HRP20000153A2 - Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them - Google Patents
Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them Download PDFInfo
- Publication number
- HRP20000153A2 HRP20000153A2 HR20000153A HRP20000153A HRP20000153A2 HR P20000153 A2 HRP20000153 A2 HR P20000153A2 HR 20000153 A HR20000153 A HR 20000153A HR P20000153 A HRP20000153 A HR P20000153A HR P20000153 A2 HRP20000153 A2 HR P20000153A2
- Authority
- HR
- Croatia
- Prior art keywords
- chloro
- mixture
- cyclohexylethyl
- dimethoxyphenyl
- ylcarbamoyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 99
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 343
- -1 acetyloxy, methoxy, ethoxy, methylthio Chemical group 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 36
- 101800001982 Cholecystokinin Proteins 0.000 claims description 35
- 102100025841 Cholecystokinin Human genes 0.000 claims description 35
- 229940107137 cholecystokinin Drugs 0.000 claims description 35
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 239000012453 solvate Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 24
- 108010089335 Cholecystokinin A Receptor Proteins 0.000 claims description 23
- 102100034927 Cholecystokinin receptor type A Human genes 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- NFDFTMICKVDYLQ-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-5,7-dimethylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(C)C=C(C)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC NFDFTMICKVDYLQ-UHFFFAOYSA-N 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- ITSFURYNWBMEFN-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-5-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(C)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC ITSFURYNWBMEFN-UHFFFAOYSA-N 0.000 claims description 4
- 208000012661 Dyskinesia Diseases 0.000 claims description 4
- 210000003169 central nervous system Anatomy 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- KNMAHODWYDYBNW-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4,5-dimethoxyindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(OC)C(OC)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC KNMAHODWYDYBNW-UHFFFAOYSA-N 0.000 claims description 2
- JBGFIZSFYCETDI-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4,7-dimethoxyindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(OC)C=CC(OC)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC JBGFIZSFYCETDI-UHFFFAOYSA-N 0.000 claims description 2
- PQAPEXJKQQHFKZ-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4,7-dimethylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(C)C=CC(C)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC PQAPEXJKQQHFKZ-UHFFFAOYSA-N 0.000 claims description 2
- IXSKIUYWZMHWPS-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4-methoxy-7-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(C)C=CC(OC)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC IXSKIUYWZMHWPS-UHFFFAOYSA-N 0.000 claims description 2
- WYNBPYGACGYHSD-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4-methoxyindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=CC(OC)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC WYNBPYGACGYHSD-UHFFFAOYSA-N 0.000 claims description 2
- VZVMSBUIQNSYBC-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=CC(C)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC VZVMSBUIQNSYBC-UHFFFAOYSA-N 0.000 claims description 2
- LSXGNWUBWRFTCY-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-5-methoxy-7-methylindol-1-yl]acetic acid Chemical compound C=1C2=CC(OC)=CC(C)=C2N(CC(O)=O)C=1C(=O)NC(S1)=NC(C=2C(=CC(Cl)=C(OC)C=2)OC)=C1CCC1CCCCC1 LSXGNWUBWRFTCY-UHFFFAOYSA-N 0.000 claims description 2
- HYGJUCCSZDXPRF-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-5-methoxyindol-1-yl]acetic acid Chemical compound C=1C2=CC(OC)=CC=C2N(CC(O)=O)C=1C(=O)NC(S1)=NC(C=2C(=CC(Cl)=C(OC)C=2)OC)=C1CCC1CCCCC1 HYGJUCCSZDXPRF-UHFFFAOYSA-N 0.000 claims description 2
- AXDWNJKERZGTNC-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-7-methoxyindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(OC)C=CC=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC AXDWNJKERZGTNC-UHFFFAOYSA-N 0.000 claims description 2
- MFWRPGPURWSDCK-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-7-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(C)C=CC=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC MFWRPGPURWSDCK-UHFFFAOYSA-N 0.000 claims description 2
- SXINCQCTZSUDRH-UHFFFAOYSA-N 2-[4,5-dichloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(Cl)C(Cl)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC SXINCQCTZSUDRH-UHFFFAOYSA-N 0.000 claims description 2
- NZNSWXRZLJRSGW-UHFFFAOYSA-N 2-[5,7-dichloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(Cl)C=C(Cl)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC NZNSWXRZLJRSGW-UHFFFAOYSA-N 0.000 claims description 2
- CUUMWIRAPXOFQO-UHFFFAOYSA-N 2-[5-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(Cl)C(C)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC CUUMWIRAPXOFQO-UHFFFAOYSA-N 0.000 claims description 2
- YJYRFYGFCXFFOQ-UHFFFAOYSA-N 2-[5-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-7-(trifluoromethyl)indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(C=C(Cl)C=C4C=3)C(F)(F)F)CC(O)=O)=N2)CCC2CCCCC2)=C1OC YJYRFYGFCXFFOQ-UHFFFAOYSA-N 0.000 claims description 2
- FYGGTVJAHJMXGR-UHFFFAOYSA-N 2-[5-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-7-fluoroindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(F)C=C(Cl)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC FYGGTVJAHJMXGR-UHFFFAOYSA-N 0.000 claims description 2
- CFQABQGBWXICEA-UHFFFAOYSA-N 2-[5-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-7-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(C)C=C(Cl)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC CFQABQGBWXICEA-UHFFFAOYSA-N 0.000 claims description 2
- VBRYWAAVGGWBTI-UHFFFAOYSA-N 2-[5-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(Cl)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC VBRYWAAVGGWBTI-UHFFFAOYSA-N 0.000 claims description 2
- IKZBMDGXMKKSFD-UHFFFAOYSA-N 2-[7-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(Cl)C=CC(C)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC IKZBMDGXMKKSFD-UHFFFAOYSA-N 0.000 claims description 2
- ZGZDMSJKGUFBMR-UHFFFAOYSA-N 2-[7-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-5-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(Cl)C=C(C)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC ZGZDMSJKGUFBMR-UHFFFAOYSA-N 0.000 claims description 2
- 210000005095 gastrointestinal system Anatomy 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 230000000638 stimulation Effects 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000000203 mixture Substances 0.000 description 259
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 164
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 140
- 239000000243 solution Substances 0.000 description 132
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 114
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 113
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 109
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 103
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 88
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 68
- 235000019439 ethyl acetate Nutrition 0.000 description 68
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
- 239000003480 eluent Substances 0.000 description 55
- 239000000741 silica gel Substances 0.000 description 55
- 229910002027 silica gel Inorganic materials 0.000 description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 49
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 48
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 46
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 44
- 235000019341 magnesium sulphate Nutrition 0.000 description 44
- 239000002244 precipitate Substances 0.000 description 43
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 41
- 239000011541 reaction mixture Substances 0.000 description 40
- 239000007832 Na2SO4 Substances 0.000 description 37
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 37
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 37
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 37
- 229910052938 sodium sulfate Inorganic materials 0.000 description 37
- 235000011152 sodium sulphate Nutrition 0.000 description 37
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
- 238000003756 stirring Methods 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 31
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 26
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- 150000002148 esters Chemical class 0.000 description 22
- 235000017550 sodium carbonate Nutrition 0.000 description 22
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 20
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
- 238000001704 evaporation Methods 0.000 description 17
- 229910000104 sodium hydride Inorganic materials 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
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- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 12
- 239000000556 agonist Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 229910052736 halogen Chemical group 0.000 description 12
- 150000002367 halogens Chemical group 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- 102000005962 receptors Human genes 0.000 description 12
- 108020003175 receptors Proteins 0.000 description 12
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 12
- 239000013543 active substance Substances 0.000 description 11
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 9
- 230000030136 gastric emptying Effects 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 230000033228 biological regulation Effects 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
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- MJPLUXLNYQHWIU-UHFFFAOYSA-N tert-butyl n-(3-methylpyridin-2-yl)carbamate Chemical compound CC1=CC=CN=C1NC(=O)OC(C)(C)C MJPLUXLNYQHWIU-UHFFFAOYSA-N 0.000 description 1
- RZPXITSRAQPKRU-UHFFFAOYSA-N tert-butyl n-(3-methylpyridin-4-yl)carbamate Chemical compound CC1=CN=CC=C1NC(=O)OC(C)(C)C RZPXITSRAQPKRU-UHFFFAOYSA-N 0.000 description 1
- DIHCQPPXAIYZOO-UHFFFAOYSA-N tert-butyl n-(4-methylpyridin-3-yl)carbamate Chemical compound CC1=CC=NC=C1NC(=O)OC(C)(C)C DIHCQPPXAIYZOO-UHFFFAOYSA-N 0.000 description 1
- ZUTGOBZDHFXKHW-UHFFFAOYSA-N tert-butyl n-(6-methoxy-4-methylpyridin-3-yl)carbamate Chemical compound COC1=CC(C)=C(NC(=O)OC(C)(C)C)C=N1 ZUTGOBZDHFXKHW-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9711718A FR2768737B1 (fr) | 1997-09-19 | 1997-09-19 | Derives de carboxamidothiazoles, leur preparation, les compositions pharmaceutiques en contenant |
FR9805106A FR2777887B3 (fr) | 1998-04-23 | 1998-04-23 | Derives de carboxamidothiazoles, leur preparation, les compositions pharmaceutiques en contenant |
PCT/FR1998/002007 WO1999015525A1 (fr) | 1997-09-19 | 1998-09-18 | Derives de carboxamidothiazoles, leur preparation, les compositions pharmaceutiques en contenant |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20000153A2 true HRP20000153A2 (en) | 2001-04-30 |
Family
ID=26233812
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20000153A HRP20000153A2 (en) | 1997-09-19 | 2000-03-17 | Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them |
Country Status (27)
Country | Link |
---|---|
US (1) | US6380230B1 (es) |
EP (1) | EP1017693A1 (es) |
JP (1) | JP3456970B2 (es) |
KR (1) | KR20010030629A (es) |
CN (1) | CN1276790A (es) |
AR (1) | AR013494A1 (es) |
AU (1) | AU746707B2 (es) |
BG (1) | BG104254A (es) |
BR (1) | BR9812653A (es) |
CA (1) | CA2304397A1 (es) |
CO (1) | CO4970713A1 (es) |
EA (1) | EA003093B1 (es) |
EE (1) | EE200000168A (es) |
HR (1) | HRP20000153A2 (es) |
HU (1) | HUP0100225A3 (es) |
ID (1) | ID25528A (es) |
IL (1) | IL134961A (es) |
IS (1) | IS5409A (es) |
MY (1) | MY141444A (es) |
NO (1) | NO314455B1 (es) |
NZ (1) | NZ503339A (es) |
PL (1) | PL339292A1 (es) |
SK (1) | SK4052000A3 (es) |
TR (1) | TR200001218T2 (es) |
TW (1) | TW430664B (es) |
UY (1) | UY25180A1 (es) |
WO (1) | WO1999015525A1 (es) |
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IE68593B1 (en) | 1989-12-06 | 1996-06-26 | Sanofi Sa | Heterocyclic substituted acylaminothiazoles their preparation and pharmaceutical compositions containing them |
FR2677356B1 (fr) | 1991-06-05 | 1995-03-17 | Sanofi Sa | Derives heterocycliques d'acylamino-2 thiazoles-5 substitues, leur preparation et compositions pharmaceutiques en contenant. |
FR2701708B1 (fr) | 1993-02-19 | 1995-05-19 | Sanofi Elf | Dérivés de 2-amido-4-phénylthiazoles polysubstitués, procédé de préparation, composition pharmaceutique et utilisation de ces dérivés pour la préparation d'un médicament. |
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1998
- 1998-09-09 CO CO98051671A patent/CO4970713A1/es unknown
- 1998-09-12 MY MYPI98004185A patent/MY141444A/en unknown
- 1998-09-14 UY UY25180A patent/UY25180A1/es unknown
- 1998-09-16 AR ARP980104588A patent/AR013494A1/es not_active Application Discontinuation
- 1998-09-18 WO PCT/FR1998/002007 patent/WO1999015525A1/fr not_active Application Discontinuation
- 1998-09-18 AU AU91705/98A patent/AU746707B2/en not_active Ceased
- 1998-09-18 TW TW087115602A patent/TW430664B/zh active
- 1998-09-18 NZ NZ503339A patent/NZ503339A/en unknown
- 1998-09-18 CA CA002304397A patent/CA2304397A1/fr not_active Abandoned
- 1998-09-18 CN CN98810341A patent/CN1276790A/zh active Pending
- 1998-09-18 KR KR1020007002905A patent/KR20010030629A/ko not_active Application Discontinuation
- 1998-09-18 EA EA200000334A patent/EA003093B1/ru not_active IP Right Cessation
- 1998-09-18 BR BR9812653-9A patent/BR9812653A/pt not_active IP Right Cessation
- 1998-09-18 IL IL13496198A patent/IL134961A/en not_active IP Right Cessation
- 1998-09-18 JP JP2000512830A patent/JP3456970B2/ja not_active Expired - Fee Related
- 1998-09-18 US US09/508,830 patent/US6380230B1/en not_active Expired - Fee Related
- 1998-09-18 TR TR2000/01218T patent/TR200001218T2/xx unknown
- 1998-09-18 SK SK405-2000A patent/SK4052000A3/sk unknown
- 1998-09-18 EP EP98944024A patent/EP1017693A1/fr not_active Withdrawn
- 1998-09-18 ID IDW20000504A patent/ID25528A/id unknown
- 1998-09-18 PL PL98339292A patent/PL339292A1/xx unknown
- 1998-09-18 HU HU0100225A patent/HUP0100225A3/hu unknown
- 1998-09-18 EE EEP200000168A patent/EE200000168A/xx unknown
-
2000
- 2000-03-16 IS IS5409A patent/IS5409A/is unknown
- 2000-03-17 HR HR20000153A patent/HRP20000153A2/hr not_active Application Discontinuation
- 2000-03-17 BG BG104254A patent/BG104254A/xx unknown
- 2000-03-17 NO NO20001409A patent/NO314455B1/no not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
MY141444A (en) | 2010-04-30 |
TR200001218T2 (tr) | 2001-05-21 |
SK4052000A3 (en) | 2001-03-12 |
EA003093B1 (ru) | 2002-12-26 |
HUP0100225A3 (en) | 2003-05-28 |
US6380230B1 (en) | 2002-04-30 |
CA2304397A1 (fr) | 1999-04-01 |
CN1276790A (zh) | 2000-12-13 |
AU9170598A (en) | 1999-04-12 |
UY25180A1 (es) | 2001-06-29 |
NZ503339A (en) | 2002-03-28 |
TW430664B (en) | 2001-04-21 |
IL134961A (en) | 2002-07-25 |
JP2001517667A (ja) | 2001-10-09 |
IS5409A (is) | 2000-03-16 |
ID25528A (id) | 2000-10-12 |
AU746707B2 (en) | 2002-05-02 |
EP1017693A1 (fr) | 2000-07-12 |
IL134961A0 (en) | 2001-05-20 |
AR013494A1 (es) | 2000-12-27 |
CO4970713A1 (es) | 2000-11-07 |
JP3456970B2 (ja) | 2003-10-14 |
KR20010030629A (ko) | 2001-04-16 |
BG104254A (en) | 2001-08-31 |
EE200000168A (et) | 2001-04-16 |
NO20001409L (no) | 2000-05-16 |
HUP0100225A2 (hu) | 2001-09-28 |
BR9812653A (pt) | 2000-08-22 |
PL339292A1 (en) | 2000-12-04 |
EA200000334A1 (ru) | 2000-10-30 |
WO1999015525A1 (fr) | 1999-04-01 |
NO314455B1 (no) | 2003-03-24 |
NO20001409D0 (no) | 2000-03-17 |
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