HRP20030141A2 - Phenoxybenzylamine derivatives as selective serotonin re-uptake inhibitors - Google Patents
Phenoxybenzylamine derivatives as selective serotonin re-uptake inhibitors Download PDFInfo
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- HRP20030141A2 HRP20030141A2 HR20030141A HRP20030141A HRP20030141A2 HR P20030141 A2 HRP20030141 A2 HR P20030141A2 HR 20030141 A HR20030141 A HR 20030141A HR P20030141 A HRP20030141 A HR P20030141A HR P20030141 A2 HRP20030141 A2 HR P20030141A2
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- pharmaceutically acceptable
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- 230000000697 serotonin reuptake Effects 0.000 title description 11
- 239000003112 inhibitor Substances 0.000 title description 5
- YXMXAXHPRPWBJB-UHFFFAOYSA-N n-phenoxy-1-phenylmethanamine Chemical class C=1C=CC=CC=1CNOC1=CC=CC=C1 YXMXAXHPRPWBJB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 282
- 238000000034 method Methods 0.000 claims description 98
- 238000006243 chemical reaction Methods 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 239000001257 hydrogen Substances 0.000 claims description 65
- 239000002904 solvent Substances 0.000 claims description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- -1 NH 2 Chemical group 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 41
- 150000002431 hydrogen Chemical group 0.000 claims description 36
- 239000011541 reaction mixture Substances 0.000 claims description 26
- 239000012453 solvate Substances 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 239000003638 chemical reducing agent Substances 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 206010036596 premature ejaculation Diseases 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 230000002411 adverse Effects 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 239000012442 inert solvent Substances 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 11
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 11
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- QIWQQMZFTOCFGF-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-(3-methyl-4-methylsulfanylphenoxy)benzenesulfonamide Chemical compound C1=C(C)C(SC)=CC=C1OC1=CC=C(S(N)(=O)=O)C=C1CN(C)C QIWQQMZFTOCFGF-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 7
- YKUFJPGUCDDEEY-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzothiophen-5-yloxy)-3-(methylaminomethyl)benzamide Chemical compound CNCC1=CC(C(N)=O)=CC=C1OC1=CC=C(SCC2)C2=C1 YKUFJPGUCDDEEY-UHFFFAOYSA-N 0.000 claims description 7
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 7
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- JCNJJQOCZPBSDY-UHFFFAOYSA-N 3-(methylaminomethyl)-4-(3-methyl-4-methylsulfanylphenoxy)benzamide Chemical compound CNCC1=CC(C(N)=O)=CC=C1OC1=CC=C(SC)C(C)=C1 JCNJJQOCZPBSDY-UHFFFAOYSA-N 0.000 claims description 6
- SLWDKAHRQIGZDY-UHFFFAOYSA-N 3-(methylaminomethyl)-4-quinolin-6-yloxybenzenesulfonamide Chemical compound CNCC1=CC(S(N)(=O)=O)=CC=C1OC1=CC=C(N=CC=C2)C2=C1 SLWDKAHRQIGZDY-UHFFFAOYSA-N 0.000 claims description 6
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 6
- 230000033228 biological regulation Effects 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 150000004678 hydrides Chemical class 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 6
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 6
- 208000011117 substance-related disease Diseases 0.000 claims description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
- QEIZOHJXMQOJAP-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzothiophen-5-yloxy)-3-(methylaminomethyl)benzenesulfonamide Chemical compound CNCC1=CC(S(N)(=O)=O)=CC=C1OC1=CC=C(SCC2)C2=C1 QEIZOHJXMQOJAP-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- OXGNKSRPOAVQJK-UHFFFAOYSA-N n,n-dimethyl-1-(2-quinolin-6-yloxyphenyl)methanamine Chemical compound CN(C)CC1=CC=CC=C1OC1=CC=C(N=CC=C2)C2=C1 OXGNKSRPOAVQJK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- PQZIPHYCFJZBMI-UHFFFAOYSA-N 3-(methylaminomethyl)-4-quinolin-6-yloxybenzamide Chemical compound CNCC1=CC(C(N)=O)=CC=C1OC1=CC=C(N=CC=C2)C2=C1 PQZIPHYCFJZBMI-UHFFFAOYSA-N 0.000 claims description 4
- ANIFHKBWUXCCBH-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-(3-fluoro-4-methylsulfanylphenoxy)benzenesulfonamide Chemical compound C1=C(F)C(SC)=CC=C1OC1=CC=C(S(N)(=O)=O)C=C1CN(C)C ANIFHKBWUXCCBH-UHFFFAOYSA-N 0.000 claims description 4
- WFSZGLDEZANSFJ-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-quinolin-6-yloxybenzamide Chemical compound CN(C)CC1=CC(C(N)=O)=CC=C1OC1=CC=C(N=CC=C2)C2=C1 WFSZGLDEZANSFJ-UHFFFAOYSA-N 0.000 claims description 4
- IHINHVZKTRUFRD-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzothiophen-5-yloxy)-3-[(dimethylamino)methyl]benzenesulfonamide Chemical compound CN(C)CC1=CC(S(N)(=O)=O)=CC=C1OC1=CC=C(SCC2)C2=C1 IHINHVZKTRUFRD-UHFFFAOYSA-N 0.000 claims description 4
- IAMXGMFQJDRJFP-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzothiophen-5-yloxy)-n-methyl-3-(methylaminomethyl)benzamide Chemical compound CNCC1=CC(C(=O)NC)=CC=C1OC1=CC=C(SCC2)C2=C1 IAMXGMFQJDRJFP-UHFFFAOYSA-N 0.000 claims description 4
- SNFPHAIZQSQJBE-UHFFFAOYSA-N 4-(3-chloro-4-methylsulfanylphenoxy)-3-[(dimethylamino)methyl]benzenesulfonamide Chemical compound C1=C(Cl)C(SC)=CC=C1OC1=CC=C(S(N)(=O)=O)C=C1CN(C)C SNFPHAIZQSQJBE-UHFFFAOYSA-N 0.000 claims description 4
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 4
- OMHSYKYTYRKAQR-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-(3-fluoro-4-methylsulfanylphenoxy)phenyl]methanol Chemical compound C1=C(F)C(SC)=CC=C1OC1=CC=C(CO)C=C1CN(C)C OMHSYKYTYRKAQR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
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- 238000002955 isolation Methods 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- VOWIWPZFWTVLOO-UHFFFAOYSA-N n-[[3-(methylaminomethyl)-4-(3-methyl-4-methylsulfanylphenoxy)phenyl]methyl]methanesulfonamide Chemical compound CNCC1=CC(CNS(C)(=O)=O)=CC=C1OC1=CC=C(SC)C(C)=C1 VOWIWPZFWTVLOO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical group FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 3
- 206010013654 Drug abuse Diseases 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 2
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- KPDONORYYAGKME-UHFFFAOYSA-N n-methyl-n-[3-(methylaminomethyl)-4-(3-methyl-4-methylsulfanylphenoxy)phenyl]methanesulfonamide Chemical compound CNCC1=CC(N(C)S(C)(=O)=O)=CC=C1OC1=CC=C(SC)C(C)=C1 KPDONORYYAGKME-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 4
- IRWJTTNPJDLUOM-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzoxathiin-7-yloxy)-3-[(dimethylamino)methyl]benzamide Chemical compound CN(C)CC1=CC(C(N)=O)=CC=C1OC1=CC=C(SCCO2)C2=C1 IRWJTTNPJDLUOM-UHFFFAOYSA-N 0.000 claims 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 2
- OKRFWLHFFMDJDB-UHFFFAOYSA-N n-[4-(2,3-dihydro-1,4-benzoxathiin-7-yloxy)-3-[(dimethylamino)methyl]phenyl]methanesulfonamide Chemical compound CN(C)CC1=CC(NS(C)(=O)=O)=CC=C1OC1=CC=C(SCCO2)C2=C1 OKRFWLHFFMDJDB-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
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- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- 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
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
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- 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
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
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- Reproductive Health (AREA)
- Pain & Pain Management (AREA)
- Gynecology & Obstetrics (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Quinoline Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
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GB0021593A GB0021593D0 (en) | 2000-08-31 | 2000-08-31 | Diphenyl ether compounds useful in therapy |
GB0107116A GB0107116D0 (en) | 2001-03-21 | 2001-03-21 | Novel compounds |
PCT/IB2001/001521 WO2002018333A1 (en) | 2000-08-31 | 2001-08-22 | Phenoxybenzylamine derivatives as selective serotonin re-uptake inhibitors |
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HR20030141A HRP20030141A2 (en) | 2000-08-31 | 2003-02-26 | Phenoxybenzylamine derivatives as selective serotonin re-uptake inhibitors |
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JP (1) | JP2004507523A (pt) |
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US6403597B1 (en) * | 1997-10-28 | 2002-06-11 | Vivus, Inc. | Administration of phosphodiesterase inhibitors for the treatment of premature ejaculation |
US6436938B1 (en) * | 2001-01-22 | 2002-08-20 | Pfizer Inc. | Combination treatment for depression |
US20020107244A1 (en) * | 2001-02-02 | 2002-08-08 | Howard Harry R. | Combination treatment for depression |
US20020183306A1 (en) * | 2001-05-30 | 2002-12-05 | Pfizer Inc. | Combination treatment for sleep disorders including sleep apnea |
GB0318706D0 (en) * | 2003-08-08 | 2003-09-10 | Pfizer Ltd | Selective serotonin reuptake inhibitors in the treatment of disease |
CA2554696C (en) | 2004-02-13 | 2009-06-30 | Warner-Lambert Company Llc | Androgen receptor modulators |
US7507860B2 (en) | 2004-04-13 | 2009-03-24 | Pfizer Inc. | Androgen modulators |
CA2562672C (en) | 2004-04-22 | 2009-09-29 | Warner-Lambert Company Llc | 4-cyano-phenoxy derivatives as androgen modulators |
CA2570047C (en) | 2004-07-08 | 2010-09-28 | Warner-Lambert Company Llc | 4-cycloalkoxy benzonitriles as androgen modulators |
BRPI0514405A (pt) * | 2004-08-18 | 2008-06-10 | Warner Lambert Co | moduladores de androgênio |
JP2008512438A (ja) * | 2004-09-10 | 2008-04-24 | ファイザー・プロダクツ・インク | 療法用ジフェニルエーテル系リガンド |
TW200724139A (en) | 2005-05-05 | 2007-07-01 | Warner Lambert Co | Androgen modulators |
WO2007010350A1 (en) * | 2005-07-19 | 2007-01-25 | Pfizer Products Inc. | Synthesis of therapeutic diphenyl ethers |
CN101331120A (zh) | 2005-10-13 | 2008-12-24 | 史密丝克莱恩比彻姆公司 | 作为阿片样物质受体调节剂的酚醚化合物 |
WO2007076875A2 (en) * | 2006-01-06 | 2007-07-12 | Aarhus Universitet | Compounds acting on the serotonin transporter |
CN101511775A (zh) * | 2006-06-29 | 2009-08-19 | 詹森药业有限公司 | 丁基和丁炔基苄基胺化合物 |
AU2007265240A1 (en) * | 2006-06-29 | 2008-01-03 | Janssen Pharmaceutica N.V. | Substituted aminomethyl benzamide compounds |
AU2007265242A1 (en) | 2006-06-29 | 2008-01-03 | Janssen Pharmaceutica N.V. | Substituted benzyl amine compounds |
WO2010059393A1 (en) | 2008-10-30 | 2010-05-27 | Janssen Pharmaceutica Nv | Serotonin receptor modulators |
US8575364B2 (en) | 2008-10-30 | 2013-11-05 | Janssen Pharmaceutica Nv | Modulators of serotonin receptor |
KR101043200B1 (ko) * | 2010-11-08 | 2011-06-21 | 성시민 | 호흡용 공기탱크의 공기 충전장치 |
US9092242B2 (en) | 2011-01-27 | 2015-07-28 | Hewlett-Packard Development Company, L.P. | Computing device to connect to a portable device |
JP7413346B2 (ja) | 2019-03-06 | 2024-01-15 | 第一三共株式会社 | ピロロピラゾール誘導体 |
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ZA923283B (en) * | 1991-05-29 | 1993-01-27 | Akzo Nv | Phenoxyphenyl derivatives |
AU693110B2 (en) * | 1993-08-19 | 1998-06-25 | Warner-Lambert Company | Substituted 2(5H)furanone, 2(5H)thiophenone and 2(5H)pyrrolone derivatives, their preparation and their use as endothelin antagonists |
CZ293595A3 (cs) * | 1995-11-09 | 1999-12-15 | Farmak A. S. | Deriváty N,N-dimethyl-2-(arylthio)benzylaminu, jejich soli, způsoby jejich přípravy a jejich použití v léčivých přípravcích |
WO1999047497A2 (en) * | 1998-03-13 | 1999-09-23 | Merck Frosst Canada & Co. | Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment |
CN1157365C (zh) * | 1999-02-23 | 2004-07-14 | 辉瑞产品公司 | 治疗cns疾病的一元胺摄取抑制剂 |
GB0007884D0 (en) * | 2000-03-31 | 2000-05-17 | Pfizer Ltd | Diphenyl ether compounds useful in therapy |
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Also Published As
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KR20030029889A (ko) | 2003-04-16 |
AU2001278650A1 (en) | 2002-03-13 |
EA200300206A1 (ru) | 2003-06-26 |
EP1313701A1 (en) | 2003-05-28 |
NZ523951A (en) | 2004-09-24 |
DZ3414A1 (fr) | 2002-03-07 |
AP2001002265A0 (en) | 2001-09-30 |
DOP2001000242A (es) | 2002-05-15 |
BR0113610A (pt) | 2003-06-24 |
EE200300084A (et) | 2005-02-15 |
AR031867A1 (es) | 2003-10-08 |
WO2002018333A1 (en) | 2002-03-07 |
NO20030842D0 (no) | 2003-02-24 |
PL360743A1 (en) | 2004-09-20 |
SK2012003A3 (en) | 2004-06-08 |
PE20020346A1 (es) | 2002-05-08 |
IL154343A0 (en) | 2003-09-17 |
HUP0303385A2 (hu) | 2004-03-01 |
TNSN01131A1 (fr) | 2005-11-10 |
BG107544A (bg) | 2003-10-31 |
CA2420969A1 (en) | 2002-03-07 |
JP2004507523A (ja) | 2004-03-11 |
OA12372A (en) | 2006-04-17 |
PA8526701A1 (es) | 2003-07-28 |
CZ2003467A3 (cs) | 2004-04-14 |
HN2001000191A (es) | 2002-03-11 |
MXPA03001848A (es) | 2003-06-04 |
MA26945A1 (fr) | 2004-12-20 |
UY26924A1 (es) | 2002-03-22 |
CN1449380A (zh) | 2003-10-15 |
IS6704A (is) | 2003-01-30 |
NO20030842L (no) | 2003-04-28 |
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