Inorganic materials 0.000 description 44
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 42
239000007787 solid Substances 0.000 description 41
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 40
238000002360 preparation method Methods 0.000 description 37
230000008569 process Effects 0.000 description 36
230000008878 coupling Effects 0.000 description 33
238000007429 general method Methods 0.000 description 32
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 28
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 27
102400001132 Melanin-concentrating hormone Human genes 0.000 description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 25
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
238000004128 high performance liquid chromatography Methods 0.000 description 22
QWZAGTBLJQGFHZ-UHFFFAOYSA-N 3-[4-(2-phenoxyethylsulfanylmethyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC(CSCCOC=3C=CC=CC=3)=CC=2)=C1 QWZAGTBLJQGFHZ-UHFFFAOYSA-N 0.000 description 21
239000012458 free base Substances 0.000 description 21
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
239000002585 base Substances 0.000 description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 19
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150000002431 hydrogen Chemical group 0.000 description 18
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 18
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150000001412 amines Chemical class 0.000 description 16
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125000002524 organometallic group Chemical group 0.000 description 16
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 16
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235000019502 Orange oil Nutrition 0.000 description 15
239000003054 catalyst Substances 0.000 description 15
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 15
239000010502 orange oil Substances 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
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238000005160 1H NMR spectroscopy Methods 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
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