NO20023293L - Piperidin- og piperazinderivater som virker som 5-HT2A- reseptorantagonister - Google Patents
Piperidin- og piperazinderivater som virker som 5-HT2A- reseptorantagonister Download PDFInfo
- Publication number
- NO20023293L NO20023293L NO20023293A NO20023293A NO20023293L NO 20023293 L NO20023293 L NO 20023293L NO 20023293 A NO20023293 A NO 20023293A NO 20023293 A NO20023293 A NO 20023293A NO 20023293 L NO20023293 L NO 20023293L
- Authority
- NO
- Norway
- Prior art keywords
- ethyl
- fluorophenyl
- hydrochloride
- piperidine
- formula
- Prior art date
Links
- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 title claims description 15
- 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 title claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title description 9
- 150000004885 piperazines Chemical class 0.000 title description 5
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 4
- 239000002464 receptor antagonist Substances 0.000 title description 2
- 229940044551 receptor antagonist Drugs 0.000 title description 2
- -1 2,1,3-benzothiadiazolyl Chemical group 0.000 claims description 210
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 230000003042 antagnostic effect Effects 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 208000032841 Bulimia Diseases 0.000 claims description 5
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 5
- 208000030814 Eating disease Diseases 0.000 claims description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 5
- 208000026139 Memory disease Diseases 0.000 claims description 5
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
- 231100000867 compulsive behavior Toxicity 0.000 claims description 5
- 235000014632 disordered eating Nutrition 0.000 claims description 5
- CEJTYFPNPXFZBP-UHFFFAOYSA-N 5-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]sulfonyl-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CCN1CCN(S(=O)(=O)C=2C=C3C(C#N)=CNC3=CC=2)CC1 CEJTYFPNPXFZBP-UHFFFAOYSA-N 0.000 claims description 4
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 4
- 208000025966 Neurological disease Diseases 0.000 claims description 4
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 229940126601 medicinal product Drugs 0.000 claims 2
- XBTPCUWXQJXEGE-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-methoxyphenyl)sulfanylpiperidine Chemical compound COC1=CC=CC=C1SC1CCN(CCC=2C=CC(F)=CC=2)CC1 XBTPCUWXQJXEGE-UHFFFAOYSA-N 0.000 claims 1
- LMYWKVOVJZTPHG-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfonylpiperidine Chemical compound C1=CC(F)=CC=C1CCN1CCC(S(=O)(=O)C=2C=CC(F)=CC=2)CC1 LMYWKVOVJZTPHG-UHFFFAOYSA-N 0.000 claims 1
- CIMWGXCDTMKAFL-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methylphenyl)sulfinylpiperidine Chemical compound C1=CC(C)=CC=C1S(=O)C1CCN(CCC=2C=CC(F)=CC=2)CC1 CIMWGXCDTMKAFL-UHFFFAOYSA-N 0.000 claims 1
- PYCGESBPLWWWGR-UHFFFAOYSA-N 2-chloro-6-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylpyridine Chemical compound C1=CC(F)=CC=C1CCN1CCC(S(=O)(=O)C=2N=C(Cl)C=CC=2)CC1 PYCGESBPLWWWGR-UHFFFAOYSA-N 0.000 claims 1
- FCPUVKHADOMADH-UHFFFAOYSA-N 8-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]sulfonylquinoline Chemical compound C1=CC(F)=CC=C1CCN1CCN(S(=O)(=O)C=2C3=NC=CC=C3C=CC=2)CC1 FCPUVKHADOMADH-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 8
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- 101150104779 HTR2A gene Proteins 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- SUYACMGBSMDVAT-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-nitrophenyl)sulfonylpiperazine hydrochloride Chemical compound Cl.[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)N1CCN(CC1)CCC1=CC=C(C=C1)F SUYACMGBSMDVAT-UHFFFAOYSA-N 0.000 description 3
- SEUMFTZWUNHUAY-UHFFFAOYSA-N 2-chloro-6-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylpyridine hydrochloride Chemical compound Cl.ClC1=NC(=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F SEUMFTZWUNHUAY-UHFFFAOYSA-N 0.000 description 3
- AWOGYKQLZGNICG-UHFFFAOYSA-N 2-pyrrol-1-ylpyridine Chemical compound C1=CC=CN1C1=CC=CC=N1 AWOGYKQLZGNICG-UHFFFAOYSA-N 0.000 description 3
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004683 dihydrates Chemical class 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- CGOSSTZGNLMTNP-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-4-(2-phenylethyl)piperazine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CCN(CCC=2C=CC=CC=2)CC1 CGOSSTZGNLMTNP-UHFFFAOYSA-N 0.000 description 2
- DPEYDNNDMKSLGQ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfonylpiperazine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)S(=O)(=O)N1CCN(CC1)CCC1=CC=C(C=C1)F DPEYDNNDMKSLGQ-UHFFFAOYSA-N 0.000 description 2
- ISPRGISEAPTUCJ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=CC=C(C=C2)F)CCC3=CC=C(C=C3)F.Cl ISPRGISEAPTUCJ-UHFFFAOYSA-N 0.000 description 2
- VCIRMYZIFYLEEU-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-naphthalen-1-ylsulfonylpiperazine hydrochloride Chemical compound C1CN(CCN1CCC2=CC=C(C=C2)F)S(=O)(=O)C3=CC=CC4=CC=CC=C43.Cl VCIRMYZIFYLEEU-UHFFFAOYSA-N 0.000 description 2
- HGUKTSNCEPXFET-UHFFFAOYSA-N 1-ethylpiperidin-1-ium;chloride Chemical compound Cl.CCN1CCCCC1 HGUKTSNCEPXFET-UHFFFAOYSA-N 0.000 description 2
- BVHCCXBFHAXYPT-UHFFFAOYSA-N 2-(4-fluorophenyl)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCC1=CC=C(F)C=C1 BVHCCXBFHAXYPT-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- TVTLKUCDBMASKE-UHFFFAOYSA-N 2-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]sulfonylaniline dihydrochloride Chemical compound Cl.Cl.NC1=C(C=CC=C1)S(=O)(=O)N1CCN(CC1)CCC1=CC=C(C=C1)F TVTLKUCDBMASKE-UHFFFAOYSA-N 0.000 description 2
- RXSJYCBBADSOGD-UHFFFAOYSA-N 2-chloro-6-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylpyridine hydrochloride Chemical compound Cl.ClC1=NC(=CC=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F RXSJYCBBADSOGD-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- VRLBWYPAIICKLL-UHFFFAOYSA-N Cl.N=1ON=C2C1C=CC=C2S(=O)(=O)N2CCN(CC2)CCC2=CC=C(C=C2)F Chemical compound Cl.N=1ON=C2C1C=CC=C2S(=O)(=O)N2CCN(CC2)CCC2=CC=C(C=C2)F VRLBWYPAIICKLL-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NKCATSWPOYBPPE-UHFFFAOYSA-N N-[5-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]sulfonylnaphthalen-1-yl]acetamide hydrochloride Chemical compound Cl.C(C)(=O)NC1=C2C=CC=C(C2=CC=C1)S(=O)(=O)N1CCN(CC1)CCC1=CC=C(C=C1)F NKCATSWPOYBPPE-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- BFIWZEKPARJYJE-UHFFFAOYSA-N isoquinoline-5-sulfonamide Chemical class N1=CC=C2C(S(=O)(=O)N)=CC=CC2=C1 BFIWZEKPARJYJE-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 2
- GPVVBCKMCIOPMN-UHFFFAOYSA-N quinolin-1-ium;hydroxide Chemical compound O.N1=CC=CC2=CC=CC=C21 GPVVBCKMCIOPMN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- BARIUTVIHIEYIB-UHFFFAOYSA-N 1-(2,5-difluorophenyl)sulfonyl-4-[2-(4-fluorophenyl)ethyl]piperazine hydrochloride Chemical compound Cl.FC1=C(C=C(C=C1)F)S(=O)(=O)N1CCN(CC1)CCC1=CC=C(C=C1)F BARIUTVIHIEYIB-UHFFFAOYSA-N 0.000 description 1
- OPWKFMWBVUVEHU-UHFFFAOYSA-N 1-(2-phenylethenylsulfonyl)-4-(2-phenylethyl)piperazine Chemical compound C1CN(CCC=2C=CC=CC=2)CCN1S(=O)(=O)C=CC1=CC=CC=C1 OPWKFMWBVUVEHU-UHFFFAOYSA-N 0.000 description 1
- XVQUSMTXBHSSKB-UHFFFAOYSA-N 1-(2-phenylethyl)-4-(2,4,6-trimethylphenyl)sulfonylpiperazine Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)N1CCN(CCC=2C=CC=CC=2)CC1 XVQUSMTXBHSSKB-UHFFFAOYSA-N 0.000 description 1
- OEUONHWMPFAJFU-UHFFFAOYSA-N 1-(2-phenylethyl)-4-(4-phenylphenyl)sulfonylpiperazine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1S(=O)(=O)N(CC1)CCN1CCC1=CC=CC=C1 OEUONHWMPFAJFU-UHFFFAOYSA-N 0.000 description 1
- MEQGSUWGKKHOEP-UHFFFAOYSA-N 1-(2-phenylethyl)-4-(4-propylphenyl)sulfonylpiperazine Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)N1CCN(CCC=2C=CC=CC=2)CC1 MEQGSUWGKKHOEP-UHFFFAOYSA-N 0.000 description 1
- ZJGYIAJKCCSPSQ-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)sulfonyl-4-(2-phenylethyl)piperazine Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1CCN(CCC=2C=CC=CC=2)CC1 ZJGYIAJKCCSPSQ-UHFFFAOYSA-N 0.000 description 1
- YBRBYPLRQMSJIS-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-4-(2-phenylethyl)piperazine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1CCN(CCC=2C=CC=CC=2)CC1 YBRBYPLRQMSJIS-UHFFFAOYSA-N 0.000 description 1
- XOSQNVCLDMEASZ-UHFFFAOYSA-N 1-(5-chloronaphthalen-1-yl)sulfonyl-4-[2-(4-fluorophenyl)ethyl]piperazine hydrochloride Chemical compound Cl.ClC1=C2C=CC=C(C2=CC=C1)S(=O)(=O)N1CCN(CC1)CCC1=CC=C(C=C1)F XOSQNVCLDMEASZ-UHFFFAOYSA-N 0.000 description 1
- UBXWQPSWVBOKJB-UHFFFAOYSA-N 1-(6-chloronaphthalen-2-yl)sulfonyl-4-(2-phenylethyl)piperazine Chemical compound C1=CC2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1)CCN1CCC1=CC=CC=C1 UBXWQPSWVBOKJB-UHFFFAOYSA-N 0.000 description 1
- BMIWDBWHODUZSX-UHFFFAOYSA-N 1-(6-chloronaphthalen-2-yl)sulfonyl-4-[2-(3,5-dimethoxyphenyl)ethyl]piperazine Chemical compound COC1=CC(OC)=CC(CCN2CCN(CC2)S(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)=C1 BMIWDBWHODUZSX-UHFFFAOYSA-N 0.000 description 1
- PZNMJEJGRMIZOO-UHFFFAOYSA-N 1-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylisoquinoline hydrochloride Chemical compound Cl.C1(=NC=CC2=CC=CC=C12)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F PZNMJEJGRMIZOO-UHFFFAOYSA-N 0.000 description 1
- NYHGBDYSZKKZLT-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)ethyl]-4-(2-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.FC1=C(C=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=C(C=C(C=C1)F)F NYHGBDYSZKKZLT-UHFFFAOYSA-N 0.000 description 1
- ZMMKUFNZZOXWHM-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)ethyl]-4-(2-methoxyphenyl)sulfonylpiperidine hydrochloride Chemical compound COC1=CC=CC=C1S(=O)(=O)C2CCN(CC2)CCC3=C(C=C(C=C3)F)F.Cl ZMMKUFNZZOXWHM-UHFFFAOYSA-N 0.000 description 1
- IOKOUKSRJWEGNW-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)ethyl]-4-(2-methylphenyl)sulfonylpiperidine hydrochloride Chemical compound CC1=CC=CC=C1S(=O)(=O)C2CCN(CC2)CCC3=C(C=C(C=C3)F)F.Cl IOKOUKSRJWEGNW-UHFFFAOYSA-N 0.000 description 1
- VUGIULCWVDEFEF-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)ethyl]-4-(4-fluorophenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)SC1CCN(CC1)CCC1=C(C=C(C=C1)F)F VUGIULCWVDEFEF-UHFFFAOYSA-N 0.000 description 1
- DOCJTNVMETXMJI-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)ethyl]-4-(4-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=C(C=C(C=C1)F)F DOCJTNVMETXMJI-UHFFFAOYSA-N 0.000 description 1
- MMHAHUXPBPSYHZ-UHFFFAOYSA-N 1-[2-(2-fluorophenyl)ethyl]-4-(2-methylphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.C1(=C(C=CC=C1)SC1CCN(CC1)CCC1=C(C=CC=C1)F)C MMHAHUXPBPSYHZ-UHFFFAOYSA-N 0.000 description 1
- LYKLILOKUIMVSZ-UHFFFAOYSA-N 1-[2-(2-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)SC1CCN(CC1)CCC1=C(C=CC=C1)F LYKLILOKUIMVSZ-UHFFFAOYSA-N 0.000 description 1
- SZXHABQDSKZVKI-UHFFFAOYSA-N 1-[2-(2-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=C(C=CC=C1)F SZXHABQDSKZVKI-UHFFFAOYSA-N 0.000 description 1
- HGBDKLDELRWAJU-UHFFFAOYSA-N 1-[2-(3,5-dimethoxyphenyl)ethyl]-4-(4-methoxyphenyl)sulfonylpiperazine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CCN(CCC=2C=C(OC)C=C(OC)C=2)CC1 HGBDKLDELRWAJU-UHFFFAOYSA-N 0.000 description 1
- XMGKHFKVBBDKJQ-UHFFFAOYSA-N 1-[2-(3,5-dimethoxyphenyl)ethyl]-4-(4-phenylphenyl)sulfonylpiperazine Chemical compound COC1=CC(OC)=CC(CCN2CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 XMGKHFKVBBDKJQ-UHFFFAOYSA-N 0.000 description 1
- ALLJIVCFCITAPF-UHFFFAOYSA-N 1-[2-(3,5-dimethoxyphenyl)ethyl]-4-(4-propan-2-ylphenyl)sulfonylpiperazine Chemical compound COC1=CC(OC)=CC(CCN2CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C(C)C)=C1 ALLJIVCFCITAPF-UHFFFAOYSA-N 0.000 description 1
- ATEFYOKGCFHDOD-UHFFFAOYSA-N 1-[2-(3,5-dimethoxyphenyl)ethyl]-4-naphthalen-2-ylsulfonylpiperazine Chemical compound COC1=CC(OC)=CC(CCN2CCN(CC2)S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=C1 ATEFYOKGCFHDOD-UHFFFAOYSA-N 0.000 description 1
- WBPCFKMIBOREDQ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(1-methylimidazol-4-yl)sulfonylpiperazine Chemical compound CN1C=NC(S(=O)(=O)N2CCN(CCC=3C=CC(F)=CC=3)CC2)=C1 WBPCFKMIBOREDQ-UHFFFAOYSA-N 0.000 description 1
- AMOMGUYPXKNABL-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2,4,6-trimethylphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.CC1=C(C(=CC(=C1)C)C)SC1CCN(CC1)CCC1=CC=C(C=C1)F AMOMGUYPXKNABL-UHFFFAOYSA-N 0.000 description 1
- KYJOIFGVJQNUDR-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2,4,6-trimethylphenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=C(C=C(C=C1C)C)C KYJOIFGVJQNUDR-UHFFFAOYSA-N 0.000 description 1
- SGWGKNOSVXXNJG-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.FC1=C(C=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F SGWGKNOSVXXNJG-UHFFFAOYSA-N 0.000 description 1
- DRVKYHPBDOXVKN-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-methoxyphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.COC1=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F DRVKYHPBDOXVKN-UHFFFAOYSA-N 0.000 description 1
- VKOBHBKRAGJMAX-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-methoxyphenyl)sulfinylpiperidine hydrochloride Chemical compound Cl.COC1=C(C=CC=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F VKOBHBKRAGJMAX-UHFFFAOYSA-N 0.000 description 1
- FWXQTBWENSXSMV-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-methoxyphenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.COC1=C(C=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F FWXQTBWENSXSMV-UHFFFAOYSA-N 0.000 description 1
- IHTSYYVNJHENFJ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-methylphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.C1(=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F)C IHTSYYVNJHENFJ-UHFFFAOYSA-N 0.000 description 1
- SRPHBSKLOVTFFH-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-propan-2-ylphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.C(C)(C)C1=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F SRPHBSKLOVTFFH-UHFFFAOYSA-N 0.000 description 1
- SFADWGAXLXDXMX-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-propan-2-ylphenyl)sulfinylpiperidine hydrochloride Chemical compound CC(C)C1=CC=CC=C1S(=O)C2CCN(CC2)CCC3=CC=C(C=C3)F.Cl SFADWGAXLXDXMX-UHFFFAOYSA-N 0.000 description 1
- OYYKBPLEOWIIKJ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F OYYKBPLEOWIIKJ-UHFFFAOYSA-N 0.000 description 1
- GAGIVQRSLZTRRZ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methoxyphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.COC1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F GAGIVQRSLZTRRZ-UHFFFAOYSA-N 0.000 description 1
- SNBDASOMTZYWQR-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methoxyphenyl)sulfinylpiperidine hydrochloride Chemical compound Cl.COC1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F SNBDASOMTZYWQR-UHFFFAOYSA-N 0.000 description 1
- OSSRRYPJGPPDJT-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methoxyphenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.COC1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F OSSRRYPJGPPDJT-UHFFFAOYSA-N 0.000 description 1
- XIVPHUDHXJWUOM-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methylphenyl)sulfinylpiperidine hydrochloride Chemical compound Cl.C1(=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)C XIVPHUDHXJWUOM-UHFFFAOYSA-N 0.000 description 1
- KDUYNDJMQQVEAG-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methylphenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.C1(=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)C KDUYNDJMQQVEAG-UHFFFAOYSA-N 0.000 description 1
- LALCOTDRPDMGQR-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methylsulfanylphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.CSC1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F LALCOTDRPDMGQR-UHFFFAOYSA-N 0.000 description 1
- ZTNVNGAHIMRZQM-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methylsulfinylphenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.CS(=O)C1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F ZTNVNGAHIMRZQM-UHFFFAOYSA-N 0.000 description 1
- IXMDFPSKGMIBQQ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-[4-(trifluoromethoxy)phenyl]sulfonylpiperidine hydrochloride Chemical compound Cl.FC(OC1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)(F)F IXMDFPSKGMIBQQ-UHFFFAOYSA-N 0.000 description 1
- KBPYBKNQGMYYJN-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-[4-(trifluoromethyl)phenyl]sulfanylpiperidine hydrochloride Chemical compound Cl.FC(C1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F)(F)F KBPYBKNQGMYYJN-UHFFFAOYSA-N 0.000 description 1
- KWAYQFPSPIOJBJ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-[4-(trifluoromethyl)phenyl]sulfinylpiperidine hydrochloride Chemical compound Cl.FC(C1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)(F)F KWAYQFPSPIOJBJ-UHFFFAOYSA-N 0.000 description 1
- WKTGIFGYHASLPN-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-[4-(trifluoromethyl)phenyl]sulfonylpiperidine hydrochloride Chemical compound Cl.FC(C1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)(F)F WKTGIFGYHASLPN-UHFFFAOYSA-N 0.000 description 1
- UAAZOZKSFYCKOB-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-naphthalen-2-ylsulfonylpiperidine hydrochloride Chemical compound Cl.C1=C(C=CC2=CC=CC=C12)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F UAAZOZKSFYCKOB-UHFFFAOYSA-N 0.000 description 1
- VVQHLYGFPBCQKR-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-thiophen-2-ylsulfonylpiperidine hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=CC=CS2)CCC3=CC=C(C=C3)F.Cl VVQHLYGFPBCQKR-UHFFFAOYSA-N 0.000 description 1
- BJMPGMOWXAYATG-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]piperazine;dihydrochloride Chemical compound Cl.Cl.C1=CC(F)=CC=C1CCN1CCNCC1 BJMPGMOWXAYATG-UHFFFAOYSA-N 0.000 description 1
- NLXTVNBGKKZNGS-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)ethyl]-4-(2-methoxyphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.COC1=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)OC NLXTVNBGKKZNGS-UHFFFAOYSA-N 0.000 description 1
- BZASUYKKGCQFBT-UHFFFAOYSA-N 1-[2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylphenyl]ethanone hydrochloride Chemical compound Cl.C(C)(=O)C1=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F BZASUYKKGCQFBT-UHFFFAOYSA-N 0.000 description 1
- MTHVQXPMLUTZKL-UHFFFAOYSA-N 1-[4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylphenyl]ethanone hydrochloride Chemical compound Cl.C(C)(=O)C1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F MTHVQXPMLUTZKL-UHFFFAOYSA-N 0.000 description 1
- OHHRXZBEJQLZOR-UHFFFAOYSA-N 1-[4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylphenyl]ethanone hydrochloride Chemical compound Cl.C(C)(=O)C1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F OHHRXZBEJQLZOR-UHFFFAOYSA-N 0.000 description 1
- MGGMMOZXZBVBQX-UHFFFAOYSA-N 1-[5-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]sulfonyl-2,3-dihydroindol-1-yl]ethanone Chemical compound C=1C=C2N(C(=O)C)CCC2=CC=1S(=O)(=O)N(CC1)CCN1CCC1=CC=C(F)C=C1 MGGMMOZXZBVBQX-UHFFFAOYSA-N 0.000 description 1
- IANSBLAVWUSRNU-UHFFFAOYSA-N 1-butylsulfonyl-4-(2-phenylethyl)piperazine Chemical compound C1CN(S(=O)(=O)CCCC)CCN1CCC1=CC=CC=C1 IANSBLAVWUSRNU-UHFFFAOYSA-N 0.000 description 1
- MTZKXEUVSFOMBP-UHFFFAOYSA-N 1-dibenzofuran-1-ylsulfonyl-4-[2-(4-fluorophenyl)ethyl]piperazine hydrochloride Chemical compound Cl.C1(=CC=CC=2OC3=C(C21)C=CC=C3)S(=O)(=O)N3CCN(CC3)CCC3=CC=C(C=C3)F MTZKXEUVSFOMBP-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- KBASTFJBCZIRRI-UHFFFAOYSA-N 1-naphthalen-2-ylsulfonyl-4-(2-phenylethyl)piperazine Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)N(CC1)CCN1CCC1=CC=CC=C1 KBASTFJBCZIRRI-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
- ZLWUHKGDLQOHDE-UHFFFAOYSA-N 2-[1-[2-(2,4-difluorophenyl)ethyl]piperidin-4-yl]sulfanylphenol hydrochloride Chemical compound Cl.FC1=C(C=CC(=C1)F)CCN1CCC(CC1)SC1=C(C=CC=C1)O ZLWUHKGDLQOHDE-UHFFFAOYSA-N 0.000 description 1
- MKHBRKZCSSKSCR-UHFFFAOYSA-N 2-[1-[2-(2,4-difluorophenyl)ethyl]piperidin-4-yl]sulfonylphenol hydrochloride Chemical compound Cl.FC1=C(C=CC(=C1)F)CCN1CCC(CC1)S(=O)(=O)C1=C(C=CC=C1)O MKHBRKZCSSKSCR-UHFFFAOYSA-N 0.000 description 1
- XEPSCRQHSQBIRK-UHFFFAOYSA-N 2-[1-[2-(2-fluorophenyl)ethyl]piperidin-4-yl]sulfanylphenol Chemical compound OC1=CC=CC=C1SC1CCN(CCC=2C(=CC=CC=2)F)CC1 XEPSCRQHSQBIRK-UHFFFAOYSA-N 0.000 description 1
- UUKKGDSYADVGSL-UHFFFAOYSA-N 2-[1-[2-(3,4-difluorophenyl)ethyl]piperidin-4-yl]sulfanylphenol Chemical compound OC1=CC=CC=C1SC1CCN(CCC=2C=C(F)C(F)=CC=2)CC1 UUKKGDSYADVGSL-UHFFFAOYSA-N 0.000 description 1
- YKRLMTIDVDTLEP-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanyl-1,3-benzothiazole hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC=1SC2=C(N1)C=CC=C2 YKRLMTIDVDTLEP-UHFFFAOYSA-N 0.000 description 1
- YEMPZPQMOFOTOT-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanyl-1,3-thiazole hydrochloride Chemical compound Cl.S1C(=NC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F YEMPZPQMOFOTOT-UHFFFAOYSA-N 0.000 description 1
- ZAPIAFGFYRUTNP-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanyl-1H-benzimidazole hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=NC2=C(N1)C=CC=C2 ZAPIAFGFYRUTNP-UHFFFAOYSA-N 0.000 description 1
- HBFZMJJHODHPEJ-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=C(C=CC=C1)O HBFZMJJHODHPEJ-UHFFFAOYSA-N 0.000 description 1
- ZIWASQCQKWGHMV-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylpyridine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=NC=CC=C1 ZIWASQCQKWGHMV-UHFFFAOYSA-N 0.000 description 1
- VVLDBVSQAYUKRW-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylpyrimidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=NC=CC=N1 VVLDBVSQAYUKRW-UHFFFAOYSA-N 0.000 description 1
- DWCMNEJKCMQYBP-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylquinoline hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=NC2=CC=CC=C2C=C1 DWCMNEJKCMQYBP-UHFFFAOYSA-N 0.000 description 1
- GGIVKJCWSXWAHT-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)C1=C(C=CC=C1)O GGIVKJCWSXWAHT-UHFFFAOYSA-N 0.000 description 1
- BPLBZFRNBNNOIU-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylpyrimidine hydrochloride Chemical compound C1CN(CCC1S(=O)C2=NC=CC=N2)CCC3=CC=C(C=C3)F.Cl BPLBZFRNBNNOIU-UHFFFAOYSA-N 0.000 description 1
- KYTCCYXFRRLEAV-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonyl-1,3-benzothiazole hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C=1SC2=C(N1)C=CC=C2 KYTCCYXFRRLEAV-UHFFFAOYSA-N 0.000 description 1
- NLHQQWVIEAAPMB-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonyl-1,3-thiazole hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=NC=CS2)CCC3=CC=C(C=C3)F.Cl NLHQQWVIEAAPMB-UHFFFAOYSA-N 0.000 description 1
- MPNWIAAXNVURTF-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonyl-6-methoxypyridine hydrochloride Chemical compound Cl.COC1=CC=CC(=N1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F MPNWIAAXNVURTF-UHFFFAOYSA-N 0.000 description 1
- GNQIOPSDOQAKIV-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=C(C=CC=C1)O GNQIOPSDOQAKIV-UHFFFAOYSA-N 0.000 description 1
- APHCXDRBCIUTIF-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylpyrimidine hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=NC=CC=N2)CCC3=CC=C(C=C3)F.Cl APHCXDRBCIUTIF-UHFFFAOYSA-N 0.000 description 1
- PWCXGDJFAIRPEO-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylquinoline hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=NC2=CC=CC=C2C=C1 PWCXGDJFAIRPEO-UHFFFAOYSA-N 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- PWPRTWDLSGNUBD-UHFFFAOYSA-N 2-chloro-6-[1-[2-(2-fluorophenyl)ethyl]piperidin-4-yl]sulfanylpyridine hydrochloride Chemical compound Cl.ClC1=NC(=CC=C1)SC1CCN(CC1)CCC1=C(C=CC=C1)F PWPRTWDLSGNUBD-UHFFFAOYSA-N 0.000 description 1
- GRXDJABVNGUGCW-UHFFFAOYSA-N 2-chloro-6-piperidin-4-ylsulfanylpyridine;hydrochloride Chemical compound Cl.ClC1=CC=CC(SC2CCNCC2)=N1 GRXDJABVNGUGCW-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- YRNVVCKAZGTRKX-UHFFFAOYSA-N 3-[1-[2-(2,4-difluorophenyl)ethyl]piperidin-4-yl]sulfonyl-1H-indole hydrochloride Chemical compound Cl.N1C=C(C2=CC=CC=C12)S(=O)(=O)C1CCN(CC1)CCC1=C(C=C(C=C1)F)F YRNVVCKAZGTRKX-UHFFFAOYSA-N 0.000 description 1
- YRZLGNJXTPRKSS-UHFFFAOYSA-N 3-[1-[2-(2-fluorophenyl)ethyl]piperidin-4-yl]sulfanyl-1H-indole hydrochloride Chemical compound Cl.N1C=C(C2=CC=CC=C12)SC1CCN(CC1)CCC1=C(C=CC=C1)F YRZLGNJXTPRKSS-UHFFFAOYSA-N 0.000 description 1
- IIOQEQFWPNPJEG-UHFFFAOYSA-N 3-[1-[2-(2-methylphenyl)ethyl]piperidin-4-yl]sulfanyl-1H-indole hydrochloride Chemical compound Cl.N1C=C(C2=CC=CC=C12)SC1CCN(CC1)CCC1=C(C=CC=C1)C IIOQEQFWPNPJEG-UHFFFAOYSA-N 0.000 description 1
- VYFJZHJFVXYQCJ-UHFFFAOYSA-N 3-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanyl-1H-indole hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=CNC2=CC=CC=C12 VYFJZHJFVXYQCJ-UHFFFAOYSA-N 0.000 description 1
- LFMHDGQPTJZHSO-UHFFFAOYSA-N 3-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonyl-1H-indole hydrochloride Chemical compound Cl.N1C=C(C2=CC=CC=C12)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F LFMHDGQPTJZHSO-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- FJECARWTSYXFDL-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC=C1Cl)SC1CCN(CC1)CCC1=CC=C(C=C1)F FJECARWTSYXFDL-UHFFFAOYSA-N 0.000 description 1
- KNCZNTXLPHHAEL-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)sulfinyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC=C1Cl)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F KNCZNTXLPHHAEL-UHFFFAOYSA-N 0.000 description 1
- NVAXRWWKLXHHNT-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC(=C1)Cl)SC1CCN(CC1)CCC1=CC=C(C=C1)F NVAXRWWKLXHHNT-UHFFFAOYSA-N 0.000 description 1
- XQJWTBPTHYLSOK-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)sulfinyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC(=C1)Cl)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F XQJWTBPTHYLSOK-UHFFFAOYSA-N 0.000 description 1
- DSIIQFFVAVNQJT-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)sulfonyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC(=C1)Cl)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F DSIIQFFVAVNQJT-UHFFFAOYSA-N 0.000 description 1
- BAPFMLZNFOKSOI-UHFFFAOYSA-N 4-(2,4-difluorophenyl)sulfinyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.FC1=C(C=CC(=C1)F)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F BAPFMLZNFOKSOI-UHFFFAOYSA-N 0.000 description 1
- TXFFDFCVZTVIQW-UHFFFAOYSA-N 4-(2,4-dimethoxyphenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.COC1=C(C=CC(=C1)OC)SC1CCN(CC1)CCC1=CC=C(C=C1)F TXFFDFCVZTVIQW-UHFFFAOYSA-N 0.000 description 1
- WXMTZGJUCVZZNV-UHFFFAOYSA-N 4-(2,4-dimethoxyphenyl)sulfonyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.COC1=C(C=CC(=C1)OC)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F WXMTZGJUCVZZNV-UHFFFAOYSA-N 0.000 description 1
- FMLMOPSRTRPILA-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.CC1=C(C=CC(=C1)C)SC1CCN(CC1)CCC1=CC=C(C=C1)F FMLMOPSRTRPILA-UHFFFAOYSA-N 0.000 description 1
- TYFPDOLMNCEERB-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)sulfinyl-1-[2-(2-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.FC1=C(C=CC=C1)CCN1CCC(CC1)S(=O)C1=C(C=C(C=C1)C)C TYFPDOLMNCEERB-UHFFFAOYSA-N 0.000 description 1
- ITDOUFIBTWCKGD-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F ITDOUFIBTWCKGD-UHFFFAOYSA-N 0.000 description 1
- BFJNBULNMSZKDS-UHFFFAOYSA-N 4-(2-ethylphenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine Chemical compound CCC1=CC=CC=C1SC1CCN(CCC=2C=CC(F)=CC=2)CC1 BFJNBULNMSZKDS-UHFFFAOYSA-N 0.000 description 1
- YUNVJVHFPCBPEE-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.COC=1C=C(C=CC1OC)SC1CCN(CC1)CCC1=CC=C(C=C1)F YUNVJVHFPCBPEE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VSBTUHUTKWCQMX-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F VSBTUHUTKWCQMX-UHFFFAOYSA-N 0.000 description 1
- AIVPBNAVFZREPX-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfonyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=CC=C(C=C2)Cl)CCC3=CC=C(C=C3)F.Cl AIVPBNAVFZREPX-UHFFFAOYSA-N 0.000 description 1
- UKFYELLYJRVBHI-UHFFFAOYSA-N 4-(4-tert-butylphenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.C(C)(C)(C)C1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F UKFYELLYJRVBHI-UHFFFAOYSA-N 0.000 description 1
- AFDZRSQBXBVTOJ-UHFFFAOYSA-N 4-(4-tert-butylphenyl)sulfinyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.C(C)(C)(C)C1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F AFDZRSQBXBVTOJ-UHFFFAOYSA-N 0.000 description 1
- CQCVOAKYPXEZPH-UHFFFAOYSA-N 4-(4-tert-butylphenyl)sulfonyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F CQCVOAKYPXEZPH-UHFFFAOYSA-N 0.000 description 1
- CSYQIIIFIGQBJD-UHFFFAOYSA-N 4-(benzenesulfinyl)-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.C1(=CC=CC=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F CSYQIIIFIGQBJD-UHFFFAOYSA-N 0.000 description 1
- KXFOIKITNHSIFV-UHFFFAOYSA-N 4-(benzenesulfonyl)-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.C1(=CC=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F KXFOIKITNHSIFV-UHFFFAOYSA-N 0.000 description 1
- PMIWSPDQRMEORO-UHFFFAOYSA-N 4-(benzenesulfonyl)piperidine Chemical class C=1C=CC=CC=1S(=O)(=O)C1CCNCC1 PMIWSPDQRMEORO-UHFFFAOYSA-N 0.000 description 1
- RMPRMZDUTXSHSS-UHFFFAOYSA-N 4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=CC=C(C=C1)O RMPRMZDUTXSHSS-UHFFFAOYSA-N 0.000 description 1
- VLGHXWKAHKGOIO-UHFFFAOYSA-N 4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)C1=CC=C(C=C1)O VLGHXWKAHKGOIO-UHFFFAOYSA-N 0.000 description 1
- JBEOOYKLQDCTQV-UHFFFAOYSA-N 4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=CC=C(C=C1)O JBEOOYKLQDCTQV-UHFFFAOYSA-N 0.000 description 1
- PMSWKOVWENXTPW-UHFFFAOYSA-N 4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylpyridine dihydrochloride Chemical compound Cl.Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=CC=NC=C1 PMSWKOVWENXTPW-UHFFFAOYSA-N 0.000 description 1
- PEJMCXKIVQXEBO-UHFFFAOYSA-N 4-[1-[2-(5-chlorothiophen-2-yl)ethyl]piperidin-4-yl]sulfanylbenzonitrile hydrochloride Chemical compound Cl.ClC1=CC=C(S1)CCN1CCC(CC1)SC1=CC=C(C#N)C=C1 PEJMCXKIVQXEBO-UHFFFAOYSA-N 0.000 description 1
- YDUDBQYACJBEOI-UHFFFAOYSA-N 4-[1-[2-(5-chlorothiophen-2-yl)ethyl]piperidin-4-yl]sulfonylbenzonitrile hydrochloride Chemical compound Cl.ClC1=CC=C(S1)CCN1CCC(CC1)S(=O)(=O)C1=CC=C(C#N)C=C1 YDUDBQYACJBEOI-UHFFFAOYSA-N 0.000 description 1
- XLUKKKAHJAYXID-UHFFFAOYSA-N 4-[2-[4-(2-methoxyphenyl)sulfonylpiperidin-1-yl]ethyl]pyridine dihydrochloride Chemical compound Cl.Cl.COC1=C(C=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=NC=C1 XLUKKKAHJAYXID-UHFFFAOYSA-N 0.000 description 1
- CCPLKOQQBWBIDF-UHFFFAOYSA-N 4-[2-[4-(benzenesulfinyl)piperidin-1-yl]ethyl]pyridine dihydrochloride Chemical compound Cl.Cl.C1(=CC=CC=C1)S(=O)C1CCN(CC1)CCC1=CC=NC=C1 CCPLKOQQBWBIDF-UHFFFAOYSA-N 0.000 description 1
- GQSWUEFZLHWONY-UHFFFAOYSA-N 4-[2-[4-(benzenesulfonyl)piperidin-1-yl]ethyl]pyridine dihydrochloride Chemical compound Cl.Cl.C1(=CC=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=NC=C1 GQSWUEFZLHWONY-UHFFFAOYSA-N 0.000 description 1
- UVWCUCNEXMKSAD-UHFFFAOYSA-N 4-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]sulfonyl-2,1,3-benzothiadiazole Chemical compound C1=CC(F)=CC=C1CCN1CCN(S(=O)(=O)C=2C3=NSN=C3C=CC=2)CC1 UVWCUCNEXMKSAD-UHFFFAOYSA-N 0.000 description 1
- IBCMLJMDEHVMPM-UHFFFAOYSA-N 4-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]sulfonyl-2,1,3-benzoxadiazole Chemical compound C1=CC(F)=CC=C1CCN1CCN(S(=O)(=O)C=2C3=NON=C3C=CC=2)CC1 IBCMLJMDEHVMPM-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- JSJXZHIPLNHNCF-UHFFFAOYSA-N 7-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]sulfonyl-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CCN1CCN(S(=O)(=O)C=2C=3NC=C(C=3C=CC=2)C#N)CC1 JSJXZHIPLNHNCF-UHFFFAOYSA-N 0.000 description 1
- YXRLBORRAOIKIX-UHFFFAOYSA-N 8-[1-(2-naphthalen-2-ylethyl)piperidin-4-yl]sulfonylquinoline hydrochloride Chemical compound Cl.N1=CC=CC2=CC=CC(=C12)S(=O)(=O)C1CCN(CC1)CCC1=CC2=CC=CC=C2C=C1 YXRLBORRAOIKIX-UHFFFAOYSA-N 0.000 description 1
- ZIGFLVDSXQFLNH-UHFFFAOYSA-N 8-[1-[2-(2,4-difluorophenyl)ethyl]piperidin-4-yl]sulfanylquinoline hydrochloride Chemical compound Cl.FC1=C(C=CC(=C1)F)CCN1CCC(CC1)SC=1C=CC=C2C=CC=NC12 ZIGFLVDSXQFLNH-UHFFFAOYSA-N 0.000 description 1
- NDMQGSADJVHUKD-UHFFFAOYSA-N 8-[1-[2-(2-chloro-4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylquinoline dihydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=CC=CC3=C2N=CC=C3)CCC4=C(C=C(C=C4)F)Cl.Cl.Cl NDMQGSADJVHUKD-UHFFFAOYSA-N 0.000 description 1
- IYPASFBFWSGMLG-UHFFFAOYSA-N 8-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylquinoline Chemical compound C1=CC(F)=CC=C1CCN1CCC(SC=2C3=NC=CC=C3C=CC=2)CC1 IYPASFBFWSGMLG-UHFFFAOYSA-N 0.000 description 1
- VYHUKFAQKPLRAI-UHFFFAOYSA-N 8-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylquinoline hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)C=1C=CC=C2C=CC=NC12 VYHUKFAQKPLRAI-UHFFFAOYSA-N 0.000 description 1
- ATVFLQICEREMBA-UHFFFAOYSA-N 8-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylquinoline hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C=1C=CC=C2C=CC=NC12 ATVFLQICEREMBA-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 208000008811 Agoraphobia Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- LFKYAFSMQXMEPK-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)S(=O)(=O)C=1C(=CSC1)S(=O)(=O)N1CCN(CC1)CCC1=CC=C(C=C1)F Chemical compound Cl.C1(=CC=CC=C1)S(=O)(=O)C=1C(=CSC1)S(=O)(=O)N1CCN(CC1)CCC1=CC=C(C=C1)F LFKYAFSMQXMEPK-UHFFFAOYSA-N 0.000 description 1
- LEZFQQAQYAYPOL-UHFFFAOYSA-N Cl.CN1N=NN=C1SC1CCN(CC1)CCC1=CC=C(C=C1)F Chemical compound Cl.CN1N=NN=C1SC1CCN(CC1)CCC1=CC=C(C=C1)F LEZFQQAQYAYPOL-UHFFFAOYSA-N 0.000 description 1
- KMWQULVQXTVOKL-UHFFFAOYSA-N Cl.COC1=C(C=CC(=C1)OC)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F Chemical compound Cl.COC1=C(C=CC(=C1)OC)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F KMWQULVQXTVOKL-UHFFFAOYSA-N 0.000 description 1
- NMBUGKXNEXBYKE-UHFFFAOYSA-N Cl.COC=1C=C(C=CC1OC)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F Chemical compound Cl.COC=1C=C(C=CC1OC)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F NMBUGKXNEXBYKE-UHFFFAOYSA-N 0.000 description 1
- ZRZXMVJREYKSJQ-UHFFFAOYSA-N Cl.CS(=O)C1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F Chemical compound Cl.CS(=O)C1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F ZRZXMVJREYKSJQ-UHFFFAOYSA-N 0.000 description 1
- YSYHZTNTRWHEGC-UHFFFAOYSA-N Cl.Cl.COC1=C(C=CC=C1)S(=O)C1CCN(CC1)CCC1=CC=NC=C1 Chemical compound Cl.Cl.COC1=C(C=CC=C1)S(=O)C1CCN(CC1)CCC1=CC=NC=C1 YSYHZTNTRWHEGC-UHFFFAOYSA-N 0.000 description 1
- SRNNXZLGELKMCL-UHFFFAOYSA-N Cl.Cl.COC=1C=C(C=CC1OC)S(=O)(=O)C1CCN(CC1)CCC1=CC=NC=C1 Chemical compound Cl.Cl.COC=1C=C(C=CC1OC)S(=O)(=O)C1CCN(CC1)CCC1=CC=NC=C1 SRNNXZLGELKMCL-UHFFFAOYSA-N 0.000 description 1
- YDMCATSDXCPEPS-UHFFFAOYSA-N Cl.Cl.COC=1C=C(C=CC1OC)S(=O)C1CCN(CC1)CCC1=CC=NC=C1 Chemical compound Cl.Cl.COC=1C=C(C=CC1OC)S(=O)C1CCN(CC1)CCC1=CC=NC=C1 YDMCATSDXCPEPS-UHFFFAOYSA-N 0.000 description 1
- YQADIQYCKPBVDX-UHFFFAOYSA-N Cl.Cl.N1C(=NC2=C1C=CC=C2)S(=O)(=O)C2CCN(CC2)CCC2=CC=C(C=C2)F Chemical compound Cl.Cl.N1C(=NC2=C1C=CC=C2)S(=O)(=O)C2CCN(CC2)CCC2=CC=C(C=C2)F YQADIQYCKPBVDX-UHFFFAOYSA-N 0.000 description 1
- WLPQKSSTSKPOIC-UHFFFAOYSA-N Cl.ClC1=CC2=C(SC(=C2C)S(=O)(=O)N2CCN(CC2)CCC2=CC=C(C=C2)F)C=C1 Chemical compound Cl.ClC1=CC2=C(SC(=C2C)S(=O)(=O)N2CCN(CC2)CCC2=CC=C(C=C2)F)C=C1 WLPQKSSTSKPOIC-UHFFFAOYSA-N 0.000 description 1
- XPTKFRBHTRCGAW-UHFFFAOYSA-N Cl.FC(OC1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)(F)F Chemical compound Cl.FC(OC1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)(F)F XPTKFRBHTRCGAW-UHFFFAOYSA-N 0.000 description 1
- WMZCLTFMRZTGDQ-UHFFFAOYSA-N Cl.FC1=C(C=CC(=C1)F)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F Chemical compound Cl.FC1=C(C=CC(=C1)F)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F WMZCLTFMRZTGDQ-UHFFFAOYSA-N 0.000 description 1
- IMMRJPZFYULARW-UHFFFAOYSA-N Cl.N1CCC2=CC(=CC=C12)S(=O)(=O)N1CCN(CC1)CCC1=CC=C(C=C1)F Chemical compound Cl.N1CCC2=CC(=CC=C12)S(=O)(=O)N1CCN(CC1)CCC1=CC=C(C=C1)F IMMRJPZFYULARW-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 206010012239 Delusion Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- BGHDUTQZGWOQIA-VQSKNWBGSA-N Ergovaline Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)C(C)C)C)C2)=C3C2=CNC3=C1 BGHDUTQZGWOQIA-VQSKNWBGSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 208000027776 Extrapyramidal disease Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000020358 Learning disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 206010047163 Vasospasm Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 231100000868 delusion Toxicity 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- SOVFVZVAXJHGFT-UHFFFAOYSA-N ditert-butyl piperazine-1,2-dicarboxylate Chemical compound CC(C)(C)OC(=O)C1CNCCN1C(=O)OC(C)(C)C SOVFVZVAXJHGFT-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 208000030172 endocrine system disease Diseases 0.000 description 1
- BGHDUTQZGWOQIA-RKUMIMICSA-N ergovaline Natural products O=C(N[C@@]1(C)C(=O)N2[C@H](C(C)C)C(=O)N3[C@@H]([C@]2(O)O1)CCC3)[C@@H]1C=C2[C@H](N(C)C1)Cc1c3c([nH]c1)cccc23 BGHDUTQZGWOQIA-RKUMIMICSA-N 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MYURNPLIPIFRLB-UHFFFAOYSA-N ethyl 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylbenzoate hydrochloride Chemical compound Cl.C(C)OC(=O)C1=C(C=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F MYURNPLIPIFRLB-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 1
- 208000031424 hyperprolactinemia Diseases 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 229960005417 ketanserin Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 201000003723 learning disability Diseases 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- OHEDMAIVEXQCOZ-UHFFFAOYSA-N piperidine;dihydrochloride Chemical compound Cl.Cl.C1CCNCC1 OHEDMAIVEXQCOZ-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- JUYUYCIJACTHMK-UHFFFAOYSA-N quinoline-8-sulfonyl chloride Chemical compound C1=CN=C2C(S(=O)(=O)Cl)=CC=CC2=C1 JUYUYCIJACTHMK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002400 serotonin 2A antagonist Substances 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRLBGINRRYSZMY-UHFFFAOYSA-N tert-butyl 4-[2-(4-fluorophenyl)ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CCC1=CC=C(F)C=C1 JRLBGINRRYSZMY-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/54—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/12—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
-
- 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
- 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
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- 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
- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (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)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10000739A DE10000739A1 (de) | 2000-01-11 | 2000-01-11 | Piperidin- und Piperazinderivate |
PCT/EP2001/000080 WO2001051469A1 (de) | 2000-01-11 | 2001-01-05 | Piperidin- und piperazinderivate als 5-ht2a rezeptor antagonisten |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20023293L true NO20023293L (no) | 2002-07-08 |
NO20023293D0 NO20023293D0 (no) | 2002-07-08 |
Family
ID=7627124
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20023293A NO20023293D0 (no) | 2000-01-11 | 2002-07-08 | Piperidin- og piperazinderivater som virker som 5-HT2A- reseptorantagonister |
Country Status (19)
Country | Link |
---|---|
US (1) | US20030130287A1 (ru) |
EP (1) | EP1246803A1 (ru) |
JP (1) | JP2004500373A (ru) |
KR (1) | KR20020073492A (ru) |
CN (1) | CN1394203A (ru) |
AR (1) | AR030181A1 (ru) |
AU (1) | AU2001233685A1 (ru) |
BR (1) | BR0107578A (ru) |
CA (1) | CA2396007A1 (ru) |
CZ (1) | CZ20022309A3 (ru) |
DE (1) | DE10000739A1 (ru) |
HU (1) | HUP0300052A3 (ru) |
MX (1) | MXPA02006809A (ru) |
NO (1) | NO20023293D0 (ru) |
PL (1) | PL355654A1 (ru) |
RU (1) | RU2002120906A (ru) |
SK (1) | SK9712002A3 (ru) |
WO (1) | WO2001051469A1 (ru) |
ZA (1) | ZA200206361B (ru) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0007907D0 (en) * | 2000-03-31 | 2000-05-17 | Merck Sharp & Dohme | Therapeutic agents |
AU2002360561A1 (en) | 2001-12-11 | 2003-06-23 | Sepracor, Inc. | 4-substituted piperidines, and methods of use thereof |
US7408067B2 (en) | 2002-01-17 | 2008-08-05 | Merck + Co., Inc. | Aza-cyclic compounds as modulators of acetylcholine receptors |
DE10201550A1 (de) * | 2002-01-17 | 2003-07-31 | Merck Patent Gmbh | Phenoxy-Piperidine |
CN100445276C (zh) | 2002-03-13 | 2008-12-24 | 詹森药业有限公司 | 用作组蛋白去乙酰酶抑制剂的磺酰基衍生物 |
WO2003099265A2 (de) * | 2002-05-24 | 2003-12-04 | Coester Carl-Fr | Pharmazeutische wirkstoffkombination sowie deren verwendung |
US7378525B2 (en) | 2002-12-23 | 2008-05-27 | Millennium Pharmaceuticals, Inc. | CCR8 inhibitors |
TW200510311A (en) | 2002-12-23 | 2005-03-16 | Millennium Pharm Inc | CCr8 inhibitors |
US7491827B2 (en) | 2002-12-23 | 2009-02-17 | Millennium Pharmaceuticals, Inc. | Aryl sulfonamides useful as inhibitors of chemokine receptor activity |
GB0311349D0 (en) * | 2003-05-16 | 2003-06-25 | Merck Sharp & Dohme | Therapeutic agents, compositions, preparations and uses |
US7365075B2 (en) * | 2003-12-22 | 2008-04-29 | Amgen Inc. | Aryl sulfonamide compounds and uses related thereto |
JP2007533749A (ja) * | 2004-04-20 | 2007-11-22 | アムゲン インコーポレイティッド | アリールスルホンアミドおよびそれに関連する使用方法 |
TWI391387B (zh) * | 2004-05-12 | 2013-04-01 | Eisai R&D Man Co Ltd | 具有哌啶環之吲哚衍生物 |
US20050282818A1 (en) * | 2004-06-22 | 2005-12-22 | Rigel Pharmaceuticals, Inc. | Ubiquitin ligase inhibitors |
GB0419192D0 (en) * | 2004-08-27 | 2004-09-29 | Merck Sharp & Dohme | Therapeutic agents |
US20080119518A1 (en) * | 2005-02-04 | 2008-05-22 | Yuichi Suzuki | 1-(Piperidin-4- Yl)-1H-Indole Derivatives |
GB0504828D0 (en) * | 2005-03-09 | 2005-04-13 | Merck Sharp & Dohme | Therapeutic agents |
JP4932717B2 (ja) * | 2005-05-11 | 2012-05-16 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピペリジン環を有するインドール誘導体の製造方法 |
JPWO2006121104A1 (ja) * | 2005-05-11 | 2008-12-18 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピペリジン環を有するインドール誘導体の結晶およびその製法 |
US8071602B2 (en) * | 2005-08-09 | 2011-12-06 | M's Science Corporation | Piperidine and piperazine derivatives |
WO2008096189A2 (en) | 2005-09-23 | 2008-08-14 | M's Science Corporation | Piperidine and piperazine derivatives |
EP2340835A1 (en) | 2006-01-27 | 2011-07-06 | M's Science Corporation | Piperidine and piperazine derivatives |
US20070238876A1 (en) * | 2006-04-10 | 2007-10-11 | Neera Tewari | Process for the preparation of aripiprazole |
AU2008285652B2 (en) * | 2007-08-07 | 2013-09-05 | AbbVie Deutschland GmbH & Co. KG | Quinoline compounds suitable for treating disorders that respond to modulation of the serotonin 5-HT6 receptor |
US20110281890A1 (en) * | 2008-03-19 | 2011-11-17 | M's Science Corporation | Piperidine and piperazine derivatives |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2439195A2 (fr) * | 1978-10-16 | 1980-05-16 | Synthelabo | Derives du naphtalene et leur application en therapeutique |
ZA848275B (en) * | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
US4695575A (en) * | 1984-11-13 | 1987-09-22 | Janssen Pharmaceutica, N.V. | 4-[(bicycle heterocyclyl)-methyl and -hetero]-piperidines |
US5643995A (en) * | 1987-06-11 | 1997-07-01 | Amoco Corporation | Method for improving the processabilty of polyphthalamides |
JPH01131158A (ja) * | 1987-08-03 | 1989-05-24 | Ss Pharmaceut Co Ltd | 置換アルキルピペラジン誘導体 |
PH25458A (en) * | 1987-08-24 | 1991-07-01 | Eisai Co Ltd | Piperidine derivatives, therapeutic, preventive agents |
FR2642069B1 (fr) * | 1989-01-20 | 1991-04-12 | Rhone Poulenc Sante | Nouveaux derives du benzopyranne, leur preparation et les compositions pharmaceutiques qui les contiennent |
JP3036789B2 (ja) * | 1990-06-22 | 2000-04-24 | 三井化学株式会社 | 新規な複素環式化合物及び医薬組成物 |
JP2983257B2 (ja) * | 1990-06-22 | 1999-11-29 | 三井化学株式会社 | 新規複素環式化合物及び医薬組成物 |
US5418242A (en) * | 1993-05-18 | 1995-05-23 | Laboratoires Upsa | Piperidinylthioindole derivatives, their methods of preparation and pharmaceutical compositions in which they are present, useful especially as analgesics |
US5567711A (en) * | 1995-04-19 | 1996-10-22 | Abbott Laboratories | Indole-3-carbonyl and indole-3-sulfonyl derivatives as platelet activating factor antagonists |
GB9901147D0 (en) * | 1999-01-19 | 1999-03-10 | Merck Sharp & Dohme | Therapeutic agents |
-
2000
- 2000-01-11 DE DE10000739A patent/DE10000739A1/de not_active Withdrawn
-
2001
- 2001-01-05 JP JP2001551851A patent/JP2004500373A/ja active Pending
- 2001-01-05 HU HU0300052A patent/HUP0300052A3/hu unknown
- 2001-01-05 US US10/169,399 patent/US20030130287A1/en not_active Abandoned
- 2001-01-05 KR KR1020027008493A patent/KR20020073492A/ko not_active Application Discontinuation
- 2001-01-05 BR BR0107578-0A patent/BR0107578A/pt not_active Application Discontinuation
- 2001-01-05 AU AU2001233685A patent/AU2001233685A1/en not_active Abandoned
- 2001-01-05 CZ CZ20022309A patent/CZ20022309A3/cs unknown
- 2001-01-05 SK SK971-2002A patent/SK9712002A3/sk unknown
- 2001-01-05 CA CA002396007A patent/CA2396007A1/en not_active Abandoned
- 2001-01-05 WO PCT/EP2001/000080 patent/WO2001051469A1/de not_active Application Discontinuation
- 2001-01-05 PL PL01355654A patent/PL355654A1/xx unknown
- 2001-01-05 CN CN01803348A patent/CN1394203A/zh active Pending
- 2001-01-05 RU RU2002120906/04A patent/RU2002120906A/ru not_active Application Discontinuation
- 2001-01-05 EP EP01905650A patent/EP1246803A1/de not_active Withdrawn
- 2001-01-05 MX MXPA02006809A patent/MXPA02006809A/es unknown
- 2001-01-10 AR ARP010100092A patent/AR030181A1/es unknown
-
2002
- 2002-07-08 NO NO20023293A patent/NO20023293D0/no not_active Application Discontinuation
- 2002-08-08 ZA ZA200206361A patent/ZA200206361B/en unknown
Also Published As
Publication number | Publication date |
---|---|
CZ20022309A3 (cs) | 2002-10-16 |
SK9712002A3 (en) | 2002-12-03 |
HUP0300052A3 (en) | 2004-03-01 |
DE10000739A1 (de) | 2001-07-12 |
US20030130287A1 (en) | 2003-07-10 |
PL355654A1 (en) | 2004-05-04 |
MXPA02006809A (es) | 2002-10-23 |
NO20023293D0 (no) | 2002-07-08 |
JP2004500373A (ja) | 2004-01-08 |
AR030181A1 (es) | 2003-08-13 |
RU2002120906A (ru) | 2004-04-10 |
ZA200206361B (en) | 2003-11-10 |
HUP0300052A2 (en) | 2003-05-28 |
BR0107578A (pt) | 2002-10-01 |
WO2001051469A1 (de) | 2001-07-19 |
KR20020073492A (ko) | 2002-09-26 |
AU2001233685A1 (en) | 2001-07-24 |
CN1394203A (zh) | 2003-01-29 |
CA2396007A1 (en) | 2001-07-19 |
EP1246803A1 (de) | 2002-10-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO20023293L (no) | Piperidin- og piperazinderivater som virker som 5-HT2A- reseptorantagonister | |
TWI481601B (zh) | 含氮化合物及藥學組成物 | |
CZ200268A3 (cs) | Derivát N-(indolkarbonyl)piperazinu, způsob jeho přípravy, jeho pouľití a farmaceutický prostředek, který ho obsahuje | |
KR20070114762A (ko) | 염증 질환 치료를 위한 pgd2 수용체 길항제 | |
KR20070092297A (ko) | Kv4 이온 채널 활성을 갖는 화합물 | |
IL137517A (en) | Oxase trotocyclic converting factor Xa inhibitors, medicinal products containing them and their use | |
KR20030019555A (ko) | 프로판-1,3-디온 유도체 | |
NO341064B1 (no) | Tieno-pyridinderivater eller et farmasøytisk akseptabelt salt, solvat eller N-oksyd derav, og deres anvendelse i terapi, og til fremstilling av et medikament, samt et farmasøytisk preparat derav. | |
AU2015226578A1 (en) | Heterocyclic compounds, process for preparation of the same and use thereof | |
NZ552283A (en) | New compounds useful for the treatment of obesity, type II diabetes and CNS disorders | |
WO2012044090A2 (ko) | 단백질 키나제 억제 활성을 갖는 신규한 아미노퀴나졸린 화합물 | |
KR20180100227A (ko) | 퀴놀린-2-온 유도체 | |
NO179007B (no) | Analogifremgangsmåte for fremstilling av (aza)naftalensultamderivater | |
WO2013100672A1 (ko) | 단백질 키나아제 저해활성을 가지는 3,6-이치환된 인다졸 유도체 | |
WO2008053863A1 (fr) | Nouveau composé ayant un squelette de 1,4-benzothiazin-3-one ou un squelette de 3,4-dihydroquinolin-2-one | |
NO322152B1 (no) | Indolderivater, fremgangsmate for fremstilling derav, farmakologisk preparat som omfatter minst ±n slik forbindelse, samt anvendelse derav til fremstilling av medikamenter | |
CZ304144B6 (cs) | Derivát piperazinylkarbonylchinolinu nebo | |
SK6942002A3 (en) | Sulfonyl oxazole amine derivative, process for the preparation thereof, its use and pharmaceutical composition containing same | |
NO882321L (no) | Forbindelser. | |
KR20050024358A (ko) | 비만증, 타입 ⅱ 당뇨병 및 cns 장애의 치료에 유용한신규 화합물 | |
CZ2000343A3 (cs) | O-Substituované hydroxykumaronové deriváty jako protinádorová a protimetastázová činidla |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FC2A | Withdrawal, rejection or dismissal of laid open patent application |