JP2001504128A - Ｎ―（イミダゾリルブチル）ベンゼンスルホンアミド誘導体、その製造法およびその治療上の応用 - Google Patents

Ｎ―（イミダゾリルブチル）ベンゼンスルホンアミド誘導体、その製造法およびその治療上の応用

Info

Publication number: JP2001504128A
Authority: JP; Japan
Prior art keywords: group; alkyl; compound; formula; 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.): Pending

Application number

JP52328498A

Other languages

English (en)

Japanese (ja)

Inventor

ジャン―ミッシェルアルタンビュルジェ

ジルベールラサール

ヴァレリマルタン

ダニエルガルティエ

Original Assignee

サンテラボ

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

2001-03-27

1997-11-19 Application filed by サンテラボ filed Critical サンテラボ

2001-03-27 Publication of JP2001504128A publication Critical patent/JP2001504128A/ja

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 8
230000001225 therapeutic effect Effects 0.000 title description 6
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 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 166
-1 1,2,3,6-tetra-hydropyridin-1-yl group Chemical group 0.000 claims abstract description 164
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 50
125000005843 halogen group Chemical group 0.000 claims abstract description 48
229910052757 nitrogen Chemical group 0.000 claims abstract description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
229910052799 carbon Inorganic materials 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
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 8
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 178
239000000203 mixture Substances 0.000 claims description 130
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
238000010992 reflux Methods 0.000 claims description 23
125000003545 alkoxy group Chemical group 0.000 claims description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 18
230000002378 acidificating effect Effects 0.000 claims description 15
125000001544 thienyl group Chemical group 0.000 claims description 15
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 11
125000003003 spiro group Chemical group 0.000 claims description 9
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 8
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
150000002825 nitriles Chemical class 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
125000002541 furyl group Chemical group 0.000 claims description 7
125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
150000001413 amino acids Chemical class 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 claims description 3
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 26
229910052736 halogen Inorganic materials 0.000 abstract description 4
150000002367 halogens Chemical class 0.000 abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 181
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 170
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 156
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 128
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 123
239000000047 product Substances 0.000 description 111
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 79
239000011541 reaction mixture Substances 0.000 description 67
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 65
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 53
239000012141 concentrate Substances 0.000 description 51
238000002844 melting Methods 0.000 description 50
230000008018 melting Effects 0.000 description 50
238000003756 stirring Methods 0.000 description 46
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 41
238000004587 chromatography analysis Methods 0.000 description 41
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 39
238000000034 method Methods 0.000 description 36
229910052938 sodium sulfate Inorganic materials 0.000 description 35
235000011152 sodium sulphate Nutrition 0.000 description 35
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 34
239000003921 oil Substances 0.000 description 34
239000000741 silica gel Substances 0.000 description 34
229910002027 silica gel Inorganic materials 0.000 description 34
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 33
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 31
239000012074 organic phase Substances 0.000 description 31
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
239000000843 powder Substances 0.000 description 22
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 22
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
235000010290 biphenyl Nutrition 0.000 description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
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 10
239000000706 filtrate Substances 0.000 description 10
VHWJSJBTUWUEAL-UHFFFAOYSA-N propanamide;hydrochloride Chemical compound Cl.CCC(N)=O VHWJSJBTUWUEAL-UHFFFAOYSA-N 0.000 description 10
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 9
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229910052776 Thorium Inorganic materials 0.000 description 9
125000004429 atom Chemical group 0.000 description 9
230000002140 halogenating effect Effects 0.000 description 9
229910052943 magnesium sulfate Inorganic materials 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 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
101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 8
101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 8
102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 8
238000004108 freeze drying Methods 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
239000000284 extract Substances 0.000 description 7
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
125000004356 hydroxy functional group Chemical group O* 0.000 description 6
238000000746 purification Methods 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
241001024304 Mino Species 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
229910052744 lithium Inorganic materials 0.000 description 5
239000011259 mixed solution Substances 0.000 description 5
GPYYAXKOVKZFPY-CZCBIWLKSA-N (2S)-2-amino-N-methyl-5-(5-methyl-1-tritylimidazol-4-yl)-N-pyrrolidin-1-ylpentanamide hydrochloride Chemical compound CC1=C(N=CN1C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)CCC[C@@H](C(=O)N(C)N5CCCC5)N.Cl GPYYAXKOVKZFPY-CZCBIWLKSA-N 0.000 description 4
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
150000005333 N,N-diethylethanamines Chemical class 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 4
GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 3
WOSZTROLFNNEIW-UHFFFAOYSA-N 1,4-diazepan-5-one;hydrochloride Chemical compound Cl.O=C1CCNCCN1 WOSZTROLFNNEIW-UHFFFAOYSA-N 0.000 description 3
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
RGXCXVJYDBNGMU-UHFFFAOYSA-N 4-(difluoromethylidene)piperidine;hydrochloride Chemical compound Cl.FC(F)=C1CCNCC1 RGXCXVJYDBNGMU-UHFFFAOYSA-N 0.000 description 3
NCNVPWCTEBODPS-UHFFFAOYSA-N 4-cyclopropylpiperidine Chemical compound C1CC1C1CCNCC1 NCNVPWCTEBODPS-UHFFFAOYSA-N 0.000 description 3
UQDYMLLPZKJOKZ-UHFFFAOYSA-N 4-cyclopropylpiperidine;hydrochloride Chemical compound Cl.C1CC1C1CCNCC1 UQDYMLLPZKJOKZ-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
NKIFUNYRSQUCGF-YNMZEGNTSA-N CC1=C(N=CN1C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)CCC[C@@H](C(=O)N5CCC(=C)CC5)N.Cl Chemical compound CC1=C(N=CN1C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)CCC[C@@H](C(=O)N5CCC(=C)CC5)N.Cl NKIFUNYRSQUCGF-YNMZEGNTSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 description 3
238000010828 elution Methods 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
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
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
229960003766 thrombin (human) Drugs 0.000 description 3
CCQVJGXOSBNFLM-YTTGMZPUSA-N (2S)-2-amino-1-(4-ethylpiperidin-1-yl)-5-(5-methyl-1-tritylimidazol-4-yl)pentan-1-one Chemical compound C1CC(CC)CCN1C(=O)[C@@H](N)CCCC1=C(C)N(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=N1 CCQVJGXOSBNFLM-YTTGMZPUSA-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
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 2
FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 2
RDRQUUWCJTYHCT-UHFFFAOYSA-N 4-(trifluoromethyl)piperidine Chemical compound FC(F)(F)C1CCNCC1 RDRQUUWCJTYHCT-UHFFFAOYSA-N 0.000 description 2
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229910002651 NO3 Inorganic materials 0.000 description 1
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208000007536 Thrombosis Diseases 0.000 description 1
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125000003368 amide group 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
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238000001035 drying Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
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GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
KTVYGDJRKCXTRA-UHFFFAOYSA-N hydron;pyrrolidin-1-amine;chloride Chemical compound Cl.NN1CCCC1 KTVYGDJRKCXTRA-UHFFFAOYSA-N 0.000 description 1
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238000002329 infrared spectrum Methods 0.000 description 1
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239000002198 insoluble material Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
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229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
239000002502 liposome Substances 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
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
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238000004452 microanalysis Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
QRNLNOWVUPVUQK-UHFFFAOYSA-N n-[4-bromo-2-chlorosulfonyl-6-(3-nitrophenyl)phenyl]propanimidoyl chloride Chemical compound C1=C(Br)C=C(S(Cl)(=O)=O)C(N=C(Cl)CC)=C1C1=CC=CC([N+]([O-])=O)=C1 QRNLNOWVUPVUQK-UHFFFAOYSA-N 0.000 description 1
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238000007911 parenteral administration Methods 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
230000000144 pharmacologic effect Effects 0.000 description 1
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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
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000001294 propane Substances 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
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
229940124530 sulfonamide Drugs 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
DDTCBHPOGWRJIZ-UHFFFAOYSA-N tert-butyl 4-cyclopropylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CC1 DDTCBHPOGWRJIZ-UHFFFAOYSA-N 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
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 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
MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-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
239000003868 thrombin inhibitor Substances 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
125000003944 tolyl group Chemical group 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
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
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
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Hematology (AREA)
Pharmacology & Pharmacy (AREA)
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Animal Behavior & Ethology (AREA)
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Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP52328498A 1996-11-22 1997-11-19 Ｎ―（イミダゾリルブチル）ベンゼンスルホンアミド誘導体、その製造法およびその治療上の応用 Pending JP2001504128A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR96/14309		1996-11-22
FR9614309A FR2756285B1 (fr)	1996-11-22	1996-11-22	Derives de n-(imidazolylbutyle)benzenesulfonamide, leur preparation et leur application en therapeutique
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
JP2001504128A true JP2001504128A (ja)	2001-03-27

Family

ID=9497920

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP52328498A Pending JP2001504128A (ja)	1996-11-22	1997-11-19	Ｎ―（イミダゾリルブチル）ベンゼンスルホンアミド誘導体、その製造法およびその治療上の応用

Country Status (20)

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

Families Citing this family (3)

* 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
ES2799309T3 (es)	2014-09-29	2020-12-16	Cellix Bio Private Ltd	Compuestos y composiciones para el tratamiento de esclerosis múltiple

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 CA CA002270478A patent/CA2270478A1/fr not_active Abandoned
- 1997-11-19 EE EEP199900201A patent/EE9900201A/xx unknown
- 1997-11-19 IL IL12954697A patent/IL129546A0/xx unknown
- 1997-11-19 JP JP52328498A patent/JP2001504128A/ja active Pending
- 1997-11-19 KR KR1019997004485A patent/KR20000069063A/ko not_active Application Discontinuation
- 1997-11-19 CN CN97199986A patent/CN1238765A/zh active Pending
- 1997-11-19 CZ CZ991782A patent/CZ178299A3/cs unknown
- 1997-11-19 WO PCT/FR1997/002079 patent/WO1998022443A1/fr not_active Application Discontinuation
- 1997-11-19 AU AU52264/98A patent/AU5226498A/en not_active Abandoned
- 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 EP EP97947089A patent/EP0946517A1/fr not_active Ceased
- 1997-11-19 BR BR9713291-8A patent/BR9713291A/pt 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
NO992436L (no)	1999-07-22
FR2756285B1 (fr)	1998-12-18
WO1998022443A1 (fr)	1998-05-28
NO992436D0 (no)	1999-05-20
IL129546A0 (en)	2000-02-29
EP0946517A1 (fr)	1999-10-06
BR9713291A (pt)	1999-10-26
AU5226498A (en)	1998-06-10
KR20000069063A (ko)	2000-11-25
CN1238765A (zh)	1999-12-15
CZ178299A3 (cs)	1999-08-11
ZA9710515B (en)	1998-06-10
BG103414A (en)	2000-01-31
TR199901143T2 (xx)	1999-08-23
EE9900201A (et)	1999-12-15
SK66799A3 (en)	2000-02-14
HUP9904599A2 (hu)	2000-06-28
AR009627A1 (es)	2000-04-26
CO4910158A1 (es)	2000-04-24
CA2270478A1 (fr)	1998-05-28
FR2756285A1 (fr)	1998-05-29

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