ES2309514T3 - Derivados de 4-(2-fenilsufanil-fenil)-piperidina como inhibidores de la recaptacion de serotonina. - Google Patents
Derivados de 4-(2-fenilsufanil-fenil)-piperidina como inhibidores de la recaptacion de serotonina. Download PDFInfo
- Publication number
- ES2309514T3 ES2309514T3 ES04725291T ES04725291T ES2309514T3 ES 2309514 T3 ES2309514 T3 ES 2309514T3 ES 04725291 T ES04725291 T ES 04725291T ES 04725291 T ES04725291 T ES 04725291T ES 2309514 T3 ES2309514 T3 ES 2309514T3
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- Prior art keywords
- ilo
- alky
- hydrogen
- alkyl
- halogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title description 30
- 229940076279 serotonin Drugs 0.000 title description 8
- 239000003112 inhibitor Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 208
- 239000001257 hydrogen Substances 0.000 claims abstract description 151
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 151
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 99
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 88
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 86
- 150000002367 halogens Chemical class 0.000 claims abstract description 86
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 57
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 54
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 9
- -1 4- [2- (2,4-Dimethyl-phenylsulfanyl) -5-methyl-phenyl] -piperidine 4- [2- (4-Fluoro-2-methyl-phenylsulfanyl) -5-methyl-phenyl] -piperidine Chemical compound 0.000 claims description 83
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 19
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 208000019022 Mood disease Diseases 0.000 claims description 5
- GPPVRPYPXSWQDB-UHFFFAOYSA-N 4-[2-(4-methoxyphenyl)sulfanyl-5-methylphenyl]piperidine Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(C)C=C1C1CCNCC1 GPPVRPYPXSWQDB-UHFFFAOYSA-N 0.000 claims description 4
- 208000008811 Agoraphobia Diseases 0.000 claims description 4
- UZDAQFSRONMWEG-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)sulfanyl-5-fluorophenyl]piperidine Chemical compound C1CNCCC1C1=CC(F)=CC=C1SC1=CC=C(Cl)C=C1 UZDAQFSRONMWEG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
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- 229940079593 drug Drugs 0.000 claims description 3
- 208000013200 Stress disease Diseases 0.000 claims description 2
- 201000001716 specific phobia Diseases 0.000 claims description 2
- KHGKUMKIFUCNFY-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)sulfanyl-4-fluorophenyl]piperidine 4-[2-(2,4-dimethylphenyl)sulfanyl-5-(trifluoromethyl)phenyl]piperidine Chemical compound ClC1=CC=C(C=C1)SC1=C(C=CC(=C1)F)C1CCNCC1.CC1=C(C=CC(=C1)C)SC1=C(C=C(C=C1)C(F)(F)F)C1CCNCC1 KHGKUMKIFUCNFY-UHFFFAOYSA-N 0.000 claims 1
- LWELJNLNEZLVCK-UHFFFAOYSA-N 4-[4-fluoro-2-(4-methoxyphenyl)sulfanylphenyl]piperidine 4-[5-methyl-2-(4-methylphenyl)sulfanylphenyl]piperidine Chemical compound CC1=CC=C(C=C1)SC1=C(C=C(C=C1)C)C1CCNCC1.COC1=CC=C(C=C1)SC1=C(C=CC(=C1)F)C1CCNCC1 LWELJNLNEZLVCK-UHFFFAOYSA-N 0.000 claims 1
- RVMNGJMEDMJXHC-UHFFFAOYSA-N COC1=CC=C(C=C1)SC1=C(C=CC=C1)C1CCNCC1.ClC1=CC=C(C=C1)SC1=C(C=C(C=C1)C(F)(F)F)C1CCNCC1 Chemical compound COC1=CC=C(C=C1)SC1=C(C=CC=C1)C1CCNCC1.ClC1=CC=C(C=C1)SC1=C(C=C(C=C1)C(F)(F)F)C1CCNCC1 RVMNGJMEDMJXHC-UHFFFAOYSA-N 0.000 claims 1
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- XPTDYAQWRPQBFX-UHFFFAOYSA-N tert-butyl 4-[2-(2,4-dimethylphenyl)sulfanyl-5-methylphenyl]-4-hydroxypiperidine-1-carboxylate Chemical compound CC1=CC(C)=CC=C1SC1=CC=C(C)C=C1C1(O)CCN(C(=O)OC(C)(C)C)CC1 XPTDYAQWRPQBFX-UHFFFAOYSA-N 0.000 description 1
- SSESDXOBOUGTJI-UHFFFAOYSA-N tert-butyl 4-[2-(4-chlorophenyl)sulfanyl-4-fluorophenyl]-4-hydroxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(O)C1=CC=C(F)C=C1SC1=CC=C(Cl)C=C1 SSESDXOBOUGTJI-UHFFFAOYSA-N 0.000 description 1
- VTEBIISDNLVJNS-UHFFFAOYSA-N tert-butyl 4-[2-(4-chlorophenyl)sulfanyl-5-fluorophenyl]-4-hydroxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(O)C1=CC(F)=CC=C1SC1=CC=C(Cl)C=C1 VTEBIISDNLVJNS-UHFFFAOYSA-N 0.000 description 1
- ADWUUAPFMVXJFQ-UHFFFAOYSA-N tert-butyl 4-[2-(4-fluoro-2-methylphenyl)sulfanyl-5-methylphenyl]-4-hydroxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(O)C1=CC(C)=CC=C1SC1=CC=C(F)C=C1C ADWUUAPFMVXJFQ-UHFFFAOYSA-N 0.000 description 1
- UVELELIDCDLCQW-UHFFFAOYSA-N tert-butyl 4-[4-fluoro-2-(4-methoxyphenyl)sulfanylphenyl]-4-hydroxypiperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1SC1=CC(F)=CC=C1C1(O)CCN(C(=O)OC(C)(C)C)CC1 UVELELIDCDLCQW-UHFFFAOYSA-N 0.000 description 1
- VAZSLTVEQCBZSA-UHFFFAOYSA-N tert-butyl 4-[5-fluoro-2-(4-methoxyphenyl)sulfanylphenyl]-4-hydroxypiperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(F)C=C1C1(O)CCN(C(=O)OC(C)(C)C)CC1 VAZSLTVEQCBZSA-UHFFFAOYSA-N 0.000 description 1
- BELMAIBJXNZSCY-UHFFFAOYSA-N tert-butyl 4-hydroxy-4-[2-(4-methoxyphenyl)sulfanyl-5-methylphenyl]piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(C)C=C1C1(O)CCN(C(=O)OC(C)(C)C)CC1 BELMAIBJXNZSCY-UHFFFAOYSA-N 0.000 description 1
- YMOJNTBURHGNDC-UHFFFAOYSA-N tert-butyl 4-hydroxy-4-[2-(4-methoxyphenyl)sulfanylphenyl]piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1SC1=CC=CC=C1C1(O)CCN(C(=O)OC(C)(C)C)CC1 YMOJNTBURHGNDC-UHFFFAOYSA-N 0.000 description 1
- WJNBZLHTXSZMSW-UHFFFAOYSA-N tert-butyl 4-hydroxy-4-[5-methyl-2-(4-methylphenyl)sulfanylphenyl]piperidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C)C=C1C1(O)CCN(C(=O)OC(C)(C)C)CC1 WJNBZLHTXSZMSW-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
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
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- 229940035722 triiodothyronine Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- 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
- C07D211/06—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
- C07D211/24—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 by sulfur atoms to which a second hetero atom is attached
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46052803P | 2003-04-04 | 2003-04-04 | |
| DKPA200300520 | 2003-04-04 | ||
| US460528P | 2003-04-04 | ||
| DK200300520 | 2003-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2309514T3 true ES2309514T3 (es) | 2008-12-16 |
Family
ID=33132909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04725291T Expired - Lifetime ES2309514T3 (es) | 2003-04-04 | 2004-04-02 | Derivados de 4-(2-fenilsufanil-fenil)-piperidina como inhibidores de la recaptacion de serotonina. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7732463B2 (https=) |
| EP (1) | EP1626720B1 (https=) |
| JP (1) | JP4667366B2 (https=) |
| AT (1) | ATE406894T1 (https=) |
| AU (1) | AU2004226838B8 (https=) |
| CA (1) | CA2521258C (https=) |
| CO (1) | CO5700748A2 (https=) |
| CY (1) | CY1108464T1 (https=) |
| DE (1) | DE602004016316D1 (https=) |
| DK (1) | DK1626720T3 (https=) |
| ES (1) | ES2309514T3 (https=) |
| HR (1) | HRP20080478T3 (https=) |
| IL (1) | IL171087A (https=) |
| MX (1) | MXPA05009592A (https=) |
| NO (1) | NO20055208L (https=) |
| PL (1) | PL1626720T3 (https=) |
| PT (1) | PT1626720E (https=) |
| SI (1) | SI1626720T1 (https=) |
| WO (1) | WO2004087156A1 (https=) |
Families Citing this family (18)
| 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 |
| JP5173190B2 (ja) | 2004-08-25 | 2013-03-27 | 武田薬品工業株式会社 | 腹圧性尿失禁の予防・治療剤及びそのスクリーニング方法 |
| EP2727585A1 (en) | 2006-05-16 | 2014-05-07 | Takeda Pharmaceutical Company Limited | In-vivo screening method |
| PL2044043T5 (pl) | 2006-06-16 | 2022-05-02 | H. Lundbeck A/S | Bromowodorek 1-[2-(2,4-dimetylofenylosulfanylo)fenylo]piperazyny jako związek o połączonym działaniu wychwytu zwrotnego serotoniny i działaniu na 5-ht3 i 5-ht1a do leczenia upośledzenia funckji poznawczych |
| 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 |
| 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 |
| 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 |
| EP2789338A3 (en) | 2007-11-15 | 2015-01-14 | Takeda Pharmaceutical Company Limited | Condensed pyridine derivate and use thereof |
| 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 |
| UA98698C2 (en) * | 2008-03-03 | 2012-06-11 | Х. Луннбек А/С | Phenylsulfanylphenyl-piperidines and process for the preparation thereof |
| SG175124A1 (en) | 2009-04-24 | 2011-12-29 | Lundbeck & Co As H | Liquid formulations of salts of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine |
| EP2510949A4 (en) | 2009-12-11 | 2013-11-13 | Astellas Pharma Inc | THERAPEUTICS FOR FIBROMYALGIA |
| PH12012502153A1 (en) * | 2010-04-30 | 2013-02-04 | Takeda Pharmaceuticals Co | Enteric tablet |
| CN103096879B (zh) * | 2010-04-30 | 2014-12-10 | 武田药品工业株式会社 | 肠溶片剂 |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
| EP3762379A1 (en) | 2018-03-07 | 2021-01-13 | Bayer Aktiengesellschaft | Identification and use of erk5 inhibitors |
| KR20250011137A (ko) | 2022-05-11 | 2025-01-21 | 피아이 인더스트리스 엘티디. | 바이사이클릭 화합물 및 해충 방제제로서 이의 용도 |
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| US3803143A (en) | 1969-09-08 | 1974-04-09 | Eisai Co Ltd | 6-amino alkylene 6,7-dihydro-5h-dibenzo (b,g),(1,5)thiazocines |
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| GEP20043296B (en) | 1999-02-23 | 2004-01-12 | Pfizer Prod Inc | Monoamine Reuptake Inhibitors for Treatment of CNS Disorders |
| CN1351588A (zh) | 1999-04-02 | 2002-05-29 | 伊科斯公司 | 白细胞功能相关抗原与细胞间粘着分子结合的抑制剂及其用途 |
| CA2372481A1 (en) | 1999-04-30 | 2000-11-09 | The Trustees Of The University Of Pennsylvania | Spect imaging agents for serotonin transporters |
| BR0012984A (pt) | 1999-08-04 | 2002-07-16 | Millennium Pharm Inc | Método para tratar um estado associado com o mc4-r em um mamìfero, composto de ligação ao mc4-r, e, composição farmacêutica |
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| BR0210929A (pt) | 2001-06-07 | 2004-06-08 | Hoffmann La Roche | Derivados de indol com afinidade para o receptor 5-ht6 |
| UA81749C2 (uk) | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
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| WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
-
2004
- 2004-04-02 WO PCT/DK2004/000244 patent/WO2004087156A1/en not_active Ceased
- 2004-04-02 DK DK04725291T patent/DK1626720T3/da active
- 2004-04-02 JP JP2006504349A patent/JP4667366B2/ja not_active Expired - Fee Related
- 2004-04-02 US US10/551,883 patent/US7732463B2/en not_active Expired - Fee Related
- 2004-04-02 AU AU2004226838A patent/AU2004226838B8/en not_active Ceased
- 2004-04-02 EP EP04725291A patent/EP1626720B1/en not_active Expired - Lifetime
- 2004-04-02 AT AT04725291T patent/ATE406894T1/de active
- 2004-04-02 DE DE602004016316T patent/DE602004016316D1/de not_active Expired - Lifetime
- 2004-04-02 HR HR20080478T patent/HRP20080478T3/xx unknown
- 2004-04-02 SI SI200430864T patent/SI1626720T1/sl unknown
- 2004-04-02 ES ES04725291T patent/ES2309514T3/es not_active Expired - Lifetime
- 2004-04-02 CA CA002521258A patent/CA2521258C/en not_active Expired - Fee Related
- 2004-04-02 MX MXPA05009592A patent/MXPA05009592A/es active IP Right Grant
- 2004-04-02 PL PL04725291T patent/PL1626720T3/pl unknown
- 2004-04-02 PT PT04725291T patent/PT1626720E/pt unknown
-
2005
- 2005-09-25 IL IL171087A patent/IL171087A/en not_active IP Right Cessation
- 2005-11-03 CO CO05112440A patent/CO5700748A2/es not_active Application Discontinuation
- 2005-11-04 NO NO20055208A patent/NO20055208L/no not_active Application Discontinuation
-
2008
- 2008-10-30 CY CY20081101225T patent/CY1108464T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CO5700748A2 (es) | 2006-11-30 |
| US20060100242A1 (en) | 2006-05-11 |
| JP2006522030A (ja) | 2006-09-28 |
| EP1626720A1 (en) | 2006-02-22 |
| DE602004016316D1 (de) | 2008-10-16 |
| WO2004087156A1 (en) | 2004-10-14 |
| HRP20080478T3 (hr) | 2009-02-28 |
| SI1626720T1 (sl) | 2008-12-31 |
| CY1108464T1 (el) | 2014-04-09 |
| MXPA05009592A (es) | 2005-10-18 |
| AU2004226838A1 (en) | 2004-10-14 |
| IL171087A (en) | 2011-01-31 |
| PT1626720E (pt) | 2008-11-10 |
| EP1626720B1 (en) | 2008-09-03 |
| AU2004226838B2 (en) | 2009-02-12 |
| US7732463B2 (en) | 2010-06-08 |
| AU2004226838B8 (en) | 2009-06-11 |
| CA2521258A1 (en) | 2004-10-14 |
| DK1626720T3 (da) | 2008-12-01 |
| NO20055208L (no) | 2005-11-04 |
| CA2521258C (en) | 2009-12-01 |
| PL1626720T3 (pl) | 2009-02-27 |
| ATE406894T1 (de) | 2008-09-15 |
| JP4667366B2 (ja) | 2011-04-13 |
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