UA81300C2 - Derivates of 4-(2-fenilsulfanilfenil)-1,2,3,6-tetrahydropiridin as retarding agents of serotonin recapture - Google Patents
Derivates of 4-(2-fenilsulfanilfenil)-1,2,3,6-tetrahydropiridin as retarding agents of serotonin recapture Download PDFInfo
- Publication number
- UA81300C2 UA81300C2 UAA200508779A UA2005008779A UA81300C2 UA 81300 C2 UA81300 C2 UA 81300C2 UA A200508779 A UAA200508779 A UA A200508779A UA 2005008779 A UA2005008779 A UA 2005008779A UA 81300 C2 UA81300 C2 UA 81300C2
- Authority
- UA
- Ukraine
- Prior art keywords
- tetrahydropyridine
- phenyl
- hydrogen
- halogen
- alk
- Prior art date
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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 5
- 239000003340 retarding agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
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- 239000001257 hydrogen Substances 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 129
- 150000002431 hydrogen Chemical class 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
- -1 C1-6C-Alkoxy Chemical class 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 59
- 150000002367 halogens Chemical class 0.000 claims description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 14
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- PUEZOCGQEOXEFL-UHFFFAOYSA-N 4-(5-fluoro-2-phenylsulfanylphenyl)-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(F)=CC=C1SC1=CC=CC=C1 PUEZOCGQEOXEFL-UHFFFAOYSA-N 0.000 claims description 3
- GWOIXIXFXJRSEE-UHFFFAOYSA-N 4-[2-(2-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC=CC=C1SC1=CC=CC=C1C1=CCNCC1 GWOIXIXFXJRSEE-UHFFFAOYSA-N 0.000 claims description 3
- BVFBNCRYXIKJMP-UHFFFAOYSA-N 4-[2-(3-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC=CC(SC=2C(=CC=CC=2)C=2CCNCC=2)=C1 BVFBNCRYXIKJMP-UHFFFAOYSA-N 0.000 claims description 3
- XOWCKPZUHHALSB-UHFFFAOYSA-N 4-[2-(4-methylphenyl)sulfanyl-5-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(F)(F)F)C=C1C1=CCNCC1 XOWCKPZUHHALSB-UHFFFAOYSA-N 0.000 claims description 3
- ZGISTZRYULTIMS-UHFFFAOYSA-N 4-[5-fluoro-2-(2-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC=CC=C1SC1=CC=C(F)C=C1C1=CCNCC1 ZGISTZRYULTIMS-UHFFFAOYSA-N 0.000 claims description 3
- YRLHHXMJCNCMLO-UHFFFAOYSA-N 4-[5-fluoro-2-(3-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC=CC(SC=2C(=CC(F)=CC=2)C=2CCNCC=2)=C1 YRLHHXMJCNCMLO-UHFFFAOYSA-N 0.000 claims description 3
- OILORYGCCZFWTL-UHFFFAOYSA-N 4-[5-fluoro-2-(4-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(C)=CC=C1SC1=CC=C(F)C=C1C1=CCNCC1 OILORYGCCZFWTL-UHFFFAOYSA-N 0.000 claims description 3
- ZYRXNMJLYBQAMP-UHFFFAOYSA-N 4-[5-methyl-2-(2-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=CC=C1C ZYRXNMJLYBQAMP-UHFFFAOYSA-N 0.000 claims description 3
- JSHLHLNSXPCBPT-UHFFFAOYSA-N 4-[5-methyl-2-(4-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C)C=C1C1=CCNCC1 JSHLHLNSXPCBPT-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- DROZTWRQGIRTLE-UHFFFAOYSA-N 4-[2-(2-bromo-4-fluorophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=C(F)C=C1Br DROZTWRQGIRTLE-UHFFFAOYSA-N 0.000 claims description 2
- HPRWJGRYXXTSLD-UHFFFAOYSA-N 4-[2-(2-bromo-4-methylphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound BrC1=CC(C)=CC=C1SC1=CC=C(C)C=C1C1=CCNCC1 HPRWJGRYXXTSLD-UHFFFAOYSA-N 0.000 claims description 2
- DOGQTRQFXHQXHL-UHFFFAOYSA-N 4-[2-(2-chloro-4-methylphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound ClC1=CC(C)=CC=C1SC1=CC=C(C)C=C1C1=CCNCC1 DOGQTRQFXHQXHL-UHFFFAOYSA-N 0.000 claims description 2
- PHDZOIVGCWIKAA-UHFFFAOYSA-N 4-[2-(3-fluoro-2-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=C(F)C=CC=C1SC1=CC=CC=C1C1=CCNCC1 PHDZOIVGCWIKAA-UHFFFAOYSA-N 0.000 claims description 2
- TUVCDLWJOSIGRL-UHFFFAOYSA-N 4-[5-bromo-2-(2,4-dimethylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=CC(C)=CC=C1SC1=CC=C(Br)C=C1C1=CCNCC1 TUVCDLWJOSIGRL-UHFFFAOYSA-N 0.000 claims description 2
- VKUZTLZWFWTBJJ-UHFFFAOYSA-N 4-[2-(2-bromophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=CC=C1Br VKUZTLZWFWTBJJ-UHFFFAOYSA-N 0.000 claims 1
- VPFHQAFQSMMVFA-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=CC=C1Cl VPFHQAFQSMMVFA-UHFFFAOYSA-N 0.000 claims 1
- WOSFZNBDNYRRPS-UHFFFAOYSA-N 4-[2-(2-fluoro-4-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound FC1=CC(C)=CC=C1SC1=CC=CC=C1C1=CCNCC1 WOSFZNBDNYRRPS-UHFFFAOYSA-N 0.000 claims 1
- YUUZWPWDOCQTJZ-UHFFFAOYSA-N 4-[2-(2-fluorophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=CC=C1F YUUZWPWDOCQTJZ-UHFFFAOYSA-N 0.000 claims 1
- QNJYLSDKYNIIRZ-UHFFFAOYSA-N 4-[2-(2-methoxyphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound COC1=CC=CC=C1SC1=CC=C(C)C=C1C1=CCNCC1 QNJYLSDKYNIIRZ-UHFFFAOYSA-N 0.000 claims 1
- BPEKNTQEJVLZHM-UHFFFAOYSA-N 4-[2-(3-chloro-2-methylphenyl)sulfanylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound CC1=C(Cl)C=CC=C1SC1=CC=CC=C1C1=CCNCC1 BPEKNTQEJVLZHM-UHFFFAOYSA-N 0.000 claims 1
- ZLYAFBWNHUOJMU-UHFFFAOYSA-N 4-[2-(4-chloro-2-fluorophenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=C(Cl)C=C1F ZLYAFBWNHUOJMU-UHFFFAOYSA-N 0.000 claims 1
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- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 239000004050 mood stabilizer Substances 0.000 description 1
- 229940127237 mood stabilizer Drugs 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960003057 nialamide Drugs 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 238000001308 synthesis method Methods 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
- 229950002139 talsupram Drugs 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
- JDXHOOVUGZTNEH-UHFFFAOYSA-N tert-butyl 2-oxopiperidine-3-carboxylate Chemical compound CC(C)(C)OC(=O)C1CCCNC1=O JDXHOOVUGZTNEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 229940035722 triiodothyronine Drugs 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- 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
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200300518 | 2003-04-04 | ||
| PCT/DK2004/000243 WO2004087662A1 (en) | 2003-04-04 | 2004-04-02 | 4-(2-phenylsulfanyl-phenyl)-1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA81300C2 true UA81300C2 (en) | 2007-12-25 |
Family
ID=35432910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200508779A UA81300C2 (en) | 2003-04-04 | 2004-02-04 | Derivates of 4-(2-fenilsulfanilfenil)-1,2,3,6-tetrahydropiridin as retarding agents of serotonin recapture |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US20070173522A1 (pl) |
| EP (1) | EP1613594B1 (pl) |
| JP (1) | JP2006522029A (pl) |
| KR (1) | KR20060021825A (pl) |
| CN (1) | CN100384822C (pl) |
| AR (1) | AR043964A1 (pl) |
| AT (1) | ATE390413T1 (pl) |
| AU (1) | AU2004226319A1 (pl) |
| BR (1) | BRPI0408453A (pl) |
| CA (1) | CA2521172A1 (pl) |
| CL (1) | CL2004000730A1 (pl) |
| CO (1) | CO5700777A2 (pl) |
| DE (1) | DE602004012724T2 (pl) |
| DK (1) | DK1613594T3 (pl) |
| EA (1) | EA009282B1 (pl) |
| ES (1) | ES2301979T3 (pl) |
| HK (1) | HK1090051A1 (pl) |
| HR (1) | HRP20080243T3 (pl) |
| IS (1) | IS8007A (pl) |
| MX (1) | MXPA05010678A (pl) |
| NO (1) | NO20055205L (pl) |
| NZ (1) | NZ541944A (pl) |
| PL (1) | PL1613594T3 (pl) |
| PT (1) | PT1613594E (pl) |
| SI (1) | SI1613594T1 (pl) |
| UA (1) | UA81300C2 (pl) |
| WO (1) | WO2004087662A1 (pl) |
| ZA (1) | ZA200507182B (pl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1626720T1 (sl) | 2003-04-04 | 2008-12-31 | Lundbeck & Co As H | Derivati 4-(2-fenilsulfanil-fenil)-piperidina kotzaviralci ponovnega vnosa serotonina |
| EP2400300A1 (en) | 2004-08-25 | 2011-12-28 | Takeda Pharmaceutical Company Limited | Method of screening preventives/remedies for stress urinary incontinence |
| US8158617B2 (en) | 2006-05-16 | 2012-04-17 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound and use thereof |
| WO2009063992A1 (ja) | 2007-11-15 | 2009-05-22 | Takeda Pharmaceutical Company Limited | 縮合ピリジン誘導体およびその用途 |
| UA98698C2 (en) * | 2008-03-03 | 2012-06-11 | Х. Луннбек А/С | Phenylsulfanylphenyl-piperidines and process for the preparation thereof |
| JPWO2011071136A1 (ja) | 2009-12-11 | 2013-04-22 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| EP2930171A1 (en) * | 2014-04-07 | 2015-10-14 | LEK Pharmaceuticals d.d. | Synthesis of vortioxetine via (2,4-dimethylphenyl)(2-iodophenyl)sulfane intermediate |
| CN105294554B (zh) * | 2015-11-18 | 2017-11-07 | 乳源瑶族自治县大众药品贸易有限公司 | 苯基哌嗪衍生物及其使用方法和用途 |
| EP3733204A4 (en) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | THERAPEUTIC FOR EXERCISE INCONTINENCE AND STAIR INCONTINENCE |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3803143A (en) * | 1969-09-08 | 1974-04-09 | Eisai Co Ltd | 6-amino alkylene 6,7-dihydro-5h-dibenzo (b,g),(1,5)thiazocines |
| US4018830A (en) * | 1969-09-22 | 1977-04-19 | Merck & Co., Inc. | Phenylthioaralkylamines |
| US4055665A (en) * | 1974-11-25 | 1977-10-25 | Merck & Co., Inc. | Treating arrythmia with phenylthioaralkylamines |
| US4066654A (en) * | 1975-04-16 | 1978-01-03 | G. D. Searle & Co. | 1-triarylalkyl-4-phenyl-4-piperidine carboxylic acids and derivatives |
| US4056632A (en) * | 1975-07-21 | 1977-11-01 | Burroughs Wellcome Co. | 2-Hydroxymethyl-2'-aminomethyl-diphenylsulfides and method of use |
| DE2802306A1 (de) * | 1977-01-27 | 1978-08-10 | Hoechst Ag | Azacycloalkane, azacycloalkene und ihre derivate |
| US4241071A (en) * | 1977-01-27 | 1980-12-23 | American Hoechst Corporation | Antidepressant (α-phenyl-2-tolyl)azacycloalkanes |
| US4198417A (en) * | 1979-01-10 | 1980-04-15 | American Hoechst Corporation | Phenoxyphenylpiperidines |
| US4198419A (en) * | 1979-01-10 | 1980-04-15 | American Hoechst Corporation | Phenylthiophenylpiperidines |
| GB8912971D0 (en) * | 1989-06-06 | 1989-07-26 | Wellcome Found | Halogen substituted diphenylsulfides |
| AU769430B2 (en) * | 1999-10-13 | 2004-01-29 | Pfizer Products Inc. | Biaryl ether derivatives useful as monoamine reuptake inhibitors |
| US6410736B1 (en) * | 1999-11-29 | 2002-06-25 | Pfizer Inc. | Biaryl ether derivatives useful as monoamine reuptake inhibitors |
| WO2001049678A1 (en) * | 1999-12-30 | 2001-07-12 | H. Lundbeck A/S | Substituted phenyl-piperazine derivatives, their preparation and use |
| US6436938B1 (en) * | 2001-01-22 | 2002-08-20 | Pfizer Inc. | Combination treatment for depression |
| US20020107244A1 (en) * | 2001-02-02 | 2002-08-08 | Howard Harry R. | Combination treatment for depression |
| UA81749C2 (uk) * | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
-
2004
- 2004-02-04 UA UAA200508779A patent/UA81300C2/uk unknown
- 2004-04-02 DE DE602004012724T patent/DE602004012724T2/de not_active Expired - Fee Related
- 2004-04-02 AR ARP040101130A patent/AR043964A1/es not_active Application Discontinuation
- 2004-04-02 JP JP2006504348A patent/JP2006522029A/ja active Pending
- 2004-04-02 EP EP04725299A patent/EP1613594B1/en not_active Expired - Lifetime
- 2004-04-02 ZA ZA200507182A patent/ZA200507182B/en unknown
- 2004-04-02 BR BRPI0408453-5A patent/BRPI0408453A/pt not_active IP Right Cessation
- 2004-04-02 CN CNB2004800094713A patent/CN100384822C/zh not_active Expired - Fee Related
- 2004-04-02 NZ NZ541944A patent/NZ541944A/en unknown
- 2004-04-02 MX MXPA05010678A patent/MXPA05010678A/es active IP Right Grant
- 2004-04-02 PL PL04725299T patent/PL1613594T3/pl unknown
- 2004-04-02 AU AU2004226319A patent/AU2004226319A1/en not_active Abandoned
- 2004-04-02 AT AT04725299T patent/ATE390413T1/de not_active IP Right Cessation
- 2004-04-02 US US10/551,869 patent/US20070173522A1/en not_active Abandoned
- 2004-04-02 WO PCT/DK2004/000243 patent/WO2004087662A1/en active IP Right Grant
- 2004-04-02 KR KR1020057018870A patent/KR20060021825A/ko not_active Application Discontinuation
- 2004-04-02 SI SI200430727T patent/SI1613594T1/sl unknown
- 2004-04-02 EA EA200501579A patent/EA009282B1/ru not_active IP Right Cessation
- 2004-04-02 PT PT04725299T patent/PT1613594E/pt unknown
- 2004-04-02 CA CA002521172A patent/CA2521172A1/en not_active Abandoned
- 2004-04-02 CL CL200400730A patent/CL2004000730A1/es unknown
- 2004-04-02 DK DK04725299T patent/DK1613594T3/da active
- 2004-04-02 ES ES04725299T patent/ES2301979T3/es not_active Expired - Lifetime
-
2005
- 2005-08-29 IS IS8007A patent/IS8007A/is unknown
- 2005-11-02 CO CO05111852A patent/CO5700777A2/es unknown
- 2005-11-04 NO NO20055205A patent/NO20055205L/no unknown
-
2006
- 2006-09-26 HK HK06110721A patent/HK1090051A1/xx not_active IP Right Cessation
-
2008
- 2008-06-03 HR HR20080243T patent/HRP20080243T3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE602004012724D1 (de) | 2008-05-08 |
| PL1613594T3 (pl) | 2008-09-30 |
| CL2004000730A1 (es) | 2005-02-18 |
| DE602004012724T2 (de) | 2009-04-09 |
| IS8007A (is) | 2005-08-29 |
| DK1613594T3 (da) | 2008-07-14 |
| AR043964A1 (es) | 2005-08-17 |
| NZ541944A (en) | 2008-05-30 |
| ES2301979T3 (es) | 2008-07-01 |
| US20070173522A1 (en) | 2007-07-26 |
| SI1613594T1 (sl) | 2008-08-31 |
| EP1613594A1 (en) | 2006-01-11 |
| ZA200507182B (en) | 2006-12-27 |
| CN100384822C (zh) | 2008-04-30 |
| AU2004226319A1 (en) | 2004-10-14 |
| PT1613594E (pt) | 2008-07-01 |
| CO5700777A2 (es) | 2006-11-30 |
| EP1613594B1 (en) | 2008-03-26 |
| EA200501579A1 (ru) | 2006-04-28 |
| MXPA05010678A (es) | 2005-12-12 |
| CN1777585A (zh) | 2006-05-24 |
| KR20060021825A (ko) | 2006-03-08 |
| HRP20080243T3 (en) | 2009-04-30 |
| HK1090051A1 (en) | 2006-12-15 |
| EA009282B1 (ru) | 2007-12-28 |
| JP2006522029A (ja) | 2006-09-28 |
| ATE390413T1 (de) | 2008-04-15 |
| CA2521172A1 (en) | 2004-10-14 |
| WO2004087662A1 (en) | 2004-10-14 |
| BRPI0408453A (pt) | 2006-04-04 |
| NO20055205L (no) | 2005-11-04 |
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