SI20473A - Tienilazolilalkoksietanamini, njihova priprava in njihova uporaba kot zdravila - Google Patents

Tienilazolilalkoksietanamini, njihova priprava in njihova uporaba kot zdravila Download PDF

Info

Publication number: SI20473A
Authority: SI; Slovenia
Prior art keywords: methyl; general formula; pyrazole; thienylmethyl; dimethylamino
Prior art date: 1998-04-15

Application number

SI9920030A

Other languages

English (en)

Slovenian (sl)

Inventor

Ramon Merce-Vidal

Blas Andaluz-Mataro

Constansa Jordi Frigola

Original Assignee

Laboratorios Del Dr. Esteve, S.A.

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.)

1998-04-15

Filing date

1999-04-15

Publication date

2001-08-31

1999-04-15 Application filed by Laboratorios Del Dr. Esteve, S.A. filed Critical Laboratorios Del Dr. Esteve, S.A.

2001-08-31 Publication of SI20473A publication Critical patent/SI20473A/sl

Links

239000003814 drug Substances 0.000 title claims abstract description 8
238000002360 preparation method Methods 0.000 title claims description 27
150000001875 compounds Chemical class 0.000 claims abstract description 66
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
230000000202 analgesic effect Effects 0.000 claims abstract description 7
241000282414 Homo sapiens Species 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
241000124008 Mammalia Species 0.000 claims abstract 2
125000003118 aryl group Chemical group 0.000 claims abstract 2
125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 36
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 35
238000000034 method Methods 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 14
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 10
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000001728 carbonyl compounds Chemical class 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
125000002524 organometallic group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
150000004795 grignard reagents Chemical class 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
150000002641 lithium Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
239000013543 active substance Substances 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
SEIUDSIYAJOZRA-UHFFFAOYSA-N n,n-dimethyl-2-[1-(2-methylpyrazol-3-yl)-1-thiophen-2-ylethoxy]ethanamine Chemical compound C=1C=NN(C)C=1C(C)(OCCN(C)C)C1=CC=CS1 SEIUDSIYAJOZRA-UHFFFAOYSA-N 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
229940095064 tartrate Drugs 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
229910052987 metal hydride Inorganic materials 0.000 claims 1
150000004681 metal hydrides Chemical class 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 6
230000015572 biosynthetic process Effects 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 4
CQJWCJSXVVREST-UHFFFAOYSA-N 2-thiophen-2-yl-1h-pyrrol-3-ol Chemical class C1=CNC(C=2SC=CC=2)=C1O CQJWCJSXVVREST-UHFFFAOYSA-N 0.000 abstract 3
QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
-1 aminoalkyl radical Chemical class 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000007924 injection Substances 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical class O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 5
208000002193 Pain Diseases 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
241001465754 Metazoa Species 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
208000005392 Spasm Diseases 0.000 description 4
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
208000007101 Muscle Cramp Diseases 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229950005499 carbon tetrachloride Drugs 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
230000036461 convulsion Effects 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
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GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
229910010277 boron hydride Inorganic materials 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000003983 crown ethers Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000005905 mesyloxy group Chemical group 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000003444 phase transfer catalyst Substances 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000935 solvent evaporation Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WIRBLSBIUFJYGF-UHFFFAOYSA-N 1-(2-methylpyrazol-3-yl)-1-thiophen-2-ylethanol Chemical compound CN1N=CC=C1C(C)(O)C1=CC=CS1 WIRBLSBIUFJYGF-UHFFFAOYSA-N 0.000 description 1
ZIELEIJWNRPJIZ-UHFFFAOYSA-N 2-chloro-n,n-dimethylethanamine;hypochlorous acid Chemical compound ClO.CN(C)CCCl ZIELEIJWNRPJIZ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
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FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
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229960001138 acetylsalicylic acid Drugs 0.000 description 1
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229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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239000008346 aqueous phase Substances 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005251 capillar electrophoresis Methods 0.000 description 1
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238000001311 chemical methods and process Methods 0.000 description 1
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229960002303 citric acid monohydrate Drugs 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000003821 enantio-separation Methods 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
CPEXMLRNLBFIHJ-UHFFFAOYSA-N phenyl(1h-pyrazol-5-yl)methanol Chemical class C=1C=CC=CC=1C(O)C1=CC=NN1 CPEXMLRNLBFIHJ-UHFFFAOYSA-N 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
208000004371 toothache Diseases 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- 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
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

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

SI9920030A 1998-04-15 1999-04-15 Tienilazolilalkoksietanamini, njihova priprava in njihova uporaba kot zdravila SI20473A (sl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES009800793A ES2150353B1 (es)	1998-04-15	1998-04-15	Tienilazolilalcoxietanaminas, su preparacion y su aplicacion como medicamentos.
PCT/ES1999/000098 WO1999052525A1 (fr)	1998-04-15	1999-04-15	Thienylazolylalcoxyethanamines, leur preparation et leur application en tant que medicaments

Publications (1)

Publication Number	Publication Date
SI20473A true SI20473A (sl)	2001-08-31

Family

ID=8303465

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI9920030A SI20473A (sl)	1998-04-15	1999-04-15	Tienilazolilalkoksietanamini, njihova priprava in njihova uporaba kot zdravila

Country Status (31)

Country	Link
US (3)	US6410582B1 (fr)
EP (1)	EP1072266B8 (fr)
JP (1)	JP2002511412A (fr)
KR (1)	KR100523366B1 (fr)
CN (1)	CN1189170C (fr)
AR (1)	AR016210A1 (fr)
AT (1)	ATE302604T1 (fr)
AU (1)	AU754705B2 (fr)
BG (1)	BG64891B1 (fr)
BR (1)	BR9910124A (fr)
CA (1)	CA2328878A1 (fr)
CO (1)	CO5011045A1 (fr)
CU (1)	CU22960A3 (fr)
CZ (1)	CZ298222B6 (fr)
EE (1)	EE04739B1 (fr)
ES (1)	ES2150353B1 (fr)
GE (1)	GEP20032913B (fr)
HU (1)	HUP0102585A3 (fr)
IS (1)	IS5662A (fr)
LT (1)	LT4830B (fr)
LV (1)	LV12624B (fr)
NO (1)	NO320313B1 (fr)
NZ (1)	NZ507573A (fr)
PL (1)	PL343512A1 (fr)
RO (1)	RO121690B1 (fr)
RU (1)	RU2213743C2 (fr)
SI (1)	SI20473A (fr)
SK (1)	SK285039B6 (fr)
TW (1)	TW528756B (fr)
UA (1)	UA58589C2 (fr)
WO (1)	WO1999052525A1 (fr)

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* Cited by examiner, † Cited by third party
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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.
US6432954B1 (en) *	2000-07-14	2002-08-13	Targacept, Inc.	Pharmaceutical compositions and methods for use
ES2174756B2 (es) *	2001-04-06	2003-11-16	Esteve Labor Dr	Derivados de aril (o heteroaril) azolilcarbinoles para el tratamiento de enfermedades respiratorias.
US20040142929A1 (en) *	2001-07-06	2004-07-22	Ramon Merce-Vidal	Derivatives of aryl (or heteroaryl) azolylcarbinoles for the treatment of urinary incontinence
ES2180449B1 (es) *	2001-07-06	2004-01-16	Esteve Labor Dr	Derivados de aril (o heteroaril) azolilcarbinoles para el tratamiento de la incontinencia urinaria.
CL2004001034A1 (es) *	2003-05-14	2005-03-28	Teijin Pharma Ltd	Formas cristalinas de acido 4-(1-((,etilbenzotiofen-3-il)me til)benzimidazol-2-iltio)butanoico; procedimiento de preparacion de las formas cristalinas; composicion farmaceutica; y su uso para el tratamiento de enfermedades inflamatorias, alergicas, r
TW200533657A (en) *	2004-02-17	2005-10-16	Esteve Labor Dr	Substituted pyrazoline compounds, their preparation and use as medicaments
EP1584335A3 (fr) *	2004-04-05	2006-02-22	Laboratorios Del Dr. Esteve, S.A.	Combinaison de substances actives comprenant un composé carbinol et un opioïde
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
WO2006010627A1 (fr) *	2004-07-30	2006-02-02	Laboratorios Del Dr. Esteve, S.A.	Aryl (ou heteroaryl) azolylcarbinols
EP1632227A1 (fr) *	2004-09-07	2006-03-08	Laboratorios del Dr. Esteve S.A.	Dérivés des aryl (ou des heteroaryl) azolylcarbinols (en particulier cizolirtin citrate) pour le traitement de la dépendance des opioides
EP1671968A1 (fr)	2004-12-17	2006-06-21	Laboratorios Del Dr. Esteve, S.A.	Procédé pour la préparation des énantiomères de thiénylazolylalcoxyéthanamines
WO2006063860A2 (fr) *	2004-12-17	2006-06-22	Laboratorios Del Dr. Esteve, S.A.	Procede d'obtention d'enantiomeres de thienylazolylalcoxyethanamines
EP1674465A1 (fr) *	2004-12-27	2006-06-28	Laboratorios Del Dr. Esteve, S.A.	Procédé pour l'obtention des enanntiomères des thienylazolylalkoxyethanamines.
ES2303795B1 (es) *	2004-12-27	2009-06-12	Laboratorios Del Dr. Esteve, S.A.	Procedimiento para obtener enantiomeros de tienilazolilalcoxietanaminas.
WO2006069767A1 (fr) *	2004-12-27	2006-07-06	Laboratorios Del Dr. Esteve, S.A.	Procede pour obtenir des enantiomeres de thienylazolylalcoxyethanamines
EP1743892A1 (fr) *	2005-07-15	2007-01-17	Laboratorios del Dr. Esteve S.A.	Composés pyrazoline substitués, leur préparation et utilisation comme médicaments
EP1743890A1 (fr) *	2005-07-15	2007-01-17	Laboratorios Del Dr. Esteve, S.A.	Dérivés 4,5-dihydro-1H-pyrazole, leur, préparation et utilisation comme médicaments.
US7897589B2 (en) *	2005-07-15	2011-03-01	Laboratorios Del Dr. Esteve, S.A.	Substituted pyrazoline compounds, their preparation and use as medicaments
EP1757587A1 (fr) *	2005-07-15	2007-02-28	Laboratorios Del Dr. Esteve, S.A.	Composés de pyrazoline substituée, leur préparation et leur usage comme médicaments
US20070149590A1 (en) *	2005-08-05	2007-06-28	Garcia Francisco J L	Controlled release dosage form of pirazole compounds
EP1820502A1 (fr)	2006-02-10	2007-08-22	Laboratorios Del Dr. Esteve, S.A.	Combinaisons de principes actifs comprenant de dérivés d' azolylcarbinol
EP2151234A1 (fr) *	2008-07-28	2010-02-10	Laboratorios Del. Dr. Esteve, S.A.	Formulation pharmaceutique comprenant un composé récepteur CB1 dans une solution solide et/ou une dispersion solide
CN102432845B (zh) *	2011-08-22	2013-03-13	电子科技大学	聚3,4-双乙基羟基噻吩气敏材料及其制备方法
WO2016096127A1 (fr) *	2014-12-15	2016-06-23	Laboratorios Del Dr. Esteve, S.A.	Composés méthyl-1h-pyrazole-alkylamines ayant une activité multimodale contre la douleur

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2613720B1 (fr) *	1987-04-10	1990-01-19	Esteve Labor Dr	Derives d'aryl-heteroaryl carbinols avec activite analgesique
RU2027716C1 (ru) *	1988-09-15	1995-01-27	Эбеве Арцнаймиттель ГмбХ	Производные тиенилоксиалкиламина или их фармацевтически совместимые кислые аддитивные соли
RU2088573C1 (ru) *	1993-03-18	1997-08-27	Научно-исследовательский институт фармакологии РАМН	1-[w-(n,n-замещенные амино) алкил]-2-(2*991-ацилэтенил) пирролы или их фармацевтически приемлемые соли, обладающие антиаритмической и противоишемической активностью
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.

1998
- 1998-04-15 ES ES009800793A patent/ES2150353B1/es not_active Expired - Fee Related
1999
- 1999-04-14 AR ARP990101712A patent/AR016210A1/es unknown
- 1999-04-14 CO CO99022015A patent/CO5011045A1/es unknown
- 1999-04-15 SI SI9920030A patent/SI20473A/sl not_active IP Right Cessation
- 1999-04-15 JP JP2000543135A patent/JP2002511412A/ja active Pending
- 1999-04-15 RU RU2000128658/04A patent/RU2213743C2/ru not_active IP Right Cessation
- 1999-04-15 AT AT99913321T patent/ATE302604T1/de not_active IP Right Cessation
- 1999-04-15 EE EEP200000596A patent/EE04739B1/xx not_active IP Right Cessation
- 1999-04-15 AU AU31483/99A patent/AU754705B2/en not_active Ceased
- 1999-04-15 HU HU0102585A patent/HUP0102585A3/hu unknown
- 1999-04-15 CZ CZ20003764A patent/CZ298222B6/cs not_active IP Right Cessation
- 1999-04-15 RO ROA200000995A patent/RO121690B1/ro unknown
- 1999-04-15 US US09/673,186 patent/US6410582B1/en not_active Expired - Fee Related
- 1999-04-15 PL PL99343512A patent/PL343512A1/xx not_active IP Right Cessation
- 1999-04-15 BR BR9910124-6A patent/BR9910124A/pt not_active Application Discontinuation
- 1999-04-15 GE GEAP19995625A patent/GEP20032913B/en unknown
- 1999-04-15 SK SK1528-2000A patent/SK285039B6/sk unknown
- 1999-04-15 NZ NZ507573A patent/NZ507573A/en unknown
- 1999-04-15 KR KR10-2000-7011466A patent/KR100523366B1/ko not_active Expired - Fee Related
- 1999-04-15 UA UA2000105809A patent/UA58589C2/uk unknown
- 1999-04-15 CN CNB998068098A patent/CN1189170C/zh not_active Expired - Fee Related
- 1999-04-15 CA CA002328878A patent/CA2328878A1/fr not_active Abandoned
- 1999-04-15 EP EP99913321A patent/EP1072266B8/fr not_active Expired - Lifetime
- 1999-04-15 WO PCT/ES1999/000098 patent/WO1999052525A1/fr not_active Ceased
- 1999-04-19 TW TW088106199A patent/TW528756B/zh not_active IP Right Cessation
2000
- 2000-10-09 CU CU20000215A patent/CU22960A3/es unknown
- 2000-10-12 LT LT2000097A patent/LT4830B/lt unknown
- 2000-10-13 NO NO20005146A patent/NO320313B1/no not_active IP Right Cessation
- 2000-10-13 IS IS5662A patent/IS5662A/is unknown
- 2000-10-13 BG BG104853A patent/BG64891B1/bg unknown
- 2000-11-03 LV LV000135A patent/LV12624B/xx unknown
2002
- 2002-05-06 US US10/139,674 patent/US20020188017A1/en not_active Abandoned
2004
- 2004-02-13 US US10/779,287 patent/US7129361B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU3148399A (en)	1999-11-01
TW528756B (en)	2003-04-21
JP2002511412A (ja)	2002-04-16
IS5662A (is)	2000-10-13
AR016210A1 (es)	2001-06-20
LV12624B (lv)	2001-09-20
RO121690B1 (ro)	2008-02-28
CU22960A3 (es)	2004-06-21
CO5011045A1 (es)	2001-02-28
HUP0102585A3 (en)	2002-04-29
BR9910124A (pt)	2001-01-09
WO1999052525A1 (fr)	1999-10-21
RU2213743C2 (ru)	2003-10-10
US6410582B1 (en)	2002-06-25
NO20005146L (no)	2000-12-14
KR20010042739A (ko)	2001-05-25
UA58589C2 (uk)	2003-08-15
LT4830B (lt)	2001-08-27
GEP20032913B (en)	2003-03-25
HUP0102585A2 (hu)	2001-12-28
NO320313B1 (no)	2005-11-21
SK15282000A3 (sk)	2001-12-03
NZ507573A (en)	2002-07-26
LT2000097A (en)	2001-03-26
CZ298222B6 (cs)	2007-07-25
ATE302604T1 (de)	2005-09-15
CA2328878A1 (fr)	1999-10-21
CZ20003764A3 (en)	2001-05-16
ES2150353B1 (es)	2001-07-01
EE200000596A (et)	2002-06-17
BG64891B1 (bg)	2006-08-31
CN1303283A (zh)	2001-07-11
EP1072266A1 (fr)	2001-01-31
US20020188017A1 (en)	2002-12-12
LV12624A (lv)	2001-03-20
EE04739B1 (et)	2006-12-15
NO20005146D0 (no)	2000-10-13
EP1072266B1 (fr)	2005-08-24
SK285039B6 (sk)	2006-05-04
EP1072266B8 (fr)	2006-10-18
KR100523366B1 (ko)	2005-10-20
CN1189170C (zh)	2005-02-16
US7129361B2 (en)	2006-10-31
ES2150353A1 (es)	2000-11-16
AU754705B2 (en)	2002-11-21
PL343512A1 (en)	2001-08-27
US20040162324A1 (en)	2004-08-19
BG104853A (en)	2001-04-30

Publication	Publication Date	Title
SI20473A (sl)	2001-08-31	Tienilazolilalkoksietanamini, njihova priprava in njihova uporaba kot zdravila
US5948777A (en)	1999-09-07	Cannabinoid receptor agonists
CA3017388C (fr)	2024-03-12	Modulateurs du recepteur des oestrogenes
EP1641763B1 (fr)	2009-09-02	Derives de 4-cyanopyrazole-3-carboxamide, leur preparation et leur application comme antagonistes des recepteurs aux cannabinoides cb1
EP0477049B1 (fr)	1999-12-01	Dérivés d'amido-3 pyrazole, procédé pour leur préparation et compositions pharmaceutiques les contenant
FR2741621A1 (fr)	1997-05-30	Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant
NZ229239A (en)	1991-06-25	Substituted diperazine derivatives and pharmaceutical compositions
FI86175B (fi)	1992-04-15	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara fenolderivat.
FR2595695A1 (fr)	1987-09-18	Derives de n-(((hydroxy-2 phenyl) (phenyl) methylene) amino-2) ethyl) acetamide, leur preparation et leur application en therapeutique
WO2009004171A2 (fr)	2009-01-08	Dérives de 1 -benzylpyrazole, leur preparation et leur application en therapeutique
JPH09508917A (ja)	1997-09-09	フェニルピロール誘導体およびそのドーパミンｄ▲下３▼アンタゴニストとしての使用
FR2911136A1 (fr)	2008-07-11	Derives de n-(4-cyano-1h-pyrazol-3-yl)methylamine substitues leur preparation et leur application en therapeutique.
FR2888236A1 (fr)	2007-01-12	Derives de n-[(1,5-diphenyl-1h-pyrazol-3-yl)methyl] sulfonamide, leur preparation et leur application en therapeutique
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