ZA200105190B - Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression. - Google Patents
Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression. Download PDFInfo
- Publication number
- ZA200105190B ZA200105190B ZA200105190A ZA200105190A ZA200105190B ZA 200105190 B ZA200105190 B ZA 200105190B ZA 200105190 A ZA200105190 A ZA 200105190A ZA 200105190 A ZA200105190 A ZA 200105190A ZA 200105190 B ZA200105190 B ZA 200105190B
- Authority
- ZA
- South Africa
- Prior art keywords
- indole
- cyclohexyl
- piperazin
- cis
- fluoro
- Prior art date
Links
- 208000020401 Depressive disease Diseases 0.000 title description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 29
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 11
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 230000001430 anti-depressive effect Effects 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- -1 2,3-Dihydro-benzo[1,4]dioxin-5-yl Chemical group 0.000 claims description 4
- ORDLTNPENGIZSO-UHFFFAOYSA-N 3-[4-[4-(1h-indol-4-yl)piperazin-1-yl]cyclohexyl]-2-methyl-1h-indole Chemical compound CC=1NC2=CC=CC=C2C=1C(CC1)CCC1N(CC1)CCN1C1=CC=CC2=C1C=CN2 ORDLTNPENGIZSO-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- DOLPIUHNWIPHSB-UHFFFAOYSA-N C12=CC(F)=CC=C2NC=C1C(CC1)CCC1N(CC1)CCN1C1=CC=CC2=C1C=CN2 Chemical compound C12=CC(F)=CC=C2NC=C1C(CC1)CCC1N(CC1)CCN1C1=CC=CC2=C1C=CN2 DOLPIUHNWIPHSB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- HNDDWMZUMFRVLD-UHFFFAOYSA-N 3-[4-(4-quinolin-8-ylpiperazin-1-yl)cyclohexyl]-1h-indole-5-carbonitrile Chemical compound C1=CN=C2C(N3CCN(CC3)C3CCC(CC3)C3=CNC4=CC=C(C=C43)C#N)=CC=CC2=C1 HNDDWMZUMFRVLD-UHFFFAOYSA-N 0.000 claims description 2
- OZGLYAGDXDOWME-UHFFFAOYSA-N 3-[4-[4-(1h-indol-4-yl)piperazin-1-yl]cyclohexen-1-yl]-1h-indole-5-carbonitrile Chemical compound C12=CC(C#N)=CC=C2NC=C1C(CC1)=CCC1N(CC1)CCN1C1=CC=CC2=C1C=CN2 OZGLYAGDXDOWME-UHFFFAOYSA-N 0.000 claims description 2
- SMBPHGSMOKBXEX-UHFFFAOYSA-N 3-[4-[4-(1h-indol-4-yl)piperazin-1-yl]cyclohexyl]-5-methoxy-1h-indole Chemical compound C12=CC(OC)=CC=C2NC=C1C(CC1)CCC1N(CC1)CCN1C1=CC=CC2=C1C=CN2 SMBPHGSMOKBXEX-UHFFFAOYSA-N 0.000 claims description 2
- SHVCWBIQZXNONP-UHFFFAOYSA-N 5-chloro-3-[4-[4-(1H-indol-4-yl)piperazin-1-yl]cyclohexyl]-1H-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1C(CC1)CCC1N(CC1)CCN1C1=CC=CC2=C1C=CN2 SHVCWBIQZXNONP-UHFFFAOYSA-N 0.000 claims description 2
- PKKXQKIYTJVFFJ-UHFFFAOYSA-N C1=CC=C2C(C3CCC(CC3)N3CCN(CC3)C=3C=4C=CNC=4C=CC=3)=CNC2=C1 Chemical compound C1=CC=C2C(C3CCC(CC3)N3CCN(CC3)C=3C=4C=CNC=4C=CC=3)=CNC2=C1 PKKXQKIYTJVFFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 8
- 238000000034 method Methods 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- KYRUDMLLMDKVOX-UHFFFAOYSA-N 8-[4-[4-(5-fluoro-1h-indol-3-yl)cyclohexyl]piperazin-1-yl]quinoline Chemical compound C1=CN=C2C(N3CCN(CC3)C3CCC(CC3)C3=CNC4=CC=C(C=C43)F)=CC=CC2=C1 KYRUDMLLMDKVOX-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- OTRPSWLBRPYFGX-UHFFFAOYSA-N 3-[4-[4-(1h-indol-4-yl)piperazin-1-yl]cyclohexyl]-1-methylindole-5-carbonitrile Chemical compound C12=CC(C#N)=CC=C2N(C)C=C1C1CCC(N2CCN(CC2)C=2C=3C=CNC=3C=CC=2)CC1 OTRPSWLBRPYFGX-UHFFFAOYSA-N 0.000 claims 1
- MCPMBLGHBQTMIY-UHFFFAOYSA-N 3-[4-[4-(1h-indol-4-yl)piperazin-1-yl]cyclohexyl]-1-propylindole-5-carbonitrile Chemical compound C12=CC(C#N)=CC=C2N(CCC)C=C1C1CCC(N2CCN(CC2)C=2C=3C=CNC=3C=CC=2)CC1 MCPMBLGHBQTMIY-UHFFFAOYSA-N 0.000 claims 1
- OYJYQLZNASJVKA-KESTWPANSA-N C1CN([C@H]2CC[C@@H](CC2)C2=CNC3=CC=C(C=C32)Br)CCN1C1=CC=CC2=C1C=CN2 Chemical compound C1CN([C@H]2CC[C@@H](CC2)C2=CNC3=CC=C(C=C32)Br)CCN1C1=CC=CC2=C1C=CN2 OYJYQLZNASJVKA-KESTWPANSA-N 0.000 claims 1
- KZTVKOKDELMIOA-MSEWRSJXSA-N COC1=CC=C(F)C=C1N1CCN([C@@H]2CC[C@@H](CC2)C=2C3=CC(F)=CC=C3NC=2)CC1 Chemical compound COC1=CC=C(F)C=C1N1CCN([C@@H]2CC[C@@H](CC2)C=2C3=CC(F)=CC=C3NC=2)CC1 KZTVKOKDELMIOA-MSEWRSJXSA-N 0.000 claims 1
- YHTVPWYPSMYPLD-GRGXKFILSA-N FC1=CC=C2C([C@@H]3CC[C@@H](CC3)N3CCN(CC3)C3=C4C=CN(C4=CC=C3)C)=CN(C)C2=C1 Chemical compound FC1=CC=C2C([C@@H]3CC[C@@H](CC3)N3CCN(CC3)C3=C4C=CN(C4=CC=C3)C)=CN(C)C2=C1 YHTVPWYPSMYPLD-GRGXKFILSA-N 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- MVXVYAKCVDQRLW-UHFFFAOYSA-N azain Natural products C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 208000035475 disorder Diseases 0.000 description 5
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 4
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 4
- 102000007527 Autoreceptors Human genes 0.000 description 3
- 108010071131 Autoreceptors Proteins 0.000 description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 2
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 230000005062 synaptic transmission Effects 0.000 description 2
- KPSXQZRHHYIOJN-UHFFFAOYSA-N 5-fluoro-3-[4-[4-(2-methoxyphenyl)piperazin-1-yl]cyclohexen-1-yl]-1h-indole Chemical compound COC1=CC=CC=C1N1CCN(C2CC=C(CC2)C=2C3=CC(F)=CC=C3NC=2)CC1 KPSXQZRHHYIOJN-UHFFFAOYSA-N 0.000 description 1
- 210000002348 5-ht neuron Anatomy 0.000 description 1
- AAURBPVIEGZGKT-UHFFFAOYSA-N 6-fluoro-3-[4-[4-(1H-indol-4-yl)piperazin-1-yl]cyclohexyl]-1H-indole Chemical compound C=1NC2=CC(F)=CC=C2C=1C(CC1)CCC1N(CC1)CCN1C1=CC=CC2=C1C=CN2 AAURBPVIEGZGKT-UHFFFAOYSA-N 0.000 description 1
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 description 1
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- PXPDZPCPTSKVAX-PUZFROQSSA-N chembl181784 Chemical compound COC1=CC=CC=C1N1CCN([C@@H]2CC[C@@H](CC2)C=2C3=CC(F)=CC=C3NC=2)CC1 PXPDZPCPTSKVAX-PUZFROQSSA-N 0.000 description 1
- BKCXSHHVYOXEJX-TYKWCNGQSA-N chembl522529 Chemical compound C12=CC(F)=CC=C2N(C)C=C1[C@H]1CC[C@@H](N2CCN(CC2)C=2C=3C=CNC=3C=CC=2)CC1 BKCXSHHVYOXEJX-TYKWCNGQSA-N 0.000 description 1
- 238000000586 desensitisation Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000008517 inhibition of serotonin uptake Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 230000013275 serotonin uptake Effects 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D401/08—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 carbon chain containing alicyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D295/02—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- 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
- C07D403/14—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 three or more hetero rings
-
- 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
-
- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22658399A | 1999-01-07 | 1999-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200105190B true ZA200105190B (en) | 2002-09-23 |
Family
ID=22849500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200105190A ZA200105190B (en) | 1999-01-07 | 2001-06-22 | Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression. |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP1147083B1 (es) |
| JP (1) | JP2002534411A (es) |
| KR (1) | KR20010086163A (es) |
| CN (1) | CN1166636C (es) |
| AR (1) | AR028810A1 (es) |
| AT (1) | ATE269303T1 (es) |
| AU (1) | AU2490900A (es) |
| BR (1) | BR0007424A (es) |
| CA (1) | CA2355342A1 (es) |
| CZ (1) | CZ20012444A3 (es) |
| DE (1) | DE60011570T2 (es) |
| DK (1) | DK1147083T3 (es) |
| ES (1) | ES2219302T3 (es) |
| HU (1) | HUP0200309A3 (es) |
| IL (1) | IL143979A0 (es) |
| NO (1) | NO20013369L (es) |
| PT (1) | PT1147083E (es) |
| WO (1) | WO2000040554A1 (es) |
| ZA (1) | ZA200105190B (es) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1228065A1 (en) * | 1999-11-08 | 2002-08-07 | Wyeth | (indol-3-yl)-cycloalkyl]-3-substituted azetidines for the treatment of central nervous system disorders |
| US6337326B1 (en) * | 1999-11-08 | 2002-01-08 | American Home Products Corporation | N-aryl-(homopiperazinyl)-cyclohexyl amines |
| CN1821236B (zh) * | 2001-01-16 | 2010-06-23 | 阿斯特拉曾尼卡有限公司 | 治疗性杂环化合物 |
| AU2002217742B2 (en) * | 2001-01-16 | 2008-02-21 | Astrazeneca Ab | Therapeutic heterocyclic compounds |
| US6777437B2 (en) | 2001-03-29 | 2004-08-17 | Bristol-Myers Squibb Company | Cyclopropylindole derivatives as selective serotonin reuptake inhibitors |
| SE0103648D0 (sv) * | 2001-11-01 | 2001-11-01 | Astrazeneca Ab | Therapeutic quinolone compounds |
| SE0103649D0 (sv) * | 2001-11-01 | 2001-11-01 | Astrazeneca Ab | Therapeutic quinoline compounds |
| GB0227240D0 (en) * | 2002-11-21 | 2002-12-31 | Glaxo Group Ltd | Compounds |
| US7276603B2 (en) | 2003-05-02 | 2007-10-02 | Wyeth | Benzofuranyl-and benzothienyl-piperazinyl quinolines and methods of their use |
| WO2006009734A1 (en) | 2004-06-17 | 2006-01-26 | Wyeth | Gonadotropin releasing hormone receptor antagonists |
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| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| EP3068776B1 (en) | 2013-11-13 | 2019-05-29 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| SG10201804021TA (en) | 2013-11-13 | 2018-07-30 | Vertex Pharma | Methods of preparing inhibitors of influenza viruses replication |
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| CN104725363B (zh) * | 2013-12-20 | 2019-03-01 | 广东东阳光药业有限公司 | 取代的哌嗪化合物及其使用方法和用途 |
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| JP6857617B2 (ja) | 2015-05-13 | 2021-04-14 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4954502A (en) * | 1988-06-10 | 1990-09-04 | Bristol-Myers Squibb Company | 1-indolyalkyl-4-(substituted-pyridinyl)piperazines |
| US5468767A (en) * | 1994-01-06 | 1995-11-21 | Bristol-Myers Squibb Company | Antidepressant 3-(aminocycloalkenyl)-indole-5-nitrile derivatives |
| DE19512639A1 (de) * | 1995-04-05 | 1996-10-10 | Merck Patent Gmbh | Benzonitrile und -fluoride |
-
2000
- 2000-01-06 JP JP2000592263A patent/JP2002534411A/ja not_active Withdrawn
- 2000-01-06 CN CNB008026084A patent/CN1166636C/zh not_active Expired - Fee Related
- 2000-01-06 AT AT00903114T patent/ATE269303T1/de not_active IP Right Cessation
- 2000-01-06 CA CA002355342A patent/CA2355342A1/en not_active Abandoned
- 2000-01-06 KR KR1020017008567A patent/KR20010086163A/ko not_active Application Discontinuation
- 2000-01-06 CZ CZ20012444A patent/CZ20012444A3/cs unknown
- 2000-01-06 ES ES00903114T patent/ES2219302T3/es not_active Expired - Lifetime
- 2000-01-06 AU AU24909/00A patent/AU2490900A/en not_active Abandoned
- 2000-01-06 DK DK00903114T patent/DK1147083T3/da active
- 2000-01-06 WO PCT/US2000/000223 patent/WO2000040554A1/en not_active Application Discontinuation
- 2000-01-06 AR ARP000100049A patent/AR028810A1/es not_active Application Discontinuation
- 2000-01-06 EP EP00903114A patent/EP1147083B1/en not_active Expired - Lifetime
- 2000-01-06 DE DE60011570T patent/DE60011570T2/de not_active Expired - Fee Related
- 2000-01-06 BR BR0007424-1A patent/BR0007424A/pt not_active Application Discontinuation
- 2000-01-06 IL IL14397900A patent/IL143979A0/xx unknown
- 2000-01-06 HU HU0200309A patent/HUP0200309A3/hu unknown
- 2000-01-06 PT PT00903114T patent/PT1147083E/pt unknown
-
2001
- 2001-06-22 ZA ZA200105190A patent/ZA200105190B/en unknown
- 2001-07-06 NO NO20013369A patent/NO20013369L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60011570D1 (de) | 2004-07-22 |
| IL143979A0 (en) | 2002-04-21 |
| EP1147083A1 (en) | 2001-10-24 |
| BR0007424A (pt) | 2001-10-09 |
| DE60011570T2 (de) | 2004-11-25 |
| CN1166636C (zh) | 2004-09-15 |
| EP1147083B1 (en) | 2004-06-16 |
| KR20010086163A (ko) | 2001-09-08 |
| AU2490900A (en) | 2000-07-24 |
| HUP0200309A2 (en) | 2002-06-29 |
| NO20013369D0 (no) | 2001-07-06 |
| CN1336916A (zh) | 2002-02-20 |
| ATE269303T1 (de) | 2004-07-15 |
| WO2000040554A1 (en) | 2000-07-13 |
| JP2002534411A (ja) | 2002-10-15 |
| PT1147083E (pt) | 2004-09-30 |
| CA2355342A1 (en) | 2000-07-13 |
| ES2219302T3 (es) | 2004-12-01 |
| HUP0200309A3 (en) | 2003-05-28 |
| DK1147083T3 (da) | 2004-08-16 |
| NO20013369L (no) | 2001-09-03 |
| AR028810A1 (es) | 2003-05-28 |
| CZ20012444A3 (cs) | 2002-02-13 |
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