EP1070063A1 - Derives d'amine indol-3-yl-cyclhexyle utilises dans le traitement de la depression (antagonistes du recepteur 5-ht1) - Google Patents
Derives d'amine indol-3-yl-cyclhexyle utilises dans le traitement de la depression (antagonistes du recepteur 5-ht1)Info
- Publication number
- EP1070063A1 EP1070063A1 EP99916450A EP99916450A EP1070063A1 EP 1070063 A1 EP1070063 A1 EP 1070063A1 EP 99916450 A EP99916450 A EP 99916450A EP 99916450 A EP99916450 A EP 99916450A EP 1070063 A1 EP1070063 A1 EP 1070063A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydrogen
- lower alkyl
- independently
- indol
- phenyl
- 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.)
- Withdrawn
Links
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- 208000020401 Depressive disease Diseases 0.000 title description 4
- 102000035038 5-HT1 receptors Human genes 0.000 title description 2
- 108091005478 5-HT1 receptors Proteins 0.000 title description 2
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 230000001430 anti-depressive effect Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- OENICUBCLXKLJQ-UHFFFAOYSA-N ethyl 2,3-dibromopropanoate Chemical compound CCOC(=O)C(Br)CBr OENICUBCLXKLJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
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- 150000002334 glycols Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
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- 230000008517 inhibition of serotonin uptake Effects 0.000 description 1
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- 239000011630 iodine Substances 0.000 description 1
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- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- UFYQZKLUZJZODA-UHFFFAOYSA-N n-cyclohexyl-1h-indol-3-amine Chemical class C1CCCCC1NC1=CNC2=CC=CC=C12 UFYQZKLUZJZODA-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
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- 229940049954 penicillin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000013275 serotonin uptake Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
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- 229960005322 streptomycin Drugs 0.000 description 1
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- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
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- 229960000278 theophylline Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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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
- A61P25/24—Antidepressants
Definitions
- the compounds of the present invention are selected from the following:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
On décrit des composés qui sont efficaces dans le traitement des troubles des symptômes neurologiques affectés par la sérotonine (le récepteur 5-HT1A étant actif), ces composés étant représentés par la formule (I). Dans cette formule, R1 et R5 représentent chacun indépendamment, hydrogène, halogène, alcoxy inférieur, alkyle inférieur, cyano ou trifluorométhyle; R2 et R4 représentent chacun indépendamment hydrogène, alkyle inférieur, phényle ou phényle substitué; R3 représente hydrogène ou alkyle inférieur; et X et Y représentent chacun indépendamment O, NR6 ou Ch2, R6 représentant hydrogène, alkyle inférieur, phényle ou phényle substitué. Cette invention concerne lesdits composés de formule (I) ainsi que leurs sels pharmaceutiquement acceptables. formule (I)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57244 | 1993-05-03 | ||
| US5724498A | 1998-04-08 | 1998-04-08 | |
| PCT/US1999/007606 WO1999051592A1 (fr) | 1998-04-08 | 1999-04-07 | Derives d'amine indol-3-yl-cyclhexyle utilises dans le traitement de la depression (antagonistes du recepteur 5-ht1) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1070063A1 true EP1070063A1 (fr) | 2001-01-24 |
Family
ID=22009404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP99916450A Withdrawn EP1070063A1 (fr) | 1998-04-08 | 1999-04-07 | Derives d'amine indol-3-yl-cyclhexyle utilises dans le traitement de la depression (antagonistes du recepteur 5-ht1) |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1070063A1 (fr) |
| JP (1) | JP2002510682A (fr) |
| CN (1) | CN1304409A (fr) |
| AU (1) | AU3476599A (fr) |
| CA (1) | CA2327360A1 (fr) |
| WO (1) | WO1999051592A1 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6221863B1 (en) | 1999-01-07 | 2001-04-24 | American Home Products Corp. | 3,4-dihydro-2H-benzo[1,4]oxazine derivatives |
| TW546299B (en) * | 1999-01-07 | 2003-08-11 | Wyeth Corp | 3,4-dihydro-2H-benzo[1,4]oxazinyl-methyl-[3-(1H-indol-3-yl)-alkyl]-amines |
| AU2494300A (en) * | 1999-01-07 | 2000-07-24 | American Home Products Corporation | 3,4-dihydro-2h-benzo(1,4)oxazine derivatives |
| GB0203804D0 (en) | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| US6911445B2 (en) * | 2002-09-12 | 2005-06-28 | Wyeth | Antidepressant cycloalkylamine derivatives of heterocycle-fused benzodioxans |
| US7041697B2 (en) | 2002-09-12 | 2006-05-09 | Wyeth | Antidepressant cycloalkylamine derivatives of 2,3-dihydro-1,4-benzodioxan |
| US7276603B2 (en) * | 2003-05-02 | 2007-10-02 | Wyeth | Benzofuranyl-and benzothienyl-piperazinyl quinolines and methods of their use |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3058980A (en) * | 1962-10-16 | Substitution products of benzo- | ||
| US4612312A (en) * | 1984-07-30 | 1986-09-16 | Merrell Dow Pharmaceuticals Inc. | Glutarimide antianxiety and antihypertensive agents |
| GB8719167D0 (en) * | 1987-08-13 | 1987-09-23 | Glaxo Group Ltd | Chemical compounds |
| DK37790A (da) * | 1990-02-13 | 1991-08-14 | Novo Nordisk As | Indolderivater, deres fremstilling og anvendelse |
| US5189179A (en) * | 1990-08-29 | 1993-02-23 | Merrell Dow Pharmaceuticals Inc. | Serotonin 5ht1a agonists |
| US5468768A (en) * | 1994-01-06 | 1995-11-21 | Bristol-Myers Squibb Company | Antimigraine derivatives of indolylcycloalkanylamines |
| US5521197A (en) * | 1994-12-01 | 1996-05-28 | Eli Lilly And Company | 3-<1-alkylenearyl>-4-<1,2,3,6-tetrahydropyridinyl>-and 3-<1-alkylenearyl>-4-piperidinyl-1h-indoles: new 5-HT1F agonists |
| NZ305166A (en) * | 1995-03-20 | 1998-12-23 | Lilly Co Eli | 5-substituted-3-(1,2,3,6-tetrahydropyridin-4-yl)- and 3-(piperidin-4-yl)-1h-indoles; preparation and medicaments |
-
1999
- 1999-04-07 AU AU34765/99A patent/AU3476599A/en not_active Abandoned
- 1999-04-07 CN CN99807010A patent/CN1304409A/zh active Pending
- 1999-04-07 WO PCT/US1999/007606 patent/WO1999051592A1/fr not_active Application Discontinuation
- 1999-04-07 CA CA002327360A patent/CA2327360A1/fr not_active Abandoned
- 1999-04-07 JP JP2000542313A patent/JP2002510682A/ja active Pending
- 1999-04-07 EP EP99916450A patent/EP1070063A1/fr not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9951592A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1304409A (zh) | 2001-07-18 |
| AU3476599A (en) | 1999-10-25 |
| CA2327360A1 (fr) | 1999-10-14 |
| JP2002510682A (ja) | 2002-04-09 |
| WO1999051592A1 (fr) | 1999-10-14 |
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