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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- C07D295/00—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
- C07D295/08—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
- C07D295/084—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
- 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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- C07D295/00—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
- C07D295/10—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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- C07—ORGANIC CHEMISTRY
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
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- 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
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- 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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DKPA200201142 | 2002-07-26 | ||
PCT/DK2003/000071 WO2003066604A2 (fr) | 2002-02-05 | 2003-02-05 | Nouvelles aryl- et heteroarylpiperazines |
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EP (1) | EP1474401A2 (fr) |
JP (1) | JP4607458B2 (fr) |
CN (1) | CN1628109A (fr) |
AU (2) | AU2003203148A1 (fr) |
BR (1) | BR0307429A (fr) |
CA (1) | CA2474214A1 (fr) |
IL (1) | IL162859A0 (fr) |
MX (1) | MXPA04007612A (fr) |
NO (1) | NO328714B1 (fr) |
PL (1) | PL372390A1 (fr) |
WO (1) | WO2003066604A2 (fr) |
ZA (1) | ZA200405694B (fr) |
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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 |
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2003
- 2003-02-05 IL IL16285903A patent/IL162859A0/xx unknown
- 2003-02-05 BR BR0307429-3A patent/BR0307429A/pt not_active Application Discontinuation
- 2003-02-05 EP EP03701482A patent/EP1474401A2/fr not_active Withdrawn
- 2003-02-05 PL PL03372390A patent/PL372390A1/xx not_active Application Discontinuation
- 2003-02-05 CN CNA038033607A patent/CN1628109A/zh active Pending
- 2003-02-05 JP JP2003565978A patent/JP4607458B2/ja not_active Expired - Fee Related
- 2003-02-05 CA CA002474214A patent/CA2474214A1/fr not_active Abandoned
- 2003-02-05 MX MXPA04007612A patent/MXPA04007612A/es not_active Application Discontinuation
- 2003-02-05 WO PCT/DK2003/000071 patent/WO2003066604A2/fr active Application Filing
- 2003-02-05 AU AU2003203148A patent/AU2003203148A1/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 |
---|---|
BR0307429A (pt) | 2004-12-28 |
MXPA04007612A (es) | 2004-11-10 |
AU2010200135A1 (en) | 2010-02-04 |
CN1628109A (zh) | 2005-06-15 |
AU2003203148A1 (en) | 2003-09-02 |
NO328714B1 (no) | 2010-05-03 |
WO2003066604A3 (fr) | 2003-12-04 |
NO20043709L (no) | 2004-09-03 |
JP4607458B2 (ja) | 2011-01-05 |
PL372390A1 (en) | 2005-07-25 |
EP1474401A2 (fr) | 2004-11-10 |
JP2005533747A (ja) | 2005-11-10 |
IL162859A0 (en) | 2005-11-20 |
WO2003066604A2 (fr) | 2003-08-14 |
CA2474214A1 (fr) | 2003-08-14 |
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