SK4052000A3 - Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them - Google Patents

Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them Download PDF

Info

Publication number: SK4052000A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; chloro; dimethoxyphenyl; cyclohexylethyl
Prior art date: 1997-09-19

Application number

SK405-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Roger Brodin

Robert Boigegrain

Eric Bignon

Jean-Charles Molimard

Dominique Olliero

Original Assignee

Sanofi Synthelabo

Priority date (The priority date 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 date listed.)

1997-09-19

Filing date

1998-09-18

Publication date

2001-03-12

1997-09-19 Priority claimed from FR9711718A external-priority patent/FR2768737B1/fr

1998-04-23 Priority claimed from FR9805106A external-priority patent/FR2777887B3/fr

1998-09-18 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

2001-03-12 Publication of SK4052000A3 publication Critical patent/SK4052000A3/sk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
238000002360 preparation method Methods 0.000 title claims description 91
238000000034 method Methods 0.000 claims abstract description 45
239000003814 drug Substances 0.000 claims abstract description 15
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims abstract description 5
125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 5
150000001875 compounds Chemical class 0.000 claims description 356
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 94
-1 2-indolyl Chemical group 0.000 claims description 86
150000003839 salts Chemical class 0.000 claims description 49
229910052739 hydrogen Inorganic materials 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 46
239000012453 solvate Substances 0.000 claims description 40
101800001982 Cholecystokinin Proteins 0.000 claims description 33
102100025841 Cholecystokinin Human genes 0.000 claims description 33
229940107137 cholecystokinin Drugs 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 32
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 32
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 26
150000002148 esters Chemical class 0.000 claims description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
238000011282 treatment Methods 0.000 claims description 21
108010089335 Cholecystokinin A Receptor Proteins 0.000 claims description 20
102100034927 Cholecystokinin receptor type A Human genes 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 17
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
230000008569 process Effects 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
238000005859 coupling reaction Methods 0.000 claims description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
ZYZXGWGQYNTGAU-UHFFFAOYSA-N dibenzyl oxalate Chemical compound C=1C=CC=CC=1COC(=O)C(=O)OCC1=CC=CC=C1 ZYZXGWGQYNTGAU-UHFFFAOYSA-N 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
KBHQUFPZXCNYKN-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=CC2=N1 KBHQUFPZXCNYKN-UHFFFAOYSA-N 0.000 claims description 6
JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 claims description 6
150000002641 lithium Chemical class 0.000 claims description 6
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 6
239000002243 precursor Substances 0.000 claims description 6
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical group 0.000 claims description 5
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 5
238000007127 saponification reaction Methods 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
208000008589 Obesity Diseases 0.000 claims description 4
230000002378 acidificating effect Effects 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
210000001035 gastrointestinal tract Anatomy 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
235000020824 obesity Nutrition 0.000 claims description 4
125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 4
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 3
208000012661 Dyskinesia Diseases 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 3
150000003901 oxalic acid esters Chemical class 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
238000007363 ring formation reaction Methods 0.000 claims description 3
230000000638 stimulation Effects 0.000 claims description 3
AGOJEFQTAMTJHV-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4,5-dimethylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(C)C(C)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC AGOJEFQTAMTJHV-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
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
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
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
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
238000010511 deprotection reaction Methods 0.000 claims description 2
LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical group C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
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 1
125000003277 amino group Chemical group 0.000 claims 1
239000000556 agonist Substances 0.000 abstract description 11
229940079593 drug Drugs 0.000 abstract description 3
125000006313 (C5-C8) alkyl group Chemical group 0.000 abstract 1
150000007979 thiazole derivatives Chemical class 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 172
239000000203 mixture Substances 0.000 description 170
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 142
239000000243 solution Substances 0.000 description 134
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 123
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 115
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 115
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 106
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 93
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
239000011734 sodium Substances 0.000 description 77
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
235000019439 ethyl acetate Nutrition 0.000 description 68
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 67
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 63
229910000041 hydrogen chloride Inorganic materials 0.000 description 63
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 60
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
239000000460 chlorine Substances 0.000 description 56
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 44
239000002244 precipitate Substances 0.000 description 43
238000003756 stirring Methods 0.000 description 42
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 41
239000000377 silicon dioxide Substances 0.000 description 41
239000012074 organic phase Substances 0.000 description 35
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
239000011541 reaction mixture Substances 0.000 description 34
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
239000002904 solvent Substances 0.000 description 32
235000019441 ethanol Nutrition 0.000 description 29
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 28
239000000284 extract Substances 0.000 description 28
239000000463 material Substances 0.000 description 28
238000010992 reflux Methods 0.000 description 28
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 26
239000000872 buffer Substances 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
229910052757 nitrogen Inorganic materials 0.000 description 19
229910052763 palladium Inorganic materials 0.000 description 18
238000001704 evaporation Methods 0.000 description 17
230000008020 evaporation Effects 0.000 description 17
239000000706 filtrate Substances 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
229910000104 sodium hydride Inorganic materials 0.000 description 17
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000012071 phase Substances 0.000 description 15
239000013078 crystal Substances 0.000 description 14
229920006395 saturated elastomer Polymers 0.000 description 14
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229910052708 sodium Inorganic materials 0.000 description 13
239000004480 active ingredient Substances 0.000 description 12
239000008346 aqueous phase Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 12
238000004062 sedimentation Methods 0.000 description 12
GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 description 12
230000000694 effects Effects 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 10
239000011575 calcium Substances 0.000 description 10
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
235000012631 food intake Nutrition 0.000 description 9
229940044601 receptor agonist Drugs 0.000 description 9
239000000018 receptor agonist Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
230000037406 food intake Effects 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
239000012429 reaction media Substances 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
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NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 1
229960000553 somatostatin Drugs 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
NQHGVLXTBYQHGX-UHFFFAOYSA-N tert-butyl 5-chloro-1-(2-ethoxy-2-oxoethyl)indole-2-carboxylate Chemical compound ClC1=CC=C2N(CC(=O)OCC)C(C(=O)OC(C)(C)C)=CC2=C1 NQHGVLXTBYQHGX-UHFFFAOYSA-N 0.000 description 1
LIQDWFIDLWBJAV-UHFFFAOYSA-N tert-butyl 5-chloro-1h-indole-2-carboxylate Chemical compound ClC1=CC=C2NC(C(=O)OC(C)(C)C)=CC2=C1 LIQDWFIDLWBJAV-UHFFFAOYSA-N 0.000 description 1
UYDXRONSKCHNAK-UHFFFAOYSA-N tert-butyl n-(2,4,5-trimethylphenyl)carbamate Chemical compound CC1=CC(C)=C(NC(=O)OC(C)(C)C)C=C1C UYDXRONSKCHNAK-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
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
BQBSTIXIDDRDHH-UHFFFAOYSA-N tert-butyl n-(6-methoxypyridin-3-yl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)(C)C)C=N1 BQBSTIXIDDRDHH-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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 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
229910052722 tritium Inorganic materials 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
229910052721 tungsten Inorganic materials 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

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)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Child & Adolescent Psychology (AREA)
Hematology (AREA)
Obesity (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

SK405-2000A 1997-09-19 1998-09-18 Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them SK4052000A3 (en)

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
SK4052000A3 true SK4052000A3 (en)	2001-03-12

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ID=26233812

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK405-2000A SK4052000A3 (en)	1997-09-19	1998-09-18	Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them

Country Status (27)

Country	Link
US (1)	US6380230B1 (id)
EP (1)	EP1017693A1 (id)
JP (1)	JP3456970B2 (id)
KR (1)	KR20010030629A (id)
CN (1)	CN1276790A (id)
AR (1)	AR013494A1 (id)
AU (1)	AU746707B2 (id)
BG (1)	BG104254A (id)
BR (1)	BR9812653A (id)
CA (1)	CA2304397A1 (id)
CO (1)	CO4970713A1 (id)
EA (1)	EA003093B1 (id)
EE (1)	EE200000168A (id)
HR (1)	HRP20000153A2 (id)
HU (1)	HUP0100225A3 (id)
ID (1)	ID25528A (id)
IL (1)	IL134961A (id)
IS (1)	IS5409A (id)
MY (1)	MY141444A (id)
NO (1)	NO314455B1 (id)
NZ (1)	NZ503339A (id)
PL (1)	PL339292A1 (id)
SK (1)	SK4052000A3 (id)
TR (1)	TR200001218T2 (id)
TW (1)	TW430664B (id)
UY (1)	UY25180A1 (id)
WO (1)	WO1999015525A1 (id)

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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 IL IL13496198A patent/IL134961A/en not_active IP Right Cessation
- 1998-09-18 HU HU0100225A patent/HUP0100225A3/hu unknown
- 1998-09-18 EE EEP200000168A patent/EE200000168A/xx unknown
- 1998-09-18 KR KR1020007002905A patent/KR20010030629A/ko not_active Ceased
- 1998-09-18 PL PL98339292A patent/PL339292A1/xx unknown
- 1998-09-18 CN CN98810341A patent/CN1276790A/zh active Pending
- 1998-09-18 SK SK405-2000A patent/SK4052000A3/sk unknown
- 1998-09-18 TW TW087115602A patent/TW430664B/zh active
- 1998-09-18 AU AU91705/98A patent/AU746707B2/en not_active Ceased
- 1998-09-18 EA EA200000334A patent/EA003093B1/ru not_active IP Right Cessation
- 1998-09-18 US US09/508,830 patent/US6380230B1/en not_active Expired - Fee Related
- 1998-09-18 ID IDW20000504A patent/ID25528A/id unknown
- 1998-09-18 CA CA002304397A patent/CA2304397A1/fr not_active Abandoned
- 1998-09-18 TR TR2000/01218T patent/TR200001218T2/xx unknown
- 1998-09-18 NZ NZ503339A patent/NZ503339A/en unknown
- 1998-09-18 HR HR20000153A patent/HRP20000153A2/hr not_active Application Discontinuation
- 1998-09-18 BR BR9812653-9A patent/BR9812653A/pt not_active IP Right Cessation
- 1998-09-18 EP EP98944024A patent/EP1017693A1/fr not_active Withdrawn
- 1998-09-18 JP JP2000512830A patent/JP3456970B2/ja not_active Expired - Fee Related
2000
- 2000-03-16 IS IS5409A patent/IS5409A/is unknown
- 2000-03-17 NO NO20001409A patent/NO314455B1/no not_active IP Right Cessation
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Also Published As

Publication number	Publication date
KR20010030629A (ko)	2001-04-16
AR013494A1 (es)	2000-12-27
US6380230B1 (en)	2002-04-30
HRP20000153A2 (en)	2001-04-30
PL339292A1 (en)	2000-12-04
NO20001409D0 (no)	2000-03-17
JP3456970B2 (ja)	2003-10-14
WO1999015525A1 (fr)	1999-04-01
HUP0100225A2 (hu)	2001-09-28
TR200001218T2 (tr)	2001-05-21
AU9170598A (en)	1999-04-12
UY25180A1 (es)	2001-06-29
EE200000168A (et)	2001-04-16
CA2304397A1 (fr)	1999-04-01
EA003093B1 (ru)	2002-12-26
MY141444A (en)	2010-04-30
CN1276790A (zh)	2000-12-13
BR9812653A (pt)	2000-08-22
EP1017693A1 (fr)	2000-07-12
NO20001409L (no)	2000-05-16
HUP0100225A3 (en)	2003-05-28
IL134961A (en)	2002-07-25
AU746707B2 (en)	2002-05-02
NO314455B1 (no)	2003-03-24
BG104254A (en)	2001-08-31
IS5409A (is)	2000-03-16
ID25528A (id)	2000-10-12
IL134961A0 (en)	2001-05-20
CO4970713A1 (es)	2000-11-07
JP2001517667A (ja)	2001-10-09
TW430664B (en)	2001-04-21
EA200000334A1 (ru)	2000-10-30
NZ503339A (en)	2002-03-28

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SK4052000A3 (en)	2001-03-12	Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them
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AU4690600A (en)	2000-12-05	Pyrazole carboxamides useful for the treatment of obesity and other disorders
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AU725530B2 (en)	2000-10-12	N-triazolyl-2-indolecarboxamides and their use as CCK-A agonists
JPH0755927B2 (ja)	1995-06-14	コレシストキニン（ｃｃｋ）拮抗剤
EP1725555B1 (en)	2010-10-06	Pyrrolopyridine-2-carboxylic acid hydrazides as inhibitors of glycogen phosphorylase
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WO2005085245A9 (en)	2006-01-05	Pyrrolopyridine-2-carboxylic acid hydrazides
CA2884708A1 (en)	2014-04-17	Indolines
CZ2000977A3 (cs)	2001-02-14	Karboxamidothiazolové deriváty, způsob jejich přípravy a farmaceutické prostředky s jejich obsahem
JP2001525398A (ja)	2001-12-11	選択的β３アドレナリン作動性アゴニスト
WO2005085194A2 (en)	2005-09-15	Indole-2-carboxylic acid hydrazides as glycogen phosphorylase inhibitors
MXPA00002767A (en)	2001-06-26	Carboxamidothiazole derivatives, preparation, pharmaceutical compositions containing them
JPS63174980A (ja)	1988-07-19	２，１−ベンゾチアゼピン−２，２−ジオキシド−５−カルボン酸誘導体
FR2768737A1 (fr)	1999-03-26	Derives de carboxamidothiazoles, leur preparation, les compositions pharmaceutiques en contenant
FR2777887A1 (fr)	1999-10-29	Derives de carboxamidothiazoles, leur preparation, les compositions pharmaceutiques en contenant
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