NO316651B1 - Nye pyridinforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem - Google Patents
Nye pyridinforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem Download PDFInfo
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- NO316651B1 NO316651B1 NO20004295A NO20004295A NO316651B1 NO 316651 B1 NO316651 B1 NO 316651B1 NO 20004295 A NO20004295 A NO 20004295A NO 20004295 A NO20004295 A NO 20004295A NO 316651 B1 NO316651 B1 NO 316651B1
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- isomers
- pharmaceutically acceptable
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- 238000002360 preparation method Methods 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims description 49
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 150000003222 pyridines Chemical class 0.000 title abstract description 3
- -1 Pyridine derivatives compounds Chemical class 0.000 claims abstract description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 117
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229910052740 iodine Chemical group 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 206010033664 Panic attack Diseases 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 208000019906 panic disease Diseases 0.000 claims description 4
- 208000019899 phobic disease Diseases 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- NWCWKSDDIUZJQM-UHFFFAOYSA-N 3-[2-(4-furo[3,2-c]pyridin-4-ylpiperazin-1-yl)ethyl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CCN(CC1)CCN1C1=NC=CC2=C1C=CO2 NWCWKSDDIUZJQM-UHFFFAOYSA-N 0.000 claims description 3
- IEBPBISRJJHYBE-UHFFFAOYSA-N 3-[2-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)ethyl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CCN(CC1)CCN1C1=NC=CC2=C1C=CS2 IEBPBISRJJHYBE-UHFFFAOYSA-N 0.000 claims description 3
- KMSCPOBOQLANCF-UHFFFAOYSA-N 4-[1-(2-naphthalen-1-ylethyl)piperidin-4-yl]furo[3,2-c]pyridine Chemical compound C=1C=CC2=CC=CC=C2C=1CCN(CC1)CCC1C1=NC=CC2=C1C=CO2 KMSCPOBOQLANCF-UHFFFAOYSA-N 0.000 claims description 3
- CUYCGVNKGOERCQ-UHFFFAOYSA-N 4-[1-(2-naphthalen-1-ylethyl)piperidin-4-yl]thieno[3,2-c]pyridine Chemical compound C=1C=CC2=CC=CC=C2C=1CCN(CC1)CCC1C1=NC=CC2=C1C=CS2 CUYCGVNKGOERCQ-UHFFFAOYSA-N 0.000 claims description 3
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 238000007796 conventional method Methods 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 150000002829 nitrogen Chemical group 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- FKIXJJIPWQTKPJ-UHFFFAOYSA-N 4-[4-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]piperazin-1-yl]furo[3,2-c]pyridine Chemical compound C=1C=C2OCCC2=CC=1CCN(CC1)CCN1C1=NC=CC2=C1C=CO2 FKIXJJIPWQTKPJ-UHFFFAOYSA-N 0.000 claims description 2
- XVXIKMSHRJQDLM-UHFFFAOYSA-N 4-[4-[2-(3,4-dihydro-1h-isochromen-1-yl)ethyl]piperazin-1-yl]thieno[3,2-c]pyridine Chemical compound O1CCC2=CC=CC=C2C1CCN1CCN(C=2C=3C=CSC=3C=CN=2)CC1 XVXIKMSHRJQDLM-UHFFFAOYSA-N 0.000 claims description 2
- HJQYOGAVLXVCMK-UHFFFAOYSA-N 4-[4-[2-[5-(1,2,4-triazol-1-ylmethyl)-1h-indol-3-yl]ethyl]piperazin-1-yl]-1h-pyrrolo[3,2-c]pyridine Chemical compound C1CN(C=2C=3C=CNC=3C=CN=2)CCN1CCC(C1=C2)=CNC1=CC=C2CN1C=NC=N1 HJQYOGAVLXVCMK-UHFFFAOYSA-N 0.000 claims description 2
- DAPVAOQEIWULLT-UHFFFAOYSA-N 4-[4-[2-[5-(1,2,4-triazol-1-ylmethyl)-1h-indol-3-yl]ethyl]piperazin-1-yl]furo[3,2-c]pyridine Chemical compound C1CN(C=2C=3C=COC=3C=CN=2)CCN1CCC(C1=C2)=CNC1=CC=C2CN1C=NC=N1 DAPVAOQEIWULLT-UHFFFAOYSA-N 0.000 claims description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 2
- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims description 2
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 2
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000004385 trihaloalkyl group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
- 239000000047 product Substances 0.000 description 99
- 239000000243 solution Substances 0.000 description 63
- 238000002844 melting Methods 0.000 description 57
- 230000008018 melting Effects 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 239000000758 substrate Substances 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000002955 isolation Methods 0.000 description 25
- 230000002829 reductive effect Effects 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 15
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 13
- 241000699666 Mus <mouse, genus> Species 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 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 6
- 238000001035 drying Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229940076279 serotonin Drugs 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ZYIXXVCNAOYWQA-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)acetic acid Chemical compound C1=CC=C2OC(CC(=O)O)=CC2=C1 ZYIXXVCNAOYWQA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 230000005593 dissociations Effects 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 230000000697 serotonin reuptake Effects 0.000 description 4
- VLVVACOWPCJHHG-UHFFFAOYSA-N 1-benzyl-4-bromopyrrolo[3,2-c]pyridine Chemical compound C1=CC=2C(Br)=NC=CC=2N1CC1=CC=CC=C1 VLVVACOWPCJHHG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 2
- GPHCPUFIWQJZOI-UHFFFAOYSA-N 1-(2-bromoethyl)naphthalene Chemical compound C1=CC=C2C(CCBr)=CC=CC2=C1 GPHCPUFIWQJZOI-UHFFFAOYSA-N 0.000 description 2
- 125000003163 2-(2-naphthyl)ethyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(C([H])=C([H])C2=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- OPFFYLJLHPZSEO-UHFFFAOYSA-N 4-chlorofuro[3,2-c]pyridine Chemical compound ClC1=NC=CC2=C1C=CO2 OPFFYLJLHPZSEO-UHFFFAOYSA-N 0.000 description 2
- VFPFMOXMHVQFNR-UHFFFAOYSA-N 4-chlorothieno[3,2-c]pyridine Chemical compound ClC1=NC=CC2=C1C=CS2 VFPFMOXMHVQFNR-UHFFFAOYSA-N 0.000 description 2
- OLFWGDMDZCFCPV-UHFFFAOYSA-N 4-piperazin-1-yl-1h-pyrrolo[3,2-c]pyridine Chemical compound C1CNCCN1C1=NC=CC2=C1C=CN2 OLFWGDMDZCFCPV-UHFFFAOYSA-N 0.000 description 2
- RVGRTFBJOXMFAX-UHFFFAOYSA-N 4-piperazin-1-ylthieno[3,2-c]pyridine Chemical group C1CNCCN1C1=NC=CC2=C1C=CS2 RVGRTFBJOXMFAX-UHFFFAOYSA-N 0.000 description 2
- AIGGEYKUXJSCGG-UHFFFAOYSA-N 4-piperidin-4-yl-1h-pyrrolo[3,2-c]pyridine Chemical compound C1CNCCC1C1=NC=CC2=C1C=CN2 AIGGEYKUXJSCGG-UHFFFAOYSA-N 0.000 description 2
- HCQVAFNLISXSJP-UHFFFAOYSA-N 7-(4-aminopiperidin-1-yl)-1,3-dihydropyrrolo[2,3-c]pyridin-2-one Chemical compound C1CC(N)CCN1C1=NC=CC2=C1NC(=O)C2 HCQVAFNLISXSJP-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9910834A FR2797874B1 (fr) | 1999-08-27 | 1999-08-27 | Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20004295D0 NO20004295D0 (no) | 2000-08-28 |
| NO20004295L NO20004295L (no) | 2001-02-28 |
| NO316651B1 true NO316651B1 (no) | 2004-03-22 |
Family
ID=9549376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20004295A NO316651B1 (no) | 1999-08-27 | 2000-08-28 | Nye pyridinforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US6399616B1 (ru) |
| EP (1) | EP1078928B1 (ru) |
| JP (1) | JP3602780B2 (ru) |
| KR (1) | KR100450317B1 (ru) |
| CN (1) | CN1163495C (ru) |
| AT (1) | ATE266664T1 (ru) |
| AU (1) | AU765661B2 (ru) |
| BR (1) | BR0003848A (ru) |
| CA (1) | CA2317053A1 (ru) |
| DE (1) | DE60010596T2 (ru) |
| DK (1) | DK1078928T3 (ru) |
| EA (1) | EA004102B1 (ru) |
| ES (1) | ES2220359T3 (ru) |
| FR (1) | FR2797874B1 (ru) |
| HK (1) | HK1034250A1 (ru) |
| HU (1) | HUP0003413A3 (ru) |
| MX (1) | MXPA00008241A (ru) |
| NO (1) | NO316651B1 (ru) |
| NZ (1) | NZ506560A (ru) |
| PL (1) | PL342178A1 (ru) |
| PT (1) | PT1078928E (ru) |
| SI (1) | SI1078928T1 (ru) |
| ZA (1) | ZA200004411B (ru) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2797874B1 (fr) * | 1999-08-27 | 2002-03-29 | Adir | Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| DE10031391A1 (de) * | 2000-07-03 | 2002-02-07 | Knoll Ag | Bicyclische Verbindungen und ihre Verwendung zur Prophylaxe und Therapie der zerebralen Ischämie |
| AU2002242996A1 (en) * | 2001-03-29 | 2002-10-15 | Tanabe Seiyaku Co., Ltd. | Spiroisoquinoline compounds, methods for their preparation and intermediates |
| DE10217006A1 (de) * | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| JP4897221B2 (ja) * | 2002-12-20 | 2012-03-14 | チバ ホールディング インコーポレーテッド | アミン類の合成及びその合成のための中間体 |
| JP4559749B2 (ja) * | 2004-02-16 | 2010-10-13 | あすか製薬株式会社 | ピペラジニルピリジン誘導体 |
| JP4596792B2 (ja) * | 2004-02-24 | 2010-12-15 | あすか製薬株式会社 | ５−ｈｔ１ａ作動作用と５−ｈｔ３拮抗作用を併有する薬剤 |
| EP1724267B1 (en) | 2004-02-26 | 2013-11-06 | ASKA Pharmaceutical Co., Ltd. | Pyrimidine derivative |
| DE102004023506A1 (de) * | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023508A1 (de) * | 2004-05-10 | 2005-12-08 | Grünenthal GmbH | Säurederivate substituierter Cyclohexyl-1,4-diamine |
| DE102004023501A1 (de) * | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate |
| US20070249690A1 (en) * | 2004-07-23 | 2007-10-25 | Darren Mansfield | N-[2-(4-Pyridinyl)Ethyl]Benzamide Derivatives as Fungicides |
| CA2585857A1 (en) | 2004-11-26 | 2006-06-01 | Janssen Pharmaceutica N.V. | Isoxazoline-indole derivatives with an improved antipsychotic and anxiolytic activity |
| FR2909670B1 (fr) * | 2006-12-12 | 2010-07-30 | Sanofi Aventis | Derive fluore de quinoleine-2(1h)-one,son procede de preparation et son utilisation comme intermediaire de synthese |
| US9598401B2 (en) | 2013-07-29 | 2017-03-21 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use thereof |
| JP2016540013A (ja) * | 2013-12-13 | 2016-12-22 | 武田薬品工業株式会社 | Ｔｌｒ阻害剤としてのピロロ［３，２−ｃ］ピリジン誘導体 |
| US9968604B2 (en) | 2015-04-16 | 2018-05-15 | Chiesi Farmaceutici S.P.A. | Chromene derivatives as phoshoinositide 3-kinases inhibitors |
| CN106243088B (zh) | 2015-06-03 | 2019-01-04 | 广东东阳光药业有限公司 | 取代的哌嗪化合物及其使用方法和用途 |
| CN106795160B (zh) * | 2015-07-23 | 2019-04-19 | 广东东阳光药业有限公司 | 取代的吲哚化合物及其使用方法和用途 |
| CA3211341A1 (en) * | 2021-03-19 | 2022-09-22 | Centre National De La Recherche Scientifique | Applications of biased ligands of the serotonin 5-ht7 receptor for the treatment of pain, multiple sclerosis and the control of thermoregulation |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2761068A (en) * | 1953-10-15 | 1956-08-28 | Gen Electric | Automatic pole figure recorder |
| FR2312498A1 (fr) * | 1975-05-30 | 1976-12-24 | Parcor | Procede de preparation de la thieno (3,2-c) pyridine et de derives de celle-ci |
| FR2395271A1 (fr) * | 1977-06-21 | 1979-01-19 | Parcor | Procede de preparation de thieno (2,3-c) et thieno (3,2-c) pyridines |
| KR830003481A (ko) * | 1980-09-22 | 1983-06-20 | 미야다께 도꾸지로 | 6-플루오로-1,8-나프티리딘 유도체의 제조방법 |
| AU553415B2 (en) * | 1983-09-19 | 1986-07-17 | Abbott Japan Co., Ltd. | 6-fluoro-1-4-dihydro-4-oxo-7-substituted piperazinyl- quinoline-3-carboxylic acids |
| CA1278792C (en) * | 1985-05-06 | 1991-01-08 | Joseph P. Yevich | Antipsychotic fused-ring pyridinylpiperazine derivatives |
| US5001130A (en) * | 1988-02-18 | 1991-03-19 | Bristol-Myers Company | Psychotropic heterobicycloalkylpiperazine derivatives |
| JP2815126B2 (ja) * | 1990-08-31 | 1998-10-27 | 日清製粉株式会社 | ピリジンカルボン酸アミド誘導体 |
| US5681954A (en) * | 1993-05-14 | 1997-10-28 | Daiichi Pharmaceutical Co., Ltd. | Piperazine derivatives |
| US5300498A (en) * | 1993-06-04 | 1994-04-05 | Hoechst-Roussel Pharmaceuticals Incorporated | 6-piperazinyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acids, esters, amides and related compounds |
| FR2721800B1 (fr) * | 1994-07-01 | 1997-12-26 | Roussel Uclaf | Nouveaux concentres emulsionnables renfermant un u plussieurs pesticides |
| WO1996001052A1 (en) * | 1994-07-06 | 1996-01-18 | Quest International B.V. | Use of dibutyl malate as insect attractant |
| DE4430593C2 (de) * | 1994-08-20 | 1999-01-14 | Max Delbrueck Centrum | Verfahren zur Herstellung von Liposomal verkapseltem Taxol |
| ATE187172T1 (de) * | 1995-09-15 | 1999-12-15 | Sanofi Synthelabo | Chinolin-2-on derivate als serotonin antagonisten |
| FR2738823B1 (fr) * | 1995-09-15 | 1997-10-31 | Synthelabo | Derives de 3-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)-3,4-dihydroquinolein-2(1h)-one,leur preparation et leur application en therapeutique |
| FR2761071B1 (fr) * | 1997-03-20 | 1999-12-03 | Synthelabo | Derives de quinolein-2(1h)-one et de dihydroquinolein-2(1h)- one, leur preparation et leur application en therapeutique |
| FR2761068B1 (fr) * | 1997-03-20 | 1999-04-23 | Synthelabo | Derives de piperazin-4-ylthieno[3,2-c]pyridin-4-yl-2- carboxamide, leur preparation et leur application en therapeutique |
| EP1020445B1 (en) * | 1997-10-02 | 2008-08-13 | Eisai R&D Management Co., Ltd. | Fused pyridine derivatives |
| FR2797874B1 (fr) * | 1999-08-27 | 2002-03-29 | Adir | Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
1999
- 1999-08-27 FR FR9910834A patent/FR2797874B1/fr not_active Expired - Fee Related
-
2000
- 2000-08-18 US US09/641,777 patent/US6399616B1/en not_active Expired - Fee Related
- 2000-08-23 MX MXPA00008241A patent/MXPA00008241A/es active IP Right Grant
- 2000-08-23 JP JP2000252191A patent/JP3602780B2/ja not_active Expired - Fee Related
- 2000-08-25 NZ NZ506560A patent/NZ506560A/en unknown
- 2000-08-25 HU HU0003413A patent/HUP0003413A3/hu unknown
- 2000-08-25 AT AT00402359T patent/ATE266664T1/de not_active IP Right Cessation
- 2000-08-25 CN CNB00124065XA patent/CN1163495C/zh not_active Expired - Fee Related
- 2000-08-25 DE DE60010596T patent/DE60010596T2/de not_active Expired - Fee Related
- 2000-08-25 ZA ZA200004411A patent/ZA200004411B/xx unknown
- 2000-08-25 CA CA002317053A patent/CA2317053A1/fr not_active Abandoned
- 2000-08-25 DK DK00402359T patent/DK1078928T3/da active
- 2000-08-25 PT PT00402359T patent/PT1078928E/pt unknown
- 2000-08-25 PL PL00342178A patent/PL342178A1/xx not_active Application Discontinuation
- 2000-08-25 ES ES00402359T patent/ES2220359T3/es not_active Expired - Lifetime
- 2000-08-25 EP EP00402359A patent/EP1078928B1/fr not_active Expired - Lifetime
- 2000-08-25 EA EA200000792A patent/EA004102B1/ru not_active IP Right Cessation
- 2000-08-25 SI SI200030387T patent/SI1078928T1/xx unknown
- 2000-08-28 NO NO20004295A patent/NO316651B1/no unknown
- 2000-08-28 KR KR10-2000-0050018A patent/KR100450317B1/ko not_active IP Right Cessation
- 2000-08-28 AU AU53642/00A patent/AU765661B2/en not_active Ceased
- 2000-08-28 BR BR0003848-2A patent/BR0003848A/pt not_active IP Right Cessation
-
2001
- 2001-07-11 HK HK01104815A patent/HK1034250A1/xx not_active IP Right Cessation
-
2002
- 2002-03-25 US US10/105,171 patent/US6486171B2/en not_active Expired - Fee Related
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