NL8301844A - Piperazinederivaten, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten. - Google Patents
Piperazinederivaten, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten. Download PDFInfo
- Publication number
- NL8301844A NL8301844A NL8301844A NL8301844A NL8301844A NL 8301844 A NL8301844 A NL 8301844A NL 8301844 A NL8301844 A NL 8301844A NL 8301844 A NL8301844 A NL 8301844A NL 8301844 A NL8301844 A NL 8301844A
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- formula
- compound
- carbon atoms
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- -1 trimethylene, tetramethylene Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000000059 bradycardiac effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000000701 neuroleptic effect Effects 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- POWKNAVDGFNMSG-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-piperazin-1-ylbutan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCNCC1 POWKNAVDGFNMSG-UHFFFAOYSA-N 0.000 description 1
- QHDXPJMOWRLLRV-UHFFFAOYSA-N 1-(4-fluorophenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=C(F)C=C1 QHDXPJMOWRLLRV-UHFFFAOYSA-N 0.000 description 1
- QLEIDMAURCRVCX-UHFFFAOYSA-N 1-propylpiperazine Chemical compound CCCN1CCNCC1 QLEIDMAURCRVCX-UHFFFAOYSA-N 0.000 description 1
- YKWBEPUOVBMENG-UHFFFAOYSA-N 2-chloro-5-nitropyridin-4-amine Chemical compound NC1=CC(Cl)=NC=C1[N+]([O-])=O YKWBEPUOVBMENG-UHFFFAOYSA-N 0.000 description 1
- WERABQRUGJIMKQ-UHFFFAOYSA-N 6-chloro-3-nitropyridin-2-amine Chemical compound NC1=NC(Cl)=CC=C1[N+]([O-])=O WERABQRUGJIMKQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 108091002531 OF-1 protein Proteins 0.000 description 1
- 102100036247 Phosphatidylinositol-glycan biosynthesis class X protein Human genes 0.000 description 1
- 101710103736 Phosphatidylinositol-glycan biosynthesis class X protein Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 125000006243 carbonyl protecting group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- RSUVYMGADVXGOU-BUHFOSPRSA-N cinanserin Chemical compound CN(C)CCCSC1=CC=CC=C1NC(=O)\C=C\C1=CC=CC=C1 RSUVYMGADVXGOU-BUHFOSPRSA-N 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000028570 negative regulation of locomotion Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
- 229960001999 phentolamine Drugs 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229960001289 prazosin Drugs 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH331782 | 1982-05-28 | ||
| CH331782 | 1982-05-28 | ||
| CH337982 | 1982-06-02 | ||
| CH337982 | 1982-06-02 | ||
| CH448582 | 1982-07-22 | ||
| CH448582 | 1982-07-22 | ||
| CH448482 | 1982-07-22 | ||
| CH448482 | 1982-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8301844A true NL8301844A (nl) | 1983-12-16 |
Family
ID=27428609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8301844A NL8301844A (nl) | 1982-05-28 | 1983-05-25 | Piperazinederivaten, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten. |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4565816A (fr) |
| AU (1) | AU573524B2 (fr) |
| CA (1) | CA1203801A (fr) |
| DE (1) | DE3318671A1 (fr) |
| DK (1) | DK237383A (fr) |
| ES (1) | ES522786A0 (fr) |
| FI (1) | FI73999C (fr) |
| FR (2) | FR2527608B1 (fr) |
| GB (1) | GB2120670B (fr) |
| HU (1) | HU191844B (fr) |
| IE (1) | IE55312B1 (fr) |
| IL (1) | IL68793A (fr) |
| NL (1) | NL8301844A (fr) |
| NZ (1) | NZ204369A (fr) |
| PH (1) | PH22871A (fr) |
| PT (1) | PT76768B (fr) |
| SE (1) | SE452766B (fr) |
| WO (1) | WO1983004254A1 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4803203A (en) * | 1986-11-05 | 1989-02-07 | Warner-Lambert Company | Phenyl and heterocyclic piperazinyl alkoxy-benzheterocyclic compounds as antipsychotic agents |
| US5502187A (en) * | 1992-04-03 | 1996-03-26 | The Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
| US6432957B1 (en) * | 2001-06-29 | 2002-08-13 | Kowa Co., Ltd. | Piperazine derivative |
| GB0215293D0 (en) * | 2002-07-03 | 2002-08-14 | Rega Foundation | Viral inhibitors |
| DK2161273T3 (en) * | 2003-12-22 | 2015-07-20 | Leuven K U Res & Dev | Imidazo [4,5-C] pyridine compounds and methods for antiviral therapy |
| PT1841765E (pt) * | 2004-12-21 | 2009-05-14 | Gilead Sciences Inc | Anticorpos para mcp-1 humano |
| US7582636B2 (en) * | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
| US7754720B2 (en) * | 2006-07-07 | 2010-07-13 | Gilead Sciences, Inc. | Pyridazine compound and use thereof |
| UA99466C2 (en) | 2007-07-06 | 2012-08-27 | Гилиад Сайенсиз, Инк. | Crystalline pyridazine compound |
| JP5960688B2 (ja) | 2010-05-17 | 2016-08-02 | インコゼン セラピューティクス プライベート リミテッド | プロテインキナーゼ調節物質としての新規３，５−二置換−３ｈ−［１，２，３］トリアゾロ［４，５−ｂ］ピリジン化合物 |
| CN102952121A (zh) * | 2012-07-27 | 2013-03-06 | 北京海步国际医药科技发展有限公司 | 一种哌嗪衍生物的一种改进的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL129219C (fr) * | 1965-12-16 | |||
| GB1165283A (en) * | 1967-01-17 | 1969-09-24 | Science Union & Cie | New Purine Derivatives and processes for prepararing them |
| US4022779A (en) * | 1974-07-25 | 1977-05-10 | E. R. Squibb & Sons, Inc. | Amino derivatives of pyrido(3,4-b)pyrazine carboxylic acids and esters |
| US4082845A (en) * | 1977-04-25 | 1978-04-04 | Merck & Co., Inc. | 3-(1-Piperazinyl)-pyrido[2,3-b]pyrazines |
-
1983
- 1983-05-19 FR FR8308484A patent/FR2527608B1/fr not_active Expired
- 1983-05-20 FI FI831790A patent/FI73999C/fi not_active IP Right Cessation
- 1983-05-21 DE DE19833318671 patent/DE3318671A1/de not_active Withdrawn
- 1983-05-25 NL NL8301844A patent/NL8301844A/nl not_active Application Discontinuation
- 1983-05-25 GB GB08314456A patent/GB2120670B/en not_active Expired
- 1983-05-25 WO PCT/CH1983/000067 patent/WO1983004254A1/fr not_active Ceased
- 1983-05-26 AU AU15012/83A patent/AU573524B2/en not_active Ceased
- 1983-05-26 NZ NZ204369A patent/NZ204369A/en unknown
- 1983-05-26 DK DK237383A patent/DK237383A/da not_active Application Discontinuation
- 1983-05-26 PH PH28969A patent/PH22871A/en unknown
- 1983-05-26 CA CA000428935A patent/CA1203801A/fr not_active Expired
- 1983-05-26 IL IL68793A patent/IL68793A/xx unknown
- 1983-05-26 PT PT76768A patent/PT76768B/fr unknown
- 1983-05-26 HU HU831873A patent/HU191844B/hu not_active IP Right Cessation
- 1983-05-26 SE SE8302979A patent/SE452766B/sv not_active IP Right Cessation
- 1983-05-27 ES ES522786A patent/ES522786A0/es active Granted
- 1983-05-27 US US06/498,952 patent/US4565816A/en not_active Expired - Fee Related
- 1983-05-27 IE IE1263/83A patent/IE55312B1/en unknown
- 1983-09-12 FR FR8314586A patent/FR2536398B1/fr not_active Expired
-
1985
- 1985-10-04 US US06/784,832 patent/US4652565A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2536398B1 (fr) | 1986-12-05 |
| FI831790A0 (fi) | 1983-05-20 |
| GB8314456D0 (en) | 1983-06-29 |
| IE831263L (en) | 1983-11-28 |
| WO1983004254A1 (fr) | 1983-12-08 |
| DK237383A (da) | 1983-11-29 |
| CA1203801A (fr) | 1986-04-29 |
| GB2120670B (en) | 1985-11-27 |
| FI73999C (fi) | 1987-12-10 |
| ES8502988A1 (es) | 1985-02-01 |
| SE8302979D0 (sv) | 1983-05-26 |
| FR2527608A1 (fr) | 1983-12-02 |
| GB2120670A (en) | 1983-12-07 |
| SE452766B (sv) | 1987-12-14 |
| FR2527608B1 (fr) | 1986-10-10 |
| IL68793A0 (en) | 1983-09-30 |
| PT76768B (fr) | 1986-01-28 |
| FR2536398A1 (fr) | 1984-05-25 |
| AU1501283A (en) | 1983-12-01 |
| SE8302979L (sv) | 1983-11-29 |
| FI831790L (fi) | 1983-11-29 |
| ES522786A0 (es) | 1985-02-01 |
| US4565816A (en) | 1986-01-21 |
| HU191844B (en) | 1987-04-28 |
| NZ204369A (en) | 1986-09-10 |
| AU573524B2 (en) | 1988-06-16 |
| IE55312B1 (en) | 1990-08-01 |
| PH22871A (en) | 1989-01-19 |
| US4652565A (en) | 1987-03-24 |
| FI73999B (fi) | 1987-08-31 |
| IL68793A (en) | 1987-03-31 |
| DE3318671A1 (de) | 1983-12-01 |
| PT76768A (fr) | 1983-06-01 |
| DK237383D0 (da) | 1983-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |