CA2270478A1 - N-(imidazolylbutyl) benzenesulphonamide derivatives, their preparation and therapeutic application - Google Patents

N-(imidazolylbutyl) benzenesulphonamide derivatives, their preparation and therapeutic application Download PDF

Info

Publication number: CA2270478A1
Authority: CA; Canada
Prior art keywords: group; formula; alkyl; compound; branched
Prior art date: 1996-11-22
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

Application number

CA002270478A

Other languages

English (en)

French (fr)

Inventor

Daniel Galtier

Gilbert Lassalle

Jean-Michel Altenburger

Valerie Martin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Synthelabo SA

Original Assignee

Individual

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.)

1996-11-22

Filing date

1997-11-19

Publication date

1998-05-28

1997-11-19 Application filed by Individual filed Critical Individual

1998-05-28 Publication of CA2270478A1 publication Critical patent/CA2270478A1/en

Status Abandoned legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims description 9
230000001225 therapeutic effect Effects 0.000 title description 4
LRQVXUYWQZZCJD-UHFFFAOYSA-N n-[4-(1h-imidazol-2-yl)butyl]benzenesulfonamide Chemical class C=1C=CC=CC=1S(=O)(=O)NCCCCC1=NC=CN1 LRQVXUYWQZZCJD-UHFFFAOYSA-N 0.000 title description 2
-1 1, 2, 3, 6-tetrahydropyridin-1-yl Chemical group 0.000 claims abstract description 119
150000001875 compounds Chemical class 0.000 claims abstract description 113
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 29
229910052757 nitrogen Chemical group 0.000 claims abstract description 18
229910052799 carbon Inorganic materials 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 35
125000006313 (C5-C8) alkyl group Chemical group 0.000 claims abstract 4
239000000203 mixture Substances 0.000 claims description 145
238000000034 method Methods 0.000 claims description 36
125000005843 halogen group Chemical group 0.000 claims description 30
238000010992 reflux Methods 0.000 claims description 17
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
125000001544 thienyl group Chemical group 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000003003 spiro group Chemical group 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 3
125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 claims 3
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
125000003275 alpha amino acid group Chemical group 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 42
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 30
229910052736 halogen Inorganic materials 0.000 abstract 2
150000002367 halogens Chemical class 0.000 abstract 2
239000003814 drug Substances 0.000 abstract 1
150000002431 hydrogen Chemical class 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 201
239000000243 solution Substances 0.000 description 194
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 177
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 159
239000000047 product Substances 0.000 description 110
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 78
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 76
239000011541 reaction mixture Substances 0.000 description 70
238000003756 stirring Methods 0.000 description 63
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 60
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 58
230000008018 melting Effects 0.000 description 56
238000002844 melting Methods 0.000 description 56
238000010828 elution Methods 0.000 description 55
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
238000004587 chromatography analysis Methods 0.000 description 52
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 45
239000000741 silica gel Substances 0.000 description 44
229910002027 silica gel Inorganic materials 0.000 description 44
229910052938 sodium sulfate Inorganic materials 0.000 description 38
235000011152 sodium sulphate Nutrition 0.000 description 38
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 26
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 25
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 24
239000000843 powder Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
239000002585 base Substances 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
239000012044 organic layer Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 14
235000010290 biphenyl Nutrition 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 11
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000004305 biphenyl Substances 0.000 description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
238000004108 freeze drying Methods 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
MLBYLEUJXUBIJJ-UHFFFAOYSA-M pent-4-ynoate Chemical compound [O-]C(=O)CCC#C MLBYLEUJXUBIJJ-UHFFFAOYSA-M 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
150000005333 N,N-diethylethanamines Chemical class 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 5
230000011514 reflex Effects 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
206010053567 Coagulopathies Diseases 0.000 description 4
208000028257 Joubert syndrome with oculorenal defect Diseases 0.000 description 4
230000035602 clotting Effects 0.000 description 4
238000000605 extraction Methods 0.000 description 4
PMHVKCGLPYCNDS-UHFFFAOYSA-N n-(2-chlorosulfonyl-6-thiophen-2-ylphenyl)propanimidoyl chloride Chemical compound C1=CC=C(S(Cl)(=O)=O)C(N=C(Cl)CC)=C1C1=CC=CS1 PMHVKCGLPYCNDS-UHFFFAOYSA-N 0.000 description 4
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 4
WOSZTROLFNNEIW-UHFFFAOYSA-N 1,4-diazepan-5-one;hydrochloride Chemical compound Cl.O=C1CCNCCN1 WOSZTROLFNNEIW-UHFFFAOYSA-N 0.000 description 3
NWIXTIYQWWLYML-UHFFFAOYSA-N 2-amino-3-thiophen-2-ylbenzenesulfonyl chloride Chemical compound C1=CC=C(S(Cl)(=O)=O)C(N)=C1C1=CC=CS1 NWIXTIYQWWLYML-UHFFFAOYSA-N 0.000 description 3
ZGMCPBIYPJEPPA-UHFFFAOYSA-N 3-cyclopentyl-2-(diacetylamino)benzenesulfonyl chloride Chemical compound C1=CC=C(S(Cl)(=O)=O)C(N(C(C)=O)C(=O)C)=C1C1CCCC1 ZGMCPBIYPJEPPA-UHFFFAOYSA-N 0.000 description 3
UQDYMLLPZKJOKZ-UHFFFAOYSA-N 4-cyclopropylpiperidine;hydrochloride Chemical compound Cl.C1CC1C1CCNCC1 UQDYMLLPZKJOKZ-UHFFFAOYSA-N 0.000 description 3
YDEDPBSOZYZWTH-UHFFFAOYSA-N 4-ethylpiperidine;hydrochloride Chemical compound Cl.CCC1CCNCC1 YDEDPBSOZYZWTH-UHFFFAOYSA-N 0.000 description 3
DMFJRRMECZFOKR-UHFFFAOYSA-N 4-methoxypiperidine;hydrochloride Chemical compound Cl.COC1CCNCC1 DMFJRRMECZFOKR-UHFFFAOYSA-N 0.000 description 3
ZCJOZBAPTJGKNC-UHFFFAOYSA-N 4-methyl-1,2,3,6-tetrahydropyridine;hydrochloride Chemical compound Cl.CC1=CCNCC1 ZCJOZBAPTJGKNC-UHFFFAOYSA-N 0.000 description 3
XGMSENVPQPNOHF-UHFFFAOYSA-N 4-methylidenepiperidine;hydrochloride Chemical compound Cl.C=C1CCNCC1 XGMSENVPQPNOHF-UHFFFAOYSA-N 0.000 description 3
VXAYZGLCMOYQFU-UHFFFAOYSA-N 4-methylsulfanylpiperidine;hydrochloride Chemical compound Cl.CSC1CCNCC1 VXAYZGLCMOYQFU-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
KDUFGJODEHTWTC-UHFFFAOYSA-N Cl.NC(C(=O)N1CCNC(CC1)=O)CCCC=1N=CN(C1C)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound Cl.NC(C(=O)N1CCNC(CC1)=O)CCCC=1N=CN(C1C)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 KDUFGJODEHTWTC-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
108090000190 Thrombin Proteins 0.000 description 3
230000002785 anti-thrombosis Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229940113088 dimethylacetamide Drugs 0.000 description 3
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
WYLHQTSQMKMTGM-UHFFFAOYSA-N n-cyclopentylformamide Chemical compound O=CNC1CCCC1 WYLHQTSQMKMTGM-UHFFFAOYSA-N 0.000 description 3
DTMTYKUCZFYAEU-UHFFFAOYSA-N n-methylcyclopentanamine;hydrochloride Chemical compound Cl.CNC1CCCC1 DTMTYKUCZFYAEU-UHFFFAOYSA-N 0.000 description 3
HMDGPWDTQHTOKU-UHFFFAOYSA-N n-methylpyrrolidin-1-amine;hydrochloride Chemical compound Cl.CNN1CCCC1 HMDGPWDTQHTOKU-UHFFFAOYSA-N 0.000 description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
150000003385 sodium Chemical class 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 3
ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 3
229960004072 thrombin Drugs 0.000 description 3
229960003766 thrombin (human) Drugs 0.000 description 3
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
AMKHAJIFPHJYMH-ZETCQYMHSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-ynoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC#C AMKHAJIFPHJYMH-ZETCQYMHSA-N 0.000 description 2
DKNOPZCYIDBMNY-UHFFFAOYSA-N 1-benzyl-1,4-diazepan-5-one Chemical compound C1CNC(=O)CCN1CC1=CC=CC=C1 DKNOPZCYIDBMNY-UHFFFAOYSA-N 0.000 description 2
PRDDIAGFPPJIQH-UHFFFAOYSA-N 2-[di(propanoyl)amino]-3-phenylbenzenesulfonyl chloride Chemical compound C1=CC=C(S(Cl)(=O)=O)C(N(C(=O)CC)C(=O)CC)=C1C1=CC=CC=C1 PRDDIAGFPPJIQH-UHFFFAOYSA-N 0.000 description 2
FVBHVBCCQLTLAJ-UHFFFAOYSA-N 3-cyclopentyl-2-(diacetylamino)benzenesulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C(N(C(C)=O)C(=O)C)=C1C1CCCC1 FVBHVBCCQLTLAJ-UHFFFAOYSA-N 0.000 description 2
WVIJOUFQYFUXAY-UHFFFAOYSA-N 4-(difluoromethylidene)piperidine Chemical compound FC(F)=C1CCNCC1 WVIJOUFQYFUXAY-UHFFFAOYSA-N 0.000 description 2
RGXCXVJYDBNGMU-UHFFFAOYSA-N 4-(difluoromethylidene)piperidine;hydrochloride Chemical compound Cl.FC(F)=C1CCNCC1 RGXCXVJYDBNGMU-UHFFFAOYSA-N 0.000 description 2
NCNVPWCTEBODPS-UHFFFAOYSA-N 4-cyclopropylpiperidine Chemical compound C1CC1C1CCNCC1 NCNVPWCTEBODPS-UHFFFAOYSA-N 0.000 description 2
WLQVBFDHWAVUJN-UHFFFAOYSA-N 4-cyclopropylpyridine Chemical compound C1CC1C1=CC=NC=C1 WLQVBFDHWAVUJN-UHFFFAOYSA-N 0.000 description 2
WEGKNBGCGIISAT-UHFFFAOYSA-N 5-ethyl-4-iodo-1-(4-methylphenyl)sulfonylimidazole Chemical compound CCC1=C(I)N=CN1S(=O)(=O)C1=CC=C(C)C=C1 WEGKNBGCGIISAT-UHFFFAOYSA-N 0.000 description 2
RQFXCHOQVKBBOK-UHFFFAOYSA-N 5-ethyl-4-iodo-1h-imidazole Chemical compound CCC=1NC=NC=1I RQFXCHOQVKBBOK-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
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SRUCGVWHSWAEOZ-XIFFEERXSA-N [(2S)-1-(4-ethylpiperidin-1-yl)-5-(5-ethyl-1-tritylimidazol-4-yl)-1-oxopentan-2-yl]carbamic acid Chemical compound CCC1CCN(CC1)C(=O)[C@H](CCCC2=C(N(C=N2)C(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)CC)NC(=O)O SRUCGVWHSWAEOZ-XIFFEERXSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000001413 amino acids Chemical group 0.000 description 1
DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000002429 anti-coagulating effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
GRCDJFHYVYUNHM-UHFFFAOYSA-N bromodifluoromethane Chemical compound FC(F)Br GRCDJFHYVYUNHM-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003593 chromogenic compound Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
DRAOLRRXKAPIQB-UHFFFAOYSA-N cyclopentylmethyl carbamate Chemical compound NC(=O)OCC1CCCC1 DRAOLRRXKAPIQB-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
KTVYGDJRKCXTRA-UHFFFAOYSA-N hydron;pyrrolidin-1-amine;chloride Chemical compound Cl.NN1CCCC1 KTVYGDJRKCXTRA-UHFFFAOYSA-N 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
PKJFDRBACJCRQM-UHFFFAOYSA-N methyl N-pyrrolidin-1-ylcarbamate Chemical compound COC(=O)NN1CCCC1 PKJFDRBACJCRQM-UHFFFAOYSA-N 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
PNUKVLQKDZRPEO-UHFFFAOYSA-N n-(1-oxo-1-piperidin-1-ylpentan-2-yl)benzenesulfonamide Chemical class C1CCCCN1C(=O)C(CCC)NS(=O)(=O)C1=CC=CC=C1 PNUKVLQKDZRPEO-UHFFFAOYSA-N 0.000 description 1
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
WIYDEVSKVYFPPV-UHFFFAOYSA-N pentanamide;hydrochloride Chemical compound Cl.CCCCC(N)=O WIYDEVSKVYFPPV-UHFFFAOYSA-N 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
DZEKXNZRIOWTHG-UHFFFAOYSA-N tert-butyl 4-ethylpiperidine-1-carboxylate Chemical compound CCC1CCN(C(=O)OC(C)(C)C)CC1 DZEKXNZRIOWTHG-UHFFFAOYSA-N 0.000 description 1
WATASAJREKAPOT-UHFFFAOYSA-N tert-butyl 4-methoxypiperidine-1-carboxylate Chemical compound COC1CCN(C(=O)OC(C)(C)C)CC1 WATASAJREKAPOT-UHFFFAOYSA-N 0.000 description 1
UPUZWYFQRARJNC-UHFFFAOYSA-N tert-butyl 4-methyl-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC1=CCN(C(=O)OC(C)(C)C)CC1 UPUZWYFQRARJNC-UHFFFAOYSA-N 0.000 description 1
RBSTYDJFVDTJPH-UHFFFAOYSA-N tert-butyl 4-methylsulfanylpiperidine-1-carboxylate Chemical compound CSC1CCN(C(=O)OC(C)(C)C)CC1 RBSTYDJFVDTJPH-UHFFFAOYSA-N 0.000 description 1
HZSZSJPYBMQMTN-DHUJRADRSA-N tert-butyl N-[(2S)-1-(4-methyl-3,6-dihydro-2H-pyridin-1-yl)-5-(5-methyl-1-tritylimidazol-4-yl)-1-oxopentan-2-yl]carbamate Chemical compound CC1=C(N=CN1C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)CCC[C@@H](C(=O)N1CCC(=CC1)C)NC(OC(C)(C)C)=O HZSZSJPYBMQMTN-DHUJRADRSA-N 0.000 description 1
MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
XKXIQBVKMABYQJ-UHFFFAOYSA-N tert-butyl hydrogen carbonate Chemical compound CC(C)(C)OC(O)=O XKXIQBVKMABYQJ-UHFFFAOYSA-N 0.000 description 1
KWALSAYHFOCNEE-UHFFFAOYSA-N tert-butyl n-(cyclopentylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCCC1 KWALSAYHFOCNEE-UHFFFAOYSA-N 0.000 description 1
RQJUQLAVWRKKRG-UHFFFAOYSA-N tert-butyl n-methyl-n-pyrrolidin-1-ylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)N1CCCC1 RQJUQLAVWRKKRG-UHFFFAOYSA-N 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
229940038773 trisodium citrate Drugs 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/68—Halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Hematology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA002270478A 1996-11-22 1997-11-19 N-(imidazolylbutyl) benzenesulphonamide derivatives, their preparation and therapeutic application Abandoned CA2270478A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR9614309A FR2756285B1 (fr)	1996-11-22	1996-11-22	Derives de n-(imidazolylbutyle)benzenesulfonamide, leur preparation et leur application en therapeutique
FR96/14309		1996-11-22
PCT/FR1997/002079 WO1998022443A1 (fr)	1996-11-22	1997-11-19	Derives de n-(imidazolylbutyle) benzenesulfonamide ayant une activite antithrombotique

Publications (1)

Publication Number	Publication Date
CA2270478A1 true CA2270478A1 (en)	1998-05-28

Family

ID=9497920

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002270478A Abandoned CA2270478A1 (en)	1996-11-22	1997-11-19	N-(imidazolylbutyl) benzenesulphonamide derivatives, their preparation and therapeutic application

Country Status (20)

Country	Link
EP (1)	EP0946517A1 (no)
JP (1)	JP2001504128A (no)
KR (1)	KR20000069063A (no)
CN (1)	CN1238765A (no)
AR (1)	AR009627A1 (no)
AU (1)	AU5226498A (no)
BG (1)	BG103414A (no)
BR (1)	BR9713291A (no)
CA (1)	CA2270478A1 (no)
CO (1)	CO4910158A1 (no)
CZ (1)	CZ178299A3 (no)
EE (1)	EE9900201A (no)
FR (1)	FR2756285B1 (no)
HU (1)	HUP9904599A2 (no)
IL (1)	IL129546A0 (no)
NO (1)	NO992436L (no)
SK (1)	SK66799A3 (no)
TR (1)	TR199901143T2 (no)
WO (1)	WO1998022443A1 (no)
ZA (1)	ZA9710515B (no)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2783521B1 (fr) *	1998-09-18	2002-04-26	Synthelabo	Derives de n-(arginyl) benzenesulfonamide, leur preparation et leur application en therapeutique
FR2806722B1 (fr) *	2000-03-23	2002-05-17	Sanofi Synthelabo	Derives de n-(heterocyclylbutyl) benzene-ou pyridine sulfonamide, leur preparation et leur application en therapeutique
JP6698643B2 (ja)	2014-09-29	2020-05-27	セリックスバイオプライヴェートリミテッドＣｅｌｌｉｘＢｉｏＰｒｉｖａｔｅＬｉｍｉｔｅｄ	多発性硬化症の治療のための組成物及び方法
CN118459425A (zh) *	2024-04-29	2024-08-09	南通华祥医药科技有限公司	一种吡咯烷-1-胺-二盐酸盐的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2689130B1 (fr) *	1992-03-30	1994-05-27	Synthelabo	Derives de 1-[2 (arylsulfonylamino)ethyl-1-oxo] piperidine, leur preparation et leur application en therapeutique.
FR2710066B1 (fr) *	1993-09-14	1995-10-20	Synthelabo	Dérivés de 1-[2-amino-5-[1-(triphénylméthyl-1H-imidazol-4-yl]-1-oxopentyl]piperidine, leur préparation et leur utilisation comme intermédiaires de synthèse.
FR2727410B1 (fr) *	1994-11-25	1996-12-20	Synthelabo	Chlorures de sulfonyles, leur preparation et leur utilisation comme intermediaires de synthese
FR2728570B1 (fr) *	1994-12-23	1997-04-11	Synthelabo	Derives de 1-oxo-2-(phenylsulfonylamino)pentylpiperidine, leur preparation et leur application en therapeutique
DE19548797A1 (de) *	1995-12-27	1997-07-03	Thomae Gmbh Dr K	Substituierte 2-Amino-imidazole, ihre Herstellung und ihre Verwendung als Arzneimittel

1996
- 1996-11-22 FR FR9614309A patent/FR2756285B1/fr not_active Expired - Fee Related
1997
- 1997-11-19 EE EEP199900201A patent/EE9900201A/xx unknown
- 1997-11-19 AU AU52264/98A patent/AU5226498A/en not_active Abandoned
- 1997-11-19 CA CA002270478A patent/CA2270478A1/en not_active Abandoned
- 1997-11-19 CN CN97199986A patent/CN1238765A/zh active Pending
- 1997-11-19 JP JP52328498A patent/JP2001504128A/ja active Pending
- 1997-11-19 BR BR9713291-8A patent/BR9713291A/pt not_active Application Discontinuation
- 1997-11-19 KR KR1019997004485A patent/KR20000069063A/ko not_active Withdrawn
- 1997-11-19 TR TR1999/01143T patent/TR199901143T2/xx unknown
- 1997-11-19 HU HU9904599A patent/HUP9904599A2/hu unknown
- 1997-11-19 SK SK667-99A patent/SK66799A3/sk unknown
- 1997-11-19 IL IL12954697A patent/IL129546A0/xx unknown
- 1997-11-19 CZ CZ991782A patent/CZ178299A3/cs unknown
- 1997-11-19 EP EP97947089A patent/EP0946517A1/fr not_active Ceased
- 1997-11-19 WO PCT/FR1997/002079 patent/WO1998022443A1/fr not_active Application Discontinuation
- 1997-11-19 CO CO97067574A patent/CO4910158A1/es unknown
- 1997-11-21 ZA ZA9710515A patent/ZA9710515B/xx unknown
- 1997-11-21 AR ARP970105455A patent/AR009627A1/es unknown
1999
- 1999-05-19 BG BG103414A patent/BG103414A/xx unknown
- 1999-05-20 NO NO992436A patent/NO992436L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
EE9900201A (et)	1999-12-15
ZA9710515B (en)	1998-06-10
SK66799A3 (en)	2000-02-14
BR9713291A (pt)	1999-10-26
HUP9904599A2 (hu)	2000-06-28
NO992436D0 (no)	1999-05-20
CZ178299A3 (cs)	1999-08-11
IL129546A0 (en)	2000-02-29
CN1238765A (zh)	1999-12-15
BG103414A (en)	2000-01-31
CO4910158A1 (es)	2000-04-24
WO1998022443A1 (fr)	1998-05-28
AU5226498A (en)	1998-06-10
AR009627A1 (es)	2000-04-26
FR2756285B1 (fr)	1998-12-18
NO992436L (no)	1999-07-22
TR199901143T2 (xx)	1999-08-23
EP0946517A1 (fr)	1999-10-06
KR20000069063A (ko)	2000-11-25
FR2756285A1 (fr)	1998-05-29
JP2001504128A (ja)	2001-03-27

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2001-11-19	FZDE	Discontinued