BG64098B1 - Заместени аза- и диазациклохептанови и циклооктанови производни и използването им - Google Patents
Заместени аза- и диазациклохептанови и циклооктанови производни и използването им Download PDFInfo
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- BG64098B1 BG64098B1 BG102616A BG10261698A BG64098B1 BG 64098 B1 BG64098 B1 BG 64098B1 BG 102616 A BG102616 A BG 102616A BG 10261698 A BG10261698 A BG 10261698A BG 64098 B1 BG64098 B1 BG 64098B1
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- Prior art keywords
- alkyl
- halogen
- compounds
- phenyl
- ring
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- 125000000640 cyclooctyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 title description 3
- QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
- 239000003446 ligand Substances 0.000 abstract description 5
- 102000004073 Dopamine D3 Receptors Human genes 0.000 abstract description 3
- 108090000525 Dopamine D3 Receptors Proteins 0.000 abstract description 3
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 40
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000460 chlorine Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 23
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 22
- 235000014121 butter Nutrition 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- -1 2-pyrimidyl group Chemical group 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- 108020003175 receptors Proteins 0.000 description 12
- 102000005962 receptors Human genes 0.000 description 12
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000003217 pyrazoles Chemical group 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000011087 fumaric acid Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000001301 oxygen 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
- 150000003230 pyrimidines Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 108050004812 Dopamine receptor Proteins 0.000 description 3
- 102000015554 Dopamine receptor Human genes 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 102000004142 Trypsin Human genes 0.000 description 3
- 108090000631 Trypsin Proteins 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000012139 lysis buffer Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000012588 trypsin Substances 0.000 description 3
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 2
- ZSPBHCKOHOVORF-UHFFFAOYSA-N 2-methylsulfonyl-4-phenylmethoxypyrimidine Chemical compound CS(=O)(=O)C1=NC=CC(OCC=2C=CC=CC=2)=N1 ZSPBHCKOHOVORF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- 101100234822 Caenorhabditis elegans ltd-1 gene Proteins 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 2
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000012980 RPMI-1640 medium Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000000164 antipsychotic agent Substances 0.000 description 2
- 206010003119 arrhythmia Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 210000003715 limbic system Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
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- 238000001525 receptor binding assay Methods 0.000 description 2
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- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
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- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
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Classifications
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19600934A DE19600934A1 (de) | 1996-01-12 | 1996-01-12 | Substituierte Aza- und Diazacycloheptan- und Cyclooctanverbindungen und deren Verwendung |
| PCT/EP1997/000106 WO1997025324A1 (de) | 1996-01-12 | 1997-01-10 | Substituierte aza- und diazacycloheptan- und -cyclooctanverbindungen und deren verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG102616A BG102616A (en) | 1999-04-30 |
| BG64098B1 true BG64098B1 (bg) | 2003-12-31 |
Family
ID=7782613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG102616A BG64098B1 (bg) | 1996-01-12 | 1998-07-09 | Заместени аза- и диазациклохептанови и циклооктанови производни и използването им |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US6214822B1 (enExample) |
| EP (1) | EP0877744B1 (enExample) |
| JP (1) | JP4349657B2 (enExample) |
| KR (1) | KR100441073B1 (enExample) |
| CN (2) | CN1075070C (enExample) |
| AR (1) | AR005868A1 (enExample) |
| AT (1) | ATE273301T1 (enExample) |
| AU (1) | AU717726B2 (enExample) |
| BG (1) | BG64098B1 (enExample) |
| CA (1) | CA2241787C (enExample) |
| CO (1) | CO4790173A1 (enExample) |
| CZ (1) | CZ297981B6 (enExample) |
| DE (2) | DE19600934A1 (enExample) |
| ES (1) | ES2225947T3 (enExample) |
| HR (1) | HRP970021A2 (enExample) |
| HU (1) | HU228457B1 (enExample) |
| IL (1) | IL125076A (enExample) |
| MX (1) | MX9805499A (enExample) |
| NO (1) | NO316753B1 (enExample) |
| NZ (1) | NZ326332A (enExample) |
| PL (1) | PL327692A1 (enExample) |
| SK (1) | SK284987B6 (enExample) |
| TR (1) | TR199801302T2 (enExample) |
| TW (1) | TW475929B (enExample) |
| WO (1) | WO1997025324A1 (enExample) |
| ZA (1) | ZA97209B (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19728996A1 (de) * | 1997-07-07 | 1999-01-14 | Basf Ag | Triazolverbindungen und deren Verwendung |
| GB9810876D0 (en) | 1998-05-20 | 1998-07-22 | Smithkline Beecham Plc | Compounds |
| IL142388A0 (en) | 1998-10-08 | 2002-03-10 | Smithkline Beecham Plc | Tetrahydrobenzazepine derivatives useful as modulators of dopamine d3 receptors (antipsychotic agents) |
| AR022230A1 (es) * | 1999-01-12 | 2002-09-04 | Abbott Gmbh & Co Kg | Compuestos de triazol, composicion farmaceutica que los comprende y uso de los mismos para preparar dicha composicion |
| DE19922443A1 (de) | 1999-05-07 | 2000-11-09 | Basf Ag | Verwendung von Dopamin-D3-Rezeptorliganden zur Herstellung von Arzneimittel für die Behandlung von Nierenfunktionsstörungen |
| US7037916B2 (en) | 1999-07-15 | 2006-05-02 | Pharmacopeia Drug Discovery, Inc. | Pyrimidine derivatives as IL-8 receptor antagonists |
| DE50114170D1 (de) * | 2000-03-27 | 2008-09-11 | Abbott Gmbh & Co Kg | Dopamin-d3-rezeptor-liganden zur behandlung von sucht |
| IL157413A0 (en) | 2001-02-16 | 2004-03-28 | Aventis Pharmaceuticals Inc Av | Heterocyclic substituted carbonyl derivatives and their use as dopamine d3 receptor ligands |
| DE10109866A1 (de) * | 2001-03-01 | 2002-09-05 | Abbott Gmbh & Co Kg | Triazolverbindungen und deren Verwendung zur Prophylaxe und Therapie neurodegenerativer Erkrankungen, Hirntrauma und zerebraler Ischämie |
| DE10131543A1 (de) * | 2001-06-29 | 2003-01-16 | Abbott Lab | Pyrimidinoxyalkylpiperazine und ihre therapeutische Verwendung |
| NZ533397A (en) * | 2001-11-28 | 2005-12-23 | Sod Conseils Rech Applic | 5-sulphanyl-4H-1,2,4-triazole derivatives and their use as a medicament |
| CN1642422A (zh) * | 2002-03-15 | 2005-07-20 | 西巴特殊化学品控股有限公司 | 4－氨基嘧啶及其在表面抗菌处理中的应用 |
| DE10304870A1 (de) | 2003-02-06 | 2004-08-19 | Abbott Gmbh & Co. Kg | Triazolverbindungen und ihre therapeutische Verwendung |
| TW200507841A (en) * | 2003-03-27 | 2005-03-01 | Glaxo Group Ltd | Antibacterial agents |
| DE10358004A1 (de) * | 2003-12-11 | 2005-07-14 | Abbott Gmbh & Co. Kg | Ketolactam-Verbindungen und ihre Verwendung |
| DE102004027358A1 (de) * | 2004-06-04 | 2005-12-29 | Abbott Gmbh & Co. Kg | Pyrimidinverbindungen und ihre Verwendung |
| FR2877005A1 (fr) * | 2004-10-22 | 2006-04-28 | Bioprojet Soc Civ Ile | Nouveaux derives d'arylpiperazine |
| US7511035B2 (en) * | 2005-01-25 | 2009-03-31 | Glaxo Group Limited | Antibacterial agents |
| JP2007106746A (ja) * | 2005-09-13 | 2007-04-26 | Tosoh Corp | 新規アリールホモピペラジン類、またはその塩と製造方法 |
| JPWO2007099828A1 (ja) * | 2006-02-23 | 2009-07-16 | 塩野義製薬株式会社 | 環式基で置換された含窒素複素環誘導体 |
| US20070293548A1 (en) * | 2006-03-31 | 2007-12-20 | Wang Eric Y | Inhibitors of semicarbazide-sensitive amine oxidase (SSAO) and VAP-1 mediated adhesion useful for treatment and prevention of diseases |
| EP1882688A1 (en) * | 2006-07-25 | 2008-01-30 | EPFL Ecole Polytechnique Fédérale de Lausanne | Labelling of fusion proteins with synthetic probes |
| JP4840440B2 (ja) * | 2008-12-24 | 2011-12-21 | ソニー株式会社 | 画像処理装置およびその方法、並びにプログラム |
| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| JP2013518046A (ja) * | 2010-01-25 | 2013-05-20 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | 特定のキヌレニン−３−モノオキシゲナーゼインヒビターおよびその医薬組成物ならびにこれらの使用方法 |
| WO2012003418A2 (en) * | 2010-07-02 | 2012-01-05 | The University Of North Carolina At Chapel Hill | Functionally selective ligands of dopamine d2 receptors |
| NZ610315A (en) | 2010-11-15 | 2015-08-28 | Univ Leuven Kath | Antiviral condensed heterocyclic compounds |
| MX2014002459A (es) | 2011-08-30 | 2014-04-10 | Chdi Foundation Inc | Inhibidores de quinurenina-3-monooxigenasa, composiciones farmaceuticas y metodos de uso de los mismos. |
| HRP20170928T1 (hr) | 2011-08-30 | 2017-09-22 | Chdi Foundation, Inc. | Inhibitori kinurenin-3-monooksigenaze, farmaceutski pripravci, i postupci za njihovu upotrebu |
| EP3756666A1 (en) | 2013-12-24 | 2020-12-30 | Oncotartis Inc. | Nicotinamide compound for use in the treatment of cancer |
| CR20170061A (es) | 2014-07-17 | 2017-07-17 | Chdi Foundation Inc | Métodos y composiciones para el tratamiento de trastornos relacionados con vih |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE628766A (enExample) | 1962-12-26 | |||
| BE792206A (enExample) | 1971-12-02 | 1973-06-01 | Byk Gulden Lomberg Chem Fab | |
| US5139998A (en) | 1988-08-31 | 1992-08-18 | Superconductor Technologies, Inc. | Controlled thallous oxide evaporation for thallium superconductor films and reactor design |
| SE8803429D0 (sv) * | 1988-09-28 | 1988-09-28 | Pharmacia Ab | Novel pyridyl- and pyrimidyl derivatives |
| US5008267A (en) | 1988-10-29 | 1991-04-16 | Mitsui Toatsu Chemicals, Incorporated | Pyrimidinedione compounds, method of producing the same and antiarrythmic agents containing the same |
| JP2815218B2 (ja) | 1990-04-13 | 1998-10-27 | 三井化学株式会社 | ピリミジンジオン誘導体、およびそれを含有する抗不整脈剤 |
| FR2663638B2 (fr) | 1990-04-06 | 1995-02-10 | Institut Nal Sante Recherc Medic | Polypeptides ayant une activite de recepteur dopaminergique, acides nucleiques codant pour ces polypeptides et utilisation de ces polypeptides pour le criblage de substances actives sur ces polypeptides. |
| JP2518965B2 (ja) | 1990-09-21 | 1996-07-31 | 三井東圧化学株式会社 | 新規ピリジン誘導体及びそれを有効成分として含有する制癌剤効果増強剤 |
| FR2668771B1 (fr) | 1990-11-06 | 1995-03-17 | Inst Nat Sante Rech Med | Acides nucleiques codant pour des polypeptides ayant une activite de recepteur dopaminergique humain et utilisation de ces polypeptides pour le criblage de substances actives sur ces polypeptides. |
| DE4425145A1 (de) | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung von Thiazol- und Thiadiazolverbindungen |
| DE4425143A1 (de) | 1994-07-15 | 1996-01-18 | Basf Ag | Substituierte Pyrimidinverbindungen und deren Verwendung |
| DE4425144A1 (de) | 1994-07-15 | 1996-01-18 | Basf Ag | Triazolverbindungen und deren Verwendung |
| DE4425146A1 (de) | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung heterocyclischer Verbindungen |
| US5635503A (en) * | 1995-06-07 | 1997-06-03 | Bristol-Myers Squibb Company | Dihydropyridine npy antagonists: piperazine derivatives |
| FR2742149B1 (fr) | 1995-12-11 | 1998-02-13 | Inst Nat Sante Rech Med | Nouveaux derives de 2-naphtamides et leurs applications therapeutiques |
-
1996
- 1996-01-12 DE DE19600934A patent/DE19600934A1/de not_active Withdrawn
-
1997
- 1997-01-10 CN CN97192755A patent/CN1075070C/zh not_active Expired - Lifetime
- 1997-01-10 CA CA002241787A patent/CA2241787C/en not_active Expired - Lifetime
- 1997-01-10 ES ES97901000T patent/ES2225947T3/es not_active Expired - Lifetime
- 1997-01-10 TR TR1998/01302T patent/TR199801302T2/xx unknown
- 1997-01-10 US US09/101,265 patent/US6214822B1/en not_active Expired - Lifetime
- 1997-01-10 ZA ZA97209A patent/ZA97209B/xx unknown
- 1997-01-10 DE DE59711847T patent/DE59711847D1/de not_active Expired - Lifetime
- 1997-01-10 NZ NZ326332A patent/NZ326332A/en not_active IP Right Cessation
- 1997-01-10 IL IL12507697A patent/IL125076A/en not_active IP Right Cessation
- 1997-01-10 SK SK941-98A patent/SK284987B6/sk not_active IP Right Cessation
- 1997-01-10 PL PL97327692A patent/PL327692A1/xx unknown
- 1997-01-10 HR HRP19600934.0A patent/HRP970021A2/hr not_active Application Discontinuation
- 1997-01-10 CZ CZ0215998A patent/CZ297981B6/cs not_active IP Right Cessation
- 1997-01-10 WO PCT/EP1997/000106 patent/WO1997025324A1/de not_active Ceased
- 1997-01-10 CO CO97000912A patent/CO4790173A1/es unknown
- 1997-01-10 AT AT97901000T patent/ATE273301T1/de not_active IP Right Cessation
- 1997-01-10 JP JP52486997A patent/JP4349657B2/ja not_active Expired - Lifetime
- 1997-01-10 AU AU14407/97A patent/AU717726B2/en not_active Expired
- 1997-01-10 EP EP97901000A patent/EP0877744B1/de not_active Expired - Lifetime
- 1997-01-10 HU HU9901590A patent/HU228457B1/hu unknown
- 1997-01-10 KR KR10-1998-0705263A patent/KR100441073B1/ko not_active Expired - Lifetime
- 1997-01-13 TW TW086100296A patent/TW475929B/zh not_active IP Right Cessation
- 1997-01-13 AR ARP970100120A patent/AR005868A1/es not_active Application Discontinuation
-
1998
- 1998-07-07 MX MX9805499A patent/MX9805499A/es unknown
- 1998-07-09 BG BG102616A patent/BG64098B1/bg unknown
- 1998-07-10 NO NO19983187A patent/NO316753B1/no not_active IP Right Cessation
-
2000
- 2000-10-27 US US09/696,941 patent/US6352981B1/en not_active Expired - Lifetime
-
2001
- 2001-04-20 CN CNB011170697A patent/CN1146551C/zh not_active Expired - Lifetime
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