ZA200408975B - Novel compounds are their use. - Google Patents
Novel compounds are their use. Download PDFInfo
- Publication number
- ZA200408975B ZA200408975B ZA200408975A ZA200408975A ZA200408975B ZA 200408975 B ZA200408975 B ZA 200408975B ZA 200408975 A ZA200408975 A ZA 200408975A ZA 200408975 A ZA200408975 A ZA 200408975A ZA 200408975 B ZA200408975 B ZA 200408975B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyridin
- trifluoromethyl
- piperazine
- acetate
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000003814 drug Substances 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 42
- -1 2-tetrahydrofuryl Chemical group 0.000 claims description 24
- 108020003175 receptors Proteins 0.000 claims description 20
- 102000005962 receptors Human genes 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 13
- 208000008589 Obesity Diseases 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 229940076279 serotonin Drugs 0.000 claims description 7
- 208000030814 Eating disease Diseases 0.000 claims description 6
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 6
- 235000014632 disordered eating Nutrition 0.000 claims description 6
- 108091005436 5-HT7 receptors Proteins 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 150000004885 piperazines Chemical class 0.000 claims description 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 34
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 238000011321 prophylaxis Methods 0.000 claims 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 206010027304 Menopausal symptoms Diseases 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000000561 anti-psychotic effect Effects 0.000 claims 2
- 208000014679 binge eating disease Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 238000001647 drug administration Methods 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 201000009032 substance abuse Diseases 0.000 claims 2
- 231100000736 substance abuse Toxicity 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 230000004584 weight gain Effects 0.000 claims 2
- 235000019786 weight gain Nutrition 0.000 claims 2
- XJXIZRHEURHPLD-GFCCVEGCSA-N (2r)-1-[6-[(2-chlorophenyl)methylsulfanyl]-5-(trifluoromethyl)pyridin-2-yl]-2-methylpiperazine Chemical compound C[C@@H]1CNCCN1C1=CC=C(C(F)(F)F)C(SCC=2C(=CC=CC=2)Cl)=N1 XJXIZRHEURHPLD-GFCCVEGCSA-N 0.000 claims 1
- OLQYIWBVVISDKZ-SSDOTTSWSA-N (2r)-1-[6-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpiperazine Chemical compound C[C@@H]1CNCCN1C1=CC=C(C(F)(F)F)C(Cl)=N1 OLQYIWBVVISDKZ-SSDOTTSWSA-N 0.000 claims 1
- SZSVGTFMHBWDFK-CYBMUJFWSA-N (2r)-2-methyl-1-[6-phenylmethoxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound C[C@@H]1CNCCN1C1=CC=C(C(F)(F)F)C(OCC=2C=CC=CC=2)=N1 SZSVGTFMHBWDFK-CYBMUJFWSA-N 0.000 claims 1
- XJXIZRHEURHPLD-LBPRGKRZSA-N (2s)-1-[6-[(2-chlorophenyl)methylsulfanyl]-5-(trifluoromethyl)pyridin-2-yl]-2-methylpiperazine Chemical compound C[C@H]1CNCCN1C1=CC=C(C(F)(F)F)C(SCC=2C(=CC=CC=2)Cl)=N1 XJXIZRHEURHPLD-LBPRGKRZSA-N 0.000 claims 1
- SGLNIXKCLOPOJJ-SSDOTTSWSA-N (3r)-1-[6-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methylpiperazine Chemical compound C1CN[C@H](C)CN1C1=CC=C(C(F)(F)F)C(Cl)=N1 SGLNIXKCLOPOJJ-SSDOTTSWSA-N 0.000 claims 1
- NTUXZOOPCXJLMQ-SECBINFHSA-N (3r)-1-[6-ethylsulfanyl-5-(trifluoromethyl)pyridin-2-yl]-3-methylpiperazine Chemical compound C1=C(C(F)(F)F)C(SCC)=NC(N2C[C@@H](C)NCC2)=C1 NTUXZOOPCXJLMQ-SECBINFHSA-N 0.000 claims 1
- MGNJRCXEEAHGRW-CYBMUJFWSA-N (3r)-3-methyl-1-[6-phenylmethoxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound C1CN[C@H](C)CN1C1=CC=C(C(F)(F)F)C(OCC=2C=CC=CC=2)=N1 MGNJRCXEEAHGRW-CYBMUJFWSA-N 0.000 claims 1
- SGLNIXKCLOPOJJ-ZETCQYMHSA-N (3s)-1-[6-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-methylpiperazine Chemical compound C1CN[C@@H](C)CN1C1=CC=C(C(F)(F)F)C(Cl)=N1 SGLNIXKCLOPOJJ-ZETCQYMHSA-N 0.000 claims 1
- NTUXZOOPCXJLMQ-VIFPVBQESA-N (3s)-1-[6-ethylsulfanyl-5-(trifluoromethyl)pyridin-2-yl]-3-methylpiperazine Chemical compound C1=C(C(F)(F)F)C(SCC)=NC(N2C[C@H](C)NCC2)=C1 NTUXZOOPCXJLMQ-VIFPVBQESA-N 0.000 claims 1
- JDBDRBLDOHFQGQ-UHFFFAOYSA-N 1-[6-(1-phenylethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound C=1C=CC=CC=1C(C)OC(C(=CC=1)C(F)(F)F)=NC=1N1CCNCC1 JDBDRBLDOHFQGQ-UHFFFAOYSA-N 0.000 claims 1
- PNJPYOVAPXMJKI-UHFFFAOYSA-N 1-[6-(2,3-dihydro-1,4-benzodioxin-6-ylmethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound N1=C(OCC=2C=C3OCCOC3=CC=2)C(C(F)(F)F)=CC=C1N1CCNCC1 PNJPYOVAPXMJKI-UHFFFAOYSA-N 0.000 claims 1
- BRXXSRUTEAWYSZ-UHFFFAOYSA-N 1-[6-(2-cyclohexylethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCCC1CCCCC1 BRXXSRUTEAWYSZ-UHFFFAOYSA-N 0.000 claims 1
- ISXKGCKVAMMYCG-UHFFFAOYSA-N 1-[6-(2-cyclopentylethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCCC1CCCC1 ISXKGCKVAMMYCG-UHFFFAOYSA-N 0.000 claims 1
- LGUCZURKPZRUKT-UHFFFAOYSA-N 1-[6-(2-naphthalen-2-yloxyethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound N1=C(OCCOC=2C=C3C=CC=CC3=CC=2)C(C(F)(F)F)=CC=C1N1CCNCC1 LGUCZURKPZRUKT-UHFFFAOYSA-N 0.000 claims 1
- CWMFJKDGYIOIEP-UHFFFAOYSA-N 1-[6-(2-phenoxyethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCCOC1=CC=CC=C1 CWMFJKDGYIOIEP-UHFFFAOYSA-N 0.000 claims 1
- GGMIYHLTSHVBCU-UHFFFAOYSA-N 1-[6-(furan-2-ylmethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCC1=CC=CO1 GGMIYHLTSHVBCU-UHFFFAOYSA-N 0.000 claims 1
- ZTWDVAVUSQVHNU-UHFFFAOYSA-N 1-[6-(thiophen-3-ylmethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCC=1C=CSC=1 ZTWDVAVUSQVHNU-UHFFFAOYSA-N 0.000 claims 1
- YYSRVJMCMWYNLJ-UHFFFAOYSA-N 1-[6-[(2,3-difluorophenyl)methoxy]-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC1=CC=CC(COC=2C(=CC=C(N=2)N2CCNCC2)C(F)(F)F)=C1F YYSRVJMCMWYNLJ-UHFFFAOYSA-N 0.000 claims 1
- KGIUCJODDPAOCP-UHFFFAOYSA-N 1-[6-[(2-chlorophenyl)methylsulfanyl]-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1SCC1=CC=CC=C1Cl KGIUCJODDPAOCP-UHFFFAOYSA-N 0.000 claims 1
- ZZSYJFBTCLSEEN-UHFFFAOYSA-N 1-[6-[(3-methylphenyl)methylsulfanyl]-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC1=CC=CC(CSC=2C(=CC=C(N=2)N2CCNCC2)C(F)(F)F)=C1 ZZSYJFBTCLSEEN-UHFFFAOYSA-N 0.000 claims 1
- OBLMRDRFYUMUQH-UHFFFAOYSA-N 1-[6-[2-(2,6-difluorophenoxy)ethoxy]-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC1=CC=CC(F)=C1OCCOC1=NC(N2CCNCC2)=CC=C1C(F)(F)F OBLMRDRFYUMUQH-UHFFFAOYSA-N 0.000 claims 1
- VLTFROJFPRTUBA-UHFFFAOYSA-N 1-[6-[[2-(phenoxymethyl)phenyl]methoxy]-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCC1=CC=CC=C1COC1=CC=CC=C1 VLTFROJFPRTUBA-UHFFFAOYSA-N 0.000 claims 1
- LADXOCROYYAJEV-UHFFFAOYSA-N 1-[6-cyclopentyloxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OC1CCCC1 LADXOCROYYAJEV-UHFFFAOYSA-N 0.000 claims 1
- GGIPYRBPIJCYSD-UHFFFAOYSA-N 1-[6-ethylsulfanyl-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound C1=C(C(F)(F)F)C(SCC)=NC(N2CCNCC2)=C1 GGIPYRBPIJCYSD-UHFFFAOYSA-N 0.000 claims 1
- OCEZFJULIYXWAR-UHFFFAOYSA-N 1-[6-phenylmethoxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCC1=CC=CC=C1 OCEZFJULIYXWAR-UHFFFAOYSA-N 0.000 claims 1
- VRGJESCGGWQCRP-UHFFFAOYSA-N 1-[6-propoxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound C1=C(C(F)(F)F)C(OCCC)=NC(N2CCNCC2)=C1 VRGJESCGGWQCRP-UHFFFAOYSA-N 0.000 claims 1
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- VREOKOJKZOOCSM-UHFFFAOYSA-N 3-[[6-piperazin-1-yl-3-(trifluoromethyl)pyridin-2-yl]oxymethyl]benzonitrile Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCC1=CC=CC(C#N)=C1 VREOKOJKZOOCSM-UHFFFAOYSA-N 0.000 claims 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 1
- BMBLRVKOLIKNPO-UHFFFAOYSA-N 8-[2-[6-piperazin-1-yl-3-(trifluoromethyl)pyridin-2-yl]oxyethoxy]quinoline Chemical compound N1=C(OCCOC=2C3=NC=CC=C3C=CC=2)C(C(F)(F)F)=CC=C1N1CCNCC1 BMBLRVKOLIKNPO-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
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- 150000001204 N-oxides Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
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- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
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- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
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- 239000000651 prodrug Chemical group 0.000 claims 1
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- 150000003839 salts Chemical class 0.000 claims 1
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
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- 239000003446 ligand Substances 0.000 description 4
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- QUERAHCHJWZYJF-UHFFFAOYSA-N 1-(1h-indol-2-yl)ethanamine Chemical class C1=CC=C2NC(C(N)C)=CC2=C1 QUERAHCHJWZYJF-UHFFFAOYSA-N 0.000 description 1
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- IGBPLIGXKQSNKV-UHFFFAOYSA-N 1-(6-ethoxypyridin-2-yl)piperazine Chemical compound CCOC1=CC=CC(N2CCNCC2)=N1 IGBPLIGXKQSNKV-UHFFFAOYSA-N 0.000 description 1
- OILYGSQXSLUZSY-UHFFFAOYSA-N 1-(6-methoxypyridin-2-yl)piperazine Chemical compound COC1=CC=CC(N2CCNCC2)=N1 OILYGSQXSLUZSY-UHFFFAOYSA-N 0.000 description 1
- SQXPLTLACATQLF-UHFFFAOYSA-N 1-(6-phenoxypyridin-2-yl)piperazine Chemical compound C1CNCCN1C1=CC=CC(OC=2C=CC=CC=2)=N1 SQXPLTLACATQLF-UHFFFAOYSA-N 0.000 description 1
- COLGTEXTAQAQGH-UHFFFAOYSA-N 1-(6-phenylmethoxypyridin-2-yl)piperazine Chemical compound C=1C=CC=CC=1COC(N=1)=CC=CC=1N1CCNCC1 COLGTEXTAQAQGH-UHFFFAOYSA-N 0.000 description 1
- VNFLCKSDQOEXJF-UHFFFAOYSA-N 1-(6-propan-2-yloxypyridin-2-yl)piperazine Chemical compound CC(C)OC1=CC=CC(N2CCNCC2)=N1 VNFLCKSDQOEXJF-UHFFFAOYSA-N 0.000 description 1
- FTLURDYNTODIEK-UHFFFAOYSA-N 1-[6-(2-methylpropoxy)pyridin-2-yl]piperazine Chemical compound CC(C)COC1=CC=CC(N2CCNCC2)=N1 FTLURDYNTODIEK-UHFFFAOYSA-N 0.000 description 1
- XVYOLPSINUUEHF-UHFFFAOYSA-N 1-[6-(2-phenylethyl)pyridin-2-yl]piperazine Chemical compound C=1C=CC=CC=1CCC(N=1)=CC=CC=1N1CCNCC1 XVYOLPSINUUEHF-UHFFFAOYSA-N 0.000 description 1
- HFTNTSJFXFBNHH-UHFFFAOYSA-N 1-[6-(cyclohexylmethoxy)pyridin-2-yl]piperazine Chemical compound C1CCCCC1COC(N=1)=CC=CC=1N1CCNCC1 HFTNTSJFXFBNHH-UHFFFAOYSA-N 0.000 description 1
- RVYSFDSBHGXYDX-UHFFFAOYSA-N 1-[6-(cyclohexylmethyl)pyridin-2-yl]piperazine Chemical compound C=1C=CC(N2CCNCC2)=NC=1CC1CCCCC1 RVYSFDSBHGXYDX-UHFFFAOYSA-N 0.000 description 1
- ZEEQFFNXWAZADS-UHFFFAOYSA-N 1-[6-(cyclopropylmethoxy)pyridin-2-yl]piperazine Chemical compound C1CC1COC(N=1)=CC=CC=1N1CCNCC1 ZEEQFFNXWAZADS-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
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- 229960002464 fluoxetine Drugs 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- XSTBCICLDQSQIQ-UHFFFAOYSA-N indeno[2,1-c]pyrazole Chemical class C1=CC=C2C3=CN=NC3=CC2=C1 XSTBCICLDQSQIQ-UHFFFAOYSA-N 0.000 description 1
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- QZYYPQAYSFBKPW-UHFFFAOYSA-N org 12962 Chemical compound N1=C(Cl)C(C(F)(F)F)=CC=C1N1CCNCC1 QZYYPQAYSFBKPW-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical class C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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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- C—CHEMISTRY; METALLURGY
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- 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
- C07D213/72—Nitrogen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- 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
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
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- Hospice & Palliative Care (AREA)
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- Gynecology & Obstetrics (AREA)
- Addiction (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Liquid Crystal Substances (AREA)
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SE0201544A SE0201544D0 (sv) | 2002-05-17 | 2002-05-17 | Novel compounds and thier use |
US41003802P | 2002-09-12 | 2002-09-12 |
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EP (1) | EP1506185B1 (de) |
JP (1) | JP4865221B2 (de) |
KR (1) | KR20050026702A (de) |
CN (1) | CN1329389C (de) |
AT (1) | ATE327229T1 (de) |
AU (1) | AU2003228196B2 (de) |
BR (1) | BR0310077A (de) |
CA (1) | CA2483619A1 (de) |
CY (1) | CY1105162T1 (de) |
DE (1) | DE60305484T2 (de) |
DK (1) | DK1506185T3 (de) |
EA (1) | EA007543B1 (de) |
ES (1) | ES2263971T3 (de) |
HK (1) | HK1084941A1 (de) |
IL (1) | IL164974A0 (de) |
MX (1) | MXPA04011437A (de) |
NO (1) | NO20045486L (de) |
NZ (1) | NZ536409A (de) |
PT (1) | PT1506185E (de) |
RS (1) | RS99804A (de) |
SE (1) | SE0201544D0 (de) |
SI (1) | SI1506185T1 (de) |
WO (1) | WO2003097636A1 (de) |
ZA (1) | ZA200408975B (de) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
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US20030236259A1 (en) * | 2002-02-05 | 2003-12-25 | Rolf Hohlweg | Novel aryl- and heteroarylpiperazines |
WO2006022420A1 (ja) * | 2004-08-25 | 2006-03-02 | Takeda Pharmaceutical Company Limited | 腹圧性尿失禁の予防・治療剤及びそのスクリーニング方法 |
GT200500317A (es) * | 2004-11-05 | 2006-10-27 | Proceso para preparar compuestos de quinolina y productos obtenidos de los mismos | |
JP5121707B2 (ja) | 2005-07-04 | 2013-01-16 | ハイ ポイント ファーマシューティカルズ,エルエルシー | 新規医薬 |
AR054849A1 (es) * | 2005-07-26 | 2007-07-18 | Wyeth Corp | Diazepinoquinolinas, sintesis de las mismas, e intermediarios para obtenerlas |
JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
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 (de) * | 2006-03-24 | 2008-12-10 | Wyeth a Corporation of the State of Delaware | Schmerzbehandlung |
WO2007132841A1 (ja) | 2006-05-16 | 2007-11-22 | Takeda Pharmaceutical Company Limited | 縮合複素環化合物およびその用途 |
SG163547A1 (en) * | 2006-05-29 | 2010-08-30 | High Point Pharmaceuticals Llc | 3- (1, 3-benz0di0x0l-5-yl) -6- (4-cyclopropylpiperazin-1-yl) -pyridazine, its salts and solvates and its use as histamine h3 receptor antagonist |
US20070293475A1 (en) * | 2006-06-20 | 2007-12-20 | Alcon Manufacturing Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
TW200823187A (en) * | 2006-10-24 | 2008-06-01 | Wyeth Corp | Benzodioxane derivatives and uses thereof |
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 |
CN101663292A (zh) | 2007-04-23 | 2010-03-03 | 詹森药业有限公司 | 作为快速解离的多巴胺2受体拮抗剂的4-烷氧基哒嗪衍生物 |
KR101506156B1 (ko) | 2007-04-23 | 2015-03-26 | 얀센 파마슈티카 엔.브이. | 속해리성 도파민 2 수용체 길항제로서의 티아(디아)졸 |
EP2014656A3 (de) * | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | Neue heterocyclische H3-Antagonisten |
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. |
WO2009063992A1 (ja) | 2007-11-15 | 2009-05-22 | Takeda Pharmaceutical Company Limited | 縮合ピリジン誘導体およびその用途 |
CA2729313C (en) | 2008-07-03 | 2016-08-30 | Janssen Pharmaceutica Nv | Substituted 6-(1-piperazinyl)-pyridazines as 5-ht6 receptor antagonists |
EA019048B1 (ru) * | 2008-07-31 | 2013-12-30 | Янссен Фармацевтика Нв | Пиперазин-1-илтрифторметилзамещенные пиридины в качестве быстро диссоциирующихся антагонистов d-рецепторов дофамина |
AU2010260847B2 (en) | 2009-06-15 | 2016-11-24 | Takeda Pharmaceutical Company Limited | Pyrazinooxazepine derivatives |
JPWO2011071136A1 (ja) | 2009-12-11 | 2013-04-22 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
WO2012030953A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
JP6263469B2 (ja) | 2011-07-15 | 2018-01-17 | ノバルティス アーゲー | アザ二環式ジ−アリールエーテルの塩およびその製造方法またはその前駆体の製造方法 |
WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
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US4078063A (en) * | 1976-09-24 | 1978-03-07 | Merck & Co., Inc. | Piperazinylpyridines |
ES2061953T3 (es) * | 1988-11-24 | 1994-12-16 | Akzo Nv | Un procedimiento para preparar una composicion farmaceutica. |
EP0580465A1 (de) | 1992-06-25 | 1994-01-26 | Sanofi | Neue therapeutische Verwendung von heterocyclischen Piperazinen als 5-HT3-Agonisten und neue Derivaten |
JPH0665203A (ja) * | 1992-06-25 | 1994-03-08 | Elf Sanofi | ピペラジンのヘテロ環誘導体 |
SE9202265D0 (sv) * | 1992-07-31 | 1992-07-31 | Kabi Pharmacia Ab | Novel- pyridyl and pyrimidylpiperazine derivatives |
JPH0797370A (ja) * | 1993-09-29 | 1995-04-11 | Asahi Chem Ind Co Ltd | 2−アルコキシピラジン誘導体およびその用途 |
WO1998033504A1 (en) * | 1997-02-03 | 1998-08-06 | Akzo Nobel N.V. | Treatment of urinary incontinence |
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 |
UA77650C2 (en) * | 1999-12-06 | 2007-01-15 | Lundbeck & Co As H | Use of serotonin reuptake inhibitor in combination with deramcyclane |
AU2426602A (en) * | 2000-11-20 | 2002-05-27 | Biovitrum Ab | Piperazinylpyrazine compounds as agonist or antagonist of serotonin 5ht-2 receptor |
US6498184B2 (en) * | 2000-12-05 | 2002-12-24 | Akzo Nobel N.V. | Serotonergic compound for a method of treatment of hot flushes in post-menopausal women |
EP1213017A3 (de) * | 2000-12-05 | 2003-11-12 | Akzo Nobel N.V. | Verwendung von einem 5-HT2C Rezeptor Agonist zur Behandlung von Hitzewallungen |
-
2002
- 2002-05-17 SE SE0201544A patent/SE0201544D0/xx unknown
-
2003
- 2003-05-16 AU AU2003228196A patent/AU2003228196B2/en not_active Expired - Fee Related
- 2003-05-16 KR KR1020047018539A patent/KR20050026702A/ko not_active Application Discontinuation
- 2003-05-16 DE DE60305484T patent/DE60305484T2/de not_active Expired - Lifetime
- 2003-05-16 SI SI200330377T patent/SI1506185T1/sl unknown
- 2003-05-16 WO PCT/SE2003/000795 patent/WO2003097636A1/en active IP Right Grant
- 2003-05-16 DK DK03725958T patent/DK1506185T3/da active
- 2003-05-16 MX MXPA04011437A patent/MXPA04011437A/es active IP Right Grant
- 2003-05-16 US US10/440,011 patent/US7229997B2/en not_active Expired - Fee Related
- 2003-05-16 CN CNB038112493A patent/CN1329389C/zh not_active Expired - Fee Related
- 2003-05-16 PT PT03725958T patent/PT1506185E/pt unknown
- 2003-05-16 JP JP2004505369A patent/JP4865221B2/ja not_active Expired - Fee Related
- 2003-05-16 EP EP03725958A patent/EP1506185B1/de not_active Expired - Lifetime
- 2003-05-16 RS YU99804A patent/RS99804A/sr unknown
- 2003-05-16 EA EA200401526A patent/EA007543B1/ru not_active IP Right Cessation
- 2003-05-16 CA CA002483619A patent/CA2483619A1/en not_active Abandoned
- 2003-05-16 ES ES03725958T patent/ES2263971T3/es not_active Expired - Lifetime
- 2003-05-16 AT AT03725958T patent/ATE327229T1/de not_active IP Right Cessation
- 2003-05-16 BR BR0310077-4A patent/BR0310077A/pt not_active IP Right Cessation
- 2003-05-16 NZ NZ536409A patent/NZ536409A/en unknown
- 2003-05-16 ZA ZA200408975A patent/ZA200408975B/en unknown
-
2004
- 2004-11-01 IL IL16497404A patent/IL164974A0/xx unknown
- 2004-12-16 NO NO20045486A patent/NO20045486L/no not_active Application Discontinuation
-
2006
- 2006-03-17 HK HK06103395A patent/HK1084941A1/xx not_active IP Right Cessation
- 2006-08-23 CY CY20061101170T patent/CY1105162T1/el unknown
Also Published As
Publication number | Publication date |
---|---|
CA2483619A1 (en) | 2003-11-27 |
JP4865221B2 (ja) | 2012-02-01 |
IL164974A0 (en) | 2005-12-18 |
NO20045486L (no) | 2005-02-02 |
EP1506185A1 (de) | 2005-02-16 |
US7229997B2 (en) | 2007-06-12 |
DK1506185T3 (da) | 2006-10-02 |
NZ536409A (en) | 2007-11-30 |
SE0201544D0 (sv) | 2002-05-17 |
CY1105162T1 (el) | 2010-03-03 |
DE60305484D1 (de) | 2006-06-29 |
JP2005529926A (ja) | 2005-10-06 |
WO2003097636A1 (en) | 2003-11-27 |
PT1506185E (pt) | 2006-10-31 |
EA200401526A1 (ru) | 2005-04-28 |
SI1506185T1 (sl) | 2006-10-31 |
AU2003228196B2 (en) | 2009-12-17 |
EP1506185B1 (de) | 2006-05-24 |
MXPA04011437A (es) | 2005-02-17 |
RS99804A (en) | 2006-12-15 |
ES2263971T3 (es) | 2006-12-16 |
BR0310077A (pt) | 2005-02-22 |
KR20050026702A (ko) | 2005-03-15 |
AU2003228196A1 (en) | 2003-12-02 |
US20030232814A1 (en) | 2003-12-18 |
DE60305484T2 (de) | 2006-11-09 |
CN1701068A (zh) | 2005-11-23 |
ATE327229T1 (de) | 2006-06-15 |
HK1084941A1 (en) | 2006-08-11 |
EA007543B1 (ru) | 2006-10-27 |
CN1329389C (zh) | 2007-08-01 |
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