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 PDF

Info

Publication number: UA81300C2
Authority: UA; Ukraine
Prior art keywords: tetrahydropyridine; phenyl; hydrogen; halogen; alk
Prior art date: 2003-04-04

Application number

UAA200508779A

Other languages

English (en)

Ukrainian (uk)

Inventor

Ask Puschl

Benny Bang-Andersen

Thomas Ruhland

Kim Andersen

Jan Kehler

Original Assignee

Lundbeck & Co As H

Priority date (The priority date 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 date listed.)

2003-04-04

Filing date

2004-02-04

Publication date

2007-12-25

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35432910&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=UA81300(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2004-02-04 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2007-12-25 Publication of UA81300C2 publication Critical patent/UA81300C2/uk

Links

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
238000011282 treatment Methods 0.000 claims abstract description 23
208000019906 panic disease Diseases 0.000 claims abstract description 16
208000019022 Mood disease Diseases 0.000 claims abstract description 9
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 9
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
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
206010041250 Social phobia Diseases 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 11
208000035475 disorder Diseases 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
229940126601 medicinal product Drugs 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 9
208000011688 Generalised anxiety disease Diseases 0.000 claims description 8
206010034912 Phobia Diseases 0.000 claims description 8
208000029364 generalized anxiety disease Diseases 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
208000008811 Agoraphobia Diseases 0.000 claims description 7
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239000003085 diluting agent Substances 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
208000028173 post-traumatic stress disease Diseases 0.000 claims description 7
201000001716 specific phobia Diseases 0.000 claims description 7
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
241001465754 Metazoa Species 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
BQSPIKKONWKLAI-UHFFFAOYSA-N 4-[2-(4-chloro-2-methylphenyl)sulfanyl-5-methylphenyl]-1,2,3,6-tetrahydropyridine Chemical compound C=1CNCCC=1C1=CC(C)=CC=C1SC1=CC=C(Cl)C=C1C BQSPIKKONWKLAI-UHFFFAOYSA-N 0.000 claims 1
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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)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

UAA200508779A 2003-04-04 2004-02-04 Derivates of 4-(2-fenilsulfanilfenil)-1,2,3,6-tetrahydropiridin as retarding agents of serotonin recapture UA81300C2 (en)

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 (27)

Country	Link
US (1)	US20070173522A1 (de)
EP (1)	EP1613594B1 (de)
JP (1)	JP2006522029A (de)
KR (1)	KR20060021825A (de)
CN (1)	CN100384822C (de)
AR (1)	AR043964A1 (de)
AT (1)	ATE390413T1 (de)
AU (1)	AU2004226319A1 (de)
BR (1)	BRPI0408453A (de)
CA (1)	CA2521172A1 (de)
CL (1)	CL2004000730A1 (de)
CO (1)	CO5700777A2 (de)
DE (1)	DE602004012724T2 (de)
DK (1)	DK1613594T3 (de)
EA (1)	EA009282B1 (de)
ES (1)	ES2301979T3 (de)
HR (1)	HRP20080243T3 (de)
IS (1)	IS8007A (de)
MX (1)	MXPA05010678A (de)
NO (1)	NO20055205L (de)
NZ (1)	NZ541944A (de)
PL (1)	PL1613594T3 (de)
PT (1)	PT1613594E (de)
SI (1)	SI1613594T1 (de)
UA (1)	UA81300C2 (de)
WO (1)	WO2004087662A1 (de)
ZA (1)	ZA200507182B (de)

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Publication number	Priority date	Publication date	Assignee	Title
WO2004087156A1 (en)	2003-04-04	2004-10-14	H. Lundbeck A/S	4-(2-phenylsulfanyl-phenyl)-piperidine derivatives as serotonin reuptake inhibitors
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
JP5528699B2 (ja)	2006-05-16	2014-06-25	武田薬品工業株式会社	縮合複素環化合物およびその用途
JP5520051B2 (ja)	2007-11-15	2014-06-11	武田薬品工業株式会社	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
WO2011071136A1 (ja)	2009-12-11	2011-06-16	アステラス製薬株式会社	線維筋痛症治療剤
EP2930171A1 (de) *	2014-04-07	2015-10-14	LEK Pharmaceuticals d.d.	Synthese von Vortioxetin über (2,4-Dimethylphenyl) (2-Iodophenyl)sulfan-Zwischenprodukt
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
WO2019131902A1 (ja)	2017-12-27	2019-07-04	武田薬品工業株式会社	腹圧性尿失禁および便失禁の治療薬

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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
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
US4241071A (en) *	1977-01-27	1980-12-23	American Hoechst Corporation	Antidepressant (α-phenyl-2-tolyl)azacycloalkanes
DE2802306A1 (de) *	1977-01-27	1978-08-10	Hoechst Ag	Azacycloalkane, azacycloalkene und ihre derivate
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
SK4732002A3 (en) *	1999-10-13	2002-12-03	Pfizer Prod 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 DK DK04725299T patent/DK1613594T3/da active
- 2004-04-02 DE DE602004012724T patent/DE602004012724T2/de not_active Expired - Fee Related
- 2004-04-02 EP EP04725299A patent/EP1613594B1/de not_active Expired - Lifetime
- 2004-04-02 MX MXPA05010678A patent/MXPA05010678A/es active IP Right Grant
- 2004-04-02 AU AU2004226319A patent/AU2004226319A1/en not_active Abandoned
- 2004-04-02 CL CL200400730A patent/CL2004000730A1/es unknown
- 2004-04-02 KR KR1020057018870A patent/KR20060021825A/ko not_active Withdrawn
- 2004-04-02 US US10/551,869 patent/US20070173522A1/en not_active Abandoned
- 2004-04-02 HR HR20080243T patent/HRP20080243T3/xx unknown
- 2004-04-02 WO PCT/DK2004/000243 patent/WO2004087662A1/en not_active Ceased
- 2004-04-02 JP JP2006504348A patent/JP2006522029A/ja active Pending
- 2004-04-02 PL PL04725299T patent/PL1613594T3/pl unknown
- 2004-04-02 AR ARP040101130A patent/AR043964A1/es not_active Application Discontinuation
- 2004-04-02 BR BRPI0408453-5A patent/BRPI0408453A/pt not_active IP Right Cessation
- 2004-04-02 SI SI200430727T patent/SI1613594T1/sl unknown
- 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 CA CA002521172A patent/CA2521172A1/en not_active Abandoned
- 2004-04-02 EA EA200501579A patent/EA009282B1/ru not_active IP Right Cessation
- 2004-04-02 ES ES04725299T patent/ES2301979T3/es not_active Expired - Lifetime
- 2004-04-02 ZA ZA200507182A patent/ZA200507182B/en unknown
- 2004-04-02 AT AT04725299T patent/ATE390413T1/de not_active IP Right Cessation
- 2004-04-02 PT PT04725299T patent/PT1613594E/pt unknown
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

Also Published As

Publication number	Publication date
DK1613594T3 (da)	2008-07-14
EA200501579A1 (ru)	2006-04-28
ATE390413T1 (de)	2008-04-15
BRPI0408453A (pt)	2006-04-04
SI1613594T1 (sl)	2008-08-31
IS8007A (is)	2005-08-29
EP1613594A1 (de)	2006-01-11
CO5700777A2 (es)	2006-11-30
DE602004012724D1 (de)	2008-05-08
NZ541944A (en)	2008-05-30
ZA200507182B (en)	2006-12-27
DE602004012724T2 (de)	2009-04-09
CA2521172A1 (en)	2004-10-14
NO20055205L (no)	2005-11-04
HRP20080243T3 (hr)	2009-04-30
PT1613594E (pt)	2008-07-01
AU2004226319A1 (en)	2004-10-14
HK1090051A1 (en)	2006-12-15
EA009282B1 (ru)	2007-12-28
ES2301979T3 (es)	2008-07-01
MXPA05010678A (es)	2005-12-12
AR043964A1 (es)	2005-08-17
JP2006522029A (ja)	2006-09-28
KR20060021825A (ko)	2006-03-08
CN100384822C (zh)	2008-04-30
US20070173522A1 (en)	2007-07-26
PL1613594T3 (pl)	2008-09-30
CL2004000730A1 (es)	2005-02-18
WO2004087662A1 (en)	2004-10-14
CN1777585A (zh)	2006-05-24
EP1613594B1 (de)	2008-03-26

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