SA98190764B1 - مثبطات التخليق الحيوي لبروستاجلاندين اندوبيروكسيد hسينثار - Google Patents

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Publication number

SA98190764B1

SA98190764B1 SA98190764A SA98190764A SA98190764B1 SA 98190764 B1 SA98190764 B1 SA 98190764B1 SA 98190764 A SA98190764 A SA 98190764A SA 98190764 A SA98190764 A SA 98190764A SA 98190764 B1 SA98190764 B1 SA 98190764B1

Authority

SA

Saudi Arabia

Prior art keywords

alkyl

aryl

cycloalkyl

amino

phenyl

Prior art date

1997-08-22

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• 150000003180 prostaglandins Chemical class 0.000 title claims description 19
• 230000015572 biosynthetic process Effects 0.000 title claims description 13
• 239000003112 inhibitor Substances 0.000 title abstract description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 316
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims abstract description 85
• 206010061218 Inflammation Diseases 0.000 claims abstract description 7
• 230000004054 inflammatory process Effects 0.000 claims abstract description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 381
• -1 hydrogen halogen Chemical class 0.000 claims description 345
• 238000000034 method Methods 0.000 claims description 306
• 125000000217 alkyl group Chemical group 0.000 claims description 287
• 239000000203 mixture Substances 0.000 claims description 143
• 125000003118 aryl group Chemical group 0.000 claims description 105
• 229910052739 hydrogen Inorganic materials 0.000 claims description 105
• 239000001257 hydrogen Substances 0.000 claims description 97
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 86
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 84
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 66
• 125000003545 alkoxy group Chemical group 0.000 claims description 53
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
• 229910052736 halogen Inorganic materials 0.000 claims description 51
• 125000000623 heterocyclic group Chemical group 0.000 claims description 50
• 125000003342 alkenyl group Chemical group 0.000 claims description 48
• 239000000651 prodrug Substances 0.000 claims description 42
• 229940002612 prodrug Drugs 0.000 claims description 42
• 125000001188 haloalkyl group Chemical group 0.000 claims description 41
• 150000003839 salts Chemical class 0.000 claims description 41
• 150000002367 halogens Chemical class 0.000 claims description 37
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 37
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 36
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 33
• 125000002947 alkylene group Chemical group 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
• 150000002148 esters Chemical class 0.000 claims description 32
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
• 125000000304 alkynyl group Chemical group 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 27
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 25
• 125000003282 alkyl amino group Chemical group 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 21
• 125000006239 protecting group Chemical group 0.000 claims description 20
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 239000002168 alkylating agent Substances 0.000 claims description 14
• 229940100198 alkylating agent Drugs 0.000 claims description 14
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 14
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 12
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 11
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 238000011282 treatment Methods 0.000 claims description 11
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 10
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 9
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 8
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 8
• 125000001769 aryl amino group Chemical group 0.000 claims description 8
• 125000005418 aryl aryl group Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 239000011737 fluorine Substances 0.000 claims description 8
• 244000198134 Agave sisalana Species 0.000 claims description 7
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 7
• 125000004450 alkenylene group Chemical group 0.000 claims description 7
• 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 7
• 229910052727 yttrium Inorganic materials 0.000 claims description 7
• 150000003973 alkyl amines Chemical class 0.000 claims description 6
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
• 125000004986 diarylamino group Chemical group 0.000 claims description 5
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 5
• 230000001681 protective effect Effects 0.000 claims description 5
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
• 125000004946 alkenylalkyl group Chemical group 0.000 claims description 4
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
• 125000002431 aminoalkoxy group Chemical group 0.000 claims description 4
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
• 125000006212 aryloxy hydroxyalkyl group Chemical group 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
• 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 4
• 125000003396 thiol group Chemical class [H]S* 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 3
• 239000002841 Lewis acid Substances 0.000 claims description 3
• 241001465754 Metazoa Species 0.000 claims description 3
• 206010037660 Pyrexia Diseases 0.000 claims description 3
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
• 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 150000007517 lewis acids Chemical class 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 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 2
• 241001024099 Olla Species 0.000 claims description 2
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
• 125000005741 alkyl alkenyl group Chemical group 0.000 claims description 2
• 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 125000005038 alkynylalkyl group Chemical group 0.000 claims description 2
• 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
• 201000008482 osteoarthritis Diseases 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 7
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims 2
• 125000004171 alkoxy aryl group Chemical group 0.000 claims 2
• 125000004948 alkyl aryl alkyl group Chemical group 0.000 claims 2
• 125000003368 amide group Chemical group 0.000 claims 2
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims 2
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 2
• 239000003795 chemical substances by application Substances 0.000 claims 2
• 125000006492 halo alkyl aryl group Chemical group 0.000 claims 2
• 230000000269 nucleophilic effect Effects 0.000 claims 2
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 2
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
• 241000124008 Mammalia Species 0.000 claims 1
• 206010028980 Neoplasm Diseases 0.000 claims 1
• 241001246312 Otis Species 0.000 claims 1
• 101710185016 Proteasome-activating nucleotidase 1 Proteins 0.000 claims 1
• DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 1
• 125000001118 alkylidene group Chemical group 0.000 claims 1
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims 1
• 239000005557 antagonist Substances 0.000 claims 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims 1
• 201000011510 cancer Diseases 0.000 claims 1
• VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 claims 1
• 230000001066 destructive effect Effects 0.000 claims 1
• 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims 1
• 125000006287 difluorobenzyl group Chemical group 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 125000004175 fluorobenzyl group Chemical group 0.000 claims 1
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
• 239000011521 glass Substances 0.000 claims 1
• 239000004615 ingredient Substances 0.000 claims 1
• 238000001783 near-resonance Rayleigh scattering spectroscopy Methods 0.000 claims 1
• YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 239000002243 precursor Substances 0.000 claims 1
• 239000003223 protective agent Substances 0.000 claims 1
• 230000001012 protector Effects 0.000 claims 1
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims 1
• 102000004190 Enzymes Human genes 0.000 abstract description 10
• 108090000790 Enzymes Proteins 0.000 abstract description 10
• 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 abstract description 8
• 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 abstract description 7
• 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 abstract description 7
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 abstract description 7
• 210000001035 gastrointestinal tract Anatomy 0.000 abstract description 5
• 108010037462 Cyclooxygenase 2 Proteins 0.000 abstract description 4
• 108010029485 Protein Isoforms Proteins 0.000 abstract description 4
• 102000001708 Protein Isoforms Human genes 0.000 abstract description 4
• 229940124639 Selective inhibitor Drugs 0.000 abstract description 4
• 230000000694 effects Effects 0.000 abstract description 4
• 210000003734 kidney Anatomy 0.000 abstract description 4
• 101000605127 Homo sapiens Prostaglandin G/H synthase 2 Proteins 0.000 abstract description 2
• 230000001939 inductive effect Effects 0.000 abstract description 2
• 102000010907 Cyclooxygenase 2 Human genes 0.000 abstract 1
• 101000725401 Homo sapiens Cytochrome c oxidase subunit 2 Proteins 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 371
• 238000004458 analytical method Methods 0.000 description 231
• 238000004519 manufacturing process Methods 0.000 description 165
• 238000002844 melting Methods 0.000 description 153
• 230000008018 melting Effects 0.000 description 153
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 124
• 239000000243 solution Substances 0.000 description 104
• 239000000047 product Substances 0.000 description 86
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 72
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 70
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 57
• 239000002253 acid Substances 0.000 description 56
• 239000011541 reaction mixture Substances 0.000 description 55
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 51
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 50
• 229910002027 silica gel Inorganic materials 0.000 description 48
• 239000000741 silica gel Substances 0.000 description 47
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
• 238000004587 chromatography analysis Methods 0.000 description 39
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 38
• 238000006243 chemical reaction Methods 0.000 description 34
• 238000010992 reflux Methods 0.000 description 31
• 239000010410 layer Substances 0.000 description 28
• NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 22
• 239000000706 filtrate Substances 0.000 description 21
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
• FKKLUOCEIANSFL-UHFFFAOYSA-N 4-methylpent-3-en-1-ol Chemical compound CC(C)=CCCO FKKLUOCEIANSFL-UHFFFAOYSA-N 0.000 description 19
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 19
• 125000004429 atom Chemical group 0.000 description 19
• 239000012267 brine Substances 0.000 description 19
• 230000004927 fusion Effects 0.000 description 19
• 230000002829 reductive effect Effects 0.000 description 19
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
• 239000007787 solid Substances 0.000 description 19
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
• 239000002585 base Substances 0.000 description 18
• 239000012141 concentrate Substances 0.000 description 18
• 235000008504 concentrate Nutrition 0.000 description 18
• 239000006196 drop Substances 0.000 description 18
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 16
• 238000004440 column chromatography Methods 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical class CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 15
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 13
• 239000000377 silicon dioxide Substances 0.000 description 13
• IVUHTLFKBDDICS-UHFFFAOYSA-N (4-methylsulfanylphenyl)boronic acid Chemical compound CSC1=CC=C(B(O)O)C=C1 IVUHTLFKBDDICS-UHFFFAOYSA-N 0.000 description 12
• AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 12
• KGNQDBQYEBMPFZ-UHFFFAOYSA-N 1-fluoro-4-iodobenzene Chemical compound FC1=CC=C(I)C=C1 KGNQDBQYEBMPFZ-UHFFFAOYSA-N 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 12
• 229960004132 diethyl ether Drugs 0.000 description 12
• 239000000284 extract Substances 0.000 description 12
• YEUYZNNBXLMFCW-UHFFFAOYSA-N 1-bromo-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(Br)C=C1 YEUYZNNBXLMFCW-UHFFFAOYSA-N 0.000 description 11
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 11
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 11
• 229940124530 sulfonamide Drugs 0.000 description 11
• 125000005309 thioalkoxy group Chemical group 0.000 description 11
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
• 238000001816 cooling Methods 0.000 description 10
• XZPVPNZTYPUODG-UHFFFAOYSA-M sodium;chloride;dihydrate Chemical compound O.O.[Na+].[Cl-] XZPVPNZTYPUODG-UHFFFAOYSA-M 0.000 description 10
• 150000003456 sulfonamides Chemical class 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
• 230000021615 conjugation Effects 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 230000003647 oxidation Effects 0.000 description 9
• 238000007254 oxidation reaction Methods 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• 150000003462 sulfoxides Chemical class 0.000 description 9
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 8
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