DE102004023501A1 - Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate - Google Patents
Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate Download PDFInfo
- Publication number
- DE102004023501A1 DE102004023501A1 DE102004023501A DE102004023501A DE102004023501A1 DE 102004023501 A1 DE102004023501 A1 DE 102004023501A1 DE 102004023501 A DE102004023501 A DE 102004023501A DE 102004023501 A DE102004023501 A DE 102004023501A DE 102004023501 A1 DE102004023501 A1 DE 102004023501A1
- Authority
- DE
- Germany
- Prior art keywords
- cyclohexyl
- dimethylamino
- benzyl
- phenyl
- oxo
- 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- Withdrawn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
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- 125000003118 aryl group Chemical group 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 21
- 125000001544 thienyl group Chemical group 0.000 claims description 20
- 208000002193 Pain Diseases 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 19
- 125000002541 furyl group Chemical group 0.000 claims description 16
- 125000001041 indolyl group Chemical group 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=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
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
- 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
- 229940079593 drug Drugs 0.000 claims description 10
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 10
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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
- 238000004519 manufacturing process Methods 0.000 claims description 8
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 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 6
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
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- SCHWABGSWZDREQ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-5-oxo-5-phenylpentanamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCCC(=O)C1=CC=CC=C1 SCHWABGSWZDREQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
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- 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 4
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 4
- VCUSYDGPHVVMDW-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-(dimethylamino)-4-phenylcyclohexyl]-4-oxobutanamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)C1=CC=C(Cl)C=C1 VCUSYDGPHVVMDW-UHFFFAOYSA-N 0.000 claims description 4
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 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
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
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- 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 3
- 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 3
- SHKWSBAVRQZYLE-UHFFFAOYSA-N 5-oxo-5-phenylpentanoic acid Chemical compound OC(=O)CCCC(=O)C1=CC=CC=C1 SHKWSBAVRQZYLE-UHFFFAOYSA-N 0.000 claims description 3
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- 239000000654 additive Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 208000022531 anorexia Diseases 0.000 claims description 3
- 238000011260 co-administration Methods 0.000 claims description 3
- 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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- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 230000008991 intestinal motility Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([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
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
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- KZDFWALHBNDHDR-UHFFFAOYSA-N N-(4-benzyl-4-piperidin-1-ylcyclohexyl)-4-oxo-4-phenylbutanamide N-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-(4-fluorophenyl)-4-oxobutanamide Chemical compound CN(C)C1(Cc2ccc(C)cc2)CCC(CC1)NC(=O)CCC(=O)c1ccc(F)cc1.O=C(CCC(=O)c1ccccc1)NC1CCC(Cc2ccccc2)(CC1)N1CCCCC1 KZDFWALHBNDHDR-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008299 semisolid dosage form Substances 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 230000013275 serotonin uptake Effects 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 208000009935 visceral pain Diseases 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/80—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms having carbon atoms of carboxamide groups and keto groups bound to the same carbon atom, e.g. acetoacetamides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Addiction (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Anesthesiology (AREA)
- Psychology (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Pregnancy & Childbirth (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023501A DE102004023501A1 (de) | 2004-05-10 | 2004-05-10 | Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate |
| PCT/EP2005/004907 WO2005110970A1 (de) | 2004-05-10 | 2005-05-06 | Oxosubstituierte cyclohexyl-1,4-diamin-derivate |
| JP2007512027A JP4896009B2 (ja) | 2004-05-10 | 2005-05-06 | オキソ置換されたシクロヘキシル−１，４−ジアミンの酸誘導体 |
| CA2566210A CA2566210C (en) | 2004-05-10 | 2005-05-06 | Oxo-substituted cyclohexyl-1,4-diamine derivatives |
| EP05738450.5A EP1751088B1 (de) | 2004-05-10 | 2005-05-06 | Oxosubstituierte cyclohexyl-1,4-diamin-derivate |
| US11/594,952 US7476763B2 (en) | 2004-05-10 | 2006-11-09 | Oxo-substituted cyclohexyl-1,4-diamine compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023501A DE102004023501A1 (de) | 2004-05-10 | 2004-05-10 | Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102004023501A1 true DE102004023501A1 (de) | 2005-12-01 |
Family
ID=34968416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102004023501A Withdrawn DE102004023501A1 (de) | 2004-05-10 | 2004-05-10 | Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7476763B2 (https=) |
| EP (1) | EP1751088B1 (https=) |
| JP (1) | JP4896009B2 (https=) |
| CA (1) | CA2566210C (https=) |
| DE (1) | DE102004023501A1 (https=) |
| WO (1) | WO2005110970A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008110351A2 (en) * | 2007-03-15 | 2008-09-18 | Dompe' Pha.R.Ma S.P.A. | Use of (r) and (s)-2-aryl-propionic acid derivatives as antiseptic agents |
| 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 |
| US20030229119A1 (en) * | 2002-02-22 | 2003-12-11 | Kym Philip R. | Antagonists of melanin concentrating hormone effects on the melanin concetrating hormone receptor |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5304479A (en) | 1991-12-06 | 1994-04-19 | Diagnostic Reagents, Inc. | Phencyclidine compounds and assays for its determination |
| 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 |
| GB0012240D0 (en) | 2000-05-19 | 2000-07-12 | Merck Sharp & Dohme | Therapeutic agents |
| 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. |
| US6571525B2 (en) | 2001-08-01 | 2003-06-03 | J. David Coleman | Construction block |
| 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 |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
| DE102004023522A1 (de) * | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Substituierte Cyclohexyl-1,4-diamin-Derivate |
-
2004
- 2004-05-10 DE DE102004023501A patent/DE102004023501A1/de not_active Withdrawn
-
2005
- 2005-05-06 WO PCT/EP2005/004907 patent/WO2005110970A1/de not_active Ceased
- 2005-05-06 EP EP05738450.5A patent/EP1751088B1/de not_active Expired - Lifetime
- 2005-05-06 CA CA2566210A patent/CA2566210C/en not_active Expired - Fee Related
- 2005-05-06 JP JP2007512027A patent/JP4896009B2/ja not_active Expired - Fee Related
-
2006
- 2006-11-09 US US11/594,952 patent/US7476763B2/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 |
| US20030229119A1 (en) * | 2002-02-22 | 2003-12-11 | Kym Philip R. | Antagonists of melanin concentrating hormone effects on the melanin concetrating hormone receptor |
Also Published As
| Publication number | Publication date |
|---|---|
| US20070088034A1 (en) | 2007-04-19 |
| JP4896009B2 (ja) | 2012-03-14 |
| EP1751088B1 (de) | 2014-10-08 |
| EP1751088A1 (de) | 2007-02-14 |
| JP2007536317A (ja) | 2007-12-13 |
| US7476763B2 (en) | 2009-01-13 |
| CA2566210A1 (en) | 2005-11-24 |
| WO2005110970A1 (de) | 2005-11-24 |
| CA2566210C (en) | 2013-08-27 |
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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 |