DD292000A5 - Pyrimidinyl-piperazinyl-alkylazolderivate mit anxiolitischer und/oder beruhigender aktivitaet - Google Patents

Pyrimidinyl-piperazinyl-alkylazolderivate mit anxiolitischer und/oder beruhigender aktivitaet Download PDF

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Publication number: DD292000A5
Authority: DD; German Democratic Republic
Prior art keywords: radical; general formula; piperazinyl; pyrimidinyl; butyl
Prior art date: 1989-02-09

Application number

DD90337677A

Other languages

German (de)

English (en)

Inventor

Augusto C Pinol

Jordi F Constansa

Juan P Corominas

Original Assignee

��@��@��K@��k�K@�Kk��

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.)

1989-02-09

Filing date

1990-02-08

Publication date

1991-07-18

1990-02-08 Application filed by ��@��@��K@��k�K@�Kk�� filed Critical ��@��@��K@��k�K@�Kk��

1991-07-18 Publication of DD292000A5 publication Critical patent/DD292000A5/de

Links

230000000949 anxiolytic effect Effects 0.000 title claims description 7
230000003020 moisturizing effect Effects 0.000 title 1
-1 alkyl radical Chemical class 0.000 claims abstract description 48
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
125000003118 aryl group Chemical group 0.000 claims abstract description 7
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 6
125000003277 amino group Chemical group 0.000 claims abstract description 6
229910052736 halogen Chemical group 0.000 claims abstract description 6
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical class [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims abstract description 5
150000002367 halogens Chemical group 0.000 claims abstract description 5
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims abstract description 4
150000003254 radicals Chemical class 0.000 claims abstract description 4
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims abstract description 3
NYOWYNSNCXRVNQ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indazole Chemical class C1=CCC2CNNC2=C1 NYOWYNSNCXRVNQ-UHFFFAOYSA-N 0.000 claims abstract description 3
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 3
150000005840 aryl radicals Chemical class 0.000 claims abstract description 3
229910052799 carbon Inorganic materials 0.000 claims abstract description 3
JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims abstract description 3
150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 3
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims abstract description 3
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
239000002249 anxiolytic agent Substances 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
230000002936 tranquilizing effect Effects 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
125000005905 mesyloxy group Chemical group 0.000 claims description 2
125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
150000003839 salts Chemical class 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
239000003204 tranquilizing agent Substances 0.000 claims description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
102000009025 Endorphins Human genes 0.000 claims 1
108010049140 Endorphins Proteins 0.000 claims 1
150000008065 acid anhydrides Chemical class 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
229940005530 anxiolytics Drugs 0.000 claims 1
150000003851 azoles Chemical class 0.000 claims 1
239000000543 intermediate Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 abstract 1
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
MVLCWTIFKARXPZ-UHFFFAOYSA-N 2-[4-(4-pyrazol-1-ylbutyl)piperazin-1-yl]pyrimidine Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCCN1C=CC=N1 MVLCWTIFKARXPZ-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
238000004611 spectroscopical analysis Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
210000003169 central nervous system Anatomy 0.000 description 4
AHCPKWJUALHOPH-UHFFFAOYSA-N lesopitron Chemical compound C1=C(Cl)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 AHCPKWJUALHOPH-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
230000009467 reduction Effects 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
ZIQGOFVRBXXVAD-UHFFFAOYSA-N 1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazol-4-amine Chemical compound C1=C(N)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 ZIQGOFVRBXXVAD-UHFFFAOYSA-N 0.000 description 2
RGDLQJUAYQRGBC-UHFFFAOYSA-N 2-[4-[4-(4-chloropyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine;dihydrochloride Chemical compound Cl.Cl.C1=C(Cl)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 RGDLQJUAYQRGBC-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000002585 base Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000009472 formulation Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002576 ketones 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
YEYPABYUNOVUGE-UHFFFAOYSA-N n-[1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazol-4-yl]methanesulfonamide Chemical compound C1=C(NS(=O)(=O)C)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 YEYPABYUNOVUGE-UHFFFAOYSA-N 0.000 description 2
NTDNRPNORCEPQE-UHFFFAOYSA-N n-butan-2-yl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazol-4-amine Chemical compound C1=C(NC(C)CC)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 NTDNRPNORCEPQE-UHFFFAOYSA-N 0.000 description 2
LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000004044 response Effects 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 1
UTTUKVYNSMQGMB-UHFFFAOYSA-N 1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]indazole Chemical compound N1=CC2=CC=CC=C2N1CCCCN(CC1)CCN1C1=NC=CC=N1 UTTUKVYNSMQGMB-UHFFFAOYSA-N 0.000 description 1
SOIYHTHGIOYGSR-UHFFFAOYSA-N 1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazole-4-carbonitrile Chemical compound C1=C(C#N)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 SOIYHTHGIOYGSR-UHFFFAOYSA-N 0.000 description 1
OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 description 1
PRBGKQGYGPXWLE-UHFFFAOYSA-N 2-[4-(4-imidazol-1-ylbutyl)piperazin-1-yl]pyrimidine Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCCN1C=CN=C1 PRBGKQGYGPXWLE-UHFFFAOYSA-N 0.000 description 1
GUEQPKHZPIQBRC-UHFFFAOYSA-N 2-[4-(4-pyrrol-1-ylbutyl)piperazin-1-yl]pyrimidine Chemical class C1CN(C=2N=CC=CN=2)CCN1CCCCN1C=CC=C1 GUEQPKHZPIQBRC-UHFFFAOYSA-N 0.000 description 1
KYLSLMHEJLBHHW-UHFFFAOYSA-N 2-[4-[4-(2-methylimidazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound CC1=NC=CN1CCCCN1CCN(C=2N=CC=CN=2)CC1 KYLSLMHEJLBHHW-UHFFFAOYSA-N 0.000 description 1
MMQKMHSNUAMZRP-UHFFFAOYSA-N 2-[4-[4-(3,5-dimethyl-4-nitropyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound CC1=C([N+]([O-])=O)C(C)=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 MMQKMHSNUAMZRP-UHFFFAOYSA-N 0.000 description 1
LKXFVDIVDAWWOF-UHFFFAOYSA-N 2-[4-[4-(3,5-dimethylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound N1=C(C)C=C(C)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 LKXFVDIVDAWWOF-UHFFFAOYSA-N 0.000 description 1
NZZOEYWJCWUKBV-UHFFFAOYSA-N 2-[4-[4-(3-chloro-4-fluoropyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound N1=C(Cl)C(F)=CN1CCCCN1CCN(C=2N=CC=CN=2)CC1 NZZOEYWJCWUKBV-UHFFFAOYSA-N 0.000 description 1
USRALLUDBDLGCW-UHFFFAOYSA-N 2-[4-[4-(3-chloro-4-methoxypyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound N1=C(Cl)C(OC)=CN1CCCCN1CCN(C=2N=CC=CN=2)CC1 USRALLUDBDLGCW-UHFFFAOYSA-N 0.000 description 1
HIJKBNNMCPXUQN-UHFFFAOYSA-N 2-[4-[4-(3-methyl-4-phenylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1=C(C=2C=CC=CC=2)C(C)=NN1CCCCN(CC1)CCN1C1=NC=CC=N1 HIJKBNNMCPXUQN-UHFFFAOYSA-N 0.000 description 1
CWWDSXQOEYQKQR-UHFFFAOYSA-N 2-[4-[4-(3-methyl-5-phenylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCCN1N=C(C)C=C1C1=CC=CC=C1 CWWDSXQOEYQKQR-UHFFFAOYSA-N 0.000 description 1
GNKMDANXMLJJMD-UHFFFAOYSA-N 2-[4-[4-(3-methylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound N1=C(C)C=CN1CCCCN1CCN(C=2N=CC=CN=2)CC1 GNKMDANXMLJJMD-UHFFFAOYSA-N 0.000 description 1
ULHRMRNNWSMWOZ-UHFFFAOYSA-N 2-[4-[4-(4,5-dichloroimidazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound ClC1=C(Cl)N=CN1CCCCN1CCN(C=2N=CC=CN=2)CC1 ULHRMRNNWSMWOZ-UHFFFAOYSA-N 0.000 description 1
KAISPBQTVCMHPN-UHFFFAOYSA-N 2-[4-[4-(4-bromo-3,5-dimethylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound CC1=C(Br)C(C)=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 KAISPBQTVCMHPN-UHFFFAOYSA-N 0.000 description 1
ZBIRDOWQBNTXKX-UHFFFAOYSA-N 2-[4-[4-(4-bromo-3-methylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1=C(Br)C(C)=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 ZBIRDOWQBNTXKX-UHFFFAOYSA-N 0.000 description 1
NXPNSIOXOJVART-UHFFFAOYSA-N 2-[4-[4-(4-bromo-5-methylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound CC1=C(Br)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 NXPNSIOXOJVART-UHFFFAOYSA-N 0.000 description 1
ATALGGVYPSLBSH-UHFFFAOYSA-N 2-[4-[4-(4-bromopyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1=C(Br)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 ATALGGVYPSLBSH-UHFFFAOYSA-N 0.000 description 1
CKDUBTXWOMBKQI-UHFFFAOYSA-N 2-[4-[4-(4-chloropyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine;hydrochloride Chemical compound Cl.C1=C(Cl)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 CKDUBTXWOMBKQI-UHFFFAOYSA-N 0.000 description 1
IFFQMBVIZCOYRH-UHFFFAOYSA-N 2-[4-[4-(4-fluoropyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1=C(F)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 IFFQMBVIZCOYRH-UHFFFAOYSA-N 0.000 description 1
SHQMTNAAGNEHIB-UHFFFAOYSA-N 2-[4-[4-(4-methoxypyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1=C(OC)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 SHQMTNAAGNEHIB-UHFFFAOYSA-N 0.000 description 1
VCNNXTSFINEAGU-UHFFFAOYSA-N 2-[4-[4-(4-methylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1=C(C)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 VCNNXTSFINEAGU-UHFFFAOYSA-N 0.000 description 1
DPHHDSRYFIOQHK-UHFFFAOYSA-N 2-[4-[4-(4-nitropyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1=C([N+](=O)[O-])C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 DPHHDSRYFIOQHK-UHFFFAOYSA-N 0.000 description 1
SUNNVVOZTVYWIZ-UHFFFAOYSA-N 2-[4-[4-(4-phenylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCCN(N=C1)C=C1C1=CC=CC=C1 SUNNVVOZTVYWIZ-UHFFFAOYSA-N 0.000 description 1
HAGDWVFGTHOQFQ-UHFFFAOYSA-N 2-[4-[4-(4-pyrrol-1-ylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCCN(N=C1)C=C1N1C=CC=C1 HAGDWVFGTHOQFQ-UHFFFAOYSA-N 0.000 description 1
YTNAZSGONJPDNT-UHFFFAOYSA-N 2-[4-[4-(5-methyl-4-phenylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound CC1=C(C=2C=CC=CC=2)C=NN1CCCCN(CC1)CCN1C1=NC=CC=N1 YTNAZSGONJPDNT-UHFFFAOYSA-N 0.000 description 1
PBFXUKZCLSPMJU-UHFFFAOYSA-N 2-[4-[4-(5-methylimidazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound CC1=CN=CN1CCCCN1CCN(C=2N=CC=CN=2)CC1 PBFXUKZCLSPMJU-UHFFFAOYSA-N 0.000 description 1
CSFAXAANQSIMRG-UHFFFAOYSA-N 2-[4-[4-(5-methylpyrazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound CC1=CC=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 CSFAXAANQSIMRG-UHFFFAOYSA-N 0.000 description 1
VBNDYCJTBGFPGX-UHFFFAOYSA-N 2-[4-[4-[4-(4-chlorophenyl)pyrazol-1-yl]butyl]piperazin-1-yl]pyrimidine Chemical compound C1=CC(Cl)=CC=C1C1=CN(CCCCN2CCN(CC2)C=2N=CC=CN=2)N=C1 VBNDYCJTBGFPGX-UHFFFAOYSA-N 0.000 description 1
SOGYBQVAZOAIGS-UHFFFAOYSA-N 2-[4-[4-[4-(4-methoxyphenyl)pyrazol-1-yl]butyl]piperazin-1-yl]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=CN(CCCCN2CCN(CC2)C=2N=CC=CN=2)N=C1 SOGYBQVAZOAIGS-UHFFFAOYSA-N 0.000 description 1
MEAWMKXNZDOKST-UHFFFAOYSA-N 5-bromo-2-[4-(4-pyrazol-1-ylbutyl)piperazin-1-yl]pyrimidine Chemical compound N1=CC(Br)=CN=C1N1CCN(CCCCN2N=CC=C2)CC1 MEAWMKXNZDOKST-UHFFFAOYSA-N 0.000 description 1
229910000497 Amalgam Inorganic materials 0.000 description 1
241000212977 Andira Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 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
241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
PNRYSZAJDPGROU-UHFFFAOYSA-N ethyl 1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazole-4-carboxylate Chemical compound C1=C(C(=O)OCC)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 PNRYSZAJDPGROU-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 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
239000011707 mineral Substances 0.000 description 1
QQFMMCKIGICJSG-UHFFFAOYSA-N n-[1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazol-4-yl]acetamide Chemical compound C1=C(NC(=O)C)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 QQFMMCKIGICJSG-UHFFFAOYSA-N 0.000 description 1
DBNKMCYXRRDLBY-UHFFFAOYSA-N n-[1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazol-4-yl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=C1)C=NN1CCCCN(CC1)CCN1C1=NC=CC=N1 DBNKMCYXRRDLBY-UHFFFAOYSA-N 0.000 description 1
GKQSZZPQFGVPBU-UHFFFAOYSA-N n-[1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazol-4-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=C1)C=NN1CCCCN(CC1)CCN1C1=NC=CC=N1 GKQSZZPQFGVPBU-UHFFFAOYSA-N 0.000 description 1
QQSKCNBQOFMEGR-UHFFFAOYSA-N n-[1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazol-4-yl]butane-1-sulfonamide Chemical compound C1=C(NS(=O)(=O)CCCC)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 QQSKCNBQOFMEGR-UHFFFAOYSA-N 0.000 description 1
DKPXAYBSQMNYQL-UHFFFAOYSA-N n-[1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazol-4-yl]ethanesulfonamide Chemical compound C1=C(NS(=O)(=O)CC)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 DKPXAYBSQMNYQL-UHFFFAOYSA-N 0.000 description 1
KFCKXTPTWUZLDL-UHFFFAOYSA-N n-[1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrazol-4-yl]propane-1-sulfonamide Chemical compound C1=C(NS(=O)(=O)CCC)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 KFCKXTPTWUZLDL-UHFFFAOYSA-N 0.000 description 1
DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
238000000053 physical method Methods 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
229940125725 tranquilizer Drugs 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- C07D401/14—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 three or more hetero rings
- 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
- 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
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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

Landscapes

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

DD90337677A 1989-02-09 1990-02-08 Pyrimidinyl-piperazinyl-alkylazolderivate mit anxiolitischer und/oder beruhigender aktivitaet DD292000A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8901700A FR2642759B1 (fr)	1989-02-09	1989-02-09	Derives de pyrimidyl-piperazinyl-alkyl azoles avec activite anxiolytique et/ou tranquillisante

Publications (1)

Publication Number	Publication Date
DD292000A5 true DD292000A5 (de)	1991-07-18

Family

ID=9378642

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90337677A DD292000A5 (de)	1989-02-09	1990-02-08	Pyrimidinyl-piperazinyl-alkylazolderivate mit anxiolitischer und/oder beruhigender aktivitaet

Country Status (18)

Country	Link
US (1)	US5128343A (ja)
EP (1)	EP0382637B1 (ja)
JP (1)	JP2521170B2 (ja)
KR (1)	KR950000779B1 (ja)
AT (1)	ATE92059T1 (ja)
AU (1)	AU623734B2 (ja)
CA (1)	CA2009480A1 (ja)
DD (1)	DD292000A5 (ja)
DE (1)	DE69002341T2 (ja)
DK (1)	DK0382637T3 (ja)
ES (1)	ES2021941A6 (ja)
FR (1)	FR2642759B1 (ja)
HU (1)	HU204817B (ja)
NO (1)	NO176880C (ja)
PT (1)	PT93095B (ja)
RU (1)	RU2071474C1 (ja)
YU (1)	YU48071B (ja)
ZA (1)	ZA90929B (ja)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5219855A (en) *	1988-01-29	1993-06-15	Mitsubishi Kasei Corporation	Anxiolytic drug
FR2654621B1 (fr) *	1989-11-22	1994-09-23	Esteve Labor Dr	Inhibition du syndrome d'abstinence.
FR2672052B1 (fr) *	1991-01-28	1995-05-24	Esteve Labor Dr	Derives d'aryl (ou heteroaryl)-piperazinyl-alkyl-azoles, leur preparation et leur application en tant que medicaments.
US5656762A (en)	1990-12-28	1997-08-12	Neurogen Corporation	4-piperidino-and piperazinomethyl-2-phenylimidazole derivatives, dopamine receptor subtype specific ligands
US5681956A (en) *	1990-12-28	1997-10-28	Neurogen Corporation	4-aryl substituted piperazinylmethyl phenylimidazole derivatives; a new class of dopamine receptor subtype specific ligands
FR2671972B1 (fr) *	1991-01-25	1995-03-03	Esteve Labor Dr	Utilisation de derives 1-h-azole-(omega-(4-(2-pyrimidinyl)-1-piperazinyl)-alkyl) pour la preparation de medicaments destines au traitement des troubles des fonctions cognitives.
FR2673628B1 (fr) *	1991-03-07	1993-07-09	Esteve Labor Dr	Procede de preparation de derives d'aryl (ou heteroaryl)-piperazinyl-butyl-azoles.
FR2701260B1 (fr) *	1993-02-05	1995-05-05	Esteve Labor Dr	Dérivés de 2-[4-(4-azolylbutyl)-1-pipérazinyl]-5-hydroxypyrimidine, leur préparation et leur application en tant que médicaments.
FR2705098B1 (fr) *	1993-05-10	1995-08-04	Esteve Labor Dr	Procédé de préparation de 2-{4-[4-(chloro-1-pyrazolyl)butyl]1-pipérazinyl}pyrimidine (Lesopitron) .
ES2099031B1 (es) *	1995-05-31	1997-12-01	Esteve Labor Dr	Nuevos polimorfos de diclorhidrato de lesopitron y sus formas hidratadas, procedimientos de preparacion y composiciones que los contienen.
FR2763950B1 (fr) *	1997-06-02	2002-09-20	Esteve Labor Dr	2- {4- [4-(4,5-dichloro-2-methylimidazol-1-yl)butyl] -1- piperazinyl }-5-fluoropyrimidine, sa preparation et son utilisation therapeutique
ES2125206B1 (es)	1997-07-21	1999-11-16	Esteve Labor Dr	Derivados de acil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos.
US6166205A (en) *	1998-09-02	2000-12-26	Neurogen Corporation	2-Aryl-4-(1-[4-heteroaryl]piperazin-1-yl)methylimidazoles: dopamine . D.sub4 receptor subtype ligands
US7332494B2 (en)	2000-08-14	2008-02-19	Janssen Pharmaceutica, N.V.	Method for treating allergies using substituted pyrazoles
EP1309591B1 (en)	2000-08-14	2007-01-24	Ortho-McNeil Pharmaceutical, Inc.	Substituted pyrazoles
NZ524192A (en)	2000-08-14	2005-02-25	Ortho Mcneil Pharm Inc	Substituted pyrazoles
RU2317988C2 (ru)	2000-08-14	2008-02-27	Орто-Макнейл Фармасьютикал, Инк.	Замещенные пиразолы, фармацевтическая композиция на их основе, применение фармацевтической композиции и способ ингибирования активности катепсина s
HK1053129A1 (zh)	2000-09-06	2003-10-10	Ortho-Mcneil Pharmaceutical, Inc.	治疗变态反应的方法
ES2167276B1 (es) *	2000-10-20	2003-04-01	Esteve Labor Dr	Nuevos derivados de cianoaril (o cianoheteroaril)-carbonil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos.

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4487773A (en) *	1981-03-16	1984-12-11	Mead Johnson & Company	1,2,4-Triazol-3-one antidepressants
US4367335A (en) *	1981-08-03	1983-01-04	Mead Johnson & Company	Thiazolidinylalkylene piperazine derivatives
DE3321969A1 (de) *	1983-06-18	1984-12-20	Troponwerke GmbH & Co KG, 5000 Köln	2-pyrimidinyl-1-piperazin-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
US4547499A (en) *	1984-05-10	1985-10-15	The Upjohn Company	2,4-Dihydro-2(omega-aminoalkyl)-1H-[1,2,4]triazolo[3,4-c]benzoxazin-1-one anti-allergy drug compounds, compositions and use
US4675403A (en) *	1985-10-16	1987-06-23	American Home Products Corporation	3-Aminoalkyl derivatives of 5,5-disubstituted hydantoins with psychotropic activity

1989
- 1989-02-09 FR FR8901700A patent/FR2642759B1/fr not_active Expired - Lifetime
1990
- 1990-01-29 NO NO900411A patent/NO176880C/no not_active IP Right Cessation
- 1990-02-07 US US07/476,815 patent/US5128343A/en not_active Expired - Fee Related
- 1990-02-07 CA CA002009480A patent/CA2009480A1/fr not_active Abandoned
- 1990-02-07 AT AT90400337T patent/ATE92059T1/de not_active IP Right Cessation
- 1990-02-07 EP EP90400337A patent/EP0382637B1/en not_active Expired - Lifetime
- 1990-02-07 DK DK90400337.3T patent/DK0382637T3/da active
- 1990-02-07 DE DE90400337T patent/DE69002341T2/de not_active Expired - Fee Related
- 1990-02-07 AU AU49192/90A patent/AU623734B2/en not_active Ceased
- 1990-02-08 ES ES9000369A patent/ES2021941A6/es not_active Expired - Lifetime
- 1990-02-08 PT PT93095A patent/PT93095B/pt not_active IP Right Cessation
- 1990-02-08 HU HU90716A patent/HU204817B/hu not_active IP Right Cessation
- 1990-02-08 ZA ZA90929A patent/ZA90929B/xx unknown
- 1990-02-08 JP JP2031353A patent/JP2521170B2/ja not_active Expired - Lifetime
- 1990-02-08 KR KR1019900001536A patent/KR950000779B1/ko not_active Expired - Fee Related
- 1990-02-08 DD DD90337677A patent/DD292000A5/de unknown
- 1990-02-09 YU YU25790A patent/YU48071B/sh unknown
1991
- 1991-09-18 RU SU915001503A patent/RU2071474C1/ru active

Also Published As

Publication number	Publication date
HUT53100A (en)	1990-09-28
JPH032179A (ja)	1991-01-08
ZA90929B (en)	1990-11-28
HU204817B (en)	1992-02-28
PT93095B (pt)	1995-12-29
NO176880C (no)	1995-06-14
JP2521170B2 (ja)	1996-07-31
KR900012929A (ko)	1990-09-03
EP0382637B1 (en)	1993-07-28
PT93095A (pt)	1990-08-31
EP0382637A1 (fr)	1990-08-16
DK0382637T3 (da)	1993-09-20
AU4919290A (en)	1990-08-16
ATE92059T1 (de)	1993-08-15
KR950000779B1 (ko)	1995-02-02
YU48071B (sh)	1997-01-08
DE69002341D1 (de)	1993-09-02
RU2071474C1 (ru)	1997-01-10
DE69002341T2 (de)	1993-12-02
FR2642759A1 (fr)	1990-08-10
US5128343A (en)	1992-07-07
ES2021941A6 (es)	1991-11-16
NO176880B (no)	1995-03-06
YU25790A (en)	1991-08-31
CA2009480A1 (fr)	1990-08-09
NO900411L (no)	1990-08-10
HU900716D0 (en)	1990-04-28
NO900411D0 (no)	1990-01-29
FR2642759B1 (fr)	1991-05-17
AU623734B2 (en)	1992-05-21

Publication	Publication Date	Title
DD292000A5 (de)	1991-07-18	Pyrimidinyl-piperazinyl-alkylazolderivate mit anxiolitischer und/oder beruhigender aktivitaet
DE69210076T2 (de)	1996-10-24	Verfahren zur Herstellung von Aryl(oder Heteroaryl)-piperazin-1-butyl-azol-derivaten
DE60121590T2 (de)	2006-11-30	Pyrazolderivate
DE60007329T2 (de)	2004-06-09	N-heterozyklische derivate als nos inhibitoren
DE3788145T2 (de)	1994-04-28	Piperidinderivate, diese enthaltende pharmazeutische Zusammensetzungen und ihre Verwendung.
DE69132340T2 (de)	2001-02-08	Kondensiertes pyrazinderivat
DE69106715T2 (de)	1995-05-11	Indolderivate als antiallergische und antiinflammatorische mittel.
DE69529142T2 (de)	2003-09-25	Tetrahydropyridin-(oder 4-hydroxypiperidin) alkylazole mit sigma und/oder 5ht 1a-rezeptor aktivität
DE3852565T2 (de)	1995-05-11	Aryl-heteroaryl-karbinol-Derivate mit analgetischer Aktivität.
DE69209679T2 (de)	1996-10-10	Aryl(oder Heteroaryl)-piperazinyl-alkyl-azol-derivate, ihre Herstellung und ihre Anwendung als Medikament
DE60207815T2 (de)	2006-08-24	1-aryl-oder 1-alkylsulfonylbenzazol-derivate als 5-hydroxytryptamin-6 liganden
DE69222595T2 (de)	1998-02-12	Pyrazolopyrimidone als Wirkstoffe gegen Angina
DE69521323T2 (de)	2001-09-20	Quinoxalindion-nmda rezeptorantagonisten
DE2009020B2 (de)	1979-01-11	Verfahren zur Herstellung von N-U,l,l-trisubstituierten)-Methylazolen
EP0908456A1 (de)	1999-04-14	Pyrazol-Derivate, ihre Herstellung und ihre Verwendung in Arzneimitteln
DE2946020A1 (de)	1980-05-29	Imidazolverbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE69203911T2 (de)	1995-12-07	Antihistaminische und nicht sedierende Benzimidazolderivate, Verfahren zu deren Herstellung und deren Anwendung als Arzneimittel.
DD282912A5 (de)	1990-09-26	Verfahren zur herstellung eines substituierten imidazols
DE1946370C3 (de)	1979-07-26	Substituierte Pyrazol-4-essigsäuren, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2834322A1 (de)	1979-02-15	4-substituierte pyrazole
DE3889974T2 (de)	1994-09-15	Pyrazol-Derivate und diese enthaltende Behandlungsmittel für cerebrovaskulare Krankheiten.
DE2023453C3 (de)	1975-04-10	Pyrazole eckige Klammer auf 3,4-e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-7(1H)one
DE69525633T2 (de)	2002-08-08	Chinoxalinderivate und ihre therapeutische verwendbarkeit
DE1595920B2 (de)	1978-08-10	4-(co-Piperazinoalkyl)-pyrazole, ihre Salze und Verfahren zu ihrer Herstellung
DE2052692A1 (de)	1971-05-06	Isothioharnstoffverbmdungen, ihre Salze mit Sauren, Verfahren zu ihrer Her stellung und ihre Verwendung zur Her stellung von Arzneimitteln