UA73126C2 - Substituted amides of phenylcyclohexanecarboxylic acid, intermedier compounds and medicaments on its base - Google Patents

Substituted amides of phenylcyclohexanecarboxylic acid, intermedier compounds and medicaments on its base Download PDF

Info

Publication number: UA73126C2
Authority: UA; Ukraine
Prior art keywords: carbon atoms; residue; alkyl containing; formula; group
Prior art date: 1999-05-29

Application number

UA2001129201A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Bayer Aktiengezellschaft

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

2000-05-16

Publication date

2005-06-15

2000-05-16 Application filed by Bayer Aktiengezellschaft filed Critical Bayer Aktiengezellschaft

2005-06-15 Publication of UA73126C2 publication Critical patent/UA73126C2/uk

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150000001408 amides Chemical class 0.000 title claims abstract description 15
150000001875 compounds Chemical class 0.000 title claims description 77
QXXHHHWXFHPNOS-UHFFFAOYSA-N 1-phenylcyclohexane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCCC1 QXXHHHWXFHPNOS-UHFFFAOYSA-N 0.000 title claims description 12
239000003814 drug Substances 0.000 title abstract description 3
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 claims abstract description 34
239000002126 C01EB10 - Adenosine Substances 0.000 claims abstract description 17
229960005305 adenosine Drugs 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 15
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
238000010521 absorption reaction Methods 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 2
229940126601 medicinal product Drugs 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
101500021168 Aplysia californica Myomodulin-F Proteins 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
238000000034 method Methods 0.000 abstract description 34
RKNUEXASLVLVSL-UHFFFAOYSA-N 1-phenylcyclohexane-1-carboxamide Chemical class C=1C=CC=CC=1C1(C(=O)N)CCCCC1 RKNUEXASLVLVSL-UHFFFAOYSA-N 0.000 abstract 1
208000014644 Brain disease Diseases 0.000 abstract 1
230000000302 ischemic effect Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
-1 1,3-dihydroxyprop-2-oxy-methyl Chemical group 0.000 description 62
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 14
229940086542 triethylamine Drugs 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
239000002904 solvent Substances 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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
230000007062 hydrolysis Effects 0.000 description 10
238000006460 hydrolysis reaction Methods 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
235000002639 sodium chloride Nutrition 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
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 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
230000003993 interaction Effects 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
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 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
230000008569 process Effects 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
238000007429 general method Methods 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
239000011734 sodium Substances 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
239000000725 suspension Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229910052784 alkaline earth metal Inorganic materials 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
210000001168 carotid artery common Anatomy 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
208000029028 brain injury Diseases 0.000 description 5
229960001701 chloroform Drugs 0.000 description 5
239000013078 crystal Substances 0.000 description 5
208000028867 ischemia Diseases 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
210000003568 synaptosome Anatomy 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
206010061216 Infarction Diseases 0.000 description 4
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 4
206010028980 Neoplasm Diseases 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
229910000288 alkali metal carbonate Inorganic materials 0.000 description 4
150000008041 alkali metal carbonates Chemical class 0.000 description 4
244000309466 calf Species 0.000 description 4
210000004004 carotid artery internal Anatomy 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000007796 conventional method Methods 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
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
239000003960 organic solvent Substances 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 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
229910000029 sodium carbonate Inorganic materials 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
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-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
208000010496 Heart Arrest Diseases 0.000 description 3
206010021143 Hypoxia Diseases 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
208000002667 Subdural Hematoma Diseases 0.000 description 3
208000027418 Wounds and injury Diseases 0.000 description 3
108010018878 adenosine transporter Proteins 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
229910001860 alkaline earth metal hydroxide Inorganic materials 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
230000015572 biosynthetic process Effects 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
150000001735 carboxylic acids Chemical class 0.000 description 3
210000003710 cerebral cortex Anatomy 0.000 description 3
206010008118 cerebral infarction Diseases 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012973 diazabicyclooctane Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
208000014674 injury Diseases 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
230000000324 neuroprotective effect Effects 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
229910052760 oxygen Inorganic materials 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
239000008363 phosphate buffer Substances 0.000 description 3
230000002980 postoperative effect Effects 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
230000007958 sleep Effects 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
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
MCSDUXSCNZIMLL-UHFFFAOYSA-N 1h-benzimidazol-2-ylmethoxy-tert-butyl-dimethylsilane Chemical compound C1=CC=C2NC(CO[Si](C)(C)C(C)(C)C)=NC2=C1 MCSDUXSCNZIMLL-UHFFFAOYSA-N 0.000 description 2
PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 2
VKCDIMUFPORXJA-UHFFFAOYSA-N 2-[2-(1h-benzimidazol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC1=NC2=CC=CC=C2N1 VKCDIMUFPORXJA-UHFFFAOYSA-N 0.000 description 2
GXBRYTMUEZNYJT-UHFFFAOYSA-N 2-anilinoacetamide Chemical compound NC(=O)CNC1=CC=CC=C1 GXBRYTMUEZNYJT-UHFFFAOYSA-N 0.000 description 2
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
206010002091 Anaesthesia Diseases 0.000 description 2
201000006474 Brain Ischemia Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
108010078791 Carrier Proteins Proteins 0.000 description 2
102000014914 Carrier Proteins Human genes 0.000 description 2
206010008111 Cerebral haemorrhage Diseases 0.000 description 2
206010008120 Cerebral ischaemia Diseases 0.000 description 2
206010008132 Cerebral thrombosis Diseases 0.000 description 2
206010008190 Cerebrovascular accident Diseases 0.000 description 2
206010010904 Convulsion Diseases 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
208000005189 Embolism Diseases 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
208000010412 Glaucoma Diseases 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
208000032843 Hemorrhage Diseases 0.000 description 2
201000001429 Intracranial Thrombosis Diseases 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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208000002193 Pain Diseases 0.000 description 2
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HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
230000008447 perception Effects 0.000 description 1
229940117803 phenethylamine Drugs 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
125000005543 phthalimide group Chemical group 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000003518 presynaptic effect Effects 0.000 description 1
150000003141 primary amines Chemical class 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
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000010410 reperfusion Effects 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000012916 structural analysis Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003356 suture material Substances 0.000 description 1
230000000946 synaptic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
229960000790 thymol Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000008733 trauma Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
230000000007 visual effect 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/08—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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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
- A61P9/04—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)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Diabetes (AREA)
Vascular Medicine (AREA)
Anesthesiology (AREA)
Pulmonology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

UA2001129201A 1999-05-29 2000-05-16 Substituted amides of phenylcyclohexanecarboxylic acid, intermedier compounds and medicaments on its base UA73126C2 (en)

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
UA73126C2 true UA73126C2 (en)	2005-06-15

Family

ID=7909712

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001129201A UA73126C2 (en)	1999-05-29	2000-05-16	Substituted amides of phenylcyclohexanecarboxylic acid, intermedier compounds and medicaments on its base

Country Status (36)

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

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
RU2524212C2 (ru) *	2008-06-16	2014-07-27	Бёрингер Ингельхайм Интернациональ Гмбх	Способ получения промежуточного продукта для синтеза этексилата дабигатрана
EP2858983B1 (en)	2012-06-11	2018-04-18	UCB Biopharma SPRL	Tnf-alpha modulating benzimidazoles
CA3120941A1 (en) *	2018-11-25	2020-05-28	Tnt Medical Corporation	Orally active prodrug of gemcitabine

Family Cites Families (7)

* 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
DK0582164T3 (da)	1992-07-31	1999-08-23	Bristol Myers Squibb Co	Adenosin-genoptagelsesinhiberende derivater af diphenyloxazoler, -thiazoler og -imidazoler
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 DK DK00925288T patent/DK1185516T3/da active
- 2000-05-16 BR BR0011061-2A patent/BR0011061A/pt not_active IP Right Cessation
- 2000-05-16 EP EP00925288A patent/EP1185516B1/de not_active Expired - Lifetime
- 2000-05-16 SK SK1705-2001A patent/SK17052001A3/sk unknown
- 2000-05-16 CN CNB008110492A patent/CN1200932C/zh not_active Expired - Fee Related
- 2000-05-16 RU RU2001135715/04A patent/RU2246490C9/ru not_active IP Right Cessation
- 2000-05-16 HU HU0201350A patent/HUP0201350A3/hu unknown
- 2000-05-16 WO PCT/EP2000/004417 patent/WO2000073275A1/de not_active Application Discontinuation
- 2000-05-16 CA CA002375186A patent/CA2375186A1/en not_active Abandoned
- 2000-05-16 MX MXPA01012241A patent/MXPA01012241A/es active IP Right Grant
- 2000-05-16 EE EEP200100634A patent/EE200100634A/xx unknown
- 2000-05-16 AU AU44055/00A patent/AU765752B2/en not_active Ceased
- 2000-05-16 SI SI200030147T patent/SI1185516T1/xx unknown
- 2000-05-16 PT PT00925288T patent/PT1185516E/pt unknown
- 2000-05-16 PL PL00352101A patent/PL352101A1/xx not_active Application Discontinuation
- 2000-05-16 US US09/980,243 patent/US6716849B1/en not_active Expired - Fee Related
- 2000-05-16 DE DE50001982T patent/DE50001982D1/de not_active Expired - Fee Related
- 2000-05-16 IL IL14639200A patent/IL146392A0/xx unknown
- 2000-05-16 UA UA2001129201A patent/UA73126C2/uk unknown
- 2000-05-16 ES ES00925288T patent/ES2197870T3/es not_active Expired - Lifetime
- 2000-05-16 CZ CZ20014288A patent/CZ20014288A3/cs unknown
- 2000-05-16 JP JP2000621341A patent/JP2003500475A/ja active Pending
- 2000-05-16 KR KR1020017015263A patent/KR20020003397A/ko active IP Right Grant
- 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 SV SV2000000087A patent/SV2004000087A/es unknown
- 2000-05-26 MY MYPI20002352A patent/MY122576A/en unknown
- 2000-05-26 GT GT200000083A patent/GT200000083A/es unknown
- 2000-05-26 PE PE2000000506A patent/PE20010167A1/es not_active Application Discontinuation
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
- 2001-12-24 HR HR20010955A patent/HRP20010955A2/hr not_active Application Discontinuation
2003
- 2003-02-07 HK HK03100922.0A patent/HK1048810A1/zh unknown
2004
- 2004-03-18 US US10/805,548 patent/US20040186106A1/en not_active Abandoned

Also Published As

Publication number	Publication date
GT200000083A (es)	2001-11-17
KR20020003397A (ko)	2002-01-12
ES2197870T3 (es)	2004-01-16
CN1200932C (zh)	2005-05-11
HN2000000072A (es)	2001-02-02
PL352101A1 (en)	2003-07-28
SK17052001A3 (sk)	2002-06-04
SI1185516T1 (en)	2003-10-31
HRP20010955A2 (en)	2003-08-31
CA2375186A1 (en)	2000-12-07
DK1185516T3 (da)	2003-08-11
NO20015810L (no)	2002-01-25
DE19924818A1 (de)	2000-11-30
HK1048810A1 (zh)	2003-04-17
HUP0201350A2 (en)	2002-08-28
EP1185516A1 (de)	2002-03-13
WO2000073275A1 (de)	2000-12-07
JP2003500475A (ja)	2003-01-07
MY122576A (en)	2006-04-29
CN1365356A (zh)	2002-08-21
US20040186106A1 (en)	2004-09-23
NO20015810D0 (no)	2001-11-28
US6716849B1 (en)	2004-04-06
AU765752B2 (en)	2003-09-25
MA25414A1 (fr)	2002-04-01
IL146392A0 (en)	2002-07-25
HUP0201350A3 (en)	2003-05-28
MXPA01012241A (es)	2002-08-12
ZA200109263B (en)	2003-01-29
BG106107A (bg)	2002-05-31
AR024100A1 (es)	2002-09-04
RU2246490C9 (ru)	2005-09-20
PT1185516E (pt)	2003-09-30
SV2004000087A (es)	2004-05-07
PE20010167A1 (es)	2001-04-25
DE50001982D1 (de)	2003-06-05
RU2246490C2 (ru)	2005-02-20
ATE238997T1 (de)	2003-05-15
EP1185516B1 (de)	2003-05-02
AU4405500A (en)	2000-12-18
CZ20014288A3 (cs)	2002-03-13
BR0011061A (pt)	2002-03-05
EE200100634A (et)	2003-02-17

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