HRP20020324A2 - Biaryl ether derivatives useful as monoamine reuptake inhibitors - Google Patents
Biaryl ether derivatives useful as monoamine reuptake inhibitors Download PDFInfo
- Publication number
- HRP20020324A2 HRP20020324A2 HR20020324A HRP20020324A HRP20020324A2 HR P20020324 A2 HRP20020324 A2 HR P20020324A2 HR 20020324 A HR20020324 A HR 20020324A HR P20020324 A HRP20020324 A HR P20020324A HR P20020324 A2 HRP20020324 A2 HR P20020324A2
- Authority
- HR
- Croatia
- Prior art keywords
- dichlorophenoxy
- alkyl
- disorder
- methylamine
- compound
- Prior art date
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- -1 Biaryl ether derivatives Chemical class 0.000 title claims description 41
- 239000003112 inhibitor Substances 0.000 title description 2
- 230000000407 monoamine reuptake Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 152
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 70
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 59
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 48
- 208000035475 disorder Diseases 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 37
- 229960003638 dopamine Drugs 0.000 claims description 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- 241000124008 Mammalia Species 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 229940076279 serotonin Drugs 0.000 claims description 24
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims description 22
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims description 22
- 229960002748 norepinephrine Drugs 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 241000282414 Homo sapiens Species 0.000 claims description 17
- 230000002401 inhibitory effect Effects 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 15
- 239000002464 receptor antagonist Substances 0.000 claims description 15
- 229940044551 receptor antagonist Drugs 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 208000018737 Parkinson disease Diseases 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 206010012335 Dependence Diseases 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 208000024891 symptom Diseases 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 239000004001 serotonin 1D antagonist Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
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- 206010009094 Chronic paroxysmal hemicrania Diseases 0.000 claims description 6
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- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 206010066218 Stress Urinary Incontinence Diseases 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 6
- 208000016620 Tourette disease Diseases 0.000 claims description 6
- 206010047163 Vasospasm Diseases 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
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- 231100000869 headache Toxicity 0.000 claims description 6
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- 239000011593 sulfur Substances 0.000 claims description 6
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- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 5
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- 150000003536 tetrazoles Chemical class 0.000 claims description 5
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- MGHGKQQYNNPDLG-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(triazol-2-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2N=CC=N2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 MGHGKQQYNNPDLG-UHFFFAOYSA-N 0.000 claims description 3
- KCRBGCHPNCBUCW-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-phenylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2C=CC=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 KCRBGCHPNCBUCW-UHFFFAOYSA-N 0.000 claims description 3
- WJYRLEWZANLZLM-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]pyrrolidin-2-one Chemical compound CNCC1=CC(N2C(CCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 WJYRLEWZANLZLM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- SOCXCXJYEMOKAM-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-(1,2,4-triazol-1-yl)phenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC=C(N2N=CN=C2)C=C1OC1=CC=C(Cl)C(Cl)=C1 SOCXCXJYEMOKAM-UHFFFAOYSA-N 0.000 claims description 2
- LLVVRQNZUNMHJV-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-(furan-2-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(C=2OC=CC=2)C=C1OC1=CC=C(Cl)C(Cl)=C1 LLVVRQNZUNMHJV-UHFFFAOYSA-N 0.000 claims description 2
- KBGXEJXXNBUUKO-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-phenylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(C=2C=CC=CC=2)C=C1OC1=CC=C(Cl)C(Cl)=C1 KBGXEJXXNBUUKO-UHFFFAOYSA-N 0.000 claims description 2
- YMZHLLFBCASHHB-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-thiophen-2-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(C=2SC=CC=2)C=C1OC1=CC=C(Cl)C(Cl)=C1 YMZHLLFBCASHHB-UHFFFAOYSA-N 0.000 claims description 2
- SFTJBUCEUIKDJD-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-thiophen-3-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(C2=CSC=C2)C=C1OC1=CC=C(Cl)C(Cl)=C1 SFTJBUCEUIKDJD-UHFFFAOYSA-N 0.000 claims description 2
- IQGWBOYXUSLCFT-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(1,2,4-triazol-4-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2C=NN=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 IQGWBOYXUSLCFT-UHFFFAOYSA-N 0.000 claims description 2
- QLTUAGOAYVRRPQ-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(1,3-thiazol-2-yl)phenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC(C=2SC=CN=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 QLTUAGOAYVRRPQ-UHFFFAOYSA-N 0.000 claims description 2
- APMXCCUBPMTTLK-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(1,3-thiazol-2-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2SC=CN=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 APMXCCUBPMTTLK-UHFFFAOYSA-N 0.000 claims description 2
- LYRAGSVEZOIZJQ-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(2h-tetrazol-5-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2NN=NN=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 LYRAGSVEZOIZJQ-UHFFFAOYSA-N 0.000 claims description 2
- VTOCPMQDJCNXJC-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(4-fluorophenyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2C=CC(F)=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 VTOCPMQDJCNXJC-UHFFFAOYSA-N 0.000 claims description 2
- MRHLSXLWXQUUIW-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(4-methylphenyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2C=CC(C)=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 MRHLSXLWXQUUIW-UHFFFAOYSA-N 0.000 claims description 2
- WKOZOESISFTQMB-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(5-methylthiophen-2-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2SC(C)=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 WKOZOESISFTQMB-UHFFFAOYSA-N 0.000 claims description 2
- JMPDXZXUFVZHHI-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(furan-2-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2OC=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 JMPDXZXUFVZHHI-UHFFFAOYSA-N 0.000 claims description 2
- YTEXZARZLHLRJB-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(furan-3-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C2=COC=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 YTEXZARZLHLRJB-UHFFFAOYSA-N 0.000 claims description 2
- WDOHSBCURHURPV-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(triazol-1-yl)phenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC(N2N=NC=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 WDOHSBCURHURPV-UHFFFAOYSA-N 0.000 claims description 2
- MNAHJPYGOSWSBX-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(triazol-1-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2N=NC=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 MNAHJPYGOSWSBX-UHFFFAOYSA-N 0.000 claims description 2
- ULJOCBVUVYUVEY-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(triazol-2-yl)phenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC(N2N=CC=N2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ULJOCBVUVYUVEY-UHFFFAOYSA-N 0.000 claims description 2
- NLTGIMKNKKMQPE-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-pyridin-2-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2N=CC=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 NLTGIMKNKKMQPE-UHFFFAOYSA-N 0.000 claims description 2
- JPBFWBNMQFVEEC-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-pyridin-3-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2C=NC=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 JPBFWBNMQFVEEC-UHFFFAOYSA-N 0.000 claims description 2
- JERYDYFQMRCTFJ-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-pyridin-4-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2C=CN=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 JERYDYFQMRCTFJ-UHFFFAOYSA-N 0.000 claims description 2
- MFVLUIJGQADSJH-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-thiophen-2-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2SC=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 MFVLUIJGQADSJH-UHFFFAOYSA-N 0.000 claims description 2
- GKVABNNXZNUTSR-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-thiophen-3-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C2=CSC=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 GKVABNNXZNUTSR-UHFFFAOYSA-N 0.000 claims description 2
- CBFOMONXEQWNRB-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]piperidin-2-one Chemical compound CNCC1=CC(N2C(CCCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 CBFOMONXEQWNRB-UHFFFAOYSA-N 0.000 claims description 2
- FZCQKTZYKUFNAJ-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]pyrazol-3-amine Chemical compound CNCC1=CC(N2N=C(N)C=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 FZCQKTZYKUFNAJ-UHFFFAOYSA-N 0.000 claims description 2
- QGLOKMBXFYKGID-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-[1-(methylamino)ethyl]phenyl]pyrrolidin-2-one Chemical compound CNC(C)C1=CC(N2C(CCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 QGLOKMBXFYKGID-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
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- 238000011946 reduction process Methods 0.000 description 1
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- 230000013275 serotonin uptake Effects 0.000 description 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
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- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- 108060008037 tachykinin Proteins 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 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 description 1
- AZPIHGXLGUESCA-UHFFFAOYSA-N tert-butyl n-[[2-(3,4-dichlorophenoxy)-5-(2-oxopiperidin-1-yl)phenyl]methyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC(N2C(CCCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 AZPIHGXLGUESCA-UHFFFAOYSA-N 0.000 description 1
- PUJRJPOOUPPMAU-UHFFFAOYSA-N tert-butyl n-[[2-(3,4-dichlorophenoxy)-5-(2-oxopyrrolidin-1-yl)phenyl]methyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC(N2C(CCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 PUJRJPOOUPPMAU-UHFFFAOYSA-N 0.000 description 1
- LMIBHVFPBQBSLY-UHFFFAOYSA-N tert-butyl n-[[2-(3,4-dichlorophenoxy)-5-nitrophenyl]methyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC([N+]([O-])=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 LMIBHVFPBQBSLY-UHFFFAOYSA-N 0.000 description 1
- ICRKMBCUHSREBD-UHFFFAOYSA-N tert-butyl n-[[5-amino-2-(3,4-dichlorophenoxy)phenyl]methyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC(N)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ICRKMBCUHSREBD-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229940072690 valium Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
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- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
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- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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- C07C233/00—Carboxylic acid amides
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- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
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- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
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- C07D211/76—Oxygen atoms attached in position 2 or 6
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- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/38—Nitrogen atoms
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- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
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- C—CHEMISTRY; METALLURGY
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
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- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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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
- C07D333/02—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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen 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
- C07D333/02—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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
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- Chemical & Material Sciences (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US15927699P | 1999-10-13 | 1999-10-13 | |
US16776199P | 1999-11-29 | 1999-11-29 | |
PCT/IB2000/001373 WO2001027068A1 (fr) | 1999-10-13 | 2000-09-27 | Derives de diarylether utilises comme inhibiteurs du recaptage de monoamines |
Publications (1)
Publication Number | Publication Date |
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HRP20020324A2 true HRP20020324A2 (en) | 2003-08-31 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HR20020324A HRP20020324A2 (en) | 1999-10-13 | 2002-04-12 | Biaryl ether derivatives useful as monoamine reuptake inhibitors |
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Families Citing this family (71)
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ZA923283B (en) * | 1991-05-29 | 1993-01-27 | Akzo Nv | Phenoxyphenyl derivatives |
DE4303676A1 (de) * | 1993-02-09 | 1994-08-11 | Bayer Ag | 1-Aryltriazolin(thi)one |
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 |
DE19853864A1 (de) * | 1998-07-09 | 2000-01-13 | Bayer Ag | Substituierte Phenyluracile |
DE19838706A1 (de) * | 1998-08-26 | 2000-03-02 | Bayer Ag | Substituierte 3-Aryl-pyrazole |
DE19901846A1 (de) * | 1999-01-19 | 2000-07-20 | Bayer Ag | Substituierte Arylheterocyclen |
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2000
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- 2000-09-27 JP JP2001530089A patent/JP2003511434A/ja active Pending
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- 2000-09-27 GE GEAP20006411A patent/GEP20043160B/en unknown
- 2000-09-27 TR TR2002/01004T patent/TR200201004T2/xx unknown
- 2000-09-27 MX MXPA02003793A patent/MXPA02003793A/es active IP Right Grant
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- 2000-09-27 NZ NZ517696A patent/NZ517696A/xx unknown
- 2000-09-27 PL PL00355289A patent/PL355289A1/xx not_active Application Discontinuation
- 2000-09-27 ES ES00960916T patent/ES2240155T3/es not_active Expired - Lifetime
- 2000-09-27 AP APAP/P/2002/002481A patent/AP2002002481A0/en unknown
- 2000-09-27 DZ DZ003192A patent/DZ3192A1/fr active
- 2000-09-27 DK DK00960916T patent/DK1220831T3/da active
- 2000-09-27 EE EEP200200191A patent/EE200200191A/xx unknown
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