DK169601B1 - Piperazinderivater og farmaceutisk præparat indeholdende et sådant derivat, samt piperazinderivater med mellemproduktanvendelse - Google Patents

Piperazinderivater og farmaceutisk præparat indeholdende et sådant derivat, samt piperazinderivater med mellemproduktanvendelse Download PDF

Info

Publication number: DK169601B1
Authority: DK; Denmark
Prior art keywords: group; ethyl; piperazinyl; fluoro; formula
Prior art date: 1983-10-17

Application number

DK490384A

Other languages

Danish (da)

English (en)

Other versions

DK490384A (da

DK490384D0 (da

Inventor

Jan Hartog

Wouter Wouters

Ineke Van Wijngaarden

Original Assignee

Duphar Int Res

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.)

1983-10-17

Filing date

1984-10-12

Publication date

1994-12-19

1984-10-12 Application filed by Duphar Int Res filed Critical Duphar Int Res

1984-10-12 Publication of DK490384D0 publication Critical patent/DK490384D0/da

1985-04-18 Publication of DK490384A publication Critical patent/DK490384A/da

1994-12-19 Application granted granted Critical

1994-12-19 Publication of DK169601B1 publication Critical patent/DK169601B1/da

Links

150000004885 piperazines Chemical class 0.000 title claims abstract description 9
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title claims abstract description 8
239000000825 pharmaceutical preparation Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 80
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
-1 methylene, ethylidene Chemical group 0.000 claims description 70
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 55
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 6
230000004531 blood pressure lowering effect Effects 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000004193 piperazinyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 2
BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
229920002554 vinyl polymer Polymers 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 3
229910052760 oxygen Inorganic materials 0.000 claims 1
230000036772 blood pressure Effects 0.000 abstract description 13
230000009471 action Effects 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 4
238000002360 preparation method Methods 0.000 abstract description 4
230000009956 central mechanism Effects 0.000 abstract description 2
201000010099 disease Diseases 0.000 abstract description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
230000001105 regulatory effect Effects 0.000 abstract description 2
125000001072 heteroaryl group Chemical group 0.000 abstract 1
229920006395 saturated elastomer Polymers 0.000 abstract 1
125000003107 substituted aryl group Chemical group 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 22
WJMOWGFGRONZPA-UHFFFAOYSA-N aziridin-1-yl-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC1 WJMOWGFGRONZPA-UHFFFAOYSA-N 0.000 description 19
LIOLIMKSCNQPLV-UHFFFAOYSA-N 2-fluoro-n-methyl-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1C1=NN2C(CC=3C=C4C=CC=NC4=CC=3)=CN=C2N=C1 LIOLIMKSCNQPLV-UHFFFAOYSA-N 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
238000000034 method Methods 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000012458 free base Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
239000003480 eluent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
VLDVCDDOQCONPL-UHFFFAOYSA-N n-[2-[4-(2,3-diaminophenyl)piperazin-1-yl]ethyl]-4-fluorobenzamide Chemical compound NC1=CC=CC(N2CCN(CCNC(=O)C=3C=CC(F)=CC=3)CC2)=C1N VLDVCDDOQCONPL-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
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000011699 spontaneously hypertensive rat Methods 0.000 description 3
CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
ZCZHNDFVODJBBB-UHFFFAOYSA-N aziridin-1-yl(cyclohexyl)methanone Chemical compound C1CN1C(=O)C1CCCCC1 ZCZHNDFVODJBBB-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 2
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000010992 reflux Methods 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
KFVKNZPFYQDNAE-UHFFFAOYSA-N 1-(1-benzofuran-7-yl)piperazine Chemical compound C1CNCCN1C1=CC=CC2=C1OC=C2 KFVKNZPFYQDNAE-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
DMLRSJNZORFCBD-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-5-amine Chemical compound O1CCOC2=C1C=CC=C2N DMLRSJNZORFCBD-UHFFFAOYSA-N 0.000 description 1
JSWRVDNTKPAJLB-UHFFFAOYSA-N 2,4-difluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(F)=C1 JSWRVDNTKPAJLB-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
GKTFLKJXZOYBRW-UHFFFAOYSA-N 2-ethylbenzamide Chemical compound CCC1=CC=CC=C1C(N)=O GKTFLKJXZOYBRW-UHFFFAOYSA-N 0.000 description 1
FBCZWQNVHNIQOD-UHFFFAOYSA-N 2-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC2=CC=CC=C2N1 FBCZWQNVHNIQOD-UHFFFAOYSA-N 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 1
USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 1
OIJQZCHYFXSTSL-UHFFFAOYSA-N 4-fluoro-n-[2-(4-quinolin-8-ylpiperazin-1-yl)ethyl]benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NCCN1CCN(C=2C3=NC=CC=C3C=CC=2)CC1 OIJQZCHYFXSTSL-UHFFFAOYSA-N 0.000 description 1
LCMFXXVESPPBKC-UHFFFAOYSA-N 4-fluoro-n-[2-[4-(2-oxo-1,3-dihydrobenzimidazol-4-yl)piperazin-1-yl]ethyl]benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NCCN1CCN(C=2C=3NC(=O)NC=3C=CC=2)CC1 LCMFXXVESPPBKC-UHFFFAOYSA-N 0.000 description 1
SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
CKJBQNUWRDPXBA-UHFFFAOYSA-N 5-piperazin-1-ylquinoxaline Chemical compound C1CNCCN1C1=CC=CC2=NC=CN=C12 CKJBQNUWRDPXBA-UHFFFAOYSA-N 0.000 description 1
XKDAUEWDPSMDGG-UHFFFAOYSA-N 7-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC=CC2=C1NC=C2 XKDAUEWDPSMDGG-UHFFFAOYSA-N 0.000 description 1
DCUZDOXGNVJQQL-UHFFFAOYSA-N 8-piperazin-1-ylquinoline Chemical compound C1CNCCN1C1=CC=CC2=CC=CN=C12 DCUZDOXGNVJQQL-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
YLQNZIPLHBGSMN-UHFFFAOYSA-N C1CN(CCN1)C1CCc2ccccc2O1 Chemical compound C1CN(CCN1)C1CCc2ccccc2O1 YLQNZIPLHBGSMN-UHFFFAOYSA-N 0.000 description 1
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
AIUPDSQLYGAORJ-UHFFFAOYSA-N aziridin-1-yl-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC1 AIUPDSQLYGAORJ-UHFFFAOYSA-N 0.000 description 1
239000011324 bead Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 description 1
238000009530 blood pressure measurement Methods 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229960002896 clonidine Drugs 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
FCZFPMKLLXTSNP-UHFFFAOYSA-N ethyl 2-iminoacetate Chemical compound CCOC(=O)C=N FCZFPMKLLXTSNP-UHFFFAOYSA-N 0.000 description 1
MODZVIMSNXSQIH-UHFFFAOYSA-N ethyl benzenecarboximidate;hydron;chloride Chemical compound Cl.CCOC(=N)C1=CC=CC=C1 MODZVIMSNXSQIH-UHFFFAOYSA-N 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000013213 extrapolation Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004050 homopiperazines Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
FYQJUYCGPLFWQR-UHFFFAOYSA-N n-(2-chloroethyl)benzamide Chemical compound ClCCNC(=O)C1=CC=CC=C1 FYQJUYCGPLFWQR-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- 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
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyridine Compounds (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Furan Compounds (AREA)
Pyrane Compounds (AREA)

DK490384A 1983-10-17 1984-10-12 Piperazinderivater og farmaceutisk præparat indeholdende et sådant derivat, samt piperazinderivater med mellemproduktanvendelse DK169601B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8303569		1983-10-17
NL8303569		1983-10-17

Publications (3)

Publication Number	Publication Date
DK490384D0 DK490384D0 (da)	1984-10-12
DK490384A DK490384A (da)	1985-04-18
DK169601B1 true DK169601B1 (da)	1994-12-19

Family

ID=19842575

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK490384A DK169601B1 (da)	1983-10-17	1984-10-12	Piperazinderivater og farmaceutisk præparat indeholdende et sådant derivat, samt piperazinderivater med mellemproduktanvendelse

Country Status (15)

Country	Link
US (1)	US4833142A (es)
EP (1)	EP0138280B1 (es)
JP (2)	JPH0672136B2 (es)
AT (1)	ATE34980T1 (es)
AU (1)	AU577802B2 (es)
CA (1)	CA1269375A (es)
DE (1)	DE3471932D1 (es)
DK (1)	DK169601B1 (es)
ES (5)	ES536755A0 (es)
GR (1)	GR80653B (es)
IE (1)	IE58281B1 (es)
IL (1)	IL73240A (es)
NZ (1)	NZ209876A (es)
PH (1)	PH23801A (es)
ZA (1)	ZA848005B (es)

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NL8005133A (nl) *	1980-09-12	1982-04-01	Duphar Int Res	Fenylpiperazinederivaten met antiagressieve werking.
JPS5777676A (en) *	1980-10-31	1982-05-15	Otsuka Pharmaceut Co Ltd	Carbostyril derivative
CH653021A5 (fr) *	1981-04-24	1985-12-13	Delalande Sa	Derives piperidino, piperazino et homopiperazino, n-substitues par un groupe heterocyclique aromatique, leur procede de preparation et composition therapeutique les contenant.
FR2504532A1 (fr) *	1981-04-24	1982-10-29	Delalande Sa	Nouveaux derives heterocycliques du type benzimidazole, indole et purine, leur procede de preparation et leur application en therapeutique
NZ209876A (en) *	1983-10-17	1988-03-30	Duphar Int Res	Piperazines and pharmaceutical compositions

1984
- 1984-10-12 NZ NZ209876A patent/NZ209876A/en unknown
- 1984-10-12 ZA ZA848005A patent/ZA848005B/xx unknown
- 1984-10-12 AU AU34165/84A patent/AU577802B2/en not_active Ceased
- 1984-10-12 DK DK490384A patent/DK169601B1/da not_active IP Right Cessation
- 1984-10-15 IE IE263384A patent/IE58281B1/en not_active IP Right Cessation
- 1984-10-15 ES ES536755A patent/ES536755A0/es active Granted
- 1984-10-15 GR GR80653A patent/GR80653B/el unknown
- 1984-10-15 IL IL73240A patent/IL73240A/xx not_active IP Right Cessation
- 1984-10-15 AT AT84201477T patent/ATE34980T1/de not_active IP Right Cessation
- 1984-10-15 EP EP84201477A patent/EP0138280B1/en not_active Expired
- 1984-10-15 DE DE8484201477T patent/DE3471932D1/de not_active Expired
- 1984-10-16 CA CA000465500A patent/CA1269375A/en not_active Expired - Lifetime
- 1984-10-17 PH PH31346A patent/PH23801A/en unknown
- 1984-10-17 JP JP59216461A patent/JPH0672136B2/ja not_active Expired - Fee Related
1985
- 1985-08-01 ES ES545818A patent/ES8604560A1/es not_active Expired
- 1985-08-01 ES ES545817A patent/ES8604559A1/es not_active Expired
- 1985-08-01 ES ES85545816A patent/ES8604582A1/es not_active Expired
- 1985-08-01 ES ES545815A patent/ES8604558A1/es not_active Expired
1987
- 1987-11-09 US US07/118,005 patent/US4833142A/en not_active Expired - Lifetime
1993
- 1993-07-19 JP JP5178104A patent/JPH07119210B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ES545818A0 (es)	1986-02-01
EP0138280A2 (en)	1985-04-24
GR80653B (en)	1985-02-01
ES8604559A1 (es)	1986-02-01
DK490384A (da)	1985-04-18
ES8604560A1 (es)	1986-02-01
NZ209876A (en)	1988-03-30
ES8604582A1 (es)	1986-02-01
IL73240A0 (en)	1985-01-31
JPH07119210B2 (ja)	1995-12-20
US4833142A (en)	1989-05-23
IE842633L (en)	1985-04-17
CA1269375A (en)	1990-05-22
ES545816A0 (es)	1986-02-01
ATE34980T1 (de)	1988-06-15
ES8604558A1 (es)	1986-02-01
IE58281B1 (en)	1993-08-25
ES545815A0 (es)	1986-02-01
ES8603455A1 (es)	1985-12-16
JPH0692934A (ja)	1994-04-05
AU577802B2 (en)	1988-10-06
ZA848005B (en)	1985-05-29
IL73240A (en)	1988-07-31
PH23801A (en)	1989-11-03
ES545817A0 (es)	1986-02-01
AU3416584A (en)	1986-09-11
EP0138280A3 (en)	1985-06-12
DE3471932D1 (en)	1988-07-14
JPS60104063A (ja)	1985-06-08
DK490384D0 (da)	1984-10-12
JPH0672136B2 (ja)	1994-09-14
EP0138280B1 (en)	1988-06-08
ES536755A0 (es)	1985-12-16

Publication	Publication Date	Title
DK169601B1 (da)	1994-12-19	Piperazinderivater og farmaceutisk præparat indeholdende et sådant derivat, samt piperazinderivater med mellemproduktanvendelse
US4430343A (en)	1984-02-07	Benzimidazole derivatives, process for the preparation thereof and pharmaceutical composition containing the same
US4346093A (en)	1982-08-24	Heterocyclic oxypropanolamine compounds and pharmaceutical compositions
EP0185429A1 (en)	1986-06-25	New bicyclic heteroaryl piperazines
EP0908458B1 (en)	2006-01-25	Substituted pyridylmethylpiperazine and piperidine derivatives, their preparation and their use for treating central nervous system (CNS) disorders
US4590273A (en)	1986-05-20	Isoquinoline compounds
HU177959B (en)	1982-02-28	Process for producing 1,2-dihydro-quinoline-2-one derivatives
DK164907B (da)	1992-09-07	Piperazinderivater, deres fremstilling og farmaceutiske praeparater indeholdende dem
US3917597A (en)	1975-11-04	Benzodioxole compounds
DK151017B (da)	1987-10-12	Analogifremgangsmaade til fremstiiling af substituerede n-(4-indolyl-piperidino-alkyl)-benzimidazoloner eller fysiologisk acceptable syreadditionssalte deraf
SK162798A3 (en)	1999-06-11	Benzoxazinone dopamine d4 receptor antagonists
US5534517A (en)	1996-07-09	(Aryl(alkyl)carbonyl)-heterocyclic compounds and their use in the treatment of anxiety and depression
JPH10139780A (ja)	1998-05-26	新規な複素環式アミノメチル化合物、これらの製造方法及びこれらを含む医薬組成物
DK149947B (da)	1986-11-03	Analogifremgangsmaade til fremstilling af 1,5-diphenylpyrazolin-3-on-forbindelser eller syreadditionssalte deraf
NO845169L (no)	1985-06-24	Analogifremgangsmaate for fremstilling av terapeutisk aktive benzimidazol-derivater
GB2120234A (en)	1983-11-30	Triazole and imidazole derivates having fungicidal and plant-growth regulating activity
FI75564B (fi)	1988-03-31	Foerfarande foer framstaellning av farmakologiskt verkande och saosom laekemedel anvaendbara bensazolderivat.
DK153487B (da)	1988-07-18	Analogifremgangsmaade til fremstilling af 2-(perhydro-1,4-diazino)-pyrimidooe5,4-daapyrimidinderivater
DK148806B (da)	1985-10-07	Analogifremgangsmaade til fremstilling af 1-phenyl-2-piperazinoalkyl-indazol-3-on-forbindelser eller syreadditionssalte deraf
US5773437A (en)	1998-06-30	Alkylenediamine derivatives
US3717637A (en)	1973-02-20	TRIFLUOROMETHYLTHIO SUBSTITUTED DIBENZ [b,f] [1,4] OXAZEPINES
CZ8096A3 (en)	1996-07-17	Derivative of 3-alkoxycarbonylthiadiazinone, process of its preparation and pharmaceutical composition containing thereof
FI77238C (fi)	1989-02-10	Foerfarande foer framstaellning av farmakologiskt vaerdefulla fenylalkyl(piperazinyl eller homopiperazinyl)alkyltioler eller tiokarbamater.
KR790001578B1 (ko)	1979-11-05	벤즈이미다졸류의 제조 방법
CA1215364A (en)	1986-12-16	Benzimidazole derivatives, process for the preparation thereof and pharmaceutical composition containing the same

Legal Events

Date	Code	Title	Description
1994-12-19	B1	Patent granted (law 1993)
2004-11-01	PUP	Patent expired