ZA200303599B - Piperazinylpyrazine compounds as agonist or antagonist of serotonin 5HT-2 receptor. - Google Patents
Piperazinylpyrazine compounds as agonist or antagonist of serotonin 5HT-2 receptor. Download PDFInfo
- Publication number
- ZA200303599B ZA200303599B ZA200303599A ZA200303599A ZA200303599B ZA 200303599 B ZA200303599 B ZA 200303599B ZA 200303599 A ZA200303599 A ZA 200303599A ZA 200303599 A ZA200303599 A ZA 200303599A ZA 200303599 B ZA200303599 B ZA 200303599B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrazine
- piperazinyl
- aryl
- compound according
- medical condition
- Prior art date
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- 239000000556 agonist Substances 0.000 title description 5
- HCGFLVDMFDHYJD-UHFFFAOYSA-N 2-piperazin-1-ylpyrazine Chemical class C1CNCCN1C1=CN=CC=N1 HCGFLVDMFDHYJD-UHFFFAOYSA-N 0.000 title description 4
- 239000005557 antagonist Substances 0.000 title description 4
- 108091005479 5-HT2 receptors Proteins 0.000 title description 2
- 102000056834 5-HT2 Serotonin Receptors Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 109
- -1 1-indanyloxy, 2- indanyloxy Chemical group 0.000 claims description 63
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 52
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 28
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 208000019901 Anxiety disease Diseases 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 150000003216 pyrazines Chemical class 0.000 claims description 12
- 208000008589 Obesity Diseases 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 11
- 235000020824 obesity Nutrition 0.000 claims description 11
- 229940076279 serotonin Drugs 0.000 claims description 11
- 208000030814 Eating disease Diseases 0.000 claims description 10
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 235000014632 disordered eating Nutrition 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 206010015037 epilepsy Diseases 0.000 claims description 7
- 201000009032 substance abuse Diseases 0.000 claims description 7
- 231100000736 substance abuse Toxicity 0.000 claims description 7
- 208000011117 substance-related disease Diseases 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
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- 208000019022 Mood disease Diseases 0.000 claims description 6
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000000651 prodrug Chemical group 0.000 claims description 5
- 229940002612 prodrug Drugs 0.000 claims description 5
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001204 N-oxides Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
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- CUVLQUXETABQKG-UHFFFAOYSA-N 2-(1-phenylethoxy)-6-piperazin-1-ylpyrazine Chemical compound C=1C=CC=CC=1C(C)OC(N=1)=CN=CC=1N1CCNCC1 CUVLQUXETABQKG-UHFFFAOYSA-N 0.000 claims description 3
- HSLQBXHVDRKYOM-UHFFFAOYSA-N 2-(2-methylpiperazin-1-yl)-6-phenylmethoxypyrazine Chemical compound CC1CNCCN1C1=CN=CC(OCC=2C=CC=CC=2)=N1 HSLQBXHVDRKYOM-UHFFFAOYSA-N 0.000 claims description 3
- MCEYUYLACAMCON-UHFFFAOYSA-N 2-(3,4-dihydro-2h-chromen-4-yloxy)-6-piperazin-1-ylpyrazine Chemical compound C1CNCCN1C1=CN=CC(OC2C3=CC=CC=C3OCC2)=N1 MCEYUYLACAMCON-UHFFFAOYSA-N 0.000 claims description 3
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- LBXPCVSYZSEMJR-UHFFFAOYSA-N 2-[(3,5-dimethoxyphenyl)methoxy]-6-piperazin-1-ylpyrazine Chemical compound COC1=CC(OC)=CC(COC=2N=C(C=NC=2)N2CCNCC2)=C1 LBXPCVSYZSEMJR-UHFFFAOYSA-N 0.000 claims description 3
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- YMGWSIGLNZOGPL-UHFFFAOYSA-N 2-benzyl-6-piperazin-1-ylpyrazine Chemical compound C=1N=CC(N2CCNCC2)=NC=1CC1=CC=CC=C1 YMGWSIGLNZOGPL-UHFFFAOYSA-N 0.000 claims description 3
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- PIPQCNRCBHVBNI-UHFFFAOYSA-N 3-[2-(6-piperazin-1-ylpyrazin-2-yl)oxyethyl]-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CCOC(N=1)=CN=CC=1N1CCNCC1 PIPQCNRCBHVBNI-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- XIEQLUARAUTYHZ-UHFFFAOYSA-N n,n-dimethyl-4-[2-(6-piperazin-1-ylpyrazin-2-yl)oxyethyl]aniline Chemical compound C1=CC(N(C)C)=CC=C1CCOC1=CN=CC(N2CCNCC2)=N1 XIEQLUARAUTYHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- BFOWHMGSWBDAOH-UHFFFAOYSA-N 2-(1-phenylpropan-2-yloxy)-6-piperazin-1-ylpyrazine Chemical compound C=1N=CC(N2CCNCC2)=NC=1OC(C)CC1=CC=CC=C1 BFOWHMGSWBDAOH-UHFFFAOYSA-N 0.000 claims description 2
- ZJRXYNVDTHFHHD-UHFFFAOYSA-N 2-(2-naphthalen-2-ylethoxy)-6-piperazin-1-ylpyrazine Chemical compound C=1C=C2C=CC=CC2=CC=1CCOC(N=1)=CN=CC=1N1CCNCC1 ZJRXYNVDTHFHHD-UHFFFAOYSA-N 0.000 claims description 2
- LGQFYTYRWGWUEY-UHFFFAOYSA-N 2-(2-phenylethylsulfanyl)-6-piperazin-1-ylpyrazine Chemical compound C=1N=CC(N2CCNCC2)=NC=1SCCC1=CC=CC=C1 LGQFYTYRWGWUEY-UHFFFAOYSA-N 0.000 claims description 2
- CMKZSOBBCDDCME-UHFFFAOYSA-N 2-(5-phenoxypentoxy)-6-piperazin-1-ylpyrazine Chemical compound C=1N=CC(N2CCNCC2)=NC=1OCCCCCOC1=CC=CC=C1 CMKZSOBBCDDCME-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
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US6825198B2 (en) * | 2001-06-21 | 2004-11-30 | Pfizer Inc | 5-HT receptor ligands and uses thereof |
US6989392B2 (en) * | 2002-06-18 | 2006-01-24 | Abbott Laboratories | 2-Aminoquinolines as melanin concentrating hormone receptor antagonists |
CA2493667C (en) * | 2002-08-08 | 2010-04-27 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
CA2514656A1 (en) * | 2003-01-31 | 2004-08-12 | Pfizer Products Inc. | 5ht7 antagonists and inverse agonists |
US20080146583A1 (en) * | 2003-05-15 | 2008-06-19 | Pfizer Inc | Treatment of Incontinence |
CL2004000826A1 (es) | 2003-04-25 | 2005-03-04 | Pfizer | Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129 |
US20040235856A1 (en) * | 2003-04-25 | 2004-11-25 | Pfizer Inc | Treatment of incontinence |
US7795266B2 (en) * | 2003-09-25 | 2010-09-14 | Helton David R | Tetrahydroindolone derivatives for treament of neurological conditions |
MY139645A (en) * | 2004-02-11 | 2009-10-30 | Amgen Inc | Vanilloid receptor ligands and their use in treatments |
CA2556239A1 (en) | 2004-02-11 | 2005-08-25 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
KR100635053B1 (ko) * | 2005-06-21 | 2006-10-16 | 도레이새한 주식회사 | 전자부품용 접착테이프 |
GT200500317A (es) * | 2004-11-05 | 2006-10-27 | Proceso para preparar compuestos de quinolina y productos obtenidos de los mismos | |
WO2006089311A1 (en) * | 2005-02-15 | 2006-08-24 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
MX2007012082A (es) * | 2005-03-31 | 2007-11-20 | Pfizer Prod Inc | Derivados de ciclopentapiridina y tetrahidroquinolina. |
EP1877400A1 (en) * | 2005-04-15 | 2008-01-16 | Amgen, Inc | Vanilloid receptor ligands and their use in treatments |
AR054849A1 (es) * | 2005-07-26 | 2007-07-18 | Wyeth Corp | Diazepinoquinolinas, sintesis de las mismas, e intermediarios para obtenerlas |
TW200734334A (en) * | 2006-01-13 | 2007-09-16 | Wyeth Corp | Treatment of substance abuse |
US20070225279A1 (en) * | 2006-03-24 | 2007-09-27 | Wyeth | Therapeutic combinations for the treatment of depression |
EP1998781A2 (en) * | 2006-03-24 | 2008-12-10 | Wyeth a Corporation of the State of Delaware | Treatment of pain |
CN101506172A (zh) * | 2006-07-14 | 2009-08-12 | 辉瑞产品公司 | (7S)-7-[(5-氟-2-甲基-苄基)氧基]-2-[(2R)-2-甲基哌嗪-1-基]-6,7-二氢-5H-环戊烷并[b]吡啶的酒石酸盐 |
CL2008002777A1 (es) * | 2007-09-21 | 2010-01-22 | Wyeth Corp | Metodo de preparacion de compuestos diazepinoquinolinicos quirales por recristalizacion en un sistema de solvente ternario. |
WO2009062134A1 (en) * | 2007-11-09 | 2009-05-14 | Cenomed Biosciences, Llc | Treatment of post-traumatic stress disorder with tetrahydroindolone arylpiperazine compounds |
US20090264443A1 (en) * | 2008-04-18 | 2009-10-22 | David Helton | Treatment of organophosphate exposure with tetrahydroindolone arylpiperazine compounds |
MY158927A (en) | 2008-06-12 | 2016-11-30 | Janssen Pharmaceutica Nv | Diamino-pyridine, pyrimidine, and pyridazine modulators of the histamine h4 receptor |
US20110003796A1 (en) * | 2009-07-06 | 2011-01-06 | Consejo Nacional De Investigaciones Cientificas Y Tecnicas (Conicet) | Method for the treatment of psychic disorders |
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DE60014083T2 (de) | 1999-06-15 | 2006-03-02 | Bristol-Myers Squibb Pharma Co., Wilmington | Substituierte heterocyclylkondensierte gamma carboline |
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US20020147200A1 (en) | 2002-10-10 |
EA006552B1 (ru) | 2006-02-24 |
EA200300593A1 (ru) | 2003-10-30 |
ZA200504675B (en) | 2006-05-31 |
CN1876648A (zh) | 2006-12-13 |
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