CA2156729A1 - New 4-aminopyridines, processes for their production as well as pharmaceutical agents containing these compounds - Google Patents

Info

Publication number

CA2156729A1

CA2156729A1 CA002156729A CA2156729A CA2156729A1 CA 2156729 A1 CA2156729 A1 CA 2156729A1 CA 002156729 A CA002156729 A CA 002156729A CA 2156729 A CA2156729 A CA 2156729A CA 2156729 A1 CA2156729 A1 CA 2156729A1

Authority

CA

Canada

Prior art keywords

group

methyl

phenyl

compound

pyridin

Prior art date

1993-03-03

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
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 321
• 150000003928 4-aminopyridines Chemical class 0.000 title claims abstract description 16
• 238000000034 method Methods 0.000 title claims abstract description 15
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
• 230000008569 process Effects 0.000 title claims abstract description 10
• 239000008177 pharmaceutical agent Substances 0.000 title claims abstract description 9
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
• 150000002367 halogens Chemical class 0.000 claims abstract description 16
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 14
• 150000003839 salts Chemical class 0.000 claims abstract description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
• 239000001257 hydrogen Substances 0.000 claims abstract description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
• 239000000203 mixture Substances 0.000 claims abstract description 10
• 125000005843 halogen group Chemical group 0.000 claims abstract description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 5
• 150000001412 amines Chemical class 0.000 claims abstract description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
• 239000001301 oxygen Substances 0.000 claims abstract description 5
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
• 239000012453 solvate Substances 0.000 claims abstract description 5
• 239000005864 Sulphur Substances 0.000 claims abstract description 4
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
• 150000004677 hydrates Chemical class 0.000 claims abstract description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
• -1 amino, carboxyl Chemical group 0.000 claims description 109
• 239000000460 chlorine Substances 0.000 claims description 34
• 125000003118 aryl group Chemical group 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 27
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• 229960004979 fampridine Drugs 0.000 claims description 16
• NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 239000000126 substance Substances 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 125000006193 alkinyl group Chemical group 0.000 claims description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000003277 amino group Chemical group 0.000 claims description 8
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
• 238000002360 preparation method Methods 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
• 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 239000012634 fragment Substances 0.000 claims description 5
• 150000002825 nitriles Chemical class 0.000 claims description 5
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 239000004305 biphenyl Substances 0.000 claims description 4
• 235000010290 biphenyl Nutrition 0.000 claims description 4
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 3
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
• 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 150000003222 pyridines Chemical class 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 208000001435 Thromboembolism Diseases 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 125000003368 amide group Chemical group 0.000 claims description 2
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
• 125000002560 nitrile group Chemical group 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims 1
• 125000005133 alkynyloxy group Chemical group 0.000 claims 1
• 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims 1
• 230000003287 optical effect Effects 0.000 claims 1
• 125000001931 aliphatic group Chemical group 0.000 abstract 2
• 125000004122 cyclic group Chemical group 0.000 abstract 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 230
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 92
• 239000002904 solvent Substances 0.000 description 90
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 84
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 81
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
• 229940093499 ethyl acetate Drugs 0.000 description 77
• 235000019439 ethyl acetate Nutrition 0.000 description 76
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
• 239000003921 oil Substances 0.000 description 69
• 235000019198 oils Nutrition 0.000 description 69
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
• 239000000243 solution Substances 0.000 description 62
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 44
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• 238000006243 chemical reaction Methods 0.000 description 40
• 108090000190 Thrombin Proteins 0.000 description 34
• 229960004072 thrombin Drugs 0.000 description 34
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
• 229960000583 acetic acid Drugs 0.000 description 24
• 235000011121 sodium hydroxide Nutrition 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 239000012074 organic phase Substances 0.000 description 20
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
• 238000010992 reflux Methods 0.000 description 19
• 229960003010 sodium sulfate Drugs 0.000 description 19
• 229910052938 sodium sulfate Inorganic materials 0.000 description 19
• 235000011152 sodium sulphate Nutrition 0.000 description 19
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 18
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 17
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
• 239000012071 phase Substances 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
• 239000007858 starting material Substances 0.000 description 16
• 235000011149 sulphuric acid Nutrition 0.000 description 16
• 238000005259 measurement Methods 0.000 description 15
• 230000002829 reductive effect Effects 0.000 description 15
• 239000001117 sulphuric acid Substances 0.000 description 15
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
• 125000004432 carbon atom Chemical group C* 0.000 description 14
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 14
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
• 229910021529 ammonia Inorganic materials 0.000 description 13
• 239000000843 powder Substances 0.000 description 13
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• 238000001816 cooling Methods 0.000 description 12
• 239000013543 active substance Substances 0.000 description 11
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 11
• 239000003054 catalyst Substances 0.000 description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• 239000002244 precipitate Substances 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 10
• 239000003112 inhibitor Substances 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• 239000012280 lithium aluminium hydride Substances 0.000 description 9
• OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 235000011181 potassium carbonates Nutrition 0.000 description 9
• 239000000758 substrate Substances 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• 229940122388 Thrombin inhibitor Drugs 0.000 description 8
• 239000008346 aqueous phase Substances 0.000 description 8
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 239000012362 glacial acetic acid Substances 0.000 description 8
• 235000010288 sodium nitrite Nutrition 0.000 description 8
• 239000003868 thrombin inhibitor Substances 0.000 description 8
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 7
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
• 210000002381 plasma Anatomy 0.000 description 7
• 229940012957 plasmin Drugs 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 238000002844 melting Methods 0.000 description 6
• 230000008018 melting Effects 0.000 description 6
• OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 6
• 235000011118 potassium hydroxide Nutrition 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 239000012312 sodium hydride Substances 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
• 108010049003 Fibrinogen Proteins 0.000 description 5
• 102000008946 Fibrinogen Human genes 0.000 description 5
• 229910010084 LiAlH4 Inorganic materials 0.000 description 5
• 238000009835 boiling Methods 0.000 description 5
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 229940012952 fibrinogen Drugs 0.000 description 5
• 239000005457 ice water Substances 0.000 description 5
• 230000005764 inhibitory process Effects 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 239000007868 Raney catalyst Substances 0.000 description 4
• 229910000564 Raney nickel Inorganic materials 0.000 description 4
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
• 108090000631 Trypsin Proteins 0.000 description 4
• 102000004142 Trypsin Human genes 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 230000029936 alkylation Effects 0.000 description 4
• 238000005804 alkylation reaction Methods 0.000 description 4
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
• 239000011230 binding agent Substances 0.000 description 4
• 210000001772 blood platelet Anatomy 0.000 description 4
• 229910000019 calcium carbonate Inorganic materials 0.000 description 4
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
• 230000015271 coagulation Effects 0.000 description 4
• 238000005345 coagulation Methods 0.000 description 4
• 238000001704 evaporation Methods 0.000 description 4
• 239000012458 free base Substances 0.000 description 4
• 239000012442 inert solvent Substances 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• OKRHBEPHBRPPBV-UHFFFAOYSA-N n-[3-[2-[benzyl-(2,3,5,6-tetrachloropyridin-4-yl)amino]ethoxy]-5-methylphenyl]-2-methoxybenzenesulfonamide Chemical compound COC1=CC=CC=C1S(=O)(=O)NC1=CC(C)=CC(OCCN(CC=2C=CC=CC=2)C=2C(=C(Cl)N=C(Cl)C=2Cl)Cl)=C1 OKRHBEPHBRPPBV-UHFFFAOYSA-N 0.000 description 4
• 239000002243 precursor Substances 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 239000012588 trypsin Substances 0.000 description 4
• UACZEBCMUQWIIC-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-nitropyridine Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=NC(Cl)=C1Cl UACZEBCMUQWIIC-UHFFFAOYSA-N 0.000 description 3
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• JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
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• MKYDTCMZYPTLFV-UHFFFAOYSA-N ethyl 2-[3-(benzenesulfonamido)-5-methylphenoxy]acetate Chemical compound CCOC(=O)COC1=CC(C)=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 MKYDTCMZYPTLFV-UHFFFAOYSA-N 0.000 description 1
• TVMLHSHUDCZPDX-UHFFFAOYSA-N ethyl 2-[3-(benzenesulfonamido)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 TVMLHSHUDCZPDX-UHFFFAOYSA-N 0.000 description 1
• GTXYWNZPWHQSKH-UHFFFAOYSA-N ethyl 2-[3-(benzenesulfonamido)phenoxy]propanoate Chemical compound CCOC(=O)C(C)OC1=CC=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 GTXYWNZPWHQSKH-UHFFFAOYSA-N 0.000 description 1
• COYHCDHWOYBQFH-UHFFFAOYSA-N ethyl 2-[3-(benzenesulfonyloxy)-5-methyl-N-(4-methylphenyl)sulfonylanilino]acetate Chemical compound C(C)OC(CN(C1=CC(=CC(=C1)C)OS(=O)(=O)C1=CC=CC=C1)S(=O)(=O)C1=CC=C(C=C1)C)=O COYHCDHWOYBQFH-UHFFFAOYSA-N 0.000 description 1
• MRQQZGUQMILMPS-UHFFFAOYSA-N ethyl 2-[3-(benzenesulfonyloxy)anilino]acetate Chemical compound C(C)OC(CNC1=CC(=CC=C1)OS(=O)(=O)C1=CC=CC=C1)=O MRQQZGUQMILMPS-UHFFFAOYSA-N 0.000 description 1
• QMBCWXPDURHRKW-UHFFFAOYSA-N ethyl 2-[3-(cyclohexylsulfonylamino)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(NS(=O)(=O)C2CCCCC2)=C1 QMBCWXPDURHRKW-UHFFFAOYSA-N 0.000 description 1
• RWIATBKXCKWSTQ-UHFFFAOYSA-N ethyl 2-[3-(naphthalen-1-ylsulfonylamino)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(NS(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=C1 RWIATBKXCKWSTQ-UHFFFAOYSA-N 0.000 description 1
• JKCCCAFUXLVLHU-UHFFFAOYSA-N ethyl 2-[3-(naphthalen-2-ylsulfonylamino)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=C1 JKCCCAFUXLVLHU-UHFFFAOYSA-N 0.000 description 1
• YFRXMYABJCSJDT-UHFFFAOYSA-N ethyl 2-[3-[(4-methylphenyl)sulfonylamino]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(NS(=O)(=O)C=2C=CC(C)=CC=2)=C1 YFRXMYABJCSJDT-UHFFFAOYSA-N 0.000 description 1
• HJMCDRUDBZIKQF-UHFFFAOYSA-N ethyl 2-[3-[[3-(trifluoromethyl)phenyl]sulfonylamino]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(NS(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1 HJMCDRUDBZIKQF-UHFFFAOYSA-N 0.000 description 1
• VILBSTCQGHEZGV-UHFFFAOYSA-N ethyl 2-[3-[[4-(trifluoromethyl)phenyl]sulfonylamino]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(NS(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 VILBSTCQGHEZGV-UHFFFAOYSA-N 0.000 description 1
• DTIIBXOAGSIKII-UHFFFAOYSA-N ethyl 2-[3-[benzenesulfonyl(benzyl)amino]-5-chlorophenoxy]acetate Chemical compound C(C)OC(COC1=CC(=CC(=C1)N(CC1=CC=CC=C1)S(=O)(=O)C1=CC=CC=C1)Cl)=O DTIIBXOAGSIKII-UHFFFAOYSA-N 0.000 description 1
• VTVRMKHNEGENLL-UHFFFAOYSA-N ethyl 2-[3-[benzenesulfonyl(benzyl)amino]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(N(CC=2C=CC=CC=2)S(=O)(=O)C=2C=CC=CC=2)=C1 VTVRMKHNEGENLL-UHFFFAOYSA-N 0.000 description 1
• UBDXDOFHIJNUOH-UHFFFAOYSA-N ethyl 2-[3-[benzenesulfonyl(ethyl)amino]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(N(CC)S(=O)(=O)C=2C=CC=CC=2)=C1 UBDXDOFHIJNUOH-UHFFFAOYSA-N 0.000 description 1
• RDGWKDQDWWPHBY-UHFFFAOYSA-N ethyl 2-[3-[benzenesulfonyl(methyl)amino]-5-chlorophenoxy]acetate Chemical compound C(C)OC(COC1=CC(=CC(=C1)N(C)S(=O)(=O)C1=CC=CC=C1)Cl)=O RDGWKDQDWWPHBY-UHFFFAOYSA-N 0.000 description 1
• MRFRWWPAHJVIKD-UHFFFAOYSA-N ethyl 2-[3-[benzenesulfonyl(methyl)amino]-5-methoxyphenoxy]acetate Chemical compound C(C)OC(COC1=CC(=CC(=C1)N(C)S(=O)(=O)C1=CC=CC=C1)OC)=O MRFRWWPAHJVIKD-UHFFFAOYSA-N 0.000 description 1
• QJMXFDNYKPVWRD-UHFFFAOYSA-N ethyl 2-[3-[benzenesulfonyl(methyl)amino]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(N(C)S(=O)(=O)C=2C=CC=CC=2)=C1 QJMXFDNYKPVWRD-UHFFFAOYSA-N 0.000 description 1
• WJEACMFYAPODCN-UHFFFAOYSA-N ethyl 2-[3-[benzenesulfonyl(propyl)amino]phenoxy]acetate Chemical compound C=1C=CC=CC=1S(=O)(=O)N(CCC)C1=CC=CC(OCC(=O)OCC)=C1 WJEACMFYAPODCN-UHFFFAOYSA-N 0.000 description 1
• LKAUJBGREXQLPE-UHFFFAOYSA-N ethyl 2-[3-[benzyl(phenyl)sulfamoyl]-5-chloroanilino]acetate Chemical compound C(C)OC(CNC1=CC(=CC(=C1)S(N(C1=CC=CC=C1)CC1=CC=CC=C1)(=O)=O)Cl)=O LKAUJBGREXQLPE-UHFFFAOYSA-N 0.000 description 1
• BXXHHEYWRRDOPE-UHFFFAOYSA-N ethyl 2-[3-[benzyl(phenyl)sulfamoyl]-5-chlorophenoxy]acetate Chemical compound C(C)OC(COC1=CC(=CC(=C1)S(N(C1=CC=CC=C1)CC1=CC=CC=C1)(=O)=O)Cl)=O BXXHHEYWRRDOPE-UHFFFAOYSA-N 0.000 description 1
• GZPPKFDLULLCDI-UHFFFAOYSA-N ethyl 2-[3-[benzyl(phenyl)sulfamoyl]-5-methoxyphenoxy]acetate Chemical compound C(C)OC(COC1=CC(=CC(=C1)S(N(C1=CC=CC=C1)CC1=CC=CC=C1)(=O)=O)OC)=O GZPPKFDLULLCDI-UHFFFAOYSA-N 0.000 description 1
• AUHCBHIZRTZFEP-UHFFFAOYSA-N ethyl 2-[3-methoxy-5-[methyl(phenyl)sulfamoyl]phenoxy]acetate Chemical compound C(C)OC(COC1=CC(=CC(=C1)S(N(C1=CC=CC=C1)C)(=O)=O)OC)=O AUHCBHIZRTZFEP-UHFFFAOYSA-N 0.000 description 1
• BVPNVLGZNQKDME-UHFFFAOYSA-N ethyl 2-[N-(2-methoxyphenyl)sulfonyl-3-methyl-5-[2-(pyridin-4-ylamino)ethoxy]anilino]acetate Chemical compound C(C)OC(CN(C1=CC(=CC(=C1)OCCNC1=CC=NC=C1)C)S(=O)(=O)C1=C(C=CC=C1)OC)=O BVPNVLGZNQKDME-UHFFFAOYSA-N 0.000 description 1
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• AHMOCQJEUQBCPT-UHFFFAOYSA-N ethyl 2-[N-(benzenesulfonyl)-3-methyl-5-[2-[(2,3,5,6-tetrachloropyridin-4-yl)amino]ethoxy]anilino]acetate Chemical compound C(C)OC(CN(C1=CC(=CC(=C1)OCCNC1=C(C(=NC(=C1Cl)Cl)Cl)Cl)C)S(=O)(=O)C1=CC=CC=C1)=O AHMOCQJEUQBCPT-UHFFFAOYSA-N 0.000 description 1
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