NO322220B1 - Nye forbindelser, deres anvendelse og fremstilling - Google Patents
Nye forbindelser, deres anvendelse og fremstilling Download PDFInfo
- Publication number
- NO322220B1 NO322220B1 NO20015686A NO20015686A NO322220B1 NO 322220 B1 NO322220 B1 NO 322220B1 NO 20015686 A NO20015686 A NO 20015686A NO 20015686 A NO20015686 A NO 20015686A NO 322220 B1 NO322220 B1 NO 322220B1
- Authority
- NO
- Norway
- Prior art keywords
- piperazinyl
- mmol
- ethoxy
- pyrazinyl
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 351
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- -1 (i) -O- Chemical class 0.000 claims abstract description 90
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 46
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
- 150000003839 salts Chemical group 0.000 claims abstract description 20
- 229940076279 serotonin Drugs 0.000 claims abstract description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 16
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 14
- 208000035475 disorder Diseases 0.000 claims abstract description 11
- 208000030814 Eating disease Diseases 0.000 claims abstract description 9
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 9
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 9
- 208000008589 Obesity Diseases 0.000 claims abstract description 8
- 235000020824 obesity Nutrition 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
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- 201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 5
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 5
- 231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 5
- 230000002485 urinary effect Effects 0.000 claims abstract description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 241001465754 Metazoa Species 0.000 claims abstract description 4
- 150000004677 hydrates Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 231
- 229910052799 carbon Inorganic materials 0.000 claims description 186
- 239000000203 mixture Substances 0.000 claims description 161
- 238000000034 method Methods 0.000 claims description 158
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 122
- 239000012458 free base Substances 0.000 claims description 98
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 77
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 71
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 52
- 239000002904 solvent Substances 0.000 claims description 51
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 49
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 43
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 39
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 37
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 28
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 28
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 claims description 25
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 22
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 22
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 22
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- ATCSWYASYIDBBB-UHFFFAOYSA-N tert-butyl 4-[3-(2-hydroxyethoxy)pyrazin-2-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=NC=CN=C1OCCO ATCSWYASYIDBBB-UHFFFAOYSA-N 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000012312 sodium hydride Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
- 150000004885 piperazines Chemical class 0.000 claims description 5
- 125000006413 ring segment Chemical group 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- VLSDXINSOMDCBK-BQYQJAHWSA-N (E)-1,1'-azobis(N,N-dimethylformamide) Chemical compound CN(C)C(=O)\N=N\C(=O)N(C)C VLSDXINSOMDCBK-BQYQJAHWSA-N 0.000 claims description 4
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 4
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
- JBVSIXXBZWLDPX-UHFFFAOYSA-N 2-[2-(2,5-difluorophenoxy)ethoxy]-3-piperazin-1-ylpyrazine Chemical compound FC1=CC=C(F)C(OCCOC=2C(=NC=CN=2)N2CCNCC2)=C1 JBVSIXXBZWLDPX-UHFFFAOYSA-N 0.000 claims description 3
- OWWRUMJGNQGETL-UHFFFAOYSA-N 2-[2-(2-bromopyridin-3-yl)oxyethoxy]-3-piperazin-1-ylpyrazine Chemical compound BrC1=NC=CC=C1OCCOC1=NC=CN=C1N1CCNCC1 OWWRUMJGNQGETL-UHFFFAOYSA-N 0.000 claims description 3
- UXUWDYFTOZFOBE-UHFFFAOYSA-N 2-[2-(2-chloro-4-methoxyphenoxy)ethoxy]-3-piperazin-1-ylpyrazine Chemical compound ClC1=CC(OC)=CC=C1OCCOC1=NC=CN=C1N1CCNCC1 UXUWDYFTOZFOBE-UHFFFAOYSA-N 0.000 claims description 3
- ZAMNPJWPKNCWGZ-UHFFFAOYSA-N 2-[2-(2-chloropyridin-3-yl)oxyethoxy]-3-piperazin-1-ylpyrazine Chemical compound ClC1=NC=CC=C1OCCOC1=NC=CN=C1N1CCNCC1 ZAMNPJWPKNCWGZ-UHFFFAOYSA-N 0.000 claims description 3
- IDGPVJWBBOIPLR-UHFFFAOYSA-N 2-[2-(2-methylsulfanylpyridin-3-yl)oxyethoxy]-3-piperazin-1-ylpyrazine Chemical compound CSC1=NC=CC=C1OCCOC1=NC=CN=C1N1CCNCC1 IDGPVJWBBOIPLR-UHFFFAOYSA-N 0.000 claims description 3
- UEDUFDVBGOWDCX-UHFFFAOYSA-N 2-[2-[3-(oxan-4-yloxy)phenoxy]ethoxy]-3-piperazin-1-ylpyrazine Chemical compound C=1C=CC(OC2CCOCC2)=CC=1OCCOC1=NC=CN=C1N1CCNCC1 UEDUFDVBGOWDCX-UHFFFAOYSA-N 0.000 claims description 3
- BLAMRABECWOVCK-UHFFFAOYSA-N 2-[2-[3-(oxolan-3-ylmethoxy)phenoxy]ethoxy]-3-piperazin-1-ylpyrazine Chemical compound C=1C=CC(OCC2COCC2)=CC=1OCCOC1=NC=CN=C1N1CCNCC1 BLAMRABECWOVCK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
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- UOQRKDSICWXMLF-UHFFFAOYSA-N 2-(2-methylpiperazin-1-yl)-3-(2-phenoxyethoxy)pyrazine Chemical compound CC1CNCCN1C1=NC=CN=C1OCCOC1=CC=CC=C1 UOQRKDSICWXMLF-UHFFFAOYSA-N 0.000 claims description 2
- DBFXNHWSCJHHOF-UHFFFAOYSA-N 2-(2-methylpiperazin-1-yl)-3-[2-(2-methylsulfanylpyridin-3-yl)oxyethoxy]pyrazine Chemical compound CSC1=NC=CC=C1OCCOC1=NC=CN=C1N1C(C)CNCC1 DBFXNHWSCJHHOF-UHFFFAOYSA-N 0.000 claims description 2
- SMPBFLVDGMHANH-UHFFFAOYSA-N 2-[2-(2-bromopyridin-3-yl)oxyethoxy]-3-(2-methylpiperazin-1-yl)pyrazine Chemical compound CC1CNCCN1C1=NC=CN=C1OCCOC1=CC=CN=C1Br SMPBFLVDGMHANH-UHFFFAOYSA-N 0.000 claims description 2
- PWXBIEPPLZGIKF-UHFFFAOYSA-N 2-[2-(2-ethoxypyridin-3-yl)oxyethoxy]-3-(2-methylpiperazin-1-yl)pyrazine Chemical compound CCOC1=NC=CC=C1OCCOC1=NC=CN=C1N1C(C)CNCC1 PWXBIEPPLZGIKF-UHFFFAOYSA-N 0.000 claims description 2
- MJERLJMAKUEYFF-UHFFFAOYSA-N 2-[2-(2-ethoxypyridin-3-yl)oxyethoxy]-3-piperazin-1-ylpyrazine Chemical compound CCOC1=NC=CC=C1OCCOC1=NC=CN=C1N1CCNCC1 MJERLJMAKUEYFF-UHFFFAOYSA-N 0.000 claims description 2
- WJVKNMROSXBHGA-UHFFFAOYSA-N 2-[2-[3-(2-methoxyethoxy)phenoxy]ethoxy]-3-piperazin-1-ylpyrazine Chemical compound COCCOC1=CC=CC(OCCOC=2C(=NC=CN=2)N2CCNCC2)=C1 WJVKNMROSXBHGA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- MDYFXKXGCCFIMM-UHFFFAOYSA-N 2-piperazin-1-yl-3-[2-[3-(2-pyridin-2-ylethoxy)phenoxy]ethoxy]pyrazine Chemical compound C=1C=CC(OCCC=2N=CC=CC=2)=CC=1OCCOC1=NC=CN=C1N1CCNCC1 MDYFXKXGCCFIMM-UHFFFAOYSA-N 0.000 claims description 2
- JQHLHQXHHJJXEL-UHFFFAOYSA-N 4-methyl-5-[2-[3-[2-(3-piperazin-1-ylpyrazin-2-yl)oxyethoxy]phenoxy]ethyl]-1,3-thiazole Chemical compound N1=CSC(CCOC=2C=C(OCCOC=3C(=NC=CN=3)N3CCNCC3)C=CC=2)=C1C JQHLHQXHHJJXEL-UHFFFAOYSA-N 0.000 claims description 2
- 102000056834 5-HT2 Serotonin Receptors Human genes 0.000 claims description 2
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- YMEIWFDMFLIJDP-UHFFFAOYSA-N 8-[2-[3-(2-methylpiperazin-1-yl)pyrazin-2-yl]oxyethoxy]quinolin-2-amine Chemical compound CC1CNCCN1C1=NC=CN=C1OCCOC1=CC=CC2=CC=C(N)N=C12 YMEIWFDMFLIJDP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
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- CZDVJGBXKADLCY-UHFFFAOYSA-N thieno[3,4-b]pyrazine Chemical group N1=CC=NC2=CSC=C21 CZDVJGBXKADLCY-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 191
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- 125000004474 heteroalkylene group Chemical group 0.000 abstract description 6
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/18—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
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- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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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
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9901884A SE9901884D0 (sv) | 1999-05-21 | 1999-05-21 | Novel compounds their use and preparation |
US13752799P | 1999-06-03 | 1999-06-03 | |
PCT/SE2000/001017 WO2000076984A2 (en) | 1999-05-21 | 2000-05-19 | Novel compounds, their use and preparation |
Publications (3)
Publication Number | Publication Date |
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NO20015686D0 NO20015686D0 (no) | 2001-11-21 |
NO20015686L NO20015686L (no) | 2002-01-15 |
NO322220B1 true NO322220B1 (no) | 2006-08-28 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20015686A NO322220B1 (no) | 1999-05-21 | 2001-11-21 | Nye forbindelser, deres anvendelse og fremstilling |
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EP (1) | EP1178973B1 (de) |
KR (1) | KR100722090B1 (de) |
CN (1) | CN1242995C (de) |
AT (1) | ATE313535T1 (de) |
AU (1) | AU777276C (de) |
BR (1) | BR0010783A (de) |
CA (1) | CA2374898C (de) |
DE (1) | DE60024986T2 (de) |
DK (1) | DK1178973T3 (de) |
EA (1) | EA005820B1 (de) |
ES (1) | ES2252004T3 (de) |
HK (1) | HK1048311B (de) |
IL (2) | IL146582A0 (de) |
MX (1) | MXPA01011905A (de) |
NO (1) | NO322220B1 (de) |
NZ (1) | NZ515786A (de) |
WO (1) | WO2000076984A2 (de) |
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SE0004244D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
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SE0004245D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
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WO2003045313A2 (en) * | 2001-11-27 | 2003-06-05 | Merck & Co. Inc. | 2-aminoquinoline compounds |
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US6989392B2 (en) | 2002-06-18 | 2006-01-24 | Abbott Laboratories | 2-Aminoquinolines as melanin concentrating hormone receptor antagonists |
WO2003105850A1 (en) * | 2002-06-18 | 2003-12-24 | Abbott Laboratories | 2-aminoquinolines as melanin concentrating hormone receptor antagonists |
CA2723494C (en) | 2002-06-19 | 2013-04-16 | Biovitrum Ab (Publ) | 2-methyl piperazine derivatives for treatment of serotonin-related disorders |
CA2485537A1 (en) * | 2002-06-19 | 2003-12-31 | Biovitrum Ab | Novel compounds, their use and preparation |
US7226925B2 (en) | 2002-06-19 | 2007-06-05 | Biovitrum Ab | Compounds, their use and preparation |
SI1645558T1 (sl) * | 2002-06-19 | 2008-10-31 | Biovitrum Ab Publ | Piperazinilpirazini kot modulatorji serotonin 5-HT2C receptorja |
WO2004009586A1 (en) | 2002-07-19 | 2004-01-29 | Biovitrum Ab | Novel piperazinyl-pyrazinone derivatives for the treatment of 5-ht2a receptor-related disorders |
SE0202287D0 (sv) * | 2002-07-19 | 2002-07-19 | Biovitrum Ab | New compounds |
JP4960085B2 (ja) | 2003-03-19 | 2012-06-27 | エクセリクシス, インク. | Tie−2モジュレータと使用方法 |
CL2004000826A1 (es) * | 2003-04-25 | 2005-03-04 | Pfizer | Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129 |
US7517900B2 (en) | 2003-10-10 | 2009-04-14 | Bristol-Myers Squibb Company | Pyrazole derivatives as cannabinoid receptor modulators |
US7423147B2 (en) | 2004-03-31 | 2008-09-09 | Janssen Pharmaceutical, N.V. | Pyridine compounds as histamine H3 modulators |
EP2400300A1 (de) | 2004-08-25 | 2011-12-28 | Takeda Pharmaceutical Company Limited | Screeningverfahren von Mitteln zur Prävention/Behandlung von stressbedingter Harninkontinenz |
GT200500317A (es) | 2004-11-05 | 2006-10-27 | Proceso para preparar compuestos de quinolina y productos obtenidos de los mismos | |
JP4130219B2 (ja) | 2004-11-29 | 2008-08-06 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 治療用のピラゾロ[3,4−b]ピリジンおよびインダゾール |
MX2007012082A (es) | 2005-03-31 | 2007-11-20 | Pfizer Prod Inc | Derivados de ciclopentapiridina y tetrahidroquinolina. |
AR054849A1 (es) | 2005-07-26 | 2007-07-18 | Wyeth Corp | Diazepinoquinolinas, sintesis de las mismas, e intermediarios para obtenerlas |
CA2645099A1 (en) * | 2006-03-24 | 2007-10-04 | Wyeth | Methods for modulating bladder function |
WO2007112000A2 (en) * | 2006-03-24 | 2007-10-04 | Wyeth | Treatment of pain |
WO2007132841A1 (ja) | 2006-05-16 | 2007-11-22 | Takeda Pharmaceutical Company Limited | 縮合複素環化合物およびその用途 |
WO2007143422A2 (en) | 2006-05-30 | 2007-12-13 | Janssen Pharmaceutica N.V. | Substituted pyridyl amide compounds as modulators of the histamine h3 receptor |
EP3078662A1 (de) | 2007-09-21 | 2016-10-12 | Array Biopharma, Inc. | Pyridin-2-yl-amino-1,2,4-thiadiazol derivate als glucokinase aktivatoren zur behandlung von diabetes mellitus |
EP2216023A4 (de) | 2007-11-15 | 2013-03-13 | Takeda Pharmaceutical | Kondensiertes pyridinderivat und seine verwendung |
NZ584998A (en) | 2007-11-20 | 2012-08-31 | Janssen Pharmaceutica Nv | Cycloalkyloxy-and heterocycloalkyloxypyridine compounds as modulators of the histamine h3 receptor |
US20110269759A1 (en) | 2009-10-30 | 2011-11-03 | Coats Steven J | Pyrimidine compounds as delta opioid receptor modulators |
BR112012011465A2 (pt) | 2009-10-30 | 2020-08-25 | Janssen Pharmaceutica N .V. | pirazinas como moduladores do receptor delta opioide. |
RU2554870C2 (ru) | 2009-10-30 | 2015-06-27 | Янссен Фармацевтика Нв | Феноксизамещенные пиримидины для использования в качестве модуляторов опиоидных рецепторов |
US20120253036A1 (en) | 2009-12-11 | 2012-10-04 | Yukinori Nagakura | Agent for treating fibromyalgia |
WO2012030953A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
WO2012044531A1 (en) | 2010-09-28 | 2012-04-05 | Bristol-Myers Squibb Company | Novel piperazine analogs with substituted heteroaryl groups as broad-spectrum influenza antivirals |
WO2013093095A1 (en) | 2011-12-22 | 2013-06-27 | Kancera Ab | Bisarylsulfonamides useful in the treatment of inflammation and cancer |
GB201312131D0 (en) * | 2013-07-05 | 2013-08-21 | Proximagen Ltd | Drug combination and its use in therapy |
GB201312129D0 (en) * | 2013-07-05 | 2013-08-21 | Proximagen Ltd | Drug combination and its use in therapy |
WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
CN105348204B (zh) * | 2015-11-18 | 2018-09-14 | 乳源瑶族自治县大众药品贸易有限公司 | 1-杂环基-2-(杂芳基硫基)苯衍生物及其使用方法和用途 |
CN105461635B (zh) * | 2015-11-18 | 2018-06-08 | 乳源瑶族自治县大众药品贸易有限公司 | 苯基哌嗪衍生物及其使用方法和用途 |
CN108409729B (zh) * | 2017-02-09 | 2020-11-24 | 广东东阳光药业有限公司 | 苯基八氢-1H-吡啶并[1,2-a]吡嗪衍生物及其用途 |
EP3733204A4 (de) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | Therapeutikum für belastungsinkontinenz und stuhlinkontinenz |
CN109111383B (zh) * | 2018-09-14 | 2020-11-24 | 广东东阳光药业有限公司 | 2-取代的二苯硫醚衍生物及其用途 |
US11459340B2 (en) | 2018-09-18 | 2022-10-04 | Nikang Therapeutics, Inc. | Tri-substituted heteroaryl derivatives as Src homology-2 phosphatase inhibitors |
CN114394887A (zh) * | 2022-01-28 | 2022-04-26 | 江苏锐鸣材料科技有限公司 | 一种苯基氧乙醇化合物及其制备方法 |
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FI193974A (de) * | 1973-07-13 | 1975-01-14 | Merck & Co Inc | |
GB9313913D0 (en) * | 1993-07-06 | 1993-08-18 | Smithkline Beecham Plc | Novel compounds |
GB9420999D0 (en) * | 1994-10-18 | 1994-12-07 | Smithkline Beecham Plc | Novel compounds |
AU4037699A (en) * | 1998-05-08 | 1999-11-29 | Akzo Nobel N.V. | Novel aryl-hydro naphthalenal kanamines |
-
2000
- 2000-05-19 EA EA200101223A patent/EA005820B1/ru not_active IP Right Cessation
- 2000-05-19 CN CNB008102449A patent/CN1242995C/zh not_active Expired - Fee Related
- 2000-05-19 BR BR0010783-2A patent/BR0010783A/pt not_active Application Discontinuation
- 2000-05-19 KR KR1020017014888A patent/KR100722090B1/ko not_active IP Right Cessation
- 2000-05-19 EP EP00931877A patent/EP1178973B1/de not_active Expired - Lifetime
- 2000-05-19 IL IL14658200A patent/IL146582A0/xx unknown
- 2000-05-19 CA CA002374898A patent/CA2374898C/en not_active Expired - Fee Related
- 2000-05-19 DK DK00931877T patent/DK1178973T3/da active
- 2000-05-19 AT AT00931877T patent/ATE313535T1/de active
- 2000-05-19 NZ NZ515786A patent/NZ515786A/en not_active IP Right Cessation
- 2000-05-19 ES ES00931877T patent/ES2252004T3/es not_active Expired - Lifetime
- 2000-05-19 WO PCT/SE2000/001017 patent/WO2000076984A2/en not_active Application Discontinuation
- 2000-05-19 MX MXPA01011905A patent/MXPA01011905A/es active IP Right Grant
- 2000-05-19 DE DE60024986T patent/DE60024986T2/de not_active Expired - Lifetime
- 2000-05-19 AU AU49690/00A patent/AU777276C/en not_active Ceased
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2001
- 2001-11-19 IL IL146582A patent/IL146582A/en not_active IP Right Cessation
- 2001-11-21 NO NO20015686A patent/NO322220B1/no not_active IP Right Cessation
-
2003
- 2003-01-15 HK HK03100371.6A patent/HK1048311B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE60024986T2 (de) | 2006-07-27 |
ATE313535T1 (de) | 2006-01-15 |
EA200101223A1 (ru) | 2002-06-27 |
IL146582A0 (en) | 2002-07-25 |
KR20020016795A (ko) | 2002-03-06 |
AU777276B2 (en) | 2004-10-07 |
BR0010783A (pt) | 2002-04-09 |
DK1178973T3 (da) | 2006-05-08 |
CA2374898A1 (en) | 2000-12-21 |
WO2000076984A8 (en) | 2001-07-19 |
ES2252004T3 (es) | 2006-05-16 |
NO20015686L (no) | 2002-01-15 |
NZ515786A (en) | 2004-01-30 |
MXPA01011905A (es) | 2004-03-19 |
WO2000076984A3 (en) | 2001-02-08 |
KR100722090B1 (ko) | 2007-05-25 |
WO2000076984A2 (en) | 2000-12-21 |
IL146582A (en) | 2010-04-29 |
HK1048311B (zh) | 2006-08-11 |
DE60024986D1 (de) | 2006-01-26 |
AU4969000A (en) | 2001-01-02 |
EA005820B1 (ru) | 2005-06-30 |
NO20015686D0 (no) | 2001-11-21 |
EP1178973A2 (de) | 2002-02-13 |
HK1048311A1 (en) | 2003-03-28 |
CA2374898C (en) | 2009-12-08 |
EP1178973B1 (de) | 2005-12-21 |
CN1242995C (zh) | 2006-02-22 |
CN1360583A (zh) | 2002-07-24 |
AU777276C (en) | 2005-07-07 |
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