BG106107A - Заместени амиди на фенилциклохексанкарбонова киселина с действие, инхибиращо усвояването на аденозин - Google Patents

Заместени амиди на фенилциклохексанкарбонова киселина с действие, инхибиращо усвояването на аденозин Download PDF

Info

Publication number: BG106107A
Authority: BG; Bulgaria
Prior art keywords: alkyl; compounds; general formula; radical; optionally
Prior art date: 1999-05-29

Application number

BG106107A

Other languages

Bulgarian (bg)

English (en)

Inventor

Wolf - Dietrich FREUND

Stephen Lensky

Stephan Mueller

Holger Paulsen

Joerg Keldenich

Ervin Horvath

Joachim Schuhmacher

Original Assignee

Bayer Aktiengesellschaft

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.)

1999-05-29

Filing date

2001-11-13

Publication date

2002-05-31

2001-11-13 Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft

2002-05-31 Publication of BG106107A publication Critical patent/BG106107A/bg

Links

OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 title abstract description 40
239000002126 C01EB10 - Adenosine Substances 0.000 title abstract description 20
229960005305 adenosine Drugs 0.000 title abstract description 20
RKNUEXASLVLVSL-UHFFFAOYSA-N 1-phenylcyclohexane-1-carboxamide Chemical class C=1C=CC=CC=1C1(C(=O)N)CCCCC1 RKNUEXASLVLVSL-UHFFFAOYSA-N 0.000 title abstract description 3
230000002401 inhibitory effect Effects 0.000 title description 5
238000000034 method Methods 0.000 claims abstract description 29
239000003814 drug Substances 0.000 claims abstract description 8
230000000302 ischemic effect Effects 0.000 claims abstract description 4
208000014644 Brain disease Diseases 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 94
-1 hydroxy, carboxyl Chemical group 0.000 claims description 73
229910052739 hydrogen Inorganic materials 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 30
229910052717 sulfur Inorganic materials 0.000 claims description 30
125000004434 sulfur atom Chemical group 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 27
229910052760 oxygen Inorganic materials 0.000 claims description 26
239000001301 oxygen Substances 0.000 claims description 26
125000000623 heterocyclic group Chemical group 0.000 claims description 25
125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 24
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 20
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
150000007513 acids Chemical class 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
230000007062 hydrolysis Effects 0.000 claims description 10
238000006460 hydrolysis reaction Methods 0.000 claims description 10
125000002883 imidazolyl group Chemical group 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 9
230000008569 process Effects 0.000 claims description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
239000012442 inert solvent Substances 0.000 claims description 8
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
150000001735 carboxylic acids Chemical class 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
208000029028 brain injury Diseases 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
208000006011 Stroke Diseases 0.000 claims description 5
238000007796 conventional method Methods 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
206010063837 Reperfusion injury Diseases 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
150000001408 amides Chemical class 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 110
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
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 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 11
238000005160 1H NMR spectroscopy Methods 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
239000000126 substance Substances 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
229910052783 alkali metal Inorganic materials 0.000 description 8
150000001340 alkali metals Chemical class 0.000 description 8
239000000047 product Substances 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000004649 carbonic acid derivatives Chemical class 0.000 description 6
150000004679 hydroxides Chemical class 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 description 5
101800004637 Communis Proteins 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
208000005189 Embolism Diseases 0.000 description 5
208000002667 Subdural Hematoma Diseases 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
238000001990 intravenous administration Methods 0.000 description 5
210000000225 synapse Anatomy 0.000 description 5
238000012360 testing method Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
206010061216 Infarction Diseases 0.000 description 4
206010030113 Oedema Diseases 0.000 description 4
241000700159 Rattus Species 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000004913 activation Effects 0.000 description 4
239000003513 alkali Substances 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
239000000872 buffer Substances 0.000 description 4
210000003710 cerebral cortex Anatomy 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
239000012973 diazabicyclooctane Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 4
230000007574 infarction Effects 0.000 description 4
208000028867 ischemia Diseases 0.000 description 4
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 4
239000000843 powder Substances 0.000 description 4
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 3
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 description 3
206010019280 Heart failures Diseases 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
DYCJFJRCWPVDHY-LSCFUAHRSA-N NBMPR Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(SCC=3C=CC(=CC=3)[N+]([O-])=O)=C2N=C1 DYCJFJRCWPVDHY-LSCFUAHRSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000009471 action Effects 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 3
229910001863 barium hydroxide Inorganic materials 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
229910000024 caesium carbonate Inorganic materials 0.000 description 3
206010008118 cerebral infarction Diseases 0.000 description 3
230000008859 change Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
238000001802 infusion Methods 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
230000003902 lesion Effects 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 description 3
230000000324 neuroprotective effect Effects 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000007170 pathology Effects 0.000 description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
230000002980 postoperative effect Effects 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
230000010410 reperfusion Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
RATGULGAYZCBBP-QWHCGFSZSA-N (1r,2r)-2-(4-methylphenyl)cyclohexane-1-carboxylic acid Chemical compound C1=CC(C)=CC=C1[C@H]1[C@H](C(O)=O)CCCC1 RATGULGAYZCBBP-QWHCGFSZSA-N 0.000 description 2
BFCDFTHTSVTWOG-PXNSSMCTSA-N (1r,2s)-2-(octylamino)-1-(4-propan-2-ylsulfanylphenyl)propan-1-ol Chemical compound CCCCCCCCN[C@@H](C)[C@H](O)C1=CC=C(SC(C)C)C=C1 BFCDFTHTSVTWOG-PXNSSMCTSA-N 0.000 description 2
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PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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235000015497 potassium bicarbonate Nutrition 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000003518 presynaptic effect Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000012545 processing Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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238000007127 saponification reaction Methods 0.000 description 1
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150000003335 secondary amines Chemical group 0.000 description 1
208000013220 shortness of breath Diseases 0.000 description 1
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208000019116 sleep disease Diseases 0.000 description 1
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YVPKVCGEXFEMMH-VQTJNVASSA-N tert-butyl (1r,2r)-2-[4-[(2-chlorobenzimidazol-1-yl)methyl]phenyl]cyclohexane-1-carboxylate Chemical compound CC(C)(C)OC(=O)[C@@H]1CCCC[C@H]1C(C=C1)=CC=C1CN1C2=CC=CC=C2N=C1Cl YVPKVCGEXFEMMH-VQTJNVASSA-N 0.000 description 1
UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
125000004570 thiomorpholin-3-yl group Chemical group N1C(CSCC1)* 0.000 description 1
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230000002588 toxic effect Effects 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000008733 trauma Effects 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000002792 vascular Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
- 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
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- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Ophthalmology & Optometry (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Anesthesiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pulmonology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

BG106107A 1999-05-29 2001-11-13 Заместени амиди на фенилциклохексанкарбонова киселина с действие, инхибиращо усвояването на аденозин BG106107A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19924818A DE19924818A1 (de)	1999-05-29	1999-05-29	Substituierte Phenylcyclohexancarbonsäureamide
PCT/EP2000/004417 WO2000073275A1 (de)	1999-05-29	2000-05-16	Substituierte phenylcyclohexancarbonsäureamide mit adenosinaufnahme-hemmender wirkung

Publications (1)

Publication Number	Publication Date
BG106107A true BG106107A (bg)	2002-05-31

Family

ID=7909712

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG106107A BG106107A (bg)	1999-05-29	2001-11-13	Заместени амиди на фенилциклохексанкарбонова киселина с действие, инхибиращо усвояването на аденозин

Country Status (36)

Country	Link
US (2)	US6716849B1 (es)
EP (1)	EP1185516B1 (es)
JP (1)	JP2003500475A (es)
KR (1)	KR20020003397A (es)
CN (1)	CN1200932C (es)
AR (1)	AR024100A1 (es)
AT (1)	ATE238997T1 (es)
AU (1)	AU765752B2 (es)
BG (1)	BG106107A (es)
BR (1)	BR0011061A (es)
CA (1)	CA2375186A1 (es)
CZ (1)	CZ20014288A3 (es)
DE (2)	DE19924818A1 (es)
DK (1)	DK1185516T3 (es)
EE (1)	EE200100634A (es)
ES (1)	ES2197870T3 (es)
GT (1)	GT200000083A (es)
HK (1)	HK1048810A1 (es)
HN (1)	HN2000000072A (es)
HR (1)	HRP20010955A2 (es)
HU (1)	HUP0201350A3 (es)
IL (1)	IL146392A0 (es)
MA (1)	MA25414A1 (es)
MX (1)	MXPA01012241A (es)
MY (1)	MY122576A (es)
NO (1)	NO20015810L (es)
PE (1)	PE20010167A1 (es)
PL (1)	PL352101A1 (es)
PT (1)	PT1185516E (es)
RU (1)	RU2246490C9 (es)
SI (1)	SI1185516T1 (es)
SK (1)	SK17052001A3 (es)
SV (1)	SV2004000087A (es)
UA (1)	UA73126C2 (es)
WO (1)	WO2000073275A1 (es)
ZA (1)	ZA200109263B (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1609784A1 (de) *	2004-06-25	2005-12-28	Boehringer Ingelheim Pharma GmbH & Co.KG	Verfahren zur Herstellung von 4-(Benzimidazolylmethylamino)-Benzamidinen
CN1834090B (zh) *	2005-03-18	2011-06-29	中国科学院上海药物研究所	苯并咪唑类化合物、其制备方法以及用途
EA028626B1 (ru)	2012-06-11	2017-12-29	Юсб Байофарма Спрл	БЕНЗИМИДАЗОЛЫ, МОДУЛИРУЮЩИЕ TNF-α
MX2021006121A (es) *	2018-11-25	2021-10-13	Tnt Medical Corp	Profarmaco de gemcitabina oralmente activo.

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2685918B1 (fr) *	1992-01-08	1995-06-23	Union Pharma Scient Appl	Nouveaux derives de l'adenosine, leurs procedes de preparation, compositions pharmaceutiques les contenant.
DE4221009A1 (de) *	1992-06-26	1994-01-05	Bayer Ag	Imidazolyl-substituierte Cyclohexanderivate
CA2101311A1 (en)	1992-07-31	1994-02-01	Neelakantan Balasubramanian	Adenosine re-uptake inhibiting derivatives of diphenyl oxazoles, thiazoles and imidazoles
DE4304455A1 (de) *	1993-02-15	1994-08-18	Bayer Ag	Heterocyclisch substituierte Phenyl-cyclohexan-carbonsäurederivate
DE4401893A1 (de) *	1994-01-24	1995-07-27	Bayer Ag	Substituierte Arylharnstoffe
HRP960015B1 (en)	1995-02-01	2000-12-31	Bayer Ag	Substituted indole derivatives
DE19503160A1 (de) *	1995-02-01	1996-08-08	Bayer Ag	Verwendung von Phenylcyclohexylcarbonsäureamiden

1999
- 1999-05-29 DE DE19924818A patent/DE19924818A1/de not_active Withdrawn
2000
- 2000-05-10 HN HN2000000072A patent/HN2000000072A/es unknown
- 2000-05-16 MX MXPA01012241A patent/MXPA01012241A/es active IP Right Grant
- 2000-05-16 SI SI200030147T patent/SI1185516T1/xx unknown
- 2000-05-16 UA UA2001129201A patent/UA73126C2/uk unknown
- 2000-05-16 DK DK00925288T patent/DK1185516T3/da active
- 2000-05-16 HK HK03100922.0A patent/HK1048810A1/zh unknown
- 2000-05-16 HU HU0201350A patent/HUP0201350A3/hu unknown
- 2000-05-16 PL PL00352101A patent/PL352101A1/xx not_active Application Discontinuation
- 2000-05-16 ES ES00925288T patent/ES2197870T3/es not_active Expired - Lifetime
- 2000-05-16 CZ CZ20014288A patent/CZ20014288A3/cs unknown
- 2000-05-16 CN CNB008110492A patent/CN1200932C/zh not_active Expired - Fee Related
- 2000-05-16 EP EP00925288A patent/EP1185516B1/de not_active Expired - Lifetime
- 2000-05-16 WO PCT/EP2000/004417 patent/WO2000073275A1/de not_active Ceased
- 2000-05-16 HR HR20010955A patent/HRP20010955A2/hr not_active Application Discontinuation
- 2000-05-16 SK SK1705-2001A patent/SK17052001A3/sk unknown
- 2000-05-16 KR KR1020017015263A patent/KR20020003397A/ko not_active Abandoned
- 2000-05-16 IL IL14639200A patent/IL146392A0/xx unknown
- 2000-05-16 DE DE50001982T patent/DE50001982D1/de not_active Expired - Fee Related
- 2000-05-16 BR BR0011061-2A patent/BR0011061A/pt not_active IP Right Cessation
- 2000-05-16 US US09/980,243 patent/US6716849B1/en not_active Expired - Fee Related
- 2000-05-16 EE EEP200100634A patent/EE200100634A/xx unknown
- 2000-05-16 RU RU2001135715/04A patent/RU2246490C9/ru not_active IP Right Cessation
- 2000-05-16 JP JP2000621341A patent/JP2003500475A/ja active Pending
- 2000-05-16 AU AU44055/00A patent/AU765752B2/en not_active Ceased
- 2000-05-16 CA CA002375186A patent/CA2375186A1/en not_active Abandoned
- 2000-05-16 PT PT00925288T patent/PT1185516E/pt unknown
- 2000-05-16 AT AT00925288T patent/ATE238997T1/de not_active IP Right Cessation
- 2000-05-24 AR ARP000102549A patent/AR024100A1/es not_active Application Discontinuation
- 2000-05-26 PE PE2000000506A patent/PE20010167A1/es not_active Application Discontinuation
- 2000-05-26 SV SV2000000087A patent/SV2004000087A/es unknown
- 2000-05-26 GT GT200000083A patent/GT200000083A/es unknown
- 2000-05-26 MY MYPI20002352A patent/MY122576A/en unknown
2001
- 2001-11-09 ZA ZA200109263A patent/ZA200109263B/xx unknown
- 2001-11-13 BG BG106107A patent/BG106107A/bg unknown
- 2001-11-26 MA MA26427A patent/MA25414A1/fr unknown
- 2001-11-28 NO NO20015810A patent/NO20015810L/no not_active Application Discontinuation
2004
- 2004-03-18 US US10/805,548 patent/US20040186106A1/en not_active Abandoned

Also Published As

Publication number	Publication date
JP2003500475A (ja)	2003-01-07
MA25414A1 (fr)	2002-04-01
PT1185516E (pt)	2003-09-30
GT200000083A (es)	2001-11-17
EP1185516B1 (de)	2003-05-02
ES2197870T3 (es)	2004-01-16
WO2000073275A1 (de)	2000-12-07
HUP0201350A2 (en)	2002-08-28
PL352101A1 (en)	2003-07-28
ATE238997T1 (de)	2003-05-15
MXPA01012241A (es)	2002-08-12
KR20020003397A (ko)	2002-01-12
SK17052001A3 (sk)	2002-06-04
IL146392A0 (en)	2002-07-25
HRP20010955A2 (en)	2003-08-31
US6716849B1 (en)	2004-04-06
NO20015810L (no)	2002-01-25
ZA200109263B (en)	2003-01-29
AR024100A1 (es)	2002-09-04
SV2004000087A (es)	2004-05-07
HN2000000072A (es)	2001-02-02
HUP0201350A3 (en)	2003-05-28
CZ20014288A3 (cs)	2002-03-13
CN1200932C (zh)	2005-05-11
RU2246490C2 (ru)	2005-02-20
PE20010167A1 (es)	2001-04-25
NO20015810D0 (no)	2001-11-28
RU2246490C9 (ru)	2005-09-20
EP1185516A1 (de)	2002-03-13
DK1185516T3 (da)	2003-08-11
EE200100634A (et)	2003-02-17
SI1185516T1 (en)	2003-10-31
BR0011061A (pt)	2002-03-05
CN1365356A (zh)	2002-08-21
HK1048810A1 (zh)	2003-04-17
MY122576A (en)	2006-04-29
AU4405500A (en)	2000-12-18
DE50001982D1 (de)	2003-06-05
UA73126C2 (en)	2005-06-15
DE19924818A1 (de)	2000-11-30
AU765752B2 (en)	2003-09-25
CA2375186A1 (en)	2000-12-07
US20040186106A1 (en)	2004-09-23

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