JP2005529926A5 - - Google Patents
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- Publication number
- JP2005529926A5 JP2005529926A5 JP2004505369A JP2004505369A JP2005529926A5 JP 2005529926 A5 JP2005529926 A5 JP 2005529926A5 JP 2004505369 A JP2004505369 A JP 2004505369A JP 2004505369 A JP2004505369 A JP 2004505369A JP 2005529926 A5 JP2005529926 A5 JP 2005529926A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- trifluoromethyl
- piperazine
- acetate
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 34
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 22
- -1 2-tetrahydrofuryl Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229940076279 serotonin Drugs 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000002431 hydrogen Chemical class 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
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 206010013654 Drug abuse Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 208000008589 Obesity Diseases 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 235000003642 hunger Nutrition 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 230000008058 pain sensation Effects 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000035807 sensation Effects 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
- 230000001052 transient effect Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 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
- YAINNWCNLIVZRL-SECBINFHSA-N (2r)-1-[6-ethylsulfanyl-5-(trifluoromethyl)pyridin-2-yl]-2-methylpiperazine Chemical compound C1=C(C(F)(F)F)C(SCC)=NC(N2[C@@H](CNCC2)C)=C1 YAINNWCNLIVZRL-SECBINFHSA-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
- OLQYIWBVVISDKZ-ZETCQYMHSA-N (2s)-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-ZETCQYMHSA-N 0.000 claims 1
- SZSVGTFMHBWDFK-ZDUSSCGKSA-N (2s)-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-ZDUSSCGKSA-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
- NWBUKSZRBSOPDH-LBPRGKRZSA-N (3s)-1-[6-[(2-chlorophenyl)methylsulfanyl]-5-(trifluoromethyl)pyridin-2-yl]-3-methylpiperazine Chemical compound C1CN[C@@H](C)CN1C1=CC=C(C(F)(F)F)C(SCC=2C(=CC=CC=2)Cl)=N1 NWBUKSZRBSOPDH-LBPRGKRZSA-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
- MGNJRCXEEAHGRW-ZDUSSCGKSA-N (3s)-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-ZDUSSCGKSA-N 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 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
- GJZATGDNYDSWNH-UHFFFAOYSA-N 1-[6-(3-pyridin-3-ylpropoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCCCC1=CC=CN=C1 GJZATGDNYDSWNH-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
- IEFCYRREPDRTBO-UHFFFAOYSA-N 1-[6-[(2,6-difluorophenyl)methoxy]-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound FC1=CC=CC(F)=C1COC1=NC(N2CCNCC2)=CC=C1C(F)(F)F IEFCYRREPDRTBO-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
- AOWTUWQUERQYNR-UHFFFAOYSA-N 1-[6-[(5-fluoro-2-methoxyphenyl)methoxy]-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound COC1=CC=C(F)C=C1COC1=NC(N2CCNCC2)=CC=C1C(F)(F)F AOWTUWQUERQYNR-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
- JEVYYEYMKYNXTN-UHFFFAOYSA-N 1-[6-methoxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound C1=C(C(F)(F)F)C(OC)=NC(N2CCNCC2)=C1 JEVYYEYMKYNXTN-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
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 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
- 150000001450 anions Chemical class 0.000 claims 1
- 125000005110 aryl thio 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
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 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
- 125000005368 heteroarylthio group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 150000004885 piperazines Chemical class 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000651 prodrug Chemical group 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 0 *C(C1*)N(*)CCN1c1nc(C2=CC2)c(C(F)(F)F)cc1 Chemical compound *C(C1*)N(*)CCN1c1nc(C2=CC2)c(C(F)(F)F)cc1 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0201544-4 | 2002-05-17 | ||
| SE0201544A SE0201544D0 (sv) | 2002-05-17 | 2002-05-17 | Novel compounds and thier use |
| US41003802P | 2002-09-12 | 2002-09-12 | |
| US60/410,038 | 2002-09-12 | ||
| PCT/SE2003/000795 WO2003097636A1 (en) | 2002-05-17 | 2003-05-16 | Novel compounds and their use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005529926A JP2005529926A (ja) | 2005-10-06 |
| JP2005529926A5 true JP2005529926A5 (enExample) | 2006-06-15 |
| JP4865221B2 JP4865221B2 (ja) | 2012-02-01 |
Family
ID=29552452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004505369A Expired - Fee Related JP4865221B2 (ja) | 2002-05-17 | 2003-05-16 | 新規化合物とそれらの使用 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US7229997B2 (enExample) |
| EP (1) | EP1506185B1 (enExample) |
| JP (1) | JP4865221B2 (enExample) |
| KR (1) | KR20050026702A (enExample) |
| CN (1) | CN1329389C (enExample) |
| AT (1) | ATE327229T1 (enExample) |
| AU (1) | AU2003228196B2 (enExample) |
| BR (1) | BR0310077A (enExample) |
| CA (1) | CA2483619A1 (enExample) |
| CY (1) | CY1105162T1 (enExample) |
| DE (1) | DE60305484T2 (enExample) |
| DK (1) | DK1506185T3 (enExample) |
| EA (1) | EA007543B1 (enExample) |
| ES (1) | ES2263971T3 (enExample) |
| IL (1) | IL164974A0 (enExample) |
| MX (1) | MXPA04011437A (enExample) |
| NO (1) | NO20045486L (enExample) |
| NZ (1) | NZ536409A (enExample) |
| PT (1) | PT1506185E (enExample) |
| RS (1) | RS99804A (enExample) |
| SE (1) | SE0201544D0 (enExample) |
| SI (1) | SI1506185T1 (enExample) |
| WO (1) | WO2003097636A1 (enExample) |
| ZA (1) | ZA200408975B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030236259A1 (en) * | 2002-02-05 | 2003-12-25 | Rolf Hohlweg | Novel aryl- and heteroarylpiperazines |
| EP2248524A3 (en) | 2004-08-25 | 2011-03-09 | Takeda Pharmaceutical Company Limited | Preventives/remedies for stress urinary incontinence and method of screening the same |
| GT200500317A (es) * | 2004-11-05 | 2006-10-27 | Proceso para preparar compuestos de quinolina y productos obtenidos de los mismos | |
| CA2614116A1 (en) | 2005-07-04 | 2007-01-11 | Novo Nordisk A/S | Novel medicaments |
| AR054849A1 (es) * | 2005-07-26 | 2007-07-18 | Wyeth Corp | Diazepinoquinolinas, sintesis de las mismas, e intermediarios para obtenerlas |
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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. |
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| 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 |
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2002
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2003
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- 2003-05-16 CA CA002483619A patent/CA2483619A1/en not_active Abandoned
- 2003-05-16 AT AT03725958T patent/ATE327229T1/de not_active IP Right Cessation
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- 2003-05-16 EP EP03725958A patent/EP1506185B1/en not_active Expired - Lifetime
- 2003-05-16 EA EA200401526A patent/EA007543B1/ru not_active IP Right Cessation
- 2003-05-16 US US10/440,011 patent/US7229997B2/en not_active Expired - Fee Related
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- 2003-05-16 KR KR1020047018539A patent/KR20050026702A/ko not_active Ceased
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