DK172927B1 - Aryl-heteroarylcarbinolderivater, fremgangsmåder til fremstilling af heraf og farmaceutiske præparater indeholdende ovennæv - Google Patents

Aryl-heteroarylcarbinolderivater, fremgangsmåder til fremstilling af heraf og farmaceutiske præparater indeholdende ovennæv Download PDF

Info

Publication number: DK172927B1
Authority: DK; Denmark
Prior art keywords: methyl; methanol; dimethylamino; ethyl; imidazol
Prior art date: 1987-04-10

Application number

DK198801701A

Other languages

Danish (da)

English (en)

Other versions

DK170188A (da

DK170188D0 (da

Inventor

Augusto Colombo

Juan Pares

Jordi Frigola

Original Assignee

Esteve Labor Dr

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.)

1987-04-10

Filing date

1988-03-28

Publication date

1999-10-04

1988-03-28 Application filed by Esteve Labor Dr filed Critical Esteve Labor Dr

1988-03-28 Publication of DK170188D0 publication Critical patent/DK170188D0/da

1988-10-11 Publication of DK170188A publication Critical patent/DK170188A/da

1999-10-04 Application granted granted Critical

1999-10-04 Publication of DK172927B1 publication Critical patent/DK172927B1/da

Links

238000000034 method Methods 0.000 title claims description 24
238000002360 preparation method Methods 0.000 title claims description 20
239000008194 pharmaceutical composition Substances 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 42
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 41
-1 3-trifluoromethyl-phenyl Chemical group 0.000 claims description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 12
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
208000002193 Pain Diseases 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
IDFPQEHZYBXIFO-GFCCVEGCSA-N (R)-(4-fluoro-2-propylphenyl)-(1H-imidazol-2-yl)methanol Chemical compound CCCc1cc(F)ccc1[C@@H](O)c1ncc[nH]1 IDFPQEHZYBXIFO-GFCCVEGCSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000005905 mesyloxy group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
239000002243 precursor Substances 0.000 claims description 2
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 8
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 5
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 5
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
FBXPRTWYPYHICU-UHFFFAOYSA-N 1-(1-methylimidazol-2-yl)butan-1-ol Chemical compound CCCC(O)C1=NC=CN1C FBXPRTWYPYHICU-UHFFFAOYSA-N 0.000 claims 3
MLZVEAXIKYIGJS-UHFFFAOYSA-N 1-(1-methylimidazol-2-yl)propan-1-ol Chemical compound CCC(O)C1=NC=CN1C MLZVEAXIKYIGJS-UHFFFAOYSA-N 0.000 claims 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims 3
QXLIZWQPORTNLK-UHFFFAOYSA-N 1-(2-methylpyrazol-3-yl)butan-1-ol Chemical compound CCCC(O)C1=CC=NN1C QXLIZWQPORTNLK-UHFFFAOYSA-N 0.000 claims 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
CAHDZOUSXHETAI-UHFFFAOYSA-N CCC(O)C1=CC=NN1C Chemical compound CCC(O)C1=CC=NN1C CAHDZOUSXHETAI-UHFFFAOYSA-N 0.000 claims 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
PGNUBDXGTOZIHC-UHFFFAOYSA-N 4-chloro-1-methylpyrazole Chemical compound CN1C=C(Cl)C=N1 PGNUBDXGTOZIHC-UHFFFAOYSA-N 0.000 claims 1
UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims 1
229940035676 analgesics Drugs 0.000 claims 1
239000000730 antalgic agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
229910052757 nitrogen Inorganic materials 0.000 abstract 1
125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000002904 solvent Substances 0.000 description 17
239000000243 solution Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
230000005764 inhibitory process Effects 0.000 description 12
229910052740 iodine Inorganic materials 0.000 description 12
241000699670 Mus sp. Species 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 7
101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
150000002170 ethers Chemical class 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
230000000202 analgesic effect Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 4
208000008035 Back Pain Diseases 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
ZEHGKSPCAMLJDC-UHFFFAOYSA-M acetylcholine bromide Chemical compound [Br-].CC(=O)OCC[N+](C)(C)C ZEHGKSPCAMLJDC-UHFFFAOYSA-M 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000010992 reflux Methods 0.000 description 4
235000015424 sodium Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
244000215068 Acacia senegal Species 0.000 description 3
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229920000084 Gum arabic Polymers 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 3
239000013078 crystal Substances 0.000 description 3
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239000007928 intraperitoneal injection Substances 0.000 description 3
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150000003254 radicals Chemical class 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
238000005303 weighing Methods 0.000 description 3
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
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WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000019687 Lamb Nutrition 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
101001116283 Phanerodontia chrysosporium Manganese peroxidase H4 Proteins 0.000 description 1
229920003082 Povidone K 90 Polymers 0.000 description 1
101001018261 Protopolybia exigua Mastoparan-1 Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- 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
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)
Steroid Compounds (AREA)

DK198801701A 1987-04-10 1988-03-28 Aryl-heteroarylcarbinolderivater, fremgangsmåder til fremstilling af heraf og farmaceutiske præparater indeholdende ovennæv DK172927B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8705118		1987-04-10
FR8705118A FR2613720B1 (fr)	1987-04-10	1987-04-10	Derives d'aryl-heteroaryl carbinols avec activite analgesique

Publications (3)

Publication Number	Publication Date
DK170188D0 DK170188D0 (da)	1988-03-28
DK170188A DK170188A (da)	1988-10-11
DK172927B1 true DK172927B1 (da)	1999-10-04

Family

ID=9350010

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198801701A DK172927B1 (da)	1987-04-10	1988-03-28	Aryl-heteroarylcarbinolderivater, fremgangsmåder til fremstilling af heraf og farmaceutiske præparater indeholdende ovennæv

Country Status (12)

Country	Link
US (1)	US5017596A (pt)
EP (1)	EP0289380B1 (pt)
JP (1)	JPH0651678B2 (pt)
KR (1)	KR930009442B1 (pt)
AT (1)	ATE116303T1 (pt)
BR (1)	BR1100931A (pt)
DE (1)	DE3852565T2 (pt)
DK (1)	DK172927B1 (pt)
ES (1)	ES2014523A6 (pt)
FR (1)	FR2613720B1 (pt)
GR (1)	GR3015616T3 (pt)
PT (1)	PT87183B (pt)

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FR2681322B1 (fr) *	1991-09-12	1993-12-17	Laboratorios Dr Esteve Sa	Derives d'aryl-heteroaryl-{n-[2-(3,4-dimethoxyphenyl)-ethyl]-n-methyl-3-aminopropoxy}-methane leur preparation et leur application en tant que medicaments .
EP0758323A1 (en) *	1994-05-02	1997-02-19	Zeneca Limited	Herbicidal hydroxybenzyl-substituted heteroaryl compounds and derivatives thereof
ES2150353B1 (es) *	1998-04-15	2001-07-01	Esteve Labor Dr	Tienilazolilalcoxietanaminas, su preparacion y su aplicacion como medicamentos.
ES2137136B1 (es) *	1998-05-18	2000-07-01	Esteve Labor Dr	Empleo de derivados de aril (o heteroaril) azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de la inflamacion neurogenica.
ES2150378B1 (es) *	1998-08-07	2001-07-01	Esteve Labor Dr	Empleo de derivados de aril(o heteroaril)azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de los trastornos mediados por un exceso de substancia p.
ES2180449B1 (es) *	2001-07-06	2004-01-16	Esteve Labor Dr	Derivados de aril (o heteroaril) azolilcarbinoles para el tratamiento de la incontinencia urinaria.
DE10335566A1 (de) *	2003-07-31	2005-02-24	Grünenthal GmbH	Arzneimittel enthaltend Derivate von Aryl( oder Heteroaryl)azolylcarbinolen
TW200533657A (en) *	2004-02-17	2005-10-16	Esteve Labor Dr	Substituted pyrazoline compounds, their preparation and use as medicaments
ES2245226B1 (es) *	2004-04-05	2007-02-16	Laboratorios Del Dr. Esteve, S.A.	Combinacion de substancias activas.
ES2244326B1 (es) *	2004-04-05	2007-02-16	Laboratorios Del Dr. Esteve, S.A.	Combinacion de substancias activas.
EP1584335A3 (en) *	2004-04-05	2006-02-22	Laboratorios Del Dr. Esteve, S.A.	Active substance combination comprising a carbinol composition and an opioid
CA2562231A1 (en) *	2004-04-05	2005-10-20	Laboratorios Del Dr. Esteve, S.A.	Active substance combination of a carbinol compound and an opioid
US20060040924A1 (en) *	2004-06-22	2006-02-23	Laboratorios Dr. Esteve S.A.	Derivatives of aryl (or heteroaryl) azolylcarbinols for the treatment of renal colic
EP1632227A1 (en) *	2004-09-07	2006-03-08	Laboratorios del Dr. Esteve S.A.	Derivatives of aryl (or heteroaryl) azolylcarbinols (in particular cizolirtin citrate) for the treatment of opioid addiction
EP1671953A1 (en)	2004-12-17	2006-06-21	Laboratorios Del Dr. Esteve, S.A.	Process for obtaining cizolirtine and its enantiomers
EP1671968A1 (en)	2004-12-17	2006-06-21	Laboratorios Del Dr. Esteve, S.A.	Process for obtaining enantiomers of thienylazolylalcoxyethanamines
EP1674465A1 (en)	2004-12-27	2006-06-28	Laboratorios Del Dr. Esteve, S.A.	Process for obtaining enantiomers of thienylazolylalcoxyethanamines
EP1690537A1 (en) *	2005-02-15	2006-08-16	Laboratorios Del Dr. Esteve, S.A.	Derivatives of aryl(or heteroaryl) azolycarbinols for the treatment of fibromyalgia
ES2286920B1 (es) *	2005-02-15	2008-08-16	Laboratorios Del Dr. Esteve, S.A.	Derivados de aril (o heteroaril)azolilcarbinoles para el tratamiento de la fibromialgia.
EP1695704A1 (en) *	2005-02-28	2006-08-30	Laboratorios Del Dr. Esteve, S.A.	Derivatives of aryl (or heteroaryl) azolylcarbinols for the treatment of fibromyalgia
WO2006087147A2 (en) *	2005-02-15	2006-08-24	Laboratorios Del Dr. Esteve, S.A.	Derivatives of aryl (or heteroaryl) azolylcarbinols for the treatment of fibromyalgia
US7897589B2 (en) *	2005-07-15	2011-03-01	Laboratorios Del Dr. Esteve, S.A.	Substituted pyrazoline compounds, their preparation and use as medicaments
EP1743890A1 (en)	2005-07-15	2007-01-17	Laboratorios Del Dr. Esteve, S.A.	4,5-Dihydro-1H-pyrazole derivatives, their preparation and use as medicaments
EP1743892A1 (en) *	2005-07-15	2007-01-17	Laboratorios del Dr. Esteve S.A.	Substituted pyrazoline compounds, their preparation and use as medicaments
EP1757587A1 (en) *	2005-07-15	2007-02-28	Laboratorios Del Dr. Esteve, S.A.	Substituted pyrazoline compounds, their preparation and use as medicaments
US7592362B2 (en) *	2006-01-19	2009-09-22	Pfizer Limited	Substituted imidazoles
EP1820502A1 (en)	2006-02-10	2007-08-22	Laboratorios Del Dr. Esteve, S.A.	Active substance combination comprising azolylcarbinol compounds
EP2151234A1 (en) *	2008-07-28	2010-02-10	Laboratorios Del. Dr. Esteve, S.A.	Pharmaceutical formulation comprising a CB1-receptor compound in a solid solution and/or solid dispersion
US20100291151A1 (en) *	2009-04-21	2010-11-18	Auspex Pharmaceuticals, Inc.	1-methylpyrazole modulators of substance p, calcitonin gene-related peptide, adrenergic receptor, and/or 5-ht receptor

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IL39413A0 (en) *	1971-05-13	1972-07-26	Sparamedica Ag	Benzodiazepine derivatives,their preparation and pharmaceutical compositions containing them
BE793407A (fr) *	1971-12-28	1973-06-28	Hoechst Ag	Imidazolyl - (2) -carbinols ayant une activite hypolipidemique et leur procede de preparation
JPS5118950B2 (pt) *	1972-06-30	1976-06-14
US4853404A (en) *	1986-10-13	1989-08-01	Tanabe Seiyaku Co., Ltd.	Phenoxyacetic acid derivatives composition and use

1987
- 1987-04-10 FR FR8705118A patent/FR2613720B1/fr not_active Expired - Lifetime
1988
- 1988-03-28 DK DK198801701A patent/DK172927B1/da not_active IP Right Cessation
- 1988-03-30 ES ES8800984A patent/ES2014523A6/es not_active Expired - Lifetime
- 1988-04-06 EP EP88400828A patent/EP0289380B1/fr not_active Expired - Lifetime
- 1988-04-06 AT AT88400828T patent/ATE116303T1/de not_active IP Right Cessation
- 1988-04-06 DE DE3852565T patent/DE3852565T2/de not_active Expired - Lifetime
- 1988-04-07 PT PT87183A patent/PT87183B/pt not_active IP Right Cessation
- 1988-04-08 JP JP63088020A patent/JPH0651678B2/ja not_active Expired - Lifetime
- 1988-04-11 KR KR1019880004094A patent/KR930009442B1/ko not_active Expired - Fee Related
1989
- 1989-12-21 US US07/456,077 patent/US5017596A/en not_active Expired - Lifetime
1995
- 1995-03-23 GR GR950400692T patent/GR3015616T3/el unknown
1997
- 1997-05-14 BR BR1100931-4A patent/BR1100931A/pt active IP Right Grant

Also Published As

Publication number	Publication date
KR930009442B1 (ko)	1993-10-04
JPH0651678B2 (ja)	1994-07-06
BR1100931A (pt)	1999-11-23
GR3015616T3 (en)	1995-06-30
EP0289380A1 (fr)	1988-11-02
PT87183A (pt)	1988-05-01
DE3852565D1 (de)	1995-02-09
KR880012558A (ko)	1988-11-28
ES2014523A6 (es)	1990-07-16
EP0289380B1 (fr)	1994-12-28
DE3852565T2 (de)	1995-05-11
FR2613720B1 (fr)	1990-01-19
DK170188A (da)	1988-10-11
PT87183B (pt)	1992-08-31
US5017596A (en)	1991-05-21
DK170188D0 (da)	1988-03-28
ATE116303T1 (de)	1995-01-15
FR2613720A1 (fr)	1988-10-14
JPS63267761A (ja)	1988-11-04

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JP2006511571A (ja)	2006-04-06	ピラゾール化合物
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US8153630B2 (en)	2012-04-10	Kinase inhibitors
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CZ9302010A3 (en)	1994-05-18	DERIVATIVE OF 4-AMINO-1,3,4,5/TETRAHYDROBENZ(cd)INDOLE SUBSTITUTED IN POSITION 6 BY A HETEROCYCLIC GROUP, PROCESS OF ITS PREPARATION AND A PHARMACEUTICAL PREPARATION IN IT IS COMPRISED
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Legal Events

Date	Code	Title
1995-06-06	B1	Patent granted (law 1993)
1999-10-04	B1	Patent granted (law 1993)
2008-04-14	PUP	Patent expired