HRP20110538T1 - Derivati 1,4-diazabiciklo[3.2.1]oktankarboksamida, njihovo dobivanje i njihova upotreba u terapiji - Google Patents
Derivati 1,4-diazabiciklo[3.2.1]oktankarboksamida, njihovo dobivanje i njihova upotreba u terapiji Download PDFInfo
- Publication number
- HRP20110538T1 HRP20110538T1 HR20110538T HRP20110538T HRP20110538T1 HR P20110538 T1 HRP20110538 T1 HR P20110538T1 HR 20110538 T HR20110538 T HR 20110538T HR P20110538 T HRP20110538 T HR P20110538T HR P20110538 T1 HRP20110538 T1 HR P20110538T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- group
- nr4c
- groups
- compound
- Prior art date
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- 239000003814 drug Substances 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- -1 nitro, amino Chemical group 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 239000012453 solvate Substances 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- NABZXASCLFSKLF-UHFFFAOYSA-N [1,2]oxazolo[4,3-b]pyridine Chemical compound C1=CC=NC2=CON=C21 NABZXASCLFSKLF-UHFFFAOYSA-N 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 1
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 claims 1
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims 1
- NMEPLWZDUIIAAC-UHFFFAOYSA-N 1h-pyrazolo[4,3-c]pyridazine Chemical compound C1=NN=C2C=NNC2=C1 NMEPLWZDUIIAAC-UHFFFAOYSA-N 0.000 claims 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims 1
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims 1
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical compound C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 claims 1
- PJVQPPHJEYPUDB-UHFFFAOYSA-N 2,3-dihydrofuro[3,2-b]pyridine Chemical compound C1=CC=C2OCCC2=N1 PJVQPPHJEYPUDB-UHFFFAOYSA-N 0.000 claims 1
- YBMFFLZLOZRFDD-UHFFFAOYSA-N 2,3-dihydrothieno[3,2-b]pyridine Chemical compound C1=CC=C2SCCC2=N1 YBMFFLZLOZRFDD-UHFFFAOYSA-N 0.000 claims 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 1
- MJQSRSOTRPMVKB-UHFFFAOYSA-N 5h-imidazo[4,5-c]pyridazine Chemical compound C1=NNC2=NC=NC2=C1 MJQSRSOTRPMVKB-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 208000019430 Motor disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- LUNHCIBEAIKLQJ-UHFFFAOYSA-N [1,2]oxazolo[4,3-c]pyridazine Chemical compound C1=CN=NC2=CON=C21 LUNHCIBEAIKLQJ-UHFFFAOYSA-N 0.000 claims 1
- YJMPFOXUBAJFFA-UHFFFAOYSA-N [1,2]thiazolo[4,3-b]pyridine Chemical compound C1=CC=NC2=CSN=C21 YJMPFOXUBAJFFA-UHFFFAOYSA-N 0.000 claims 1
- NXAFKXVMNVWYOF-UHFFFAOYSA-N [1,2]thiazolo[4,3-c]pyridazine Chemical group C1=CN=NC2=CSN=C21 NXAFKXVMNVWYOF-UHFFFAOYSA-N 0.000 claims 1
- BFPLMTPHDFFMTG-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridine Chemical compound C1=CN=C2OC=NC2=C1 BFPLMTPHDFFMTG-UHFFFAOYSA-N 0.000 claims 1
- FVFBQHPTVOZLNI-UHFFFAOYSA-N [1,3]oxazolo[5,4-c]pyridazine Chemical compound C1=NN=C2OC=NC2=C1 FVFBQHPTVOZLNI-UHFFFAOYSA-N 0.000 claims 1
- WFIHKLWVLPBMIQ-UHFFFAOYSA-N [1,3]thiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SC=NC2=C1 WFIHKLWVLPBMIQ-UHFFFAOYSA-N 0.000 claims 1
- WJRZTBNFQGTLRC-UHFFFAOYSA-N [1,3]thiazolo[5,4-c]pyridazine Chemical compound C1=NN=C2SC=NC2=C1 WJRZTBNFQGTLRC-UHFFFAOYSA-N 0.000 claims 1
- 210000001367 artery Anatomy 0.000 claims 1
- 125000002785 azepinyl group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 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 claims 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 1
- 239000012964 benzotriazole Substances 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 1
- 230000003920 cognitive function Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 claims 1
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 claims 1
- 210000002216 heart Anatomy 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims 1
- IZAJCEGIQMYVFM-UHFFFAOYSA-N thieno[3,2-c]pyridazine Chemical compound N1=CC=C2SC=CC2=N1 IZAJCEGIQMYVFM-UHFFFAOYSA-N 0.000 claims 1
- 229940125670 thienopyridine Drugs 0.000 claims 1
- 239000002175 thienopyridine Substances 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 210000003462 vein Anatomy 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 abstract 2
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 101710195183 Alpha-bungarotoxin Proteins 0.000 abstract 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 230000000648 anti-parkinson Effects 0.000 abstract 1
- 230000002738 anti-smoking effect Effects 0.000 abstract 1
- 230000000767 anti-ulcer Effects 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 239000000939 antiparkinson agent Substances 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- XLTANAWLDBYGFU-UHFFFAOYSA-N methyllycaconitine hydrochloride Natural products C1CC(OC)C2(C3C4OC)C5CC(C(C6)OC)C(OC)C5C6(O)C4(O)C2N(CC)CC31COC(=O)C1=CC=CC=C1N1C(=O)CC(C)C1=O XLTANAWLDBYGFU-UHFFFAOYSA-N 0.000 abstract 1
- 230000010807 negative regulation of binding Effects 0.000 abstract 1
- 239000003176 neuroleptic agent Substances 0.000 abstract 1
- 230000000701 neuroleptic effect Effects 0.000 abstract 1
- 230000000324 neuroprotective effect Effects 0.000 abstract 1
- 230000001777 nootropic effect Effects 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 229940125725 tranquilizer Drugs 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- 229910052722 tritium Inorganic materials 0.000 abstract 1
- LYTCVQQGCSNFJU-LKGYBJPKSA-N α-bungarotoxin Chemical compound C(/[C@H]1O[C@H]2C[C@H]3O[C@@H](CC(=C)C=O)C[C@H](O)[C@]3(C)O[C@@H]2C[C@@H]1O[C@@H]1C2)=C/C[C@]1(C)O[C@H]1[C@@]2(C)O[C@]2(C)CC[C@@H]3O[C@@H]4C[C@]5(C)O[C@@H]6C(C)=CC(=O)O[C@H]6C[C@H]5O[C@H]4C[C@@H](C)[C@H]3O[C@H]2C1 LYTCVQQGCSNFJU-LKGYBJPKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
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Abstract
Spoj, u obliku čistog enantiomera ili smjese enantiomera, koji ima opću formulu (I) naznačen time štoX predstavlja atom dušika ili skupina opće formule C-R2,svaki od P, Q, R i W neovisno predstavlja atom dušika ili skupinu opće formule C-R3,R1 predstavlja vodik atoma ili (C1-C6)alkilnu skupinu, R2 predstavlja (C1-C6)alkilnu skupinu, R3 predstavlja atom vodika ili halogena, ili (C1-C6)alkilnu, (C1-C6)alkoksi, nitro, amino, trifluormetilnu ili cijano skupinu, ili skupinu opće formule -NR4R5, -NR4C(=O)R5, -NR4C(=O)NR5R6, -NR4C(=O)OR5, NR4S(=O)2NR5R6,
Claims (4)
1. Spoj, u obliku čistog enantiomera ili smjese enantiomera, koji ima opću formulu (I)
[image]
naznačen time što
X predstavlja atom dušika ili skupina opće formule C-R2,
svaki od P, Q, R i W neovisno predstavlja atom dušika ili skupinu opće formule C-R3,
R1 predstavlja vodik atoma ili (C1-C6)alkilnu skupinu,
R2 predstavlja (C1-C6)alkilnu skupinu,
R3 predstavlja atom vodika ili halogena, ili (C1-C6)alkilnu, (C1-C6)alkoksi, nitro, amino, trifluormetilnu ili cijano skupinu, ili skupinu opće formule -NR4R5, -NR4C(=O)R5, -NR4C(=O)NR5R6, -NR4C(=O)OR5, NR4S(=O)2NR5R6, -OR5, -OC(=O)R5, -OC(=O)OR5, -OC(=O)ONR4R5, -OC(=O)SR5, -C(=O)OR5, C(=O)R5, -C(=O)NR4R5, SR5, -S(=O)R5, -S(=O)2R5 ili -S(=O)2NR4R6, ili fenilnu skupinu, izborno supstituiranu s jednom ili više skupina, koje se bira između atoma halogena i (C1-C6)alkilnih, (C1-C6)alkoksi, nitro, amino, trifluormetilnih ili cijano skupina ili skupina opće formule -NR4R5, -NR4C(=O)R5, -NR4C(=O)NR5R6, -NR4C(=O)OR5, NR4S(=O)2NR5R6, -OR5, -OC(=O)R5, -OC(=O)OR5, -OC(=O)ONR4R5, -OC(=O)SR5, -C(=O)OR5, -C(=O)NR4R5, SR5, -S(=O)R5, -S(=O)2R5 ili -S(=O)2NR4R6,
ili R3 predstavlja skupinu koju se bira između imidazolskog, piridinskog, piridazinskog, pirimidinskog, pirazolskog, pirazinskog, triazolskog, kinolinskog, izokinolinskog, tetrazolskog, furanskog, tiofenskog, tiazolskog, izotiazolskog, oksazolskog, izoksazolskog, pirolskog, tetrahidrokinolinskog, tetrahidroizokinolinskog, indolskog, benzimidazolskog, benzofuranskog, dihidrobenzofuranskog, cinolinskog, indazolskog, ftalazinskog, triazinskog, izoindolskog, oksadiazolskog, tiadiazolskog, furazanskog, benzofurazanskog, benzotiofenskog, dihidrobenzotiofenskog, benzotriazolskog, benzotiazolskog, benzizotiazolskog, benzoksazolskog, benzizoksazolskog, kinazolinskog, kinoksalinskog, naftiridinskog, dihidrokinolinskog, dihidroizokinolinskog, furopiridinskog, dihidrofuropiridinskog, pirolopiridinskog, tienopiridinskog, dihidrotienopiridinskog, imidazopiridinskog, pirazolopiridinskog, oksazolopiridinskog, izoksazolopiridinskog, izoksazolopiridinskog, tiazolopiridinskog, izotiazolopiridinskog, pirolopirimidinskog, furopirimidinskog, dihidrofuropirimidinskog, tienopirimidinskog, dihidrotienopirimidinskog, imidazopirimidinskog, pirazolopirimidinskog, oksazolopirimidinskog, izoksazolopirimidinskog, tiazolopirimidinskog, izotiazolopirimidinskog, furopirazinskog, dihidrofuropirazinskog, pirolopirazinskog, tienopirazinskog, dihidrotienopirazinskog, imidazopirazinskog, pirazolopirazinskog, oksazolopirazinskog, izoksazolopirazinskog, tiazolopirazinskog, izotiazolopirazinskog, furopiridazinskog, dihidrofuropiridazinskog, pirolopiridazinskog, tienopiridazinskog, dihidrotienopiridazinskog, imidazopiridazinskog, pirazolopiridazinskog, oksazolopiridazinskog, izoksazolopiridazinskog, tiazolopiridazinskog ili izotiazolopiridazinskog prstena,
svaki od R4, R5 i R6 neovisno predstavlja atom halogena, ili nerazgranatu ili razgranatu (C1-C6)alkilnu, nerazgranatu ili razgranatu (C2-C6)alkenilnu, ili nerazgranatu ili razgranatu (C2-C6)alkinilnu skupinu, ili (C3-C8)cikloalkilnu, (C3-C8)cikloalkil(C1-C3)alkilnu, (C4-C8)cikloalkenilnu ili fenilnu skupinu,
gdje skupine općih formula NR4R5 i NR5R6 mogu, s atomom dušika koji ih nosi, tvoriti skupinu koju se bira između aziridinilne, azetidinilne, pirolidinilne, piperidinilne, azepinilne, piperazinilne, morfolinilne, tiomorfolinilne, pirolinilne, indolinilne, pirazolinilne, pirazolidinilne, imidazolinilne, 3H-indolila, kinuklidinilne i kinolizinilne skupine,
u obliku baze, solvata ili adicijske soli s kiselinom.
2. Medikament, naznačen time što sadrži spoj u skladu s patentnim zahtjevom 1.
3. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s patentnim zahtjevom 1, u kombinaciji s pomoćnom tvari.
4. Upotreba spoja u skladu s patentnim zahtjevom 1, naznačena time što je navedeni spoj namijenjen pripravi medikamenta za liječenje poremećaja uzrokovanih poremećajem kognitivnih funkcija i poremećajem pažnje ili motoričkim poremećajima, neurološkim ili psihijatrijskim poremećajima, ili za sprječavanje simptoma koje uzrokuje ustezanje od tvari koje uzrokuju ovisnost, ili za liječenje patoloških pojava na srcu, krvnim žilama, arterijama i venama.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0400390A FR2865208B1 (fr) | 2004-01-16 | 2004-01-16 | Derives de 1,4-diazabicyclo[3.2.1]octanecarboxmique, leur preparation et leur application en therapeutique |
| PCT/FR2005/000027 WO2005077955A1 (fr) | 2004-01-16 | 2005-01-07 | Derives de 1,4-diazabicyclo[3.2.1]octanecarboxamide, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110538T1 true HRP20110538T1 (hr) | 2011-08-31 |
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ID=34707894
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110538T HRP20110538T1 (hr) | 2004-01-16 | 2011-07-20 | Derivati 1,4-diazabiciklo[3.2.1]oktankarboksamida, njihovo dobivanje i njihova upotreba u terapiji |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7589201B2 (hr) |
| EP (1) | EP1709052B1 (hr) |
| JP (1) | JP4781279B2 (hr) |
| KR (1) | KR101146445B1 (hr) |
| CN (1) | CN1946726B (hr) |
| AT (1) | ATE507228T1 (hr) |
| AU (1) | AU2005212867B2 (hr) |
| BR (1) | BRPI0506879A (hr) |
| CA (1) | CA2549954C (hr) |
| CY (1) | CY1111707T1 (hr) |
| DE (1) | DE602005027659D1 (hr) |
| DK (1) | DK1709052T3 (hr) |
| ES (1) | ES2365141T3 (hr) |
| FR (1) | FR2865208B1 (hr) |
| HK (1) | HK1105632A1 (hr) |
| HR (1) | HRP20110538T1 (hr) |
| IL (1) | IL176702A (hr) |
| MA (1) | MA28238A1 (hr) |
| NO (1) | NO20063666L (hr) |
| NZ (1) | NZ548046A (hr) |
| PL (1) | PL1709052T3 (hr) |
| PT (1) | PT1709052E (hr) |
| RS (1) | RS51910B (hr) |
| RU (1) | RU2361873C2 (hr) |
| SI (1) | SI1709052T1 (hr) |
| WO (1) | WO2005077955A1 (hr) |
| ZA (1) | ZA200605823B (hr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0510212A (pt) * | 2004-05-07 | 2007-10-16 | Memory Pharm Corp | 1h-indazóis, benzotiazóis, 1,2 - benzoisoxazóis, 1,2-benzoisotiazóis, e cromonas e a preparação e usos dos mesmos |
| US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7645881B2 (en) | 2004-07-22 | 2010-01-12 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US20060258691A1 (en) * | 2005-05-13 | 2006-11-16 | Joseph Barbosa | Methods and compositions for improving cognition |
| AU2006283511A1 (en) * | 2005-08-24 | 2007-03-01 | Lexicon Pharmaceuticals, Inc. | Pyrrolopyridine, pyrrolopyrimidine and pyrazolopyridine compounds, compositions comprising them, and methods of their use |
| AR079980A1 (es) * | 2010-01-13 | 2012-03-07 | Sanofi Aventis | Derivados de oxazolopirimidina sustituida en 2,5,7 |
| JO3407B1 (ar) | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9420521D0 (en) * | 1994-10-12 | 1994-11-30 | Smithkline Beecham Plc | Novel compounds |
| GB9803411D0 (en) * | 1998-02-18 | 1998-04-15 | Smithkline Beecham Plc | Novel compounds |
| FR2809730B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo[3.2.2] nonanebenzoxazole, -benzothiazole et -benzimidazole, leur preparation et leur application therapeutique |
| US6673811B1 (en) * | 2001-11-19 | 2004-01-06 | Neurogen Corporation | 1H-pyrrolo [3,2-b] pyridine-3-carboxylic acid amines as GABAA receptor ligands |
| MXPA04004711A (es) * | 2001-11-19 | 2005-08-16 | Neurogen Corp | Amidas del acido 1h-pirrolo(3,2-b(piridin-3-carboxilico. |
| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| FR2845388B1 (fr) * | 2002-10-08 | 2004-11-12 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo[3.2.2]nonanecarboxamides, leur preparation et leur application en therapeutique |
| US7456171B2 (en) * | 2002-10-08 | 2008-11-25 | Sanofi-Aventis | 1,4-Diazabicyclo[3.2.2]nonanecarboxamide derivatives, preparation and therapeutic use thereof |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
-
2004
- 2004-01-16 FR FR0400390A patent/FR2865208B1/fr not_active Expired - Fee Related
-
2005
- 2005-01-07 DK DK05717375.9T patent/DK1709052T3/da active
- 2005-01-07 AT AT05717375T patent/ATE507228T1/de active
- 2005-01-07 NZ NZ548046A patent/NZ548046A/en not_active IP Right Cessation
- 2005-01-07 BR BRPI0506879-7A patent/BRPI0506879A/pt not_active Application Discontinuation
- 2005-01-07 WO PCT/FR2005/000027 patent/WO2005077955A1/fr active Application Filing
- 2005-01-07 PT PT05717375T patent/PT1709052E/pt unknown
- 2005-01-07 ES ES05717375T patent/ES2365141T3/es active Active
- 2005-01-07 DE DE602005027659T patent/DE602005027659D1/de active Active
- 2005-01-07 AU AU2005212867A patent/AU2005212867B2/en not_active Ceased
- 2005-01-07 CA CA2549954A patent/CA2549954C/fr not_active Expired - Fee Related
- 2005-01-07 EP EP05717375A patent/EP1709052B1/fr active Active
- 2005-01-07 CN CN2005800026301A patent/CN1946726B/zh not_active Expired - Fee Related
- 2005-01-07 RS RS20110299A patent/RS51910B/en unknown
- 2005-01-07 RU RU2006129633/04A patent/RU2361873C2/ru not_active IP Right Cessation
- 2005-01-07 KR KR1020067014266A patent/KR101146445B1/ko not_active IP Right Cessation
- 2005-01-07 SI SI200531324T patent/SI1709052T1/sl unknown
- 2005-01-07 JP JP2006548338A patent/JP4781279B2/ja not_active Expired - Fee Related
- 2005-01-07 PL PL05717375T patent/PL1709052T3/pl unknown
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2006
- 2006-06-22 MA MA29129A patent/MA28238A1/fr unknown
- 2006-07-04 IL IL176702A patent/IL176702A/en not_active IP Right Cessation
- 2006-07-10 US US11/456,345 patent/US7589201B2/en not_active Expired - Fee Related
- 2006-07-14 ZA ZA2006/05823A patent/ZA200605823B/en unknown
- 2006-08-14 NO NO20063666A patent/NO20063666L/no not_active Application Discontinuation
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2007
- 2007-10-05 HK HK07110838.8A patent/HK1105632A1/xx not_active IP Right Cessation
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2011
- 2011-07-19 CY CY20111100703T patent/CY1111707T1/el unknown
- 2011-07-20 HR HR20110538T patent/HRP20110538T1/hr unknown
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