ZA200405694B - Novel aryl-and heteroarylpiperazines - Google Patents
Novel aryl-and heteroarylpiperazines Download PDFInfo
- Publication number
- ZA200405694B ZA200405694B ZA2004/05694A ZA200405694A ZA200405694B ZA 200405694 B ZA200405694 B ZA 200405694B ZA 2004/05694 A ZA2004/05694 A ZA 2004/05694A ZA 200405694 A ZA200405694 A ZA 200405694A ZA 200405694 B ZA200405694 B ZA 200405694B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound according
- aryl
- alkoxy
- halogen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 95
- -1 Ci-0-alkyl Substances 0.000 claims description 75
- 150000002367 halogens Chemical class 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 16
- 102000004384 Histamine H3 receptors Human genes 0.000 claims description 15
- 108090000981 Histamine H3 receptors Proteins 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 12
- 125000003435 aroyl group Chemical group 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 229960001340 histamine Drugs 0.000 claims description 6
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 230000001270 agonistic effect Effects 0.000 claims description 5
- 230000003042 antagnostic effect Effects 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000009286 beneficial effect Effects 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 208000037765 diseases and disorders Diseases 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- AUNLIXPDGQSPGW-UHFFFAOYSA-N (4-fluorophenyl)-[4-(4-pentan-3-ylpiperazin-1-yl)phenyl]methanone Chemical compound C1CN(C(CC)CC)CCN1C1=CC=C(C(=O)C=2C=CC(F)=CC=2)C=C1 AUNLIXPDGQSPGW-UHFFFAOYSA-N 0.000 claims description 2
- KLDRCVWDIQOOEC-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-pentan-3-ylpiperazine Chemical compound C1CN(C(CC)CC)CCN1C1=CC=C(Cl)C(Cl)=C1 KLDRCVWDIQOOEC-UHFFFAOYSA-N 0.000 claims description 2
- UESDDOLQUMWNDH-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-cyclopentylpiperazine Chemical compound ClC1=CC=CC(N2CCN(CC2)C2CCCC2)=C1 UESDDOLQUMWNDH-UHFFFAOYSA-N 0.000 claims description 2
- UKIDNCFCCFYFPT-UHFFFAOYSA-N 1-(4-benzylphenyl)-4-pentan-3-ylpiperazine Chemical compound C1CN(C(CC)CC)CCN1C(C=C1)=CC=C1CC1=CC=CC=C1 UKIDNCFCCFYFPT-UHFFFAOYSA-N 0.000 claims description 2
- GGKVTTJLMXTEHF-UHFFFAOYSA-N 1-cyclopentyl-4-[5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCN(C2CCCC2)CC1 GGKVTTJLMXTEHF-UHFFFAOYSA-N 0.000 claims description 2
- ORYGSMWIIBOVDS-UHFFFAOYSA-N 2-(4-cyclopentylpiperazin-1-yl)-7-methoxy-3-(4-methoxyphenyl)quinoline Chemical compound C1=CC(OC)=CC=C1C1=CC2=CC=C(OC)C=C2N=C1N1CCN(C2CCCC2)CC1 ORYGSMWIIBOVDS-UHFFFAOYSA-N 0.000 claims description 2
- YODKFKAHHFMXKB-UHFFFAOYSA-N 2-(4-cyclopentylpiperazin-1-yl)quinoxaline Chemical compound C1CCCC1N1CCN(C=2N=C3C=CC=CC3=NC=2)CC1 YODKFKAHHFMXKB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- ZLTRDWRTQXIMHI-UHFFFAOYSA-N 4-(4-cyclopentylpiperazin-1-yl)phenol Chemical compound C1=CC(O)=CC=C1N1CCN(C2CCCC2)CC1 ZLTRDWRTQXIMHI-UHFFFAOYSA-N 0.000 claims description 2
- DYGULAKZSWXNAY-UHFFFAOYSA-N 7-chloro-4-(4-pentan-3-ylpiperazin-1-yl)quinoline Chemical compound C1CN(C(CC)CC)CCN1C1=CC=NC2=CC(Cl)=CC=C12 DYGULAKZSWXNAY-UHFFFAOYSA-N 0.000 claims description 2
- GSHXFMNTSJJDCC-UHFFFAOYSA-N [6-(4-cyclopentylpiperazin-1-yl)pyridin-3-yl]-piperidin-1-ylmethanone Chemical compound C=1C=C(N2CCN(CC2)C2CCCC2)N=CC=1C(=O)N1CCCCC1 GSHXFMNTSJJDCC-UHFFFAOYSA-N 0.000 claims description 2
- HHSVDWCVSSZBGI-UHFFFAOYSA-N [6-[4-(2-cyclopropylpropan-2-yl)piperazin-1-yl]pyridin-3-yl]-phenylmethanone Chemical compound C1CN(C=2N=CC(=CC=2)C(=O)C=2C=CC=CC=2)CCN1C(C)(C)C1CC1 HHSVDWCVSSZBGI-UHFFFAOYSA-N 0.000 claims description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- 239000002552 dosage form Substances 0.000 claims 3
- 208000032841 Bulimia Diseases 0.000 claims 2
- 102000000543 Histamine Receptors Human genes 0.000 claims 2
- 108010002059 Histamine Receptors Proteins 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010033307 Overweight Diseases 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- JTWJBPGIEVYSGB-UHFFFAOYSA-N 1-cyclopentyl-4-[3-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=CN=C1N1CCN(C2CCCC2)CC1 JTWJBPGIEVYSGB-UHFFFAOYSA-N 0.000 claims 1
- JTYWGWMHLBKKPJ-UHFFFAOYSA-N 1-cyclopentyl-4-[4-[(4-fluorophenyl)methoxy]phenyl]piperazine Chemical compound C1=CC(F)=CC=C1COC1=CC=C(N2CCN(CC2)C2CCCC2)C=C1 JTYWGWMHLBKKPJ-UHFFFAOYSA-N 0.000 claims 1
- DMMRSMPUZJDBFI-UHFFFAOYSA-N 1-cyclopentyl-4-[6-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CC2)C2CCCC2)=N1 DMMRSMPUZJDBFI-UHFFFAOYSA-N 0.000 claims 1
- JGCMOVVEQUHZRT-UHFFFAOYSA-N 2-(4-cyclopentylpiperazin-1-yl)quinoline Chemical compound C1CCCC1N1CCN(C=2N=C3C=CC=CC3=CC=2)CC1 JGCMOVVEQUHZRT-UHFFFAOYSA-N 0.000 claims 1
- MHWHBMVPYRSQGR-UHFFFAOYSA-N 2-(4-cyclopropylpiperazin-1-yl)-6-(trifluoromethyl)quinoline Chemical compound C1=CC2=CC(C(F)(F)F)=CC=C2N=C1N(CC1)CCN1C1CC1 MHWHBMVPYRSQGR-UHFFFAOYSA-N 0.000 claims 1
- FSMPRTRJKQTCLK-UHFFFAOYSA-N 2-(4-cyclopropylpiperazin-1-yl)-6-propylquinoline Chemical compound C1=CC2=CC(CCC)=CC=C2N=C1N(CC1)CCN1C1CC1 FSMPRTRJKQTCLK-UHFFFAOYSA-N 0.000 claims 1
- HEWVIFVVKWCRML-UHFFFAOYSA-N 2-(4-ethylpiperazin-1-yl)quinoline Chemical compound C1CN(CC)CCN1C1=CC=C(C=CC=C2)C2=N1 HEWVIFVVKWCRML-UHFFFAOYSA-N 0.000 claims 1
- CMNVZVJPAQJIHB-UHFFFAOYSA-N 2-(4-pentan-3-ylpiperazin-1-yl)-4-(trifluoromethyl)quinoline Chemical compound C1CN(C(CC)CC)CCN1C1=CC(C(F)(F)F)=C(C=CC=C2)C2=N1 CMNVZVJPAQJIHB-UHFFFAOYSA-N 0.000 claims 1
- GCZGGBYOWDOXHL-UHFFFAOYSA-N 2-[4-(cyclopropylmethyl)piperazin-1-yl]-6-methoxy-4-(trifluoromethyl)quinoline Chemical compound C1=C(C(F)(F)F)C2=CC(OC)=CC=C2N=C1N(CC1)CCN1CC1CC1 GCZGGBYOWDOXHL-UHFFFAOYSA-N 0.000 claims 1
- NHMQRLGETCFQBU-UHFFFAOYSA-N 2-[4-(cyclopropylmethyl)piperazin-1-yl]quinoxaline Chemical compound C1CN(C=2N=C3C=CC=CC3=NC=2)CCN1CC1CC1 NHMQRLGETCFQBU-UHFFFAOYSA-N 0.000 claims 1
- BSEXWLKKPNSFLV-UHFFFAOYSA-N 6,7-dimethoxy-2-(4-pentan-3-ylpiperazin-1-yl)quinoline Chemical compound C1CN(C(CC)CC)CCN1C1=CC=C(C=C(OC)C(OC)=C2)C2=N1 BSEXWLKKPNSFLV-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
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- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 238000004965 Hartree-Fock calculation Methods 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- BIGIOOUWKKVMEI-UHFFFAOYSA-N [3,5-difluoro-4-(4-pentan-3-ylpiperazin-1-yl)phenyl]-(4-fluorophenyl)methanone Chemical compound C1CN(C(CC)CC)CCN1C1=C(F)C=C(C(=O)C=2C=CC(F)=CC=2)C=C1F BIGIOOUWKKVMEI-UHFFFAOYSA-N 0.000 claims 1
- HNBORJOWPIRWFD-UHFFFAOYSA-N [4-(4-cyclopentylpiperazin-1-yl)-3,5-difluorophenyl]-phenylmethanone Chemical compound FC1=CC(C(=O)C=2C=CC=CC=2)=CC(F)=C1N(CC1)CCN1C1CCCC1 HNBORJOWPIRWFD-UHFFFAOYSA-N 0.000 claims 1
- TWLQBZJVBYJZPS-UHFFFAOYSA-N [4-(4-cyclopentylpiperazin-1-yl)phenyl]-(3,4-dimethoxyphenyl)methanone Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)C1=CC=C(N2CCN(CC2)C2CCCC2)C=C1 TWLQBZJVBYJZPS-UHFFFAOYSA-N 0.000 claims 1
- ACUDYEDEHGVEKZ-UHFFFAOYSA-N [4-[4-(cyclopropylmethyl)piperazin-1-yl]-3,5-difluorophenyl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C(C=C1F)=CC(F)=C1N1CCN(CC2CC2)CC1 ACUDYEDEHGVEKZ-UHFFFAOYSA-N 0.000 claims 1
- PXGWRWMNLVKGTJ-UHFFFAOYSA-N [4-[4-(cyclopropylmethyl)piperazin-1-yl]-3,5-difluorophenyl]-phenylmethanone Chemical compound FC1=CC(C(=O)C=2C=CC=CC=2)=CC(F)=C1N(CC1)CCN1CC1CC1 PXGWRWMNLVKGTJ-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
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- 229960004217 benzyl alcohol Drugs 0.000 claims 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 208000014679 binge eating disease Diseases 0.000 claims 1
- GVCWILDLGZCPSF-UHFFFAOYSA-N cyclopropyl-[4-(4-pentan-3-ylpiperazin-1-yl)phenyl]methanone Chemical compound C1CN(C(CC)CC)CCN1C1=CC=C(C(=O)C2CC2)C=C1 GVCWILDLGZCPSF-UHFFFAOYSA-N 0.000 claims 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- ZUGDWIGHTLXJCC-UHFFFAOYSA-N n-benzyl-n-methyl-6-(4-pentan-3-ylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CN(C(CC)CC)CCN1C1=CC=C(C(=O)N(C)CC=2C=CC=CC=2)C=N1 ZUGDWIGHTLXJCC-UHFFFAOYSA-N 0.000 claims 1
- FMXXCKCIVXGUNS-UHFFFAOYSA-N n-methyl-6-(4-pentan-3-ylpiperazin-1-yl)-n-phenylpyridine-3-carboxamide Chemical compound C1CN(C(CC)CC)CCN1C1=CC=C(C(=O)N(C)C=2C=CC=CC=2)C=N1 FMXXCKCIVXGUNS-UHFFFAOYSA-N 0.000 claims 1
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- NSIYIZDVZLGOES-UHFFFAOYSA-N (4-hydroxyphenyl)-[4-(4-pentan-3-ylpiperazin-1-yl)phenyl]methanone Chemical compound C1CN(C(CC)CC)CCN1C1=CC=C(C(=O)C=2C=CC(O)=CC=2)C=C1 NSIYIZDVZLGOES-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-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
- C07D237/20—Nitrogen atoms
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- 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
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- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- 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
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- 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
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DKPA200201142 | 2002-07-26 | ||
PCT/DK2003/000071 WO2003066604A2 (en) | 2002-02-05 | 2003-02-05 | Novel aryl- and heteroarylpiperazines |
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JP (1) | JP4607458B2 (ja) |
CN (1) | CN1628109A (ja) |
AU (2) | AU2003203148A1 (ja) |
BR (1) | BR0307429A (ja) |
CA (1) | CA2474214A1 (ja) |
IL (1) | IL162859A0 (ja) |
MX (1) | MXPA04007612A (ja) |
NO (1) | NO328714B1 (ja) |
PL (1) | PL372390A1 (ja) |
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Families Citing this family (72)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7390813B1 (en) | 2001-12-21 | 2008-06-24 | Xenon Pharmaceuticals Inc. | Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents |
GB0224084D0 (en) * | 2002-10-16 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
US7279491B2 (en) | 2002-10-23 | 2007-10-09 | Janssen Pharmaceutica N.V. | Phenylpiperidines and phenylpyrrolidines |
KR20060054392A (ko) * | 2003-07-29 | 2006-05-22 | 노보 노르디스크 에이/에스 | 피리다지닐-피페라진 및 히스타민 h3 수용체 리간드로서그들의 사용 |
US7754711B2 (en) * | 2003-07-30 | 2010-07-13 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
CA2533897A1 (en) | 2003-07-30 | 2005-02-10 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
EP1648874B1 (en) | 2003-07-30 | 2011-10-05 | Xenon Pharmaceuticals Inc. | Piperazine derivatives and their use as therapeutic agents |
US7605161B2 (en) * | 2003-07-30 | 2009-10-20 | Xenon Pharmaceuticals Inc. | Pyridyl derivatives and their use as therapeutic agents |
WO2005035521A1 (en) * | 2003-10-09 | 2005-04-21 | Argenta Discovery Ltd. | Substituted quinolines as mcr modulators |
GB0324159D0 (en) | 2003-10-15 | 2003-11-19 | Glaxo Group Ltd | Novel compounds |
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 |
US7423147B2 (en) | 2004-03-31 | 2008-09-09 | Janssen Pharmaceutical, N.V. | Pyridine compounds as histamine H3 modulators |
WO2005097127A2 (en) | 2004-04-02 | 2005-10-20 | Merck & Co., Inc. | Method of treating men with metabolic and anthropometric disorders |
US20050256309A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands |
WO2006000914A1 (en) * | 2004-06-22 | 2006-01-05 | Pfizer Products Inc. | Diazabicyclic histamine-3 receptor antagonists |
JP4958787B2 (ja) * | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ヒトステアロイル−CoAデサチュラーゼを阻害するためのピリジン誘導体 |
MX2007003329A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y biciclicos y su uso como inhibidores de estearoil-coa-desaturasa (scd). |
EP1799667B1 (en) | 2004-09-20 | 2013-03-20 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
US8071603B2 (en) | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
EP1814551A2 (en) | 2004-09-20 | 2007-08-08 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
TW200626592A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
US7592343B2 (en) * | 2004-09-20 | 2009-09-22 | Xenon Pharmaceuticals Inc. | Pyridazine-piperazine compounds and their use as stearoyl-CoA desaturase inhibitors |
EP2266569A3 (en) | 2004-09-20 | 2011-03-09 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
MX2007003327A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos, y su uso como mediadores de estearoil-coa desaturasa. |
ES2441718T3 (es) * | 2004-11-02 | 2014-02-06 | Northwestern University | Compuestos de piridazina, composiciones y métodos |
US7700595B2 (en) | 2005-03-01 | 2010-04-20 | Wyeth Llc | Cinnoline compounds |
EP2540296A1 (en) | 2005-06-03 | 2013-01-02 | Xenon Pharmaceuticals Inc. | Arminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
CN103110635A (zh) | 2005-07-04 | 2013-05-22 | 海波因特制药有限责任公司 | 组胺h3受体拮抗剂 |
WO2007003521A2 (en) * | 2005-07-05 | 2007-01-11 | F. Hoffmann-La Roche Ag | Pyridazine derivatives as 11beta-hydroxysteroid dehydrogenase type 1 inhibitors |
WO2007022946A1 (de) * | 2005-08-21 | 2007-03-01 | Abbott Gmbh & Co. Kg | Heterocyclische verbindungen und ihre verwendung als bindungspartner für 5-ht5-rezeptoren |
GB0517184D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
US7687499B2 (en) * | 2005-09-16 | 2010-03-30 | Janssen Pharmaceutica Nv | Cyclopropyl amines as modulators of the histamine H3 receptor |
JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
AU2007229492B2 (en) * | 2006-03-28 | 2011-11-03 | High Point Pharmaceuticals, Llc | Benzothiazoles having histamine H3 receptor activity |
US20090325973A1 (en) * | 2006-04-28 | 2009-12-31 | Watterson D Martin | Formulations containing pyridazine compounds |
CA2653062A1 (en) * | 2006-05-23 | 2007-11-29 | Transtech Pharma, Inc. | 6- (4-cyclopropylpiperazin-1-yl) -2 ' -methyl- [3, 4 ' ] -bipyridine and its use as a medicament |
CA2659570C (en) | 2006-05-29 | 2015-10-06 | High Point Pharmaceuticals, Llc | 3-(1,3-benzodioxol-5-yl)-6-(4-cyclopropylpiperazin-1-yl)-pyridazine, its salts and solvates and its use as histamine h3 receptor antagonist |
WO2007143422A2 (en) | 2006-05-30 | 2007-12-13 | Janssen Pharmaceutica N.V. | Substituted pyridyl amide compounds as modulators of the histamine h3 receptor |
JP2009538859A (ja) * | 2006-05-30 | 2009-11-12 | エフ.ホフマン−ラ ロシュ アーゲー | ピペリジニルピリミジン誘導体 |
JP5203360B2 (ja) | 2006-06-23 | 2013-06-05 | アボット・ラボラトリーズ | ヒスタミンh3受容体調節剤としてのシクロプロピルアミン誘導体 |
US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
EP2044027A2 (en) * | 2006-07-03 | 2009-04-08 | Vereniging voor christelijk hoger onderwijs, wetenschappelijk onderzoek en patiëntenzorg | Fused bicyclic compounds interacting with the histamine h4 receptor |
JO2642B1 (en) | 2006-12-08 | 2012-06-17 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
JO2849B1 (en) * | 2007-02-13 | 2015-03-15 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
US8933101B2 (en) | 2007-04-23 | 2015-01-13 | Janssen Pharmaceutica Nv | Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists |
WO2008128995A1 (en) | 2007-04-23 | 2008-10-30 | Janssen Pharmaceutica N.V. | 4-alkoxypyridazine derivatives as fast dissociating dopamine 2 receptor antagonists |
WO2008145681A2 (en) * | 2007-05-31 | 2008-12-04 | Boehringer Ingelheim International Gmbh | Ccr2 receptor antagonists and uses thereof |
EP2014656A3 (en) * | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | New heteocyclic h3 antagonists |
AU2008281877A1 (en) * | 2007-08-02 | 2009-02-05 | F. Hoffmann-La Roche Ag | The use of benzamide derivatives for the treatment of CNS disorders |
US20090170869A1 (en) | 2007-09-06 | 2009-07-02 | Desmond John Best | Piperazine derivative having affinity for the histamine h3 receptor |
CA2706328C (en) | 2007-11-20 | 2016-04-19 | Janssen Pharmaceutica N.V. | Cycloalkyloxy- and heterocycloalkyloxypyridine compounds as modulators of the histamine h3 receptor |
WO2009079597A1 (en) * | 2007-12-17 | 2009-06-25 | Janssen Pharmaceutica N.V. | Piperazinyl derivatives useful as modulators of the neuropeptide y2 receptor |
US20120015957A1 (en) * | 2007-12-17 | 2012-01-19 | Wenying Chai | Piperazinyl derivatives useful as modulators of the neuropeptide y2 receptor |
WO2010000456A1 (en) | 2008-07-03 | 2010-01-07 | Janssen Pharmaceutica Nv | Substituted 6- (1-piperazinyl) -pyridazines as 5-ht6 receptor antagonists |
US8895562B2 (en) | 2008-07-31 | 2014-11-25 | Janssen Pharmaceutica Nv | Piperazin-1-yl-trifluoromethyl-substituted-pyridines as fast dissociating dopamine 2 receptor antagonists |
JP2012512834A (ja) | 2008-12-19 | 2012-06-07 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 炎症、喘息及びcopdの処置のためのccr2受容体アンタゴニストとしての環状ピリミジン−4−カルボキサミド |
US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
PL3091012T3 (pl) | 2009-12-17 | 2018-08-31 | Centrexion Therapeutics Corporation | Antagoniści receptora CCR2 i ich zastosowanie |
TWI510241B (zh) | 2010-02-18 | 2015-12-01 | Vtv Therapeutice Llc | 苯基-雜芳基衍生物及其使用方法 |
JP2013526507A (ja) | 2010-05-12 | 2013-06-24 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ccr2受容体アンタゴニスト、その製造方法及び薬物としてのその使用 |
US8946218B2 (en) | 2010-05-12 | 2015-02-03 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments |
WO2011144501A1 (en) | 2010-05-17 | 2011-11-24 | Boehringer Ingelheim International Gmbh | Ccr2 antagonists and uses thereof |
US9018212B2 (en) | 2010-05-25 | 2015-04-28 | Boehringer Ingelheim International Gmbh | Pyridazine carboxamides as CCR2 receptor antagonists |
JP5721242B2 (ja) | 2010-06-01 | 2015-05-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ccr2アンタゴニスト |
US8853390B2 (en) | 2010-09-16 | 2014-10-07 | Abbvie Inc. | Processes for preparing 1,2-substituted cyclopropyl derivatives |
EP2731941B1 (en) | 2011-07-15 | 2019-05-08 | Boehringer Ingelheim International GmbH | Novel and selective ccr2 antagonists |
WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
RS63190B1 (sr) | 2014-08-04 | 2022-06-30 | Nuevolution As | Opciono fuzionisani derivati pirimidina zamenjeni heterociklilom korisni za lečenje zapaljenskih, metaboličkih, onkoloških i autoimunskih bolesti |
JP6917910B2 (ja) | 2015-07-02 | 2021-08-11 | セントレクシオン セラピューティクス コーポレイション | (4−((3r,4r)−3−メトキシテトラヒドロ−ピラン−4−イルアミノ)ピペリジン−1−イル)(5−メチル−6−(((2r,6s)−6−(p−トリル)テトラヒドロ−2h−ピラン−2−イル)メチルアミノ)ピリミジン−4イル)メタノンクエン酸塩 |
EP4076657A1 (en) | 2019-12-20 | 2022-10-26 | Nuevolution A/S | Compounds active towards nuclear receptors |
EP4126875A1 (en) | 2020-03-31 | 2023-02-08 | Nuevolution A/S | Compounds active towards nuclear receptors |
US11780843B2 (en) | 2020-03-31 | 2023-10-10 | Nuevolution A/S | Compounds active towards nuclear receptors |
Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB753166A (en) * | 1953-05-22 | 1956-07-18 | Miles Lab | Improvements in or relating to substituted piperazines |
US2993899A (en) * | 1958-03-31 | 1961-07-25 | Miles Lab | Acetylenically unsaturated piperazine derivatives |
US3309370A (en) * | 1964-07-16 | 1967-03-14 | Miles Lab | Bicycloalkyl piperazine derivatives and process |
FR2306694A1 (fr) * | 1975-04-07 | 1976-11-05 | Parcor | Derives de la piperazine |
US4144346A (en) * | 1977-01-31 | 1979-03-13 | Janssen Pharmaceutica N.V. | Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles |
US4163849A (en) * | 1978-03-17 | 1979-08-07 | Merck & Co., Inc. | Piperazinylpyrazines |
JPS56118074A (en) * | 1980-02-22 | 1981-09-16 | Tanabe Seiyaku Co Ltd | Propane derivative and its preparation |
US4339579A (en) * | 1980-12-29 | 1982-07-13 | American Home Products Corporation | 2,6-Bis-(pyrrolopyrazinyl)pyrazines |
US5001125A (en) * | 1984-03-26 | 1991-03-19 | Janssen Pharmaceutica N.V. | Anti-virally active pyridazinamines |
FR2573075B1 (fr) * | 1984-09-14 | 1987-03-20 | Innothera Lab Sa | Nouvelles (pyridyl-2)-1 piperazines, leur procede de preparation et leur application en therapeutique |
JP2576862B2 (ja) * | 1986-03-05 | 1997-01-29 | 大塚製薬 株式会社 | カルボスチリル誘導体 |
DK111387A (da) * | 1986-03-05 | 1987-09-06 | Otsuka Pharma Co Ltd | Carbostyrilderivater og salte deraf, laegemiddel indeholdende saadanne derivater samt fremgangsmaade til fremstilling af derivaterne |
AU639529B2 (en) * | 1987-03-04 | 1993-07-29 | Higuchi, Yoshinari | Carbostyril derivatives and salts thereof and anti-arrhythmic agents containing the carbostyril derivatives |
DE3803860A1 (de) * | 1988-02-09 | 1989-08-17 | Basf Ag | N,n'-disubstituierte piperazine |
ES2058630T3 (es) * | 1989-03-03 | 1994-11-01 | Dainippon Pharmaceutical Co | Derivados de 2-(1-piperazinil)-4-fenilcicloalcanopiridinas, procedimientos de preparacion y composiciones farmaceuticas que los contienen. |
GB9012316D0 (en) * | 1990-06-01 | 1990-07-18 | Wellcome Found | Pharmacologically active cns compounds |
WO1997002245A1 (fr) * | 1995-07-06 | 1997-01-23 | Japan Tobacco Inc. | Derives de benzamidoxime et leur utilisation a des fins medicinales |
JPH0971564A (ja) * | 1995-07-06 | 1997-03-18 | Japan Tobacco Inc | ベンズアミドオキシム誘導体及びその医薬用途 |
DZ2376A1 (fr) * | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
ATE404539T1 (de) * | 1997-10-02 | 2008-08-15 | Eisai R&D Man Co Ltd | Kondensierte pyridinderivate |
JP3989102B2 (ja) * | 1997-10-02 | 2007-10-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 縮合ピリジン誘導体 |
AU2935200A (en) * | 1999-04-30 | 2000-11-17 | Pfizer Products Inc. | Compounds for the treatment of obesity |
GB9926302D0 (en) * | 1999-11-05 | 2000-01-12 | Smithkline Beecham Plc | Novel compounds |
GB9926303D0 (en) * | 1999-11-05 | 2000-01-12 | Smithkline Beecham Plc | Novel compounds |
PL356485A1 (en) * | 1999-12-16 | 2004-06-28 | Schering Corporation | Substituted imidazole neuropeptide y y5 receptor antagonists |
FI20000480A0 (fi) * | 2000-03-01 | 2000-03-01 | Orion Yhtymae Oyj | Kinoliini- ja naftaleenijohdannaisia alfa-2 antagonisteina |
MXPA03006812A (es) * | 2001-01-31 | 2004-10-15 | Synaptic Pharma Corp | Uso de antagonistas de receptores de gal3 para el tratamiento de depresion y/o ansiedad y compuestos utiles en los metodos de tratamiento. |
AU2003229535A1 (en) * | 2002-06-06 | 2003-12-22 | Novo Nordisk A/S | Substituted hexahydropyrrolo(1,2-a)pyrazines, octahydropyrido(1,2-a)pyrazines and decahydropyrazino(1,2-a)azepines |
-
2003
- 2003-02-05 WO PCT/DK2003/000071 patent/WO2003066604A2/en active Application Filing
- 2003-02-05 JP JP2003565978A patent/JP4607458B2/ja not_active Expired - Fee Related
- 2003-02-05 IL IL16285903A patent/IL162859A0/xx unknown
- 2003-02-05 EP EP03701482A patent/EP1474401A2/en not_active Withdrawn
- 2003-02-05 CN CNA038033607A patent/CN1628109A/zh active Pending
- 2003-02-05 PL PL03372390A patent/PL372390A1/xx not_active Application Discontinuation
- 2003-02-05 AU AU2003203148A patent/AU2003203148A1/en not_active Abandoned
- 2003-02-05 MX MXPA04007612A patent/MXPA04007612A/es not_active Application Discontinuation
- 2003-02-05 BR BR0307429-3A patent/BR0307429A/pt not_active Application Discontinuation
- 2003-02-05 CA CA002474214A patent/CA2474214A1/en not_active Abandoned
-
2004
- 2004-07-16 ZA ZA2004/05694A patent/ZA200405694B/en unknown
- 2004-09-03 NO NO20043709A patent/NO328714B1/no not_active IP Right Cessation
-
2010
- 2010-01-13 AU AU2010200135A patent/AU2010200135A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
JP2005533747A (ja) | 2005-11-10 |
PL372390A1 (en) | 2005-07-25 |
AU2003203148A1 (en) | 2003-09-02 |
JP4607458B2 (ja) | 2011-01-05 |
MXPA04007612A (es) | 2004-11-10 |
NO20043709L (no) | 2004-09-03 |
AU2010200135A1 (en) | 2010-02-04 |
EP1474401A2 (en) | 2004-11-10 |
IL162859A0 (en) | 2005-11-20 |
WO2003066604A2 (en) | 2003-08-14 |
WO2003066604A3 (en) | 2003-12-04 |
CA2474214A1 (en) | 2003-08-14 |
NO328714B1 (no) | 2010-05-03 |
BR0307429A (pt) | 2004-12-28 |
CN1628109A (zh) | 2005-06-15 |
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