CA2568897C - Saturated and unsaturated 3-pyridyl-benzocycloalkylmethyl-amines for use in the treatment of pains, depressions and anxiety states - Google Patents
Saturated and unsaturated 3-pyridyl-benzocycloalkylmethyl-amines for use in the treatment of pains, depressions and anxiety states Download PDFInfo
- Publication number
- CA2568897C CA2568897C CA2568897A CA2568897A CA2568897C CA 2568897 C CA2568897 C CA 2568897C CA 2568897 A CA2568897 A CA 2568897A CA 2568897 A CA2568897 A CA 2568897A CA 2568897 C CA2568897 C CA 2568897C
- Authority
- CA
- Canada
- Prior art keywords
- pyridin
- corresponding hydrochloride
- dimethylaminomethyl
- ylmethyl
- amine
- 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 - Fee Related
Links
- 208000002193 Pain Diseases 0.000 title claims abstract description 36
- 208000019901 Anxiety disease Diseases 0.000 title claims abstract description 25
- 230000036407 pain Effects 0.000 title claims abstract description 20
- 229920006395 saturated elastomer Polymers 0.000 title claims description 21
- 208000020401 Depressive disease Diseases 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000003814 drug Substances 0.000 claims abstract description 22
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 11
- 208000032841 Bulimia Diseases 0.000 claims abstract description 11
- 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 11
- 208000030814 Eating disease Diseases 0.000 claims abstract description 11
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 11
- 208000026139 Memory disease Diseases 0.000 claims abstract description 11
- 208000003251 Pruritus Diseases 0.000 claims abstract description 11
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 11
- 208000000323 Tourette Syndrome Diseases 0.000 claims abstract description 11
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- 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 11
- 208000010877 cognitive disease Diseases 0.000 claims abstract description 11
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 11
- 208000002271 trichotillomania Diseases 0.000 claims abstract description 11
- 229940079593 drug Drugs 0.000 claims abstract description 10
- 208000013403 hyperactivity Diseases 0.000 claims abstract description 9
- 208000004296 neuralgia Diseases 0.000 claims abstract description 9
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract 7
- 206010013663 drug dependence Diseases 0.000 claims abstract 7
- 208000011117 substance-related disease Diseases 0.000 claims abstract 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 182
- 239000000203 mixture Substances 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 25
- -1 dimethyl-(5-pyridin-3-yl-8,9-dihydro-7H-benzocyclohepten-6-ylmethyl) amine Chemical class 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229910052740 iodine Inorganic materials 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000012458 free base Substances 0.000 claims description 14
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- QRKAPEZZSALFQR-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-5-methoxy-1-pyridin-3-yl-3,4-dihydro-2h-naphthalen-1-ol Chemical compound COC1=CC=CC2=C1CCC(CN(C)C)C2(O)C1=CC=CN=C1 QRKAPEZZSALFQR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- KEAOSKLDFWJIGP-UHFFFAOYSA-N 6-[(dimethylamino)methyl]-5-pyridin-3-yl-7,8-dihydronaphthalen-1-ol Chemical compound C12=CC=CC(O)=C2CCC(CN(C)C)=C1C1=CC=CN=C1 KEAOSKLDFWJIGP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- CYHKDODPXAVVJY-UHFFFAOYSA-N 1-(5-methoxy-1-pyridin-3-yl-3,4-dihydronaphthalen-2-yl)-n,n-dimethylmethanamine Chemical compound CN(C)CC=1CCC=2C(OC)=CC=CC=2C=1C1=CC=CN=C1 CYHKDODPXAVVJY-UHFFFAOYSA-N 0.000 claims description 6
- CJZGNRDVLLHEER-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-pyridin-3-yl-3h-inden-5-ol Chemical compound C12=CC=C(O)C=C2CC(CN(C)C)=C1C1=CC=CN=C1 CJZGNRDVLLHEER-UHFFFAOYSA-N 0.000 claims description 6
- JRQUDCPZCIGPEF-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-6-methoxy-1-pyridin-3-yl-2,3-dihydroinden-1-ol Chemical compound C12=CC(OC)=CC=C2CC(CN(C)C)C1(O)C1=CC=CN=C1 JRQUDCPZCIGPEF-UHFFFAOYSA-N 0.000 claims description 6
- GDMQXYMWMGHHKE-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-pyridin-3-yl-2,3-dihydrochromen-4-ol Chemical compound CN(C)CC1COC2=CC=CC=C2C1(O)C1=CC=CN=C1 GDMQXYMWMGHHKE-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- YGCWTLJXPQFPEQ-UHFFFAOYSA-N n,n-dimethyl-1-(3-pyridin-3-yl-1h-inden-2-yl)methanamine Chemical compound C12=CC=CC=C2CC(CN(C)C)=C1C1=CC=CN=C1 YGCWTLJXPQFPEQ-UHFFFAOYSA-N 0.000 claims description 6
- JKUVGEXRZZWOFY-UHFFFAOYSA-N 1-(6-fluoro-3-pyridin-3-yl-1h-inden-2-yl)-n,n-dimethylmethanamine Chemical compound C12=CC=C(F)C=C2CC(CN(C)C)=C1C1=CC=CN=C1 JKUVGEXRZZWOFY-UHFFFAOYSA-N 0.000 claims description 5
- GQPGBYGEQXBPQQ-UHFFFAOYSA-N 1-(6-methoxy-3-pyridin-3-yl-1h-inden-2-yl)-n,n-dimethylmethanamine Chemical compound CN(C)CC=1CC2=CC(OC)=CC=C2C=1C1=CC=CN=C1 GQPGBYGEQXBPQQ-UHFFFAOYSA-N 0.000 claims description 5
- AYIMCOMVIZKFTL-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-pyridin-3-yl-2,3-dihydroinden-1-ol Chemical compound CN(C)CC1CC2=CC=CC=C2C1(O)C1=CC=CN=C1 AYIMCOMVIZKFTL-UHFFFAOYSA-N 0.000 claims description 5
- YEENLRKTQJLHGC-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-5-fluoro-1-pyridin-3-yl-2,3-dihydroinden-1-ol Chemical compound CN(C)CC1CC2=CC(F)=CC=C2C1(O)C1=CC=CN=C1 YEENLRKTQJLHGC-UHFFFAOYSA-N 0.000 claims description 5
- AHCCCKGSLZERRE-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-5-pyridin-3-yl-3,4-dihydro-2h-1-benzoxepin-5-ol Chemical compound CN(C)CC1CCOC2=CC=CC=C2C1(O)C1=CC=CN=C1 AHCCCKGSLZERRE-UHFFFAOYSA-N 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- VQEYEIUTACZWBP-UHFFFAOYSA-N n,n-dimethyl-1-[3-pyridin-3-yl-6-(trifluoromethoxy)-1h-inden-2-yl]methanamine Chemical compound C12=CC=C(OC(F)(F)F)C=C2CC(CN(C)C)=C1C1=CC=CN=C1 VQEYEIUTACZWBP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
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- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 5
- PRPULZAHTDWDFW-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-pyridin-3-yl-5-(trifluoromethoxy)-2,3-dihydroinden-1-ol Chemical compound CN(C)CC1CC2=CC(OC(F)(F)F)=CC=C2C1(O)C1=CC=CN=C1 PRPULZAHTDWDFW-UHFFFAOYSA-N 0.000 claims description 4
- HCYZQCDUOXFBGY-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-4-pyridin-3-yl-2,3-dihydrothiochromen-4-ol Chemical compound CN(C)CC1CSC2=CC=CC=C2C1(O)C1=CC=CN=C1 HCYZQCDUOXFBGY-UHFFFAOYSA-N 0.000 claims description 4
- AZFNLAWLWJOLDL-UHFFFAOYSA-N 6-[(dimethylamino)methyl]-5-pyridin-3-yl-6,7,8,9-tetrahydrobenzo[7]annulen-5-ol Chemical compound CN(C)CC1CCCC2=CC=CC=C2C1(O)C1=CC=CN=C1 AZFNLAWLWJOLDL-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- LAHZKUNEQKCMJZ-UHFFFAOYSA-N n,n-dimethyl-1-(5-pyridin-3-yl-8,9-dihydro-7h-benzo[7]annulen-6-yl)methanamine Chemical compound C12=CC=CC=C2CCCC(CN(C)C)=C1C1=CC=CN=C1 LAHZKUNEQKCMJZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- VSNLINZDYNIUSB-UHFFFAOYSA-N 1-(5-methoxy-3-pyridin-3-yl-1h-inden-2-yl)-n,n-dimethylmethanamine Chemical compound C12=CC(OC)=CC=C2CC(CN(C)C)=C1C1=CC=CN=C1 VSNLINZDYNIUSB-UHFFFAOYSA-N 0.000 claims description 3
- PWFIDZRWWJSWEM-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-pyridin-3-yl-3,4-dihydro-2h-naphthalen-1-ol Chemical compound CN(C)CC1CCC2=CC=CC=C2C1(O)C1=CC=CN=C1 PWFIDZRWWJSWEM-UHFFFAOYSA-N 0.000 claims description 3
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- AVJUYOMQAYCMCY-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-5-pyridin-3-yl-3,4-dihydro-2h-1-benzothiepin-5-ol Chemical compound CN(C)CC1CCSC2=CC=CC=C2C1(O)C1=CC=CN=C1 AVJUYOMQAYCMCY-UHFFFAOYSA-N 0.000 claims description 3
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- ZIKZSXHMGBOHMR-UHFFFAOYSA-N n,n-dimethyl-1-(1-pyridin-3-yl-1,2,3,4-tetrahydronaphthalen-2-yl)methanamine Chemical compound CN(C)CC1CCC2=CC=CC=C2C1C1=CC=CN=C1 ZIKZSXHMGBOHMR-UHFFFAOYSA-N 0.000 claims description 3
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004030099A DE102004030099A1 (de) | 2004-06-22 | 2004-06-22 | Gesättigte und ungesättigte 3-Pyridyl-benzocycloalkylmethyl-amine als Serotonin- und/oder Noradrenalin-Reuptake-Hemmer und/oder µ-Opioidrezeptor-Modulatoren |
| DE102004030099.2 | 2004-06-22 | ||
| PCT/EP2005/006624 WO2005123681A1 (de) | 2004-06-22 | 2005-06-20 | Gesättigte und ungesättigte 3-pyridyl-benzocycloalkylmethyl-amine zur behandlung von schmerzen, depressionen und angstzuständen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2568897A1 CA2568897A1 (en) | 2005-12-29 |
| CA2568897C true CA2568897C (en) | 2012-08-07 |
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Family Applications (1)
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|---|---|---|---|
| CA2568897A Expired - Fee Related CA2568897C (en) | 2004-06-22 | 2005-06-20 | Saturated and unsaturated 3-pyridyl-benzocycloalkylmethyl-amines for use in the treatment of pains, depressions and anxiety states |
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| Country | Link |
|---|---|
| US (1) | US8278338B2 (enExample) |
| EP (1) | EP1758860B1 (enExample) |
| JP (1) | JP4918486B2 (enExample) |
| AT (1) | ATE441632T1 (enExample) |
| CA (1) | CA2568897C (enExample) |
| CY (1) | CY1109519T1 (enExample) |
| DE (2) | DE102004030099A1 (enExample) |
| DK (1) | DK1758860T3 (enExample) |
| ES (1) | ES2333976T3 (enExample) |
| PL (1) | PL1758860T3 (enExample) |
| PT (1) | PT1758860E (enExample) |
| SI (1) | SI1758860T1 (enExample) |
| WO (1) | WO2005123681A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7435837B2 (en) | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| CA2604915A1 (en) | 2005-04-22 | 2006-11-02 | Wyeth | New therapeutic combinations for the treatment or prevention of depression |
| NZ569608A (en) * | 2006-01-06 | 2011-09-30 | Sepracor Inc | Tetralone-based monoamine reuptake inhibitors |
| EP2527328A1 (en) | 2008-04-01 | 2012-11-28 | Abbott GmbH & Co. KG | Tetrahydroisoquinolines, pharmaceutical compositions containing them, and their use in therapy |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8853196B2 (en) | 2011-08-05 | 2014-10-07 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CN104011028A (zh) | 2011-11-18 | 2014-08-27 | 艾伯维德国有限责任两合公司 | N-取代的氨基苯并环庚烯、氨基四氢化萘、氨基茚满和苯烷基胺衍生物、包含所述衍生物的药物组合物及其在治疗中的用途 |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9643947B2 (en) | 2013-08-28 | 2017-05-09 | Northwestern University | 7-membered fused heterocycles and methods of their synthesis |
| WO2015055770A1 (en) | 2013-10-17 | 2015-04-23 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| SG11201602935PA (en) | 2013-10-17 | 2016-05-30 | Abbvie Deutschland | Aminotetraline and aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CN104844471B (zh) * | 2015-04-21 | 2017-05-03 | 苏州远智医药科技有限公司 | 一种作为dor受体拮抗剂的化合物 |
| CN109896991B (zh) * | 2017-12-08 | 2020-11-20 | 苏州远智医药科技有限公司 | 一种δ阿片受体拮抗剂及其用途和药物组合物 |
Family Cites Families (11)
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| US3444176A (en) * | 1967-04-28 | 1969-05-13 | Mcneilab Inc | Certain 4-diloweralkylamino-lower alkyl - 5 - pyridyl (or phenyl)-2,3-dihydro - 1 - benzothiepins and derivatives thereof |
| US4845221A (en) * | 1988-04-15 | 1989-07-04 | American Home Products Corporation | Serotonergic substituted piperazinyl tetralins |
| WO1992009577A1 (en) * | 1990-11-22 | 1992-06-11 | Janssen Pharmaceutica N.V. | Isonicotinic acid derivatives and related spiro compounds with herbicidal action |
| US5668141A (en) * | 1996-04-02 | 1997-09-16 | Abbott Laboratories | Trans-2,6-,3,6-and 4,6-diaza-5,6,6a,7,8,12b-hexahydrobenzo[c]phenanthrene compounds as dopamine agonists |
| DE19805370A1 (de) * | 1997-03-14 | 1998-09-17 | Gruenenthal Gmbh | Substituierte Aminoverbindungen und ihre Verwendung als analgetisch wirksame Substanzen |
| AU4037699A (en) * | 1998-05-08 | 1999-11-29 | Akzo Nobel N.V. | Novel aryl-hydro naphthalenal kanamines |
| TW555757B (en) * | 1998-07-31 | 2003-10-01 | Akzo Nobel Nv | Aminomethylcarboxylic acid derivatives |
| CO5271697A1 (es) * | 2000-01-12 | 2003-04-30 | Pfizer Prod Inc | Composiciones y procedimientos para el tratamiento de afecciones que responden a un aumento de testosterona |
| EP1370546A2 (en) * | 2001-03-16 | 2003-12-17 | Abbott Laboratories | Novel amines as histamine-3 receptor ligands and their therapeutic applications |
| ATE527247T1 (de) * | 2001-07-05 | 2011-10-15 | Takeda Pharmaceutical | Benzokondensierte 5gliedrige heterocyclische verbindungen, verfahren zu deren herstellung und deren verwendung |
| JP2004149429A (ja) * | 2002-10-29 | 2004-05-27 | Takeda Chem Ind Ltd | インドール化合物およびその用途 |
-
2004
- 2004-06-22 DE DE102004030099A patent/DE102004030099A1/de not_active Withdrawn
-
2005
- 2005-06-20 DE DE502005008058T patent/DE502005008058D1/de not_active Expired - Lifetime
- 2005-06-20 SI SI200530854T patent/SI1758860T1/sl unknown
- 2005-06-20 ES ES05766092T patent/ES2333976T3/es not_active Expired - Lifetime
- 2005-06-20 EP EP05766092A patent/EP1758860B1/de not_active Expired - Lifetime
- 2005-06-20 DK DK05766092T patent/DK1758860T3/da active
- 2005-06-20 AT AT05766092T patent/ATE441632T1/de active
- 2005-06-20 WO PCT/EP2005/006624 patent/WO2005123681A1/de not_active Ceased
- 2005-06-20 CA CA2568897A patent/CA2568897C/en not_active Expired - Fee Related
- 2005-06-20 PT PT05766092T patent/PT1758860E/pt unknown
- 2005-06-20 PL PL05766092T patent/PL1758860T3/pl unknown
- 2005-06-20 JP JP2007517174A patent/JP4918486B2/ja not_active Expired - Fee Related
-
2006
- 2006-12-22 US US11/643,792 patent/US8278338B2/en not_active Expired - Fee Related
-
2009
- 2009-11-30 CY CY20091101251T patent/CY1109519T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT1758860E (pt) | 2009-12-07 |
| EP1758860A1 (de) | 2007-03-07 |
| SI1758860T1 (sl) | 2010-01-29 |
| US8278338B2 (en) | 2012-10-02 |
| DE102004030099A1 (de) | 2006-01-12 |
| EP1758860B1 (de) | 2009-09-02 |
| ATE441632T1 (de) | 2009-09-15 |
| JP4918486B2 (ja) | 2012-04-18 |
| PL1758860T3 (pl) | 2010-02-26 |
| CY1109519T1 (el) | 2014-08-13 |
| DE502005008058D1 (de) | 2009-10-15 |
| ES2333976T3 (es) | 2010-03-03 |
| DK1758860T3 (da) | 2010-01-11 |
| JP2008503523A (ja) | 2008-02-07 |
| US20070203192A1 (en) | 2007-08-30 |
| WO2005123681A1 (de) | 2005-12-29 |
| CA2568897A1 (en) | 2005-12-29 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140620 |