DE102004023506A1 - Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate - Google Patents
Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate Download PDFInfo
- Publication number
- DE102004023506A1 DE102004023506A1 DE102004023506A DE102004023506A DE102004023506A1 DE 102004023506 A1 DE102004023506 A1 DE 102004023506A1 DE 102004023506 A DE102004023506 A DE 102004023506A DE 102004023506 A DE102004023506 A DE 102004023506A DE 102004023506 A1 DE102004023506 A1 DE 102004023506A1
- Authority
- DE
- Germany
- Prior art keywords
- benzyl
- dimethylamino
- cyclohexyl
- chloro
- methyl
- 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- Withdrawn
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- 239000003814 drug Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 6
- -1 benzodioxolanyl Chemical group 0.000 claims description 144
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 34
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000001544 thienyl group Chemical group 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 239000005711 Benzoic acid Substances 0.000 claims description 19
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000002541 furyl group Chemical group 0.000 claims description 18
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 125000001041 indolyl group Chemical group 0.000 claims description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 14
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 14
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
- 150000001768 cations Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 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 12
- 150000007513 acids Chemical class 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 11
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 10
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
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- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 8
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
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- 238000004519 manufacturing process Methods 0.000 claims description 8
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- 239000004480 active ingredient Substances 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- KREWXDRXGISBEV-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-4-phenoxybutanamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCCOC1=CC=CC=C1 KREWXDRXGISBEV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- NULYMMSGHOWARS-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(dimethylamino)-4-phenylcyclohexyl]acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)COC1=CC=CC(Cl)=C1 NULYMMSGHOWARS-UHFFFAOYSA-N 0.000 claims description 5
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- QKOQLQWBLLMNHW-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(dimethylamino)-4-phenylcyclohexyl]acetamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)COC1=CC=CC(Cl)=C1 QKOQLQWBLLMNHW-UHFFFAOYSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
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- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012964 benzotriazole Substances 0.000 claims description 4
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical class NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 2
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- KKTCAPBKUJYTGF-UHFFFAOYSA-N 4-(4-chloro-2-methylphenoxy)-N-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]butanamide N-[4-(dimethylamino)-4-[(4-fluorophenyl)methyl]cyclohexyl]-2-phenoxybutanamide Chemical compound CCC(Oc1ccccc1)C(=O)NC1CCC(Cc2ccc(F)cc2)(CC1)N(C)C.CN(C)C1(Cc2ccc(C)cc2)CCC(CC1)NC(=O)CCCOc1ccc(Cl)cc1C KKTCAPBKUJYTGF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023506A DE102004023506A1 (de) | 2004-05-10 | 2004-05-10 | Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate |
| JP2007512032A JP5037336B2 (ja) | 2004-05-10 | 2005-05-06 | 鎖長が延ばされ、置換されたシクロヘキシル−1,4−ジアミンの酸誘導体 |
| CA2566219A CA2566219C (en) | 2004-05-10 | 2005-05-06 | Substituted cyclohexyl-1,4-diamine derivatives with a chain extension |
| EP05747800A EP1747191A1 (de) | 2004-05-10 | 2005-05-06 | Kettenverlängerte substituierte cyclohexyl-1,4-diamin-derivate |
| PCT/EP2005/004912 WO2005110975A1 (de) | 2004-05-10 | 2005-05-06 | Kettenverlängerte substituierte cyclohexyl-1,4-diamin-derivate |
| US11/594,953 US7786328B2 (en) | 2004-05-10 | 2006-11-09 | Cyclohexyl-1,4-diamine compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023506A DE102004023506A1 (de) | 2004-05-10 | 2004-05-10 | Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102004023506A1 true DE102004023506A1 (de) | 2005-12-01 |
Family
ID=34969346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102004023506A Withdrawn DE102004023506A1 (de) | 2004-05-10 | 2004-05-10 | Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7786328B2 (https=) |
| EP (1) | EP1747191A1 (https=) |
| JP (1) | JP5037336B2 (https=) |
| CA (1) | CA2566219C (https=) |
| DE (1) | DE102004023506A1 (https=) |
| WO (1) | WO2005110975A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004023635A1 (de) * | 2004-05-10 | 2006-04-13 | Grünenthal GmbH | Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate |
| AU2009228647B2 (en) | 2008-03-27 | 2013-07-04 | Grunenthal Gmbh | Substituted spirocyclic cyclohexane derivatives |
| JP5529843B2 (ja) | 2008-03-27 | 2014-06-25 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 置換シクロヘキシルジアミン |
| EP2280941B1 (de) | 2008-03-27 | 2015-05-06 | Grünenthal GmbH | (hetero-)aryl-cyclohexan-derivate |
| ES2375543T3 (es) | 2008-03-27 | 2012-03-01 | Grünenthal GmbH | Derivados de espiro(5.5)undecano. |
| ES2464102T3 (es) | 2008-03-27 | 2014-05-30 | Grünenthal GmbH | Derivados de 4-aminociclohexano sustituidos |
| CN102046591B (zh) | 2008-03-27 | 2014-12-03 | 格吕伦塔尔有限公司 | 羟甲基环己胺 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002090317A1 (de) * | 2001-05-09 | 2002-11-14 | Grünenthal GmbH | Substituierte cyclohexan-1,4-diaminderivate |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656182A (en) * | 1983-12-06 | 1987-04-07 | Warner-Lambert Company | Substituted trans-1,2-diaminocyclohexyl amide compounds |
| CA2373855A1 (en) * | 1999-05-12 | 2000-11-23 | Solvay Pharmaceuticals B.V. | Method of treating psychotic disorders |
| FR2797874B1 (fr) * | 1999-08-27 | 2002-03-29 | Adir | Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| ES2188344B1 (es) * | 2000-11-29 | 2004-09-16 | Laboratorios Vita, S.A. | Compuestos derivados de benzotiofeno, su procedimiento de obtencion y utilizacion de los mismos. |
| US7354932B2 (en) | 2001-12-21 | 2008-04-08 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds with enhanced efficacy |
| EP1458704A1 (en) * | 2001-12-21 | 2004-09-22 | H. Lundbeck A/S | Aminoindane derivatives as serotonin and norepinephrine uptake inhibitors |
| DE10252665A1 (de) * | 2002-11-11 | 2004-06-03 | Grünenthal GmbH | 4-Aminomethyl-1-aryl-cyclohexylamin-Derivate |
| JP2007522129A (ja) | 2004-01-21 | 2007-08-09 | エラン ファーマシューティカルズ,インコーポレイテッド | アスパラギン酸プロテアーゼ阻害薬を用いるアミロイドーシスの処置方法 |
| EP1736467A4 (en) * | 2004-04-06 | 2009-07-01 | Dainippon Sumitomo Pharma Co | NEW SULFONIC ACID AMID DERIVATIVE |
| DE102004023635A1 (de) * | 2004-05-10 | 2006-04-13 | Grünenthal GmbH | Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate |
-
2004
- 2004-05-10 DE DE102004023506A patent/DE102004023506A1/de not_active Withdrawn
-
2005
- 2005-05-06 WO PCT/EP2005/004912 patent/WO2005110975A1/de not_active Ceased
- 2005-05-06 CA CA2566219A patent/CA2566219C/en not_active Expired - Fee Related
- 2005-05-06 EP EP05747800A patent/EP1747191A1/de not_active Withdrawn
- 2005-05-06 JP JP2007512032A patent/JP5037336B2/ja not_active Expired - Fee Related
-
2006
- 2006-11-09 US US11/594,953 patent/US7786328B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002090317A1 (de) * | 2001-05-09 | 2002-11-14 | Grünenthal GmbH | Substituierte cyclohexan-1,4-diaminderivate |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005110975A1 (de) | 2005-11-24 |
| US20070281954A1 (en) | 2007-12-06 |
| EP1747191A1 (de) | 2007-01-31 |
| US7786328B2 (en) | 2010-08-31 |
| JP2007536322A (ja) | 2007-12-13 |
| CA2566219C (en) | 2012-08-07 |
| JP5037336B2 (ja) | 2012-09-26 |
| CA2566219A1 (en) | 2005-11-24 |
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| Date | Code | Title | Description |
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| OM8 | Search report available as to paragraph 43 lit. 1 sentence 1 patent law | ||
| R005 | Application deemed withdrawn due to failure to request examination |
Effective date: 20110510 |