NO326443B1 - Fenyl-piperazindernvater som serotonin-reopptaksinhibitorer - Google Patents
Fenyl-piperazindernvater som serotonin-reopptaksinhibitorer Download PDFInfo
- Publication number
- NO326443B1 NO326443B1 NO20041628A NO20041628A NO326443B1 NO 326443 B1 NO326443 B1 NO 326443B1 NO 20041628 A NO20041628 A NO 20041628A NO 20041628 A NO20041628 A NO 20041628A NO 326443 B1 NO326443 B1 NO 326443B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- piperazine
- alkyl
- acid
- compound according
- Prior art date
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- 239000003772 serotonin uptake inhibitor Substances 0.000 title description 8
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 60
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 208000019901 Anxiety disease Diseases 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 208000019022 Mood disease Diseases 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 208000019906 panic disease Diseases 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- OLSUXQFACZYSFC-UHFFFAOYSA-N 1-[2-(2,5-dimethylphenyl)sulfanylphenyl]piperazine Chemical compound CC1=CC=C(C)C(SC=2C(=CC=CC=2)N2CCNCC2)=C1 OLSUXQFACZYSFC-UHFFFAOYSA-N 0.000 claims description 3
- JYVRCNMQFCWSGB-UHFFFAOYSA-N 1-[2-(4-bromophenyl)sulfanylphenyl]piperazine Chemical compound C1=CC(Br)=CC=C1SC1=CC=CC=C1N1CCNCC1 JYVRCNMQFCWSGB-UHFFFAOYSA-N 0.000 claims description 3
- REFSEMZDFSMMGK-UHFFFAOYSA-N 1-[2-[2-(trifluoromethyl)phenyl]sulfanylphenyl]piperazine Chemical compound FC(F)(F)C1=CC=CC=C1SC1=CC=CC=C1N1CCNCC1 REFSEMZDFSMMGK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- VUSTZODWQQVOFM-UHFFFAOYSA-N 1-[2-(3-methylphenyl)sulfanylphenyl]-1,4-diazepane Chemical compound CC1=CC=CC(SC=2C(=CC=CC=2)N2CCNCCC2)=C1 VUSTZODWQQVOFM-UHFFFAOYSA-N 0.000 claims description 2
- CYZKHRQTZRUXRT-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)sulfanyl-5-methylphenyl]piperazine Chemical compound C1CNCCN1C1=CC(C)=CC=C1SC1=CC=C(F)C=C1 CYZKHRQTZRUXRT-UHFFFAOYSA-N 0.000 claims description 2
- CRSQHSOJDGHCHS-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)sulfanyl-4-methylphenyl]piperazine Chemical compound C1=CC(OC)=CC=C1SC1=CC(C)=CC=C1N1CCNCC1 CRSQHSOJDGHCHS-UHFFFAOYSA-N 0.000 claims description 2
- BLQTZXJLVAMXMR-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)sulfanyl-5-(trifluoromethyl)phenyl]piperazine Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(C(F)(F)F)C=C1N1CCNCC1 BLQTZXJLVAMXMR-UHFFFAOYSA-N 0.000 claims description 2
- YDFLGNNHJDQNRD-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)sulfanyl-5-methylphenyl]piperazine Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(C)C=C1N1CCNCC1 YDFLGNNHJDQNRD-UHFFFAOYSA-N 0.000 claims description 2
- VZGBPMFEQIPRPQ-UHFFFAOYSA-N 1-[2-(4-methylsulfanylphenyl)sulfanylphenyl]piperazine Chemical compound C1=CC(SC)=CC=C1SC1=CC=CC=C1N1CCNCC1 VZGBPMFEQIPRPQ-UHFFFAOYSA-N 0.000 claims description 2
- BFQPRZPUJCLIIQ-UHFFFAOYSA-N 1-[2-[2-(trifluoromethyl)phenyl]sulfanylphenyl]-1,4-diazepane Chemical compound FC(F)(F)C1=CC=CC=C1SC1=CC=CC=C1N1CCNCCC1 BFQPRZPUJCLIIQ-UHFFFAOYSA-N 0.000 claims description 2
- AQIRPOAARAHUND-UHFFFAOYSA-N 1-[4-chloro-2-(4-methoxyphenyl)sulfanylphenyl]piperazine Chemical compound C1=CC(OC)=CC=C1SC1=CC(Cl)=CC=C1N1CCNCC1 AQIRPOAARAHUND-UHFFFAOYSA-N 0.000 claims description 2
- 240000001987 Pyrus communis Species 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 238000000034 method Methods 0.000 description 22
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- 238000006243 chemical reaction Methods 0.000 description 18
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000000543 intermediate Substances 0.000 description 16
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- -1 but not limited to Chemical group 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
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- 230000005764 inhibitory process Effects 0.000 description 5
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- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000001430 anti-depressive effect Effects 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
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- 230000000697 serotonin reuptake Effects 0.000 description 4
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
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- 241000700159 Rattus Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
- 150000004985 diamines Chemical class 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- CYJAWBVQRMVFEO-UHFFFAOYSA-N piperazine-2,6-dione Chemical class O=C1CNCC(=O)N1 CYJAWBVQRMVFEO-UHFFFAOYSA-N 0.000 description 3
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- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- DEFBBVSVIMXNCP-UHFFFAOYSA-N 2-(3-methylpiperazin-1-yl)aniline Chemical compound C1CNC(C)CN1C1=CC=CC=C1N DEFBBVSVIMXNCP-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- COHLCPVRWDSZSC-UHFFFAOYSA-N tert-butyl 4-[2-(4-methylphenyl)sulfanylphenyl]-3,5-dioxopiperazine-1-carboxylate Chemical compound C1=CC(C)=CC=C1SC1=CC=CC=C1N1C(=O)CN(C(=O)OC(C)(C)C)CC1=O COHLCPVRWDSZSC-UHFFFAOYSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 229940035722 triiodothyronine Drugs 0.000 description 1
- YQNWZWMKLDQSAC-UHFFFAOYSA-N vortioxetine Chemical compound CC1=CC(C)=CC=C1SC1=CC=CC=C1N1CCNCC1 YQNWZWMKLDQSAC-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
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- 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
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- 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
- A61P25/22—Anxiolytics
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
-
- 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
- C07D211/68—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
- C07D211/70—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
-
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- 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
- C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200101466 | 2001-10-04 | ||
| PCT/DK2002/000659 WO2003029232A1 (en) | 2001-10-04 | 2002-10-02 | Phenyl-piperazine derivatives as serotonin reuptake inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20041628L NO20041628L (no) | 2004-04-21 |
| NO326443B1 true NO326443B1 (no) | 2008-12-08 |
Family
ID=8160750
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20041628A NO326443B1 (no) | 2001-10-04 | 2004-04-21 | Fenyl-piperazindernvater som serotonin-reopptaksinhibitorer |
| NO20083446A NO332355B1 (no) | 2001-10-04 | 2008-08-06 | Fenyl-piperidinderivater, deres anvendelse og farmasoytiske sammensetninger omfattende disse |
| NO2014011C NO2014011I2 (no) | 2001-10-04 | 2014-05-13 | Vortioksetin eller et farmasøytisk akseptabelt syreaddisjonssalt dera |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20083446A NO332355B1 (no) | 2001-10-04 | 2008-08-06 | Fenyl-piperidinderivater, deres anvendelse og farmasoytiske sammensetninger omfattende disse |
| NO2014011C NO2014011I2 (no) | 2001-10-04 | 2014-05-13 | Vortioksetin eller et farmasøytisk akseptabelt syreaddisjonssalt dera |
Country Status (39)
| Country | Link |
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| US (10) | US7144884B2 (ko) |
| EP (2) | EP1436271B3 (ko) |
| JP (3) | JP3896116B2 (ko) |
| KR (3) | KR100842702B1 (ko) |
| CN (1) | CN1319958C (ko) |
| AR (2) | AR036659A1 (ko) |
| AT (2) | ATE441631T1 (ko) |
| AU (2) | AU2002333220C1 (ko) |
| BE (1) | BE2014C036I2 (ko) |
| BR (3) | BRPI0212733B8 (ko) |
| CA (1) | CA2462110C (ko) |
| CO (1) | CO5580746A2 (ko) |
| CY (3) | CY1107924T1 (ko) |
| DE (2) | DE60225162T3 (ko) |
| DK (2) | DK1749818T3 (ko) |
| EA (2) | EA007537B3 (ko) |
| EG (1) | EG25095A (ko) |
| ES (2) | ES2328725T3 (ko) |
| FR (1) | FR14C0033I2 (ko) |
| HK (1) | HK1072600A1 (ko) |
| HR (1) | HRP20040220A2 (ko) |
| HU (3) | HU230189B1 (ko) |
| IL (1) | IL160655A0 (ko) |
| IS (2) | IS2578B (ko) |
| LT (1) | LTC1436271I2 (ko) |
| LU (1) | LU92397I2 (ko) |
| ME (1) | ME00039B (ko) |
| MX (1) | MXPA04002959A (ko) |
| MY (1) | MY140950A (ko) |
| NL (1) | NL300652I2 (ko) |
| NO (3) | NO326443B1 (ko) |
| NZ (1) | NZ531556A (ko) |
| PL (2) | PL210551B1 (ko) |
| PT (2) | PT1436271E (ko) |
| RS (2) | RS52865B (ko) |
| SI (1) | SI1436271T1 (ko) |
| UA (2) | UA81749C2 (ko) |
| WO (1) | WO2003029232A1 (ko) |
| ZA (1) | ZA200401583B (ko) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA81749C2 (uk) | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
| GB0305575D0 (en) * | 2003-03-11 | 2003-04-16 | Glaxo Group Ltd | Novel compounds |
| ATE406894T1 (de) * | 2003-04-04 | 2008-09-15 | Lundbeck & Co As H | 4-(2-phenylsulfanyl-phenyl)-piperidin-derivate als serotonin-wiederaufnahme-hemmer |
| UA81469C2 (en) * | 2003-04-04 | 2008-01-10 | Lundbeck & Co As H | 4-(2-phenyloxyphenyl)-piperidine or -1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors |
| EP1635828B1 (en) * | 2003-04-04 | 2008-04-23 | H. Lundbeck A/S | 4-(2-phenyloxyphenyl)-piperidine or -1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors |
| EA010869B1 (ru) * | 2003-04-04 | 2008-12-30 | Х. Лундбекк А/С | Производные 4-(2-фенилсульфанилфенил)пиперидина в качестве ингибиторов повторного поглощения серотонина |
| UA81300C2 (en) * | 2003-04-04 | 2007-12-25 | Lundbeck & Co As H | Derivates of 4-(2-fenilsulfanilfenil)-1,2,3,6-tetrahydropiridin as retarding agents of serotonin recapture |
| RS50589B (sr) | 2003-12-23 | 2010-05-07 | H. Lundbeck A/S. | 2-(1h-indolilsulfanil)-benzil amin derivati kao ssri |
| AR052308A1 (es) * | 2004-07-16 | 2007-03-14 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto |
| DE602006007550D1 (de) | 2005-02-10 | 2009-08-13 | Neurosearch As | Alkylsubstituierte homopiperazinderivate und deren verwendung als monoamin neurotransmitter wiederaufnahmeinhibitoren |
| AR054393A1 (es) * | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos. |
| US7629473B2 (en) | 2005-06-17 | 2009-12-08 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-aryl amine derivatives |
| AR054394A1 (es) * | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de 2- (1h-indolilsulfanil)-aril amina |
| JP2007106746A (ja) * | 2005-09-13 | 2007-04-26 | Tosoh Corp | 新規アリールホモピペラジン類、またはその塩と製造方法 |
| ES2361949T3 (es) * | 2006-06-16 | 2011-06-24 | H. Lundbeck A/S | Formas cristalinas de 4-[2-(4-metilfenilsulfanil)-fenil]piperidina con inhibición de la reabsorción de serotonina y norepinefrina combinada para el tratamiento del dolor neuropático. |
| WO2007144005A1 (en) | 2006-06-16 | 2007-12-21 | H. Lundbeck A/S | 1- [2- (2, 4-dimethylphenylsulfanyl) -phenyl] piperazine as a compound with combined serotonin reuptake, 5-ht3 and 5-ht1a activity for the treatment of cognitive impairment |
| CA2656057C (en) * | 2006-06-16 | 2012-10-02 | H. Lundbeck A/S | Crystalline forms of 4-[2-(4-methylphenylsulfanyl)-phenyl]piperidine with combined serotonin and norepinephrine reuptake inhibition for the treatment of neuropathic pain |
| ATE508115T1 (de) * | 2006-06-16 | 2011-05-15 | Lundbeck & Co As H | Kristalline formen von 4-ä2-(4- methylphenylsulfanyl)phenylüpiperidin mit kombinierter serotonin- und norepinephrinwiederaufnahmehemmung zur behandlung neuropathischer schmerzen |
| JP7179035B2 (ja) * | 2006-06-16 | 2022-11-28 | ハー・ルンドベック・アクチエゼルスカベット | 認識機能障害（ｃｏｇｎｉｔｉｖｅ ｉｍｐａｉｒｍｅｎｔ）を治療するための、組み合わされたセロトニン再取り込み、５－ＨＴ３および５－ＨＴ１Ａ活性を有する化合物としての１－［２－（２，４－ジメチルフェニルスルファニル）－フェニル］ピペラジン |
| TWI405588B (zh) | 2007-03-20 | 2013-08-21 | Lundbeck & Co As H | ４-〔２-（４-甲苯基硫基）-苯基〕哌啶之鹽類的液體調配物 |
| TWI432194B (zh) * | 2007-03-20 | 2014-04-01 | Lundbeck & Co As H | ４-〔２-（４-甲基苯硫基）苯基〕哌啶之新穎治療用途 |
| TW200848411A (en) * | 2007-03-20 | 2008-12-16 | Lundbeck & Co As H | Novel therapeutic uses of 1-[2-(2, 4-dimethylphenylsulfanyl)phenyl]-piperazine |
| JP5764327B2 (ja) * | 2007-06-15 | 2015-08-19 | ハー・ルンドベック・アクチエゼルスカベット | 過敏性腸症候群（ｉｂｓ）を処置するための４−［２−（４−メチルフェニルスルファニル）フェニル］ピペリジン |
| TW200932233A (en) * | 2007-11-13 | 2009-08-01 | Lundbeck & Co As H | Therapeutic uses of compounds having combined SERT, 5-HT3 and 5-HT1a activity |
| AU2014200364B2 (en) * | 2007-11-13 | 2015-09-17 | H. Lundbeck A/S | Therapeutic uses of compounds having combined SERT, 5-HT3 and 5-HT1A activity |
| TW200932225A (en) * | 2007-12-14 | 2009-08-01 | Lundbeck & Co As H | 4-[2,3-difluoro-6-(2-fluoro-4-methyl-phenylsulfanyl)-phenyl]-piperidine |
| TW200938194A (en) * | 2007-12-14 | 2009-09-16 | Lundbeck & Co As H | Therapeutic uses of compounds having affinity to the serotonin transporter, serotonin receptors and noradrenalin transporter |
| WO2009081259A1 (en) * | 2007-12-21 | 2009-07-02 | Pfizer Inc. | Phenoxy-pyridyl derivatives |
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| CA2742105C (en) | 2008-11-14 | 2016-09-13 | Theravance, Inc. | 4-[2-(2-fluorophenoxymethyl)phenyl]piperidine compounds |
| TW201033181A (en) * | 2009-02-17 | 2010-09-16 | Lundbeck & Co As H | Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine |
| JP5722879B2 (ja) | 2009-04-24 | 2015-05-27 | ハー・ルンドベック・アクチエゼルスカベット | １−［２−（２，４−ジメチルフェニルスルファニル）フェニル］ピペラジンの塩の液体製剤 |
| PL2470166T3 (pl) * | 2009-08-24 | 2013-11-29 | H Lundbeck As | Nowe kompozycje 1-[2-(2,4-dimetylofenylosulfanylo)fenylo]piperazyny |
| EP2493852B1 (en) * | 2009-10-30 | 2014-04-09 | Janssen Pharmaceutica NV | 4-substituted-2-phenoxy-phenylamine delta opioid receptor modulators |
| US8778949B2 (en) * | 2010-01-11 | 2014-07-15 | Theravance Biopharma R&D Ip, Llc | 1-(2-phenoxymethylphenyl)piperazine compounds |
| WO2011119461A1 (en) * | 2010-03-22 | 2011-09-29 | Theravance, Inc. | 1-(2-phenoxymethylheteroaryl)piperidine and piperazine compounds |
| EP2564838A4 (en) | 2010-04-30 | 2014-06-04 | Takeda Pharmaceutical | INTESTINAL DISRUPT TABLET |
| WO2011136373A1 (ja) * | 2010-04-30 | 2011-11-03 | 武田薬品工業株式会社 | 腸溶性錠剤 |
| EP2407467A1 (de) | 2010-07-14 | 2012-01-18 | Sandoz Ag | Kristalline Verbindung von 1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol und Milchsäure |
| TW201212918A (en) | 2010-08-23 | 2012-04-01 | Lundbeck & Co As H | Therapeutic uses of 1-[2-(2,4-dimethyl-phenylsulfanyl)phenyl]piperazine |
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