MXPA04011437A - Nuevos compuestos y su uso. - Google Patents
Nuevos compuestos y su uso.Info
- Publication number
- MXPA04011437A MXPA04011437A MXPA04011437A MXPA04011437A MXPA04011437A MX PA04011437 A MXPA04011437 A MX PA04011437A MX PA04011437 A MXPA04011437 A MX PA04011437A MX PA04011437 A MXPA04011437 A MX PA04011437A MX PA04011437 A MXPA04011437 A MX PA04011437A
- Authority
- MX
- Mexico
- Prior art keywords
- trifluoromethyl
- pyridin
- piperazine
- acetate
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 96
- 238000000034 method Methods 0.000 claims abstract description 45
- 239000003814 drug Substances 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- -1 2-tetrahydrofuryl Chemical group 0.000 claims description 97
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 claims description 39
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
- 208000035475 disorder Diseases 0.000 claims description 36
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229940076279 serotonin Drugs 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 208000019901 Anxiety disease Diseases 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 208000008589 Obesity Diseases 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 235000020824 obesity Nutrition 0.000 claims description 11
- 235000005686 eating Nutrition 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 206010046543 Urinary incontinence Diseases 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 208000033830 Hot Flashes Diseases 0.000 claims description 7
- 206010060800 Hot flush Diseases 0.000 claims description 7
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 7
- 206010015037 epilepsy Diseases 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 238000011321 prophylaxis Methods 0.000 claims description 7
- 102000005962 receptors Human genes 0.000 claims description 7
- 108020003175 receptors Proteins 0.000 claims description 7
- 231100000872 sexual dysfunction Toxicity 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
- 208000032841 Bulimia Diseases 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 208000010412 Glaucoma Diseases 0.000 claims description 6
- 208000026139 Memory disease Diseases 0.000 claims description 6
- 208000019022 Mood disease Diseases 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000164 antipsychotic agent Substances 0.000 claims description 6
- 150000004885 piperazines Chemical class 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- 230000004584 weight gain Effects 0.000 claims description 6
- 235000019786 weight gain Nutrition 0.000 claims description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 5
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- OSHVGUAPPIYWIS-UHFFFAOYSA-N piperazin-1-ium;acetate Chemical compound CC(O)=O.C1CNCCN1 OSHVGUAPPIYWIS-UHFFFAOYSA-N 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 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 description 3
- 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 description 3
- 150000001204 N-oxides Chemical group 0.000 claims description 3
- VBAXKJNOKUCINM-BTQNPOSSSA-N acetic acid;(3r)-3-methyl-1-[6-phenylmethoxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.C1CN[C@H](C)CN1C1=CC=C(C(F)(F)F)C(OCC=2C=CC=CC=2)=N1 VBAXKJNOKUCINM-BTQNPOSSSA-N 0.000 claims description 3
- YFOSDCDKUOPYGB-UHFFFAOYSA-N acetic acid;1-[6-[(2,3-difluorophenyl)methoxy]-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.FC1=CC=CC(COC=2C(=CC=C(N=2)N2CCNCC2)C(F)(F)F)=C1F YFOSDCDKUOPYGB-UHFFFAOYSA-N 0.000 claims description 3
- JUYFEDCVVGHNAT-UHFFFAOYSA-N acetic acid;1-[6-[(5-fluoro-2-methoxyphenyl)methoxy]-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.COC1=CC=C(F)C=C1COC1=NC(N2CCNCC2)=CC=C1C(F)(F)F JUYFEDCVVGHNAT-UHFFFAOYSA-N 0.000 claims description 3
- HQWCMZTXBPHSKW-UHFFFAOYSA-N acetic acid;1-[6-cyclopentyloxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OC1CCCC1 HQWCMZTXBPHSKW-UHFFFAOYSA-N 0.000 claims description 3
- TZUTWRSQYOIJEV-UHFFFAOYSA-N acetic acid;1-[6-propoxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.C1=C(C(F)(F)F)C(OCCC)=NC(N2CCNCC2)=C1 TZUTWRSQYOIJEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 208000014679 binge eating disease Diseases 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000651 prodrug Chemical group 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 2
- 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
- 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 description 2
- KDHPTLDTJLUDJG-YDALLXLXSA-N C(C)(=O)O.ClC1=C(CSC2=C(C=CC(=N2)N2[C@H](CNCC2)C)C(F)(F)F)C=CC=C1 Chemical compound C(C)(=O)O.ClC1=C(CSC2=C(C=CC(=N2)N2[C@H](CNCC2)C)C(F)(F)F)C=CC=C1 KDHPTLDTJLUDJG-YDALLXLXSA-N 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- SBIGGUXZJNJNDZ-ZOWNYOTGSA-N acetic acid;(2s)-2-methyl-1-[6-phenylmethoxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.C[C@H]1CNCCN1C1=CC=C(C(F)(F)F)C(OCC=2C=CC=CC=2)=N1 SBIGGUXZJNJNDZ-ZOWNYOTGSA-N 0.000 claims description 2
- JWROIXKSNPWERC-SBSPUUFOSA-N acetic acid;(3r)-1-[6-ethylsulfanyl-5-(trifluoromethyl)pyridin-2-yl]-3-methylpiperazine Chemical compound CC(O)=O.C1=C(C(F)(F)F)C(SCC)=NC(N2C[C@@H](C)NCC2)=C1 JWROIXKSNPWERC-SBSPUUFOSA-N 0.000 claims description 2
- YGLWNMNUNPREPK-YDALLXLXSA-N acetic acid;(3s)-1-[6-[(2-chlorophenyl)methylsulfanyl]-5-(trifluoromethyl)pyridin-2-yl]-3-methylpiperazine Chemical compound CC(O)=O.C1CN[C@@H](C)CN1C1=CC=C(C(F)(F)F)C(SCC=2C(=CC=CC=2)Cl)=N1 YGLWNMNUNPREPK-YDALLXLXSA-N 0.000 claims description 2
- VBHIVJWIXLYKTM-UHFFFAOYSA-N acetic acid;1-[6-(2,3-dihydro-1,4-benzodioxin-6-ylmethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.N1=C(OCC=2C=C3OCCOC3=CC=2)C(C(F)(F)F)=CC=C1N1CCNCC1 VBHIVJWIXLYKTM-UHFFFAOYSA-N 0.000 claims description 2
- PETQTBXRWNGGAZ-UHFFFAOYSA-N acetic acid;1-[6-[(2-chlorophenyl)methylsulfanyl]-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.FC(F)(F)C1=CC=C(N2CCNCC2)N=C1SCC1=CC=CC=C1Cl PETQTBXRWNGGAZ-UHFFFAOYSA-N 0.000 claims description 2
- WOMFXSVGYYKEOF-UHFFFAOYSA-N acetic acid;1-[6-phenylmethoxy-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCC1=CC=CC=C1 WOMFXSVGYYKEOF-UHFFFAOYSA-N 0.000 claims description 2
- WRFHPOSLEQWJBO-UHFFFAOYSA-N acetic acid;3-[[6-piperazin-1-yl-3-(trifluoromethyl)pyridin-2-yl]oxymethyl]benzonitrile Chemical compound CC(O)=O.FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCC1=CC=CC(C#N)=C1 WRFHPOSLEQWJBO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 3
- PNAZUQUHTIOEHF-UHFFFAOYSA-N (3-methylphenyl)methanethiol Chemical compound CC1=CC=CC(CS)=C1 PNAZUQUHTIOEHF-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- KDHPTLDTJLUDJG-UTONKHPSSA-N C(C)(=O)O.ClC1=C(CSC2=C(C=CC(=N2)N2[C@@H](CNCC2)C)C(F)(F)F)C=CC=C1 Chemical compound C(C)(=O)O.ClC1=C(CSC2=C(C=CC(=N2)N2[C@@H](CNCC2)C)C(F)(F)F)C=CC=C1 KDHPTLDTJLUDJG-UTONKHPSSA-N 0.000 claims 1
- DVMXKRKCYNEYEM-SBSPUUFOSA-N C(C)SC1=C(C=CC(=N1)N1[C@@H](CNCC1)C)C(F)(F)F.C(C)(=O)O Chemical compound C(C)SC1=C(C=CC(=N1)N1[C@@H](CNCC1)C)C(F)(F)F.C(C)(=O)O DVMXKRKCYNEYEM-SBSPUUFOSA-N 0.000 claims 1
- PCJAICHMDCZKCD-UHFFFAOYSA-N acetic acid;1-[6-(2-cyclohexylethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCCC1CCCCC1 PCJAICHMDCZKCD-UHFFFAOYSA-N 0.000 claims 1
- WJEULBVQJGFBLL-UHFFFAOYSA-N acetic acid;1-[6-(2-phenoxyethoxy)-5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound CC(O)=O.FC(F)(F)C1=CC=C(N2CCNCC2)N=C1OCCOC1=CC=CC=C1 WJEULBVQJGFBLL-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 12
- 230000008569 process Effects 0.000 abstract description 4
- 239000000883 anti-obesity agent Substances 0.000 abstract description 3
- 229940125710 antiobesity agent Drugs 0.000 abstract description 3
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 46
- 238000010586 diagram Methods 0.000 description 35
- 239000000463 material Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 238000013467 fragmentation Methods 0.000 description 11
- 238000006062 fragmentation reaction Methods 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000556 agonist Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 239000000018 receptor agonist Substances 0.000 description 7
- 229940044601 receptor agonist Drugs 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- JOMNTHCQHJPVAZ-YFKPBYRVSA-N (2s)-2-methylpiperazine Chemical compound C[C@H]1CNCCN1 JOMNTHCQHJPVAZ-YFKPBYRVSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
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- 238000000844 transformation Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
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Classifications
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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
- C07D401/02—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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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
- C07D401/02—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
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Gynecology & Obstetrics (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Nutrition Science (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Liquid Crystal Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0201544A SE0201544D0 (sv) | 2002-05-17 | 2002-05-17 | Novel compounds and thier use |
| US41003802P | 2002-09-12 | 2002-09-12 | |
| PCT/SE2003/000795 WO2003097636A1 (en) | 2002-05-17 | 2003-05-16 | Novel compounds and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA04011437A true MXPA04011437A (es) | 2005-02-17 |
Family
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Family Applications (1)
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|---|---|---|---|
| MXPA04011437A MXPA04011437A (es) | 2002-05-17 | 2003-05-16 | Nuevos compuestos y su uso. |
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| EP (1) | EP1506185B1 (enExample) |
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| AT (1) | ATE327229T1 (enExample) |
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| CA (1) | CA2483619A1 (enExample) |
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| NO (1) | NO20045486L (enExample) |
| NZ (1) | NZ536409A (enExample) |
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| RS (1) | RS99804A (enExample) |
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| 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 |
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| US20030236259A1 (en) * | 2002-02-05 | 2003-12-25 | Rolf Hohlweg | Novel aryl- and heteroarylpiperazines |
| JP5173190B2 (ja) * | 2004-08-25 | 2013-03-27 | 武田薬品工業株式会社 | 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 | |
| CN103110635A (zh) * | 2005-07-04 | 2013-05-22 | 海波因特制药有限责任公司 | 组胺h3受体拮抗剂 |
| 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 |
| EP1998781A2 (en) * | 2006-03-24 | 2008-12-10 | Wyeth a Corporation of the State of Delaware | Treatment of pain |
| JP2009531435A (ja) * | 2006-03-24 | 2009-09-03 | ワイス | うつ病の治療用の新規な治療組み合わせ |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| ATE538116T1 (de) * | 2006-05-29 | 2012-01-15 | High Point Pharmaceuticals Llc | 3-(1,3-benyodioxol-5-yl)-6- (4- cyclopropylpiperazin-1-yl)-pyridazin, dessen salze und solvate und dessen verwendung als histamin-h3-rezeptorantagonist |
| WO2007149728A2 (en) * | 2006-06-20 | 2007-12-27 | Alcon Research, 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 |
| RU2489431C2 (ru) | 2007-04-23 | 2013-08-10 | Янссен Фармацевтика Н.В. | Тиа(диа)золы как быстро диссоциирующие антагонисты рецептора допамина 2 |
| JP5431305B2 (ja) | 2007-04-23 | 2014-03-05 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 高速解離性ドパミン２受容体アンタゴニストとしての４−アルコキシピリダジン誘導体 |
| EP2014656A3 (en) * | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | New heteocyclic h3 antagonists |
| 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. |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| JP5417439B2 (ja) | 2008-07-03 | 2014-02-12 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ５−ｈｔ６受容体アンタゴニストとしての置換された６−（１−ピペラジニル）−ピリダジン類 |
| EA019048B1 (ru) * | 2008-07-31 | 2013-12-30 | Янссен Фармацевтика Нв | Пиперазин-1-илтрифторметилзамещенные пиридины в качестве быстро диссоциирующихся антагонистов d-рецепторов дофамина |
| TWI542592B (zh) | 2009-06-15 | 2016-07-21 | 武田藥品工業股份有限公司 | 吡並氮雜氧雜環庚烯衍生物 |
| WO2011071136A1 (ja) | 2009-12-11 | 2011-06-16 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| US20130267500A1 (en) | 2010-09-01 | 2013-10-10 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
| WO2013010679A1 (en) | 2011-07-15 | 2013-01-24 | Novartis Ag | Salts of aza-bicyclic di-aryl ethers and methods to make them or their precursors |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| WO2019131902A1 (ja) | 2017-12-27 | 2019-07-04 | 武田薬品工業株式会社 | 腹圧性尿失禁および便失禁の治療薬 |
| CN121866253A (zh) * | 2023-07-04 | 2026-04-14 | 杭州中美华东制药有限公司 | 一种glp1r激动剂及其中间体的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| JPH0665203A (ja) * | 1992-06-25 | 1994-03-08 | Elf Sanofi | ピペラジンのヘテロ環誘導体 |
| EP0580465A1 (fr) | 1992-06-25 | 1994-01-26 | Sanofi | Nouvelle utilisation thérapeutique d'hétérocyclyl-pipérazines comme 5-HT3 agonistes et nouveaux dérivés |
| 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 (en) | 2000-12-05 | 2003-11-12 | Akzo Nobel N.V. | Use of a 5-HT2C receptor agonist for the treatment of hot flushes |
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Also Published As
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| ZA200408975B (en) | 2005-11-14 |
| NO20045486L (no) | 2005-02-02 |
| JP4865221B2 (ja) | 2012-02-01 |
| EA007543B1 (ru) | 2006-10-27 |
| KR20050026702A (ko) | 2005-03-15 |
| NZ536409A (en) | 2007-11-30 |
| BR0310077A (pt) | 2005-02-22 |
| RS99804A (sr) | 2006-12-15 |
| AU2003228196B2 (en) | 2009-12-17 |
| IL164974A0 (en) | 2005-12-18 |
| AU2003228196A1 (en) | 2003-12-02 |
| US7229997B2 (en) | 2007-06-12 |
| DE60305484D1 (de) | 2006-06-29 |
| HK1084941A1 (en) | 2006-08-11 |
| CA2483619A1 (en) | 2003-11-27 |
| WO2003097636A1 (en) | 2003-11-27 |
| EP1506185B1 (en) | 2006-05-24 |
| CY1105162T1 (el) | 2010-03-03 |
| US20030232814A1 (en) | 2003-12-18 |
| DK1506185T3 (da) | 2006-10-02 |
| SE0201544D0 (sv) | 2002-05-17 |
| EA200401526A1 (ru) | 2005-04-28 |
| ES2263971T3 (es) | 2006-12-16 |
| SI1506185T1 (sl) | 2006-10-31 |
| ATE327229T1 (de) | 2006-06-15 |
| DE60305484T2 (de) | 2006-11-09 |
| CN1701068A (zh) | 2005-11-23 |
| CN1329389C (zh) | 2007-08-01 |
| JP2005529926A (ja) | 2005-10-06 |
| PT1506185E (pt) | 2006-10-31 |
| EP1506185A1 (en) | 2005-02-16 |
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